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Sail Away Catamarans

Key West Sailing Charters

Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Florida Keys. Our native Floridian staff knows how to find the best activities on land or at sea, to guide you as you plan a unique and customized getaway.

Our Key West Sailing Charter Fleet

Sailing cats.

Southern Cross Catamaran

Southern Cross

Indoses boat

Fountain Pajot Elba 45

dream reach leopard 44

Dream Reach

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Sugar Magnolia

Honu Kai Catamaran

Seawind 1260

Second sight.

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Stay Glassy

Nautitech 40 open.

Ever Summer Exterior

Ever Summer

Fountaine pajot my44, key west attractions.

Duval St. in Key West

Historic Duval Street

One of the most popular destinations on the island of Key West is Duval Street. Visit the Ernest Hemingway Home and Museum where you can take in some history about the writer and meet a legendary six toed cat. If you feel like taking in some nature, visit the Key West Butterfly and Nature Conservatory where there are 50 - 60 different species of live butterflies from around the world. On Duval Street, you can simply take a stroll and hear live music, see art galleries, enjoy coffee shops and great restaurants, or find unique souvenirs at one of the many boutiques.

Romantic Sunsets

Beautiful sunsets are what Key West is all about. Enjoy the soothing ocean breeze, a glass of wine, and relax to the backdrop of the setting sun on your own private catamaran cruise. Watching the sunset has become an integral part of everyday life in paradise. This is one tradition you don’t want to miss!

Key West sunset

Crystal Clear Snorkeling

Key West offers many beaches and reefs where you can experience snorkeling in warm crystal-clear water. At Cottrell Key, see the unique sponge garden and large coral reefs. It is also an excellent place to see dolphins, sharks, stingrays, and Goliath groupers. Fort Zachary Taylor is considered one of the best offshore snorkeling spots in Key West where there are a variety of tropical fish species and living coral to see. A favorite among snorkeling enthusiasts is Sand Key Lighthouse Reef. With a remote location and strict no-take policy, the Sand Key Lighthouse Reef is one of the healthiest coral gardens in Florida.

Pristine Sandy Beaches

Craving a drink in your hand and your toes in the sand? Check out the turquoise waters at Smathers Beach. Rental shops are available with beach chairs, shade umbrellas, kayaks, jet skis and much more. Try South Beach for calm, shallow waters that are excellent for swimming and great for families. Higgs Beach is unique for its historical significance. Take a wander around, and you'll find monuments dedicated to the 19th-century slave cemetery located on the site. There is also a pier at Higgs Beach, where visitors can often spot stingrays and other marine species.

Key West south beach

Catamaran Echo - Key West

What Should I Bring?

  • Directions to Echo, Cruise Ship & K.W. Passenger Info

Key West Info

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  • Sunset Cruise

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$10 Off each person – Promo Code “EchoDirect”

(for Public trips only – sold by the seat)

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Catamaran ECHO 2

Catamaran echo 3.

Free Echo 3 shuttle from downtown Key West, A&B Lobster House parking lot.

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Catamaran ECHO

…is a fast and comfortable sailing machine, providing the most stable ride on the water. naturally it’s a catamaran.

And with our big bimini top, you can get all the Key West sun or shade that you want. The fresh water shower on deck comes in handy on those hot days. A private bathroom in the cabin makes a day in the wildlife refuge civilized and helps protect our tropical waters.

ECHO is located at the “Key West Historic Seaport” which is downtown in Old Key West at the famous Key West Bight. The Historic Seaport “Harbor Walk” goes right around the water’s edge and leads right to ECHO‘s dock along side the famous “Turtle Kraals Restaurant and Tower Bar”. Spend the day on the Harbor Walk before and after your ECHO trip and visit all the great shops, restaurants and bars and galleries. This is where all the locals hang out!

So come and hang out in the coolest part of town and cruise with us at Catamaran ECHO .

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ECHO'S Official Website

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Wild Dolphin

Snorkeling & Sailing Adventure

Click here to read more!

