schooner sailboat annapolis

Schooner Woodwind Online Reservations

About online booking.

• Events depart from the Annapolis Waterfront Hotel, unless otherwise indicated.
• You MUST check-in at the Dock Office where you will be instructed where to stand in the boarding queue.
• We begin boarding 10 minutes before the departure time. Please arrive early and check in at the Dock Office.
• Parking suggestions and directions to the Annapolis Waterfront Hotel Dock can be found on our website https://www.schoonerwoodwind.com/contact-us/directionsmap/
• Please wear soft soled shoes.
• Smoking and vaping are prohibited on public cruises.
• Pets are not allowed aboard, with the exception of “working” service dogs (which are permitted).
• By law, no alcohol can be brought aboard or removed from the boat. We have a cash bar with local microbrews, wine and bubbly.
• As a Federally regulated vessel, there is a ZERO TOLERANCE policy for illegal drugs, including but not limited to marijuana (even if prescribed by a physician). Federal regulations overrule state and local laws/ordinances.
• All guests aboard agree to the Contract of Carriage - located at https://www.schoonerwoodwind.com/contract-of-carriage/

Reservation / Cancellation Policy

• Once tickets are purchased, there are no refunds or exchanges.
• We sail rain or shine unless the captain cancels the cruise due to unsafe conditions.

Policy Notices

• All guests must wear soft soled shoes aboard to preserve the sensitive wood deck
• Smoking and vaping are prohibited aboard public sailing cruises

Cookies and Privacy

This website uses cookies. Cookies help us personalize content and understand how visitors use our website. By browsing this website, you agree to our use of cookies.

By using this website or making a reservation with us, you agree to our privacy policy .

2024 Sailing Season is coming! See you April 13, 2024!

Buy Tickets for Today or This Week

• We sail rain or shine.
• There are no refunds or exchanges unless the captain cancels the cruise due to unsafe conditions.

* Everyone has loved having more room, so we are staying at just 30 people per cruise (instead of 48).

Online tickets go on sale at midnight 6 days before you want to sail.

Tickets may also be purchased, during office hours, in person or by phone (410-263-8994) beginning 6 days before the date you want to sail.

• The boat leaves on time, you will not be refunded if you miss the boat.
• We have a bar filled with local microbrews, wine and bubbly. You cannot bring your own alcohol.
• Pets are not allowed aboard, with the exception of “working” service dogs, which are permitted.

For groups buying individual tickets, that would like to sail on the same boat, please use the comment section ONLINE to alert us of the group name so we can try to keep your group together.

All policies listed in link below including parking, smoking, check in, footwear and more.

• Wheelchairs and strollers cannot be accepted aboard. See FAQS

Contract of Carriage

Accessibility

I have a mobility issue, or i am traveling with someone who has a mobility issue, is this cruise suitable.

• The Woodwind boarding ramp is approx 22″ wide with rope handlines on one side (crew members will offer their arms and hands to help guests board). The current tide determines the angle of the ramp (higher tides mean a steeper slope to the ramp).  At the end of the ramp, guests must step down (approx -11″) onto the deck.
• The cockpit area provides bench seating with a non-cushioned backrest and an area where guests can brace their legs. This is the most suitable place for guests with mobility and/or stability issues to sit and feel the most secure.  In order to access this area, guests must step (or swing legs) over and down approx 13.5″ to the bench and then down to the cockpit floor (approx 16″ down).
• As Schooner Woodwind is a sailboat, she may at times, sail heeled over at an angle of 5-20 degrees from one side to the other. Guests with mobility issues will likely find it difficult to move around the boat and/or keep themselves seated comfortably when the boat is heeling.
• The restrooms (heads) are located below deck – accessed by means of a companionway ladder (about six steps).

Can I bring my mobility aid aboard?

• Most wheelchairs and walkers do not fit aboard the Woodwind without compromising the safety of the boat and/or other passengers aboard. Mobility aids can be left at our Dock Office and retrieved following the cruise.  The captain has the authority to determine if it is safe for the other passengers aboard to allow mobility aids aboard.

Are you ADA compliant?

• The vessel configuration does not violate the law. There are no vessel configuration regulations now in place with which to comply.

Please consider all of these factors before deciding to purchase a ticket for a cruise on the Schooner Woodwind.  The captain has the right to determine if a specific person with limited mobility will be a danger to other guests aboard due to the current conditions.  In such cases that a person is not able to sail, a refund will be provided to this person and one caregiver that stays behind.

