Catamaran Sailing Vacations in Florida Keys: Upper and Lower Florida Keys - Dry Tortugas - Fort Lauderdale, Miami, Marathon and many different stops along the way! Charter a Catamaran with no crew and drive yourself or hire professional crew for your catamaran trip.
The florida keys have become a popular destination for americans looking for a tropical sailing vacation without leaving their own country. the florida keys can be considered the american caribbean and features all the same amenities as other island destinations such as world class sport fishing, scuba diving and snorkeling, boating, sailing, kayaking and eco-tours. each of the island destinations has some special features. we invite you to visit each area individually and discover the tropical paradise in the florida keys..
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Florida Keys Itinerary
Keys - one week.
Upper Florida Keys - 3 Days
Lower Florida Keys - One Week*
Sailing from Marathon Key you will experience the many pleasures and sites of the Florida Keys. The unspoiled coral reefs of the Lower Keys have many sites where you can tie up to a mooring ball and snorkel or dive. Hawks Channel provides fantastic sailing, as there is protection from the ocean swells but still great wind.
Dry Tortugas - One Week*
Bahamas itinerary, chain in the bahamas.
Across the Gulf Steam from Florida's east coast lies the Bimini Island Chain. These sub tropical low-lying islands are a fantastic destination for a weeklong sail. Bimini offers some of the finest SCUBA diving, snorkeling, fishing and beachcombing anywhere. These "islands in the stream" offer water clarity, which is nothing less than spectacular. You may rent snorkel gear at our office in Ft. Lauderdale if you have not brought your own. For those who are certified divers we recommend renting your SCUBA gear from Underseas Sports in Ft. Lauderdale before you head across the Gulf Stream.
The Bimini Chain is lightly populated with the center of village life located on North Bimini, in Alice Town. There are many small restaurants, shops, and bars, as well as the Hemingway Museum at the complete Angler. Marinas are abundant if you decide not to anchor out. The beaches on North Bimini offer miles of un-crowded fine white sand and snorkeling from the waters edge. Golf Carts and Mopeds are available for rent so you can explore the island. One of the most interesting dive and snorkel sites off of North Bimini is "Bimini Road", which some say is the ruin of the lost city of Atlantis.
South Bimini is primarily residential with only two marinas. The new Bimini Sands Marina is located at the entrance to the harbor and has a Customs and Immigration office so you can clear in there without having to take a taxi and ferry over to North Bimini. The other marina is located at the south end of the island. A new channel has been dredged in Nixon's Harbor that takes you into the marina. Not far from the south end of South Bimini lies the wreck of the "Sappona". This is a great snorkel and dive site.
The only other island in the Bimini's with a marina is on North Cat Cay. This is a private Island with some "high profile" homeowners. For this reason the local authorities limit the accessibility of the island for non-members. You are welcome at the Marina for transient dockage but they prefer for you to stay in the area of the marina where there is a fine dining restaurant a store for provisions, dock bar, and gift shop. It is a truly beautiful setting at the marina and we recommend this for your last night in the Bahamas. Just off the coast of South Cat Cay is a fantastic dive site. "Tuna Alley" has mooring balls and is 50' to 80' with deep caverns and crevasses in the coral.
There are many other Anchorages such as Honeymoon Harbour, Dollar Harbour. Moxom Rocks, and Nixon Harbour. Please call to speak with our knowledgeable staff for more details.
One Week Itinerary to the Bimini Islands
Day three -, day seven -, day eight -.
Obviously there can be a lot of variation on this itinerary, but it shows there is plenty to do in a week charter to the Bimini Island Chain. If you would like further information or would like to plan a different Bahamas trip give us a call and speak with our knowledgeable staff. We can provide you with a cruising guide to the Bahamas Islands as well as charts of the area.
Tropical Sailing
Catamaran tours in miami & fort lauderdale, florida, our most popular trips.