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Private Day Charters

2 to 19 Passengers

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Sunset Cruise - Adults Only

Private Trips Available (all ages welcome)

Towel (day trips), Sun screen applied (no oil), Hat, Camera, Sunglasses (polarized best), a jacket in fall, winter, spring (even if you think it’s warm out), a small bag to secure your things, a few bucks and a Big Smile!

Echo Upgrades

Please reserve upgrades in advance while reserving here online, or by phone or email before the trip.

Directions, Cruise Ship & K.W. Ferry Passenger Info

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Certificate of Excellence 2019

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Our Activities

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Private 4th of July Champagne Sunset and Fireworks Party Cruise - 2 Hours

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Catamaran Echo - Wild Dolphins! Snorkel & Sailing Adventure

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Catamaran Echo - Private Lighted Boat Parade Champagne Party

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Catamaran Echo - Sunset & Moët Cruise

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Catamaran Echo - Private Day Charters

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Catamaran Echo - Private 2 Hour Champagne Celebration Sunset Sail

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Bridging the space between reality & paradise.

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A luxury sailing catamaran charter with an emphasis on fun and adventure.

Sailing from Ft. Lauderdale, The Keys & The Bahamas.

Come sail with us!

Luxury Catamaran Guest accomodations

Meet The Crew

charter catamaran florida keys

Captain -  Scott Clark

He is most at home when on the water.  He enjoys tinkering with everything, but has a flair for all things electrical. He loves sharing stories, creating videos and spending time with his wife and 2 sons.

charter catamaran florida keys

First Mate - Holly Clark

She is most at home when she is spending time with friends and family. She enjoys cooking, meeting new people, yoga and snuggling with her granddog, Pugsly.

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The Ultimate Guide to an Unforgettable Key West Sailing Vacation

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Fort Lauderdale Boat Charter Tours Made Easy, Fun & Affordable

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Family Vacations are Incomplete without a Catamaran in the Bahamas

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Boat Charter Rules That You Must Be Aware of!

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A Day in the Life of a Charter Cat Owner

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Mission Accomplished!

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Our Mission

Tel. SAIL-TSB-DMB

(724) 587-2362, p.o. box 7696, sebring, fl 33872, ​ [email protected].

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SAILING SERENITY NOW

SERENITY NOW

Sailing Serenity Now Key west Catamaran

Private Charters Key West Florida

Private crewed sailing packages.

Set sail on your own private catamaran and explore the only living coral reef in the continental United States.  Sail the pristine turquoise waters of the Florida Keys and enjoy a relaxing afternoon on a secluded beach.  As a private charter you, and up to 5 of your guests, have the option to customize your adventure.

Full Day Sail  Adventure

Full Day Sail  Adventure Lunch and Optional Snorkeling

Starting at $1200

Half Day Sailing Adventure with

Optional lunch and snorkeling.

Starting at $600

Sunset Sailing Adventure with  Appetizer  and optional Snorkeling

Sailing catamaran "serenity now".

Up to 6 Passangers max

Sailing Catamaran

S/V "Serenity Now"  is a Fountaine Pajot Lipari 41.  She has a large comfortable trampoline on her bow and a spacious covered cockpit on her stern. Inside you will find a settee with seating for six along with four cabins and two large heads.

About Your Crew

Captain Tom and his wife Denise have been sailing for over two decades.   Over the course of the last three years they have sailed over 4,000 nm along the east coast of US and the Caribbean Sea.  Tom holds a USCG OUPV Captain's License.  Prior to their most recent adventure, Tom was a Research Physicist and his wife a Public Relations Manager.  Bow and Harry our French Hounds server at the pleasure of our guest or vacation at a nearby pet resort during charters.

dogs

6810 Font Street

Key West FL 33040

[email protected]

410-849-9199

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Sail the Florida Keys

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Get Away to Key West and Explore the Florida Keys by Sailboat

Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.  

Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks. 

While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business. 

charter catamaran florida keys

Some of the highlights to experience on a Florida Keys Sailing Charter Vacation 

Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.  

Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable. 

Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation. 

A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife. 

Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers. 

From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place. 

If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route. 