All Cruises

I see that only 30 people is the capacity on public cruises, but i see that the boat is uscg certified for 48 which one will it be.

The company has decided that the experience aboard with just 30 people (who may not know each other) is a better experience than the USCG capacity of 48 people.  Before the COVID-19 pandemic, we would sell out the boat with 48 people aboard. We reduced how many tickets we sold and our crew and customers have loved it.  We will be operating this way all season.

When will the decision be made to cancel a trip due to bad weather?

Unless there’s a tropical storm heading our way, the decision is typically made just prior to departure time.

Are there life jackets for my infant?

Yes. When you check-in at the dock office, let us know that you have an infant and we will hand you a special infant life jacket.

What should I wear for the cruise?

Soft-soled shoes are required and the dress is very casual and comfortable. Depending on the season, layered clothes work best. We supply complimentary ponchos should there be rain during the cruise.

What about motion sickness?

Since we sail in relatively protected waters and we have a heavy ballasted keel, it is very rare for people to get seasick (less than 1%). We recommend getting “sea bands” for your wrists if you are concerned about this. You can purchase these wristbands from our ticket office prior to your cruise. Motion Sickness pills will work too, however, the side effect is they may make you drowsy. We do not sell medication to help with motion sickness; please bring anything you may need with you.

What about being caught out in a lightning storm?

During the summertime, lightning storm forecasts are a common occurrence. Most of these do not materialize, but if one does “pop up” while sailing and when possible, we will head for the dock as soon as we can. Our captains are excellent at reading these storms; where the storms are and where they are going.

What do you typically see? Where do you go?

All cruises are dependent on weather factors. Minimally, all cruises will sail past the Naval Academy, Annapolis Harbor area, and the “Scenic Severn River”. Most trips leave the harbor and head out to the Bay, passing by osprey nests and other sailboats & powerboats. While sailing you may get to see the 4.5 miles long, Chesapeake Bay Bridge and as the Woodwind sails back into the harbor, the historic, Annapolis skyline stands out quite prominently. If the wind is light, we often sail up the Severn River where the magnificent waterfront estates meet the shoreline. Some trips are just right for a cruise under the Bay Bridge, and on less frequent occasions, we can sail to Thomas Point Lighthouse. It’s very easy for us to say “each trip is unique”, which keeps frequent sailors coming back for a new adventure!

Can we go below decks to get out of the rain and/or extreme heat?

We do encourage you to stay out on the deck where you can truly experience sailing, however, there is space below decks if you need to get out of the elements for a while.

Can I bring my own alcohol onboard?

We do sell a variety of beer, wines, and bubbly. We have a liquor license, and it does not allow for any type of alcohol to be brought on board.

Public Cruises

What if i need to cancel.

Our cruises do not allow for cancellations.  You can sell or give your ticket to someone else.  In the event that we need to cancel the cruise, all ticket monies will be refunded.

Must I buy a ticket for an infant or toddler?

Yes, they count as a passenger, according to the U.S. Coast Guard.

Can I buy tickets more than 6 days in advance?

Yes, you can. By purchasing a flat-fee Group Sail package (1-16 guests), you will be guaranteed the sail time that you want.  An added bonus, if you are checked in at the Dock Office 15 minutes prior to the sail, your group will board first to select the seating you like.  Click here for Group Sail information.

When do I need to show up?

We begin boarding 10 minutes prior to departure time. Allow plenty of time for traffic, parking, and time to check-in at our Dock Office. We cannot hold the boat if you will be late.

Can I smoke onboard?

There is no smoking of any kind or vaping permitted on any public or private cruises.

Can I bring food on board a public cruise?

If you wish to bring food on board, it must be individually packaged for each person. No spreads, buffets, and no cakes.

Private Cruises

Do you do team-building.

We have wonderful team-building programs for groups of 7-70 people, including our popular “Ultimate Team Challenge: Match Racing Program” with our two, identical schooners. Visit our Teambuilding page here to learn more.

Do you have merchandise so my guests can remember their adventure?

We have a wide variety of merchandise, from t-shirts to hooded sweatshirts, postcards to patches, we have it all. Check out our Ship’s Store for what we sell. All this merchandise can be purchased at the dock office or online in advance of the cruise. For large quantity orders, please let your sales agent know ahead of your visit, so we can make sure we have everything in stock.

Can I bring my own food?

We work with our exclusive caterer to provide your group with the best menu for your sailing event. All food is served chilled or at room temperature. Our menus include great appetizers, brunch, breakfast items, and gourmet lunch and dinner options. All food is pre-packaged for each guest and delivered to the boat and served by the extraordinary crew aboard. See our menus here.