- User All ages
- Hour Glass 2.5 Hours
Full Moon Sunset Sail Ft. Lauderdale
Join us as we cruise along the Intracoastal waterway, you’ll be treated to a tour of the magnificent waterfront mansions and spectacular yachts.
- Most popular
- Hour Glass 2 Hours
Sunset Cruise Castaway the Day – Fort Lauderdale
A perfect way to end the day, taking in the breathtaking views. This Fort Lauderdale sunset cruise calls for sun dresses, sandals and chilled wine. Take advantage of one of Florida’s finest highlights upon our comfortable catamaran as we sail out to the Atlantic Ocean.
Sunset Cruise Castaway the Day – Miami
Castaway the Day Sunset Cruise is a perfect way to end the day, cruising on the Caribbean Spirit. This Miami sunset cruise calls for sun dresses, flowered shirts, sandals, and cold refreshments.
- Hour Glass 3.5 Hours
Sail and Splash – Fort Lauderdale
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran the Spirit of Lauderdale. Sit back, relax and enjoy one of the best Fort Lauderdale boat cruises .
- Hour Glass 3 hours
Island Adventure – Miami
Enjoy an unforgettable adventure at our island destination during our day cruise from Miami. Experience the Miami lifestyle like a local on board our motor catamaran, Tranquility.
Looking for more to do? Check out these other local tours!
- Hour Glass 1 Hour
Waverunner Beach Rentals
Aloha watersports.
An excellent water sport activity for the whole family!
Seven Isles of Fort Lauderdale Tour
Blue moon outdoor center.
A sightseeing tour of the Seven Isles of Fort Lauderdale!
Kayak and SUP Rentals
2 hour – all day rentals! Choose between a single or tandem kayak, or a stand up paddleboard.
- Hour Glass 45 Min
Speedboat Tour
Thriller miami speedboat adventures.
The Thriller Speedboat Tour departs from Bayside Marketplace in Downtown Miami, Florida. The tour provides the ultimate sightseeing experience in true “Miami Vice Style”.
- Hour Glass 1.5 Hours
Parasailing
Sea rocket water adventures - ft. lauderdale.
Get ready to fly high above the Gold Coast and have a first class experience you will remember forever!
Everglades Day Safari
The Everglades Day Safari offers an in-depth, naturalist-guided day trip into the majestic Everglades! Includes an airboat ride, nature walk, mangrove wilderness boat ride and a delicious lunch!
What we do at Tropical Sailing
We offer two convenient locations Miami Marina at Bayside and Bahia Mar Resort in Fort Lauderdale providing great sailing access to South Florida’s finest destinations.
Our sailing and power vessels are Catamarans, that by nature of the design, provide a stable, comfortable platform with plenty of lounging space for your guests.
Our experienced staff consists of licensed Coast Guard Certified Master Captains and first mates certified in first aid and rescue. Every Captain and crew member has been hand picked for their exceptional skills and personality. Our entire staff consisting of charter specialists, captains, crew and mechanics share a passion for South Florida’s waterways, working on the water and sharing their enthusiasm with everyone they come in contact with.
During your trip, a professionally trained captain and crew will pamper your guests with tailor-made service while you cruise the world’s most desirable Caribbean destinations. Special menus can be arranged, transportation coordinated – everything necessary to assure an adventure that your group will remember for a long, long time!
Discover the ultimate in extravagance and personalized service as you step aboard our luxury crewed yachts. Stylish, spacious and elegant, our prestigious catamaran will delight you. Equipped to the highest standards, with special features and state-of-the-art electronic and water sports equipment, you can expect quality similar to that of a luxury five-star hotel.
We look forward to sharing our love of sailing and water sports with you, your family and your friends!
See Why We're Highly Rated!
Absolutely amazing! Cannot recommend this enough! We got to see dolphins, jumping fish, the sunset, and sit with our legs on the net of the catamaran. I can’t recommend this enough! It should be an especially part of anyone’s Ft. Lauderdale vacation!