Browse our yachts for charter in Florida Keys

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Enjoy an Adventure in the Florida Keys on this Catamaran

Key West, FL

boating guide

In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:

  • 25 boat rentals in Key West, FL
  • 25 boat rentals in Stock Island, FL
  • 25 boat rentals in Cudjoe Key, FL
  • 25 boat rentals in Summerland Key, FL
  • 25 boat rentals in Little Torch Key, FL
  • 25 boat rentals in Big Pine Key, FL
  • 10 boat rentals in Marathon, FL
  • 10 boat rentals in Key Colony Beach, FL
  • 10 boat rentals in Duck Key, FL

Catamaran Charters in Key West, FL | Sailo Boat Rental

Looking for a catamaran charter in Key West? Boat rental in Key West, Florida   is always a great way to enjoy sailing trip experience in Florida. Choose your perfect catamaran charter with Sailo and set a course for adventure! When you rent a boat in Key West, you can choose your own itinerary and explore at your leisure. Want to relax on deck? Prefer to do some fishing? Or maybe you just want to escape the crowds? Find your ideal yacht rental in Key West with Sailo.

Our finest collection of catamaran charters in Key West, FL

Key West, FL is a well-known boating destination in the US, perfect for a memorable experience on a Sailo boat. The catamaran rentals are popular for both locals and tourists and a great choice if you want to spend some quality time with your family or friends. 7 charters are currently available with or without captain, lined up in the Key West’s marinas, waiting for their guests. Rent a private catamaran in Key West with Sailo: it’s easy, quick, secured and the best choice for a fun experience in the waters of Florida.

How to find the ideal catamaran charter in Key West, Florida?

Sailo has the most advanced filters to help you find the perfect boat rental for an amazing experience on the water in Key West, FL. Start your search by choosing your start trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by boat type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Florida, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.

How much does it cost to charter a catamaran in Key West for a day?

Whether you are looking to rent a catamaran yacht in Key West for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a yacht in Key West is $1100. You can however find excellent affordable rentals from $250 and also elegant yacht charters that can go up to $6500 (service fee and mandatory extras not included).

Can I pay in installments for my Sailo catamaran rental in Key West?

A lot of our boat owners allow payment in installments, particularly for the weekly charters. First installment is always charged at the time the booking is confirmed. To find out if a boat has an installment plan, reach out to the boat representative and ask details via 'Message Owner' before you submit the booking or check out the Payment Schedule at top of the booking page.

Guidelines to responsible yachting

If you’re looking to explore our beautiful planet, a yacht charter is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto:  'Take only photos, leave only wake'  (OK, so we paraphrased). To be a responsible sailor, remember:

  • Don’t disturb coral or sealife
  • Take your trash home (and don’t throw anything in the sea)
  • Respect the locals and their customs wherever you go

Read more about responsible boating.

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Florida Keys Luxury Yacht Charter

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Florida keys yacht charter, florida keys charter guide.

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Marquesas Keys

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Yachts for Charter in Florida Keys

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charter catamaran florida keys

GOLDEN HORIZON

162m | Brodogradevna Industrija Split | 2021

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23.77m | Privilege Marine | 2016

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RECORD YEAR

26.2m | Princess | 2021

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NO MATTER WHAT

26.82m | Sanlorenzo | 2022

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30m | Ocean Alexander | 2016

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39.62m | Westport Yachts | 2007

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49.1m | Trinity Yachts | 2009

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72m | Viareggio SuperYachts | 2015

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Luxury Yacht FREEDOM

FREEDOM | From US$ 100,000/wk

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Florida Keys Yacht Charter

Often considered America 's Caribbean Islands the Florida Keys yacht charter offers spectacular locations to explore.