Who takes care of gratuities and taxes?

All gratuities and taxes are included in your private cruise contract under Service Fees.

Can I have my wedding on the Woodwind?

Small weddings are ideal aboard the Woodwind. Rehearsal dinners while sailing or a cruise to entertain and show off Annapolis to your guests is also a treat aboard. A true taste of Maryland!

What if the weather is bad?

We typically sail rain or shine unless the captain cancels the cruise due to unsafe conditions. We do offer “Rain Protection” at an additional cost on some of our private charters. See below.

What is Rain Protection?

Schooner Woodwind offers “Rain Protection” at an additional cost. This insurance gives the charterer a time period of 24 hours prior to the charter until 2 hours before the scheduled departure to cancel if there is a greater than 30% chance of rain forecasted for the time of the charter.

Rain Protection is not available:

• On any charters contracted within 14 days of the Event Date.
• If the charter originates from a port other than Annapolis, MD.
• If both Woodwinds are chartered for the same cruise time.
• Special dates like Blue Angels Fly-Over, July 4th, and other Holidays.

Scout and Student Cruises

Is a private cruise the only option for a scout or student trip aboard the woodwind.

Yes. In order for our crew and captains to be able to offer interactive programming for the Scouts, we do need it to be a private event.

If we wanted to brush up on our nautical terms, where should we go?

Go to our Educational page where they can learn terms, names of the sails, and other great information.

Does Schooner Woodwind have Scout patches? If so, how much?

We have great Participation Patches that say “Annapolis Sailing Cruises”.  Each participating scout and student will receive a patch as part of the Private Cruise Pricing. Additional patches are $4.25. Click here to see patches

Do you have merchandise so the guests can remember their adventure?

What is the life jacket policy.

According to the Girl Scout USA and BSA safety procedures, they want all Scouts, adults, and other children aboard a cruise must be outfitted in life jackets. We have additional Type III life jackets that are more comfortable for non-emergency use.

How many people can we fit on the boat?

The USCG limits us to 48 passengers, however, we are limiting the boat to 40 passengers.  We do have two Woodwinds, so if you have an extremely large group (40 to 80), we can fit them aboard both boats.

What to bring/Wear

Soft-soled shoes are required, and the dress is very casual and comfortable. Depending on the season, layered clothes work best. We supply complimentary ponchos should there be rain during the cruise.

What should I bring aboard?

Bring a smartphone to purchase bar items or an extra soda or water. Bring a real raincoat, if it is forecasted to rain, yours will far surpass the complimentary rain ponchos that we have aboard.

Can I bring a bottle of wine aboard?

No. We have a liquor license, and it does not allow any type of alcohol to be brought on board. We do sell a variety of beer, wine, and sparkling wine.

What do I do when I arrive at the Annapolis Waterfront Hotel Dock?

Check-in at our ticket office when you arrive at the dock for boarding instructions. Our ticket office staff will direct you to the boarding line for your cruise. If both Woodwind and Woodwind II are sailing, there will be two lines.

If you have not already purchased tickets, you can do so at our ticket office on the dock.

What do I need when I check in?

If you bought your tickets online, you should bring the printout of your ticket confirmation page. If you have a smartphone, you can bring up the confirmation email on your phone. If you bought your tickets over the phone, please have your confirmation number and a photo ID with you when you pick up your tickets. You will be told where to stand for which boat you are on.

When should I arrive?

Please arrive at the dock no later than 15 minutes before the scheduled departure time of the cruise. If you arrive early you can check in at any time, there is a great bar and restaurant located on the water at the Annapolis Waterfront Hotel. No alcohol may be brought aboard.

Click on the picture above to get a 360 degree view of the boat and where the Schooner Woodwind is docked.

General Policy

• Once tickets are purchased, there are no refunds or exchanges.
• We sail rain or shine, unless the captain cancels the cruise due to unsafe conditions.
• We begin boarding 10 minutes before the departure time. Please arrive early and check in at the Dock Office.
• Please wear rubber soled shoes.
• Smoking is prohibited on public cruises.
• Pets are not allowed aboard, with the exception of “working” service dogs, which are permitted.
• We have a bar with local microbrews, wine and bubbly. By law, no alcohol can be brought aboard or removed from the vessel.

In Addition to Above

For Weekday Sunset Sails:

If the scheduled entertainment cannot perform for any reason, we will continue to sail the scheduled public cruise. No adjustments will be made to the price since our crew will do our very best to make the cruise enjoyable without the scheduled entertainment.