Captain E and Nick were great on this tour! We brought our grandkids and they were very attentive to them! We all had a wonderful time! We would highly recently this sunset tour! Beautiful views and great crew!
Great time with Captain E and Nick! Absolutely worth doing, especially on a hot June night! Will book again on our next Ft. Lauderdale trip.
This is hands down a must if you have a family with kids!!! Captain Joe and Danny were amazing and we all had the best time. Super accommodating and helpful and made the whole sail from start to finish a great experience! Don’t hesitate to book this excursion you won’t regret it. The price was perfection for the experience you got.
One of the best romantic dates I could ever imagine. They sailed us out in the Miami Bay (Biscayne Bay) and we got to watch the sunset. Wow! A clear 5/5
Crew on board was amazing and indulged with the participants on board. They gave great knowledge of the houses and the city in general! The cruise was relaxing and calming all together I would definitely recommend!
Beautiful views, helpful, accommodating and entertaining crew and a nice long route all made for a great value trip
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Catamaran Charter Florida - Catamaran Rentals
Top-rated yacht charters in florida - preselected yacht rentals:.
Cat MY 6 available for charter in Vinoy Resort Marina
- MY 6 [Yacht Price incl. Taxes]
- Barbeque Grill
- Outboard engine for dinghy
- Yacht Insurance
- Bahamas charter tax
- Final cleaning
- Damage waiver
- Cancellation insurance
- Virgin Islands Search and Rescue (VISAR)
- Cruising tax
- Fuel (for outboarder)
- Maryland Amusement Tax
- VAT or sales tax
Catamaran Lucia 40 available for charter in Vinoy Resort Marina
- Lucia 40 [Yacht Price incl. Taxes]
Catamaran Lucia 40 for rent in Vinoy Resort Marina
Catamaran Catspace available for charter in Fun In The Sun Marina
- Catspace [Yacht Price incl. Taxes]
- Cockpit cushion
- Administration fee
Catamaran Lucia 40 for charter in Fort Lauderdale
Cat Leopard 40 available for charter in Key West
- Leopard 40 [Yacht Price incl. Taxes]
Cat Isla 40 for rent in Saint Petersburg
- Isla 40 [Yacht Price incl. Taxes]
Catamaran Lagoon 46 for rent in Key West
- Lagoon 46 [Yacht Price incl. Taxes]
- Skipper (food not included)
Catamaran Bali 4.2 available for charter in Key West
- Bali 4.2 [Yacht Price incl. Taxes]
Cat Lucia 40 for rent in Key West
- Rubber Dinghy
- Barbeque Grill (gas)
Catamaran Isla 40 for charter in Saint Petersburg
Cat Lagoon 450 available for charter in Fort Lauderdale
- Lagoon 450 [Yacht Price incl. Taxes]
- Cape Coral (1)
- Fort Lauderdale (12)
- Key West (14)
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- Saint Petersburg (24)
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- Florida Keys (14)
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- Key West Island (14)
- Lake Worth Lagoon (1)
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- Tampa Bay (24)
- Treasure Island (2)
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- Crab Island Adventure
- Snorkel Adventure
- Sunrise Sail
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Exclusive Catamaran Sailing Adventures
Spring break 2024.
Mins Minutes
Secs Seconds
Come explore the majestic waters of the Emerald Coast!
Catamaran sailing in the emerald coast sun..
Are you visiting the Destin, Okaloosa Island, Navarre Beach area and needing a little adventure in your life? This is what you're looking for aboard catamaran Destin Sailing Adventures. The boat is a Stiletto 27 Special Edition Catamaran, designed to provide maximum sailing pleasure and performance over a wide range of wind and sea conditions. Made for adventure and racing, so it offers plenty of excitement and comfort for any occasion. The boat is outfitted with a 20hp motor, so if the wind isn't blowing we can still get out and play! Charter comes with a local captain to take you to all the local spots, while you sit back and relax.