You will often read references to a 'jade necklace' or a 'string of pearls' in descriptions of the many (800+) islands that stretch off into the sea. The Keys have become increasingly busy over the last few years with an increase in cruise ship and other tourism. The keys feature plenty of energy ashore, but to get away into the quieter areas a charter yacht is the only way to go.

charter catamaran florida keys

Photos: 1. A diver explores the coral reef in the Florida Keys National Marine Sanctuary off Key Largo - The reef system in the Keys is the only contiguous coral barrier reef in North America - Photo by Bob Care-Florida Keys News Bureau; 2. A Florida Keys fishing guide positions his angler to cast for a bonefish off Key Largo- Photo by Bob Krist-Florida Keys News Bureau; 3. Sunset in Key Largo- Florida Keys- paints a pretty picture at the Kona Kai Resort -Photo by Bob Krist-Florida Keys News Bureau

The first Key to come across on your cruise south will be Key Largo . Over the years Key Largo has become a busy weekender retreat from the mainland. As you sail further down though the Keys you will finally come to the last one, Key West .

The Florida Keys are sheltered by the only living coral reef in the United States. The Keys are well known to yacht charterers for the spectacular scuba diving and snorkelling, kayaking and eco-tours, dolphin watching, island hoping and fishing.

The types of yacht charter available in the Florida Keys are all the main types including motor, sailing, bareboat charter, skippered, crewed yachts, catamaran, power boat, sailboat, luxury yachts and super yacht charter.

The Florida Keys features a year round calendar of special events such as fishing tournaments, international yacht races, motor yacht races, Fantasy Fest, a lighted boat parade and Florida's own 10 day long Mardi Gras. We recommend charter yachts with a draft of under 4 or 5 ft (1.3 - 1.5m), as with a catamaran, so that you can get in to all the best areas within the Florida Keys.

Key West Yacht Charter

Key West has the ideal year round climate for yacht charter. Key West is a very unique town being the southernmost US city where history and tradition meets natural beauty and serenity. This city has real estate titles that date back to the King of Spain! Within walking distance from the historic Seaport District you will find palm-lined streets, tropical gardens, Ernest Hemingway's home, fine shops, art galleries, quaint restaurants and cafes. You can walk in the footsteps of Thomas Edison, Lou Gehrig, Harry Truman, and Tennessee Williams. You will also discover lively bars and pubs along with street musicians, jugglers, mimes and artists.

It is not unusual for charter guests to day sail their charter yachts using Key West as a base. They will sail and explore the keys during the day, utilising the restful anchorages, and then return to the first class marinas at night to experience Key West's nighttime entertainment. Remember to radio ahead to reserve marina space, as Key West is a busy part of the Florida Keys.

Below is a selection of fabulous Florida Keys charter yachts - please, contact us for additional vessels and more information here .

  • Florida Keys Charter Itinerary
  • Browse Florida Keys Charter Yachts
  • Luxury Motor Yachts for Charter in Florida Keys
  • Luxury Sailing Yachts for Charter in Florida Keys
  • Luxury Catamarans for Charter in Florida Keys
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Florida Keys Yacht Charter Enquiry

"I have just emailed your post charter feedback to you. It doesn't say nearly enough about how well and hard you worked on this deal. I am a retired commercial real estate broker who understands the importance of the deal-maker in the deal. You are a deal maker of the first order." E. G - chartered in Florida Keys.

Yachting Destinations Near the Florida Keys

In close proximity to the Florida Keys are a number of exciting sailing destination.

Delta Pacific Northwest

New England

New England Lighthouse In Late Afternoon The Portland Head Light At Portland Maine USA

Napa Valley

Yachts for charter in the florida keys, queen miri | from eur€ 1,125,000/wk.

Exterior

KENSHO | From EUR€ 850,000/wk

Luxury Superyacht KENSHO By Admiral Yachts

MARIA | From US$ 230,000/wk

The 52m Yacht MARIA

LADY ELAINE | From US$ 225,000/wk

Exterior - Main

GIGI | From US$ 225,000/wk

The 49m Yacht HARMONY

TCB | From US$ 215,000/wk

Luxury Superyacht TCB

MYSORAH | From US$ 200,000/wk

MYSORAH (ex Major Wager)