For Wednesday Night Races (5:30 Departure Time):

Schooner Woodwind will depart promptly at 5:30 PM, however our starting time for the race is 6:45. We will be racing a fairly short course and there is a strong possibility that we will get back to the dock after 7:30 PM. This is bonus time so that we can finish the race. We will return to the dock no later than 8:00 PM. Schooner Woodwind will still depart even if the races have been cancelled by the yacht club, but the Captain has deemed the conditions safe to sail.

For Wednesday Night Races (6:25 Departure Time):

Schooner Woodwind will depart promptly at 6:25 PM, because our starting time for the race is 6:45. We must get to the starting line on time. Schooner Woodwind will still depart even if the races have been cancelled by the yacht club, but the Captain has deemed the conditions safe to sail.

For Public Special Event Cruises with catering:

The captain will wait up to one hour past the scheduled departure time to resolve any weather or mechanical issues before deciding if the event needs to be canceled. If the event is cancelled or shortened and food is able to be served or individually distributed, the food costs will not be refunded.

For Public Lighthouse Cruises:

We will make every attempt to see three lighthouses on this cruise, however, weather conditions, wind speed, and direction may impede our ability to do so. This is not a motor cruise to see the lighthouses. We hope it is breezy enough to sail the majority of the time. If the guest speaker is unable to perform for any reason, we will still sail the scheduled cruise. If the cruise is cancelled due to unsafe conditions, a refund will be issued for the cost of the sail but not the catering, the bagged lunch will be available for pick up.

For Public Wine in the Wind Cruises:

If the wine representative is unable to attend for any reason, we will still sail the scheduled cruise. Also, the captain will wait up to one hour past the scheduled departure time to resolve any weather or mechanical issues before deciding if the event needs to be cancelled. If the event is cancelled or shortened, a refund will be issued for the cost of the sail but not the catering, the food will be available for pick up.

You are using an outdated browser. Please upgrade your browser to improve your experience.

• Annapolis: 410.263.8234
• Cape Cod: 508.524.9121
• Booking Information
• Buy Cape Cod Tickets Now

A Grand Experience for All

Custom built for sailing, comfort and fun. Our cruising grounds are some of the most beautiful and historic in the country

Corporate Events

Special occasions, adventure & entertainment.

Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment.

USCG certified for 49 passengers. Music. Full bar. Every Sail is Unique.

One Great boat, two great locations

About the boat.

The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them.

The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser. Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design.

Get In Touch Now

• © 2024 The Liberté
• All Rights Reserved
• Website Design & Marketing provided by Adventure Web Interactive

Reservations Dates Previous month Next month Adults 1 2 3 4 5 Children 0 1 2 3 4 Marriott Rewards Number

Schooner Woodwind

Enjoy our annapolis sailing cruises.

Seeing as it's considered the “Sailing Capital of the U.S.,” no trip to Annapolis would be complete without getting out on the waters of the Chesapeake Bay. Lucky for you, we offer two 74-foot wooden schooners right here at the hotel dock. Hop aboard the Woodwind or the Woodwind II and let our expert sailing crews take you along the historic Annapolis waterfront, past the Naval Academy, and into the Chesapeake Bay. Depending on the strength of the wind, the schooners may make it all the way to the Chesapeake Bay Bridge. You may even be asked to be part of the crew during the excursion and help raise the sails or steer the boat! Sailing cruises we offer:

• Two-hour public sailing cruises
• Private cruises
• Schooner races
• Team-building events
• Student groups
• Wine and beer events
• Foodie events

Stay More Save More

Stay a little longer to make the most of long summer days in Annapolis and save up to 25% per night.

Liberte, The Schooner

• See all photos

Similar Experiences

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Liberte, The Schooner - All You Need to Know BEFORE You Go (2024)

Classic Sail Charters

Private sailing charters in maryland, choose your location, annapolis, md.

May - October

Learn More »

West River, MD

• Most Popular!

Sunset Sail - Licentia

Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!

• Users Up to 6 Passengers
• Hour Glass 2.5 Hours

Your Dream Adventure Awaits

Catering to clients seeking a unique, private sailing adventure for up to six passengers, we offer world-class sailing yachts, decades of experience, and 5-star service to ensure that your charter is truly memorable. All our charters are for private parties, so you can have it your way. is required. 