We offer an array of private tours, cruises, and adventures at a reasonable price. The longer you book the more fun you can have and the more money you’ll save. These are private charters, so you won’t be with a huge crowd during these unprecedented Covid 19 times. Just you and the people you bring. Come explore Crab Island, Sunset cruises, Sailing lessons, Dolphin Tour, Snorkeling, Marriage Proposals, Birthdays, sightseeing tours, Anniversary celebrations, and more with us today.
We are dedicated to making sure you have a great time while visiting the Emerald Coast. All trips include up to 6 Guests, Licensed Captain, cooler with ice, bean bag chairs, sound system, and a head (bathroom). Our Captain has 15 years of local experience racing/sailing along the Gulf Coast of Florida and more! Please contact us for special requests such as sailing to Navarre Beach (Juana's Sailors Grill), Sandestin (Baytown Wharf),Etc. Some of the best catamaran sailing adventures Destin, Okaloosa Island, Santa Rosa Island has to offer!
Jetty East Snorkeling
Usually one of the busiest spots during the summer, so book your trip early to beat the crowds.
Snorkeling with a Manatee.
Early bird got the manatee this day!
Spanish Mack
Up close and personal to a Spanish Mack doing its thing!
Pick up location
Adventure marina, okaloosa island.
1201A Miracle Strip Pkwy SE, Fort Walton Beach, FL 32548, USA
850-217-3448
"A ship is always safe at the shore, but that is not what it is built for."
Albert Einstein
Destin Sailing Adventures
1201B Miracle Strip Pkwy SE, Fort Walton Beach, Florida 32548, United States
Copyright © 2023 Destin Sailing Adventures - All Rights Reserved
What Should I Bring?
- Directions to Echo, Cruise Ship & K.W. Passenger Info
Key West Info
- Cancellation Policies, Terms and Conditions
- Catamaran Echo Videos
- ECHO Upgrades
- Tasting Notes
- Sunset Cruise
$10 Off each person – Promo Code “EchoDirect”
(for Public trips only – sold by the seat)
Catamaran ECHO 2
Catamaran echo 3.
Free Echo 3 shuttle from downtown Key West, A&B Lobster House parking lot.
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 .
ECHO'S Official Website
Wild Dolphin
Snorkeling & Sailing Adventure
Click here to read more!
Private Day Charters
2 to 19 Passengers
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
Certificate of Excellence 2019
Read Reviews
Call for Reservations
1-888-579-4782.
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Our Activities
Private 4th of July Champagne Sunset and Fireworks Party Cruise - 2 Hours
Catamaran Echo - Wild Dolphins! Snorkel & Sailing Adventure
Catamaran Echo - Private Lighted Boat Parade Champagne Party
Catamaran Echo - Sunset & Moët Cruise
Catamaran Echo - Private Day Charters
Catamaran Echo - Private 2 Hour Champagne Celebration Sunset Sail
Introducing Vivo Per Lei 58 Leopard Catamaran flagship model Learn More
Creating unforgettable journeys on custom designed luxury catamarans learn more, luxury catamaran sailing charters tailored in every way to suit your needs learn more, key west and key largo locations sailing the beautiful florida keys, bahamas and beyond learn more, catamaran sailing charters half day, full day & overnight learn more, welcome to calypso sailing.
Calypso Sailing was established in 1988 in the beautiful Florida Keys. With locations in both Key Largo and Key West we specialize in luxury sailing vacations on a range of Leopard Catamarans, both bareboat and Captained. Our monohull sailing charters can take groups of 6 to 38 on day, sunset and overnight trips whilst not forgetting the iconic African Queen steamboat from the 1951 movie starring Humphrey Bogart and Katharine Hepburn which operates daily in Key Largo.
Our aim is taking care of all your cruising needs
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