ASPEN ALTERNATIVE | From US$ 199,000/wk

Motor Yacht Aspen Alternative

FAM | From US$ 195,000/wk

Forward: Yacht FAM's Cruising Captured

GLORY | From US$ 179,000/wk

Luxury yacht AKULA

ZOOM ZOOM ZOOM | From US$ 175,000/wk

Running

AVALON | From US$ 155,000/wk

Running Shot

FOCUS | From US$ 150,000/wk

Yacht FOCUS - Profile Underway

AQUASITION | From US$ 150,000/wk

Profile Aspect Aboard Yacht BIG ZIP

RELENTLESS | From US$ 150,000/wk

Exterior

PERSISTENCE | From US$ 140,000/wk

Superyacht PERSISTENCE

CLAIRE | From US$ 139,500/wk

Forward Aspect On Yacht CLAIRE

ICE 5 | From US$ 135,000/wk

The 46m Yacht ICE 5

BLUE DEVIL | From US$ 130,000/wk

Motor Yacht BLUE DEVIL

PLAN A | From US$ 125,000/wk

Motor yacht PLAN A - Main shot

Florida Yacht News

Florida charter yacht REAL SUMMERTIME offering 10% discount

Florida charter yacht REAL SUMMERTIME ...

38m superyacht GLORY offering charters around Florida and the glorious Bahamas

38m superyacht GLORY offering charters ...

Remodelled superyacht PERSISTENCE offered for charter in Florida

Remodelled superyacht PERSISTENCE ...

26m Riva motor yacht GYPSEA ready for winter charters in Florida and the Bahamas

26m Riva motor yacht GYPSEA ready for ...

Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

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The Florida Keys

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Explore the southeast Florida coast and the renowned Florida Keys.  Start by exploring Key West, the most southern point in the continental USA. Take in the former residence of Ernest Hemingway, enjoy the sunset celebrations in Mallory Square, visit Smathers Beach and tour the Key West Lighthouse.  When planning your sail from Key West, make time for Key Biscayne with its breathtaking Bill Baggs State Park. Biscayne Bay offers calm cruising and Elliot Key is a popular anchorage if you want to snorkel, swim or explore.  You will be spoilt for choice when it comes to the 800 islands that make up the Florida Keys, which can offer everything if you love being out on the water, such as watersports, fishing, and incredible sunsets. You can stop by Key Largo, Islamorada and Marathon to name just a few.  At Key Largo you can explore the living barrier reef before heading to Islamorada with its six keys bursting with history and known for its fishing.  

If you worry you won’t have time to see everything you want to, you can also do a one-way charter by starting or ending your charter in Key Largo, Marathon, Key West, or Miami.  Miami offers the South Beach strip on Ocean Drive, the famous long stretch of white sand with a backdrop of Art Deco architecture and a vibrant atmosphere. There are plenty of hip restaurants and great shopping.  Miami has become a thriving arts scene too with art museums, private art collections open to the public and an annual contemporary art fair.  For those seeking a longer sail, you can head to the Dry Tortugas National Park and the uninhabited Marquesas coral reef islands. For those looking for a more challenging sail, you can head out east to Bimini in the Bahamas.

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Sample Itinerary

Day 1 Key West: Board and overnight in the marina or anchor in front of Key West.

Day 2 Key West – Bahia Honda Key: Make the most of the watersports and anchor at Rodriguez Key or Tavernier Key. If you’re looking for facilities, try the Pilot House Marina.

Day 3 Bahia Honda Key – Indian Key: Explore the Indian Key State Park – a great opportunity to paddleboard or kayak. Head to the south-west of Indian Key to overnight.

Day 4 India Key – Key Largo Reef: Snorkel with the colorful marine life – we recommend Molasses Reef, Conch Reef and French Reef in the state park. Explore Key Largo and anchor nearby or in the marina.

Day 5 Key Largo Reef – Long Key: Go ashore for a hike in Long Key State Park and see the wildlife, try a spot of fishing or swim and snorkel. We advise anchoring on the northwest of the island.

Day 6 Long Key – Marathon: Enjoy browsing the shops to find souvenirs or dine locally. Marathon has a welcoming, upmarket atmosphere which is perfect for a day out.

Day 7 Marathon – Key West: Watch the sunset in Mallory Square – it’s a must-see and one of our favorite things to do on a Key West yacht charter. Treat yourself to a delicious meal in one of the many restaurants.

Day 8 – Key West: Head back to the marina after a leisurly morning.

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Florida Keys Sailing

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The Spanish first found the Keys during Ponce de Leon's expedition in 1513. They mapped and named the Keys principally as an aid to their ships, which, full of gold and silver, used the Florida Straits to go from the New World back to the Old. The first settlement was at Key West, in 1882, a little more than two decades before Florida became a state. The other Keys pretty much stayed deserted until 1874, when the government surveyed them. After the survey, the government plotted land for businesses and homes. The early homes were primitive. They were built from the local beaches, made of wood and other materials washed up from shipwrecks. In 1912 Henry Flagler built a railroad to Key West. This greatly increased human settlement of the Keys. The railroad was destroyed by a hurricane in 1935, but in 1938 the longest over-water road in the world was built on the railroad's foundation. It includes 42 bridges--one that is seven miles long! This opened the Florida Keys up to a growing tourist trade.

charter catamaran florida keys

Florida Keys

Some of the most unique vacation destinations in the world can be found in unexpected places – such as the Florida Keys. Located just off the coast of South Florida, these islands have a relaxed feeling, stunning tropical scenery, and exotic wildlife; yet they are all located a relatively short distance from cosmopolitan Miami and the excitement of South Beach, where the journey begins.

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  • Newfound Harbour

Miami is South Florida’s playground, and for good reason – there is no where like South Beach to both enjoy the sun, sand, and surf by day, and live it up by night in the area’s many exclusive night clubs and restaurants. Whether you want to dance all night and enjoy premium bottle service or simply have a wonderful meal by the water, launching in miami ensures that you will start your voyage off in the most exciting way possible.

Visiting during one of the many major annual events that occur in Miami (including Art Basel, the South Beach Wine & Food Festival, the Orange Bowl, and more) will make your trip even more outstanding.

As the northernmost and largest island in the Florida Keys, Elliot Key was once used a refuge for pirates and today it is home to Biscayne National Park, with its lush vegetation and amazing beaches that offer both remarkable solitude and spectacular vistas – along with a variety of exotic birds and butterflies. You can also explore the island by kayak – there are many hidden lagoons, mangrove-covered shorelines, and winding creeks to discover. What’s more, you can enjoy your own catch for dinner after a day of capturing fish, lobster, or crab.

Key Largo is considered the “Diving Capital of the World”, with plenty of scuba diving, snorkeling, and sport-fishing options for avid enthusiasts – what’s more, it is located near the Everglades, allowing for easy access for kayaking and eco-tourism as well. It is the home of the only living coral barrier reef in the continental United States, and enjoys more than three thousand hours of sunshine per year, making it perhaps the quintessential island vacation destination.

Named after the original settlers’ boat the “Island Home” and now nicknamed the “Village of the Islands”, Islamorada is home to many notable residents (including Major League Baseball players Ted Williams and Miguel Cabera as well as actor Gene Hackman), this is one of the more serene island destinations in the Florida Keys as well as one of the world’s premier fishing destinations. Luxury resorts, shops, and art galleries are part of the Islamorada scene, but there are plenty of beaches that offer more solitude.

With less than two hundred residents, Duck Key is perhaps the closest version of a deserted island that’s still easily accessible from the contiguous U.S.  With world class fishing and sandy beaches, the island is also home to a luxurious spa and offers the opportunity for visitors to swim with dolphins.

Newfound Harbour not only offers spectacular scenery, it is home to the Florida Keys Sanctuary preservation area, which is partially located within the Coupon Bight Aquatic Preserve. The amazing sea life that visitors to the island will enjoy includes star corals and giant brain corals – perfect for amateur or inexperienced divers since these are located within in depths of 18 feet or less. Angelfish, butterflyfish, surgeonfish, damsels, wrasses, grunts, snappers, and parrotfish swim alongside the occasional grouper, along with many other types of fish that you’ll find colorful, striking, and unusual.

Along with some of the most interesting coral reefs in the world, Newfound Harbour is home to a sheltered tropical lagoon that serves as an oasis for a wide range of wildlife, including the tiny Florida Key deer, wading birds, and sea turtles.

Taking a little time to leave it all behind in Key West may be the ultimate form of relaxation – particularly if you happen to visit during one of the island’s most distinctive festivals (The annual Fantasy Fest held in October is the most famous). There’s excellent opportunities for scuba diving and snorkeling around the coral reefs and shipwrecks in the nearby waters, including the recently sunk USNS Gen. Hoyt S. Vandenberg, which created an artificial reef.

However, the island’s unique National Parks and wildlife refuges are perhaps the most interesting (at least for nature buffs), and the nightlife in general is not to be missed, with a variety of options that range from casual tropical dives to trendy nightclubs. All in all, Key West is the perfect culmination to your customized trip through the Florida Keys.

Sailing the Florida Keys may possibly be the very best way to unwind and explore a corner of the United States that hardly resembles anywhere else in the country – or the world, for that matter. And there’s no better way to experience this special part of the world than on your own private yacht.

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Captain Charter

Sit back and relax on your own private yacht while a professional takes the helm to show you the best of the Florida Keys. We offer multi-night yacht charter vacations. All of our Captain Charters have a minimum of 5 days/4nights which is the ideal amount of time to experience one of our Florida Keys sailing itineraries . Learn more about what to expect aboard a Captain Charter with Florida Yachts Charters.

Captain Selection

Captains, cooks & mates, life aboard, family friendly & kids aboard.

We are required under USCG regulations that define bareboat charter to allow you to choose your own captain. We will not assign one for you. We can provide more information of those captains who are familiar with our operations, the waters of the Florida Keys and our vessels. Should you already have a captain we require they complete our captain’s application for approval.

Captains, Cooks & Mates, Oh My!

Unless you are on a sailing course, when you interview potential captains to hire for your charter, they will ask you about prior boating experience and your ability in assisting with things like, picking up moorings balls, anchoring, dock lines and ability to manage the vessel in an emergency situation . If no one aboard would qualify to fulfill the role of 1st mate they will require you also hire a mate. Some mates can act as cook for an additional rate while others are only able to act as a mate. Adding a cook means they take care of all the meal planning, provisioning, cooking and clean up, a splendid addition to your experience. If you are unfamiliar with provisioning and cooking aboard a vessel this is a highly recommended choice.

Captains generally charge $450-500 a day, first mates $250 & Cooks $275.00, plus their food & beverages. For Cooks, they charge a full day for planning & provisioning time before your charter start. A 15 – 20% gratuity is industry standard for services well rendered.

Life Aboard a Captain Charter in the Florida Keys

Life aboard a yacht in the Florida Keys can take you to some beautiful anchorages, snorkel sights and secluded beaches. Your yacht will have all the comforts of a boutique hotel. The galley has just about everything your kitchen at home has so cooking aboard will be seamless. Refrigeration aboard vessels is much smaller than at home, and monohulls have very tiny freezer space. While all our vessels are equipped with Generators and ACs for comfort at anchor, while underway you will not be able to run the Generator, therefore you will not have AC until you reach a mooring ball or anchorage for the night. Most guests open the hatches while underway for a nice tropical breeze. As a result of Covid, we have taken the decision to not supply masks & snorkels for safety reasons over sanitation. We do sell good qualify snorkel/masks set and rent fins. We have local companies that can rent paddleboards & kayaks.

Families & Kids Aboard your Captain Charter

Key West & the Florida Keys is a great family friendly boating destination. The captains in this area know all the best places for spotting dolphins, snorkeling and a relaxing night at anchor. For safety reasons there are few things to note about having kids aboard when considering a captain charter with children:

  • Bring along or plan to buy children’s life jackets. They are weight specific up to a certain age and we don’t offer them. Children are required to wear a life vest at all times while on deck, if your children have never worn a life jacket we recommend purchasing ahead of time and practice wearing, otherwise they will be stuck below deck with an adult.
  • Our captains are professional and great with kids but it is important that a parent, guardian or designated adult keep an eye on them at all times. Your captain and mate will be very busy attending to navigation, sailing, and everyone’s overall safety and should not be relied upon to be watching children should you be absent. There are many things for kids to bump their heads on, interesting buttons to push and lines to grab. An interesting tip we recently read to ensure authority has been passed from one parent/guardian to the next is to use the phrase “Your Jane and John” and make sure the other adult responds “My Jane and John;” inserting your kids names into this phrase of course. This way you know that they know you are no longer watching the kids. If you are a pilot you may be familiar with this tip, as it was modified by parents who were former pilots for around the water safety at home.
  • It may also be a good idea to talk with your kids (depending on the age) about power, water and toilet management. You will potentially be away from the dock for several days at a time. All our vessels are equipped with Generators and AC’s but these items are additional amenities and should there be a mechanical failure you may not have access to additional power and AC until it can be repaired. Depending on your itinerary you may also be without WiFi or cell phone access from time to time.

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

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  2. Power Sail Catamarans in Florida Keys-All Inclusive Charter

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  3. Key West Charter Catamaran

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  4. Life On A Catamaran in the Florida Keys

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VIDEO

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COMMENTS

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  9. Key West Private Charters

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  10. Lady Susan Catamaran

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  11. Florida Keys Bareboat & Crewed Yacht Charters

    Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA. Along the Florida Keys the holidaymaking options are numerous.

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    When you set sail on a Florida yacht charter with The Moorings, the cost of your vacation will be based on several factors, such as: The duration of your relaxing vacation; When you book your Florida yacht charter for - peak sailing season months may cost more; Whether you book one of our world-class catamarans, monohulls or power yachts

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    Florida Keys Yacht Charter Experience the mesmerising tropical beauty of the Florida Keys. Consisting of 40 different islands, each with its own unique character, the Keys have become increasingly popular with charterers over the years due to its prime location, stunning array of amenities and pristine natural landscapes.

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    The types of yacht charter available in the Florida Keys are all the main types including motor, sailing, bareboat charter, skippered, crewed yachts, catamaran, power boat, sailboat, luxury yachts and super yacht charter. The Florida Keys features a year round calendar of special events such as fishing tournaments, international yacht races ...

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    Explore thee southeast Florida coast and the renowned Florida Keys. Start by exploring Key West, the most southern point in the continental USA. Take in the former residence of Ernest Hemingway, enjoy the sunset celebrations in Mallory Square, visit Smathers Beach and tour the Key West Lighthouse. ... Check out our Charter Yacht Video Website ...

  19. Sail and Power Catamarans in Florida Keys

    Fantastic Italian power catamaran with incredible range (over 1200nm) very low fuel consumption and very shallow draft , great for Bahamas term charters. Magic star is located in Miami and can travel to the Florida Keys or the Bahamas. She accommodates 8 guests in two king cabins, 1 aueen and 1 twin size cabins.

  20. Key West Bareboat Charters

    Bareboat Charter General Qualifications & Requirements. •30 days or 400 miles in the last three years as named Captain on an equivalent size & type of yacht (s). •ASA, US Sail, RYA or ICC certification to an equivalent Bareboat Charter level for Monohull & Multi Hull for Catamaran. •Physically capable of handling the vessel in all ...

  21. Florida Keys Sailing Charters

    This greatly increased human settlement of the Keys. The railroad was destroyed by a hurricane in 1935, but in 1938 the longest over-water road in the world was built on the railroad's foundation. It includes 42 bridges--one that is seven miles long! This opened the Florida Keys up to a growing tourist trade. Book Now

  22. Florida Keys

    DAY SIX. Newfound Harbour not only offers spectacular scenery, it is home to the Florida Keys Sanctuary preservation area, which is partially located within the Coupon Bight Aquatic Preserve. The amazing sea life that visitors to the island will enjoy includes star corals and giant brain corals - perfect for amateur or inexperienced divers ...

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  24. Key West Captained & Crewed Charters

    Captain Charter. Sit back and relax on your own private yacht while a professional takes the helm to show you the best of the Florida Keys. We offer multi-night yacht charter vacations. All of our Captain Charters have a minimum of 5 days/4nights which is the ideal amount of time to experience one of our Florida Keys sailing itineraries.