Charters Feature

Sunset Cruises

Daily Sails

Weekend Cruises

Milestone Celebrations

Marriage Proposals

Family Adventures

Check-out what our Guests say about us! ★★★★★

Capt. Nate & Payton were great! We did an engagement shoot on the boat and they were unbelievably helpful. They were extremely accommodating to the photographer and worked to position the boat perfectly as the sun was setting. Siena is a beautiful boat and the west river is idyllic. Can't recommend enough.

Captain Tony was great host and helped us have a fantastic experience. He even taught my husband some sailing skills, which allowed me to relax, have some snacks and drinks. Boat was clean and very well maintained. He has a strong commitment to saftey and is very knowledgable about sailing. Highly encourage others to book a trip with him.

My fiancé and I are both from New England and grew up by the water, so we knew we wanted a nautical setting for our engagement photos. We had a fabulous time with Classic Sail Charters on the beautiful Siena! Captain was so helpful in offering to angle the boat this way and that for better light and even raising or collapsing sails. We'll definitely be back!

My husband I along with our two grown children (in their 30's), had a wonderful day with decent wind in July sailing at times to 15 knots! Captain Tony was accommodating and friendly. He had a variety of snacks and beverages on board and encouraged participation in sailing the boat as well as relaxing in the sun or shade! We will definitely do this again and we're thinking of also offering this as a gift to my parents who also love to sail.

This past Friday, we joined Capt. Tony aboard the Licentia for an afternoon sailing the Bay. We had a great afternoon sailing and motoring (we lost the wind) around the Bay and through the Annapolis Harbor. Capt. Tony is very knowledgeable, friendly, and helpful. He has loads of sailing experience and all enjoyed his sea stories. Would we go again? Absolutely - planning a trip for next May.

Four of us sailed with Captain Tony on 2 different trips - one afternoon and one morning. Both days were fantastic and relaxing and lovely. The 2nd trip we lost the wind eventually so motored around the Bay and Annapolis and Tony gave us some history and stories. He is delightful and skilled and we had a terrific time. We will definitely plan another trip one of these day.

Rainbow 24 Sailboat Rental

No trip to the sailing capital of America would be complete without getting out on a sailboat. Our fleet of Rainbow 24s provides a safe and fun experience for those looking to have a relaxing time on the water. Feel free to bring lunch and turn it into a picnic as you pass by the sights with the wind carrying you along.

**Rentals are available during our sailing season: the beginning of April to the second week of October.

Weekdays – $158 (+taxes and fees) for a full day or any portion of a day between 9 am – 4 pm.

Weekends and Holidays – $225 (+taxes and fees) for a half-day between 9 am – 12:00 pm OR 1:00 pm – 4:00 pm

*A 30-minute sailing assessment is required of all new customers. The assessment costs $30 in addition to the rental fee.

Reservations

A reservation is needed to ensure that a sailboat is available when you want to go out. At least two adults are required on a rental boat, one of whom must be a qualified sailor. Up to six people are permitted on a rental boat; no children under 5 years of age are allowed. No pets are permitted.

A late fee of $75 will be charged per half-hour overdue.

• KeelBoat Club Members: Click HERE to jump to KBC Rainbow rental’s booking and information page. You can also click the drop-down labeled “KeelBoat Club Rentals” located under the “KeelBoat Club” tab. Please have your membership ID ready.

Our Rainbow 24 sloops have proven to be nimble, fast, and forgiving. Designed by Sparkman and Stephens specifically for Annapolis Sailing School, the boats are ready to please both novice and experienced sailors. The substantial fixed keel (1100 lbs), cuddy cabin design, and large cockpit combine to produce a boat that is stable, dry, and comfortable.

Qualified Renters

At least one person in the rental party needs to have an ASA 101 certification or its equivalent. New customers must complete a sailing competency evaluation with us prior to their first rental. Renters are required to rig and de-rig their boat. The Rainbows do not have engines, so sailors must be able to depart and dock under sail.

If you need a refresher on rolling and flaking our sails, check out our how-to page here !

Sailing Area

Rentals are restricted to an area close enough to the school so that help can reach you quickly in an emergency situation. Boundaries, determined by management, are subject to change depending on weather and water conditions at the time of your rental. Please understand that going beyond these boundaries makes quick retrieval of the boats difficult in case of emergency. Late returns of boats due to venturing beyond the boundaries will result in late fees. If a renter goes outside the prescribed sailing area and needs to be retrieved, there will be a fee of $75 and the renter will be unable to rent with us in the future.

Sailing is entirely dependent upon wind and weather. We recommend that renters check marine.weather.gov three days before the rental date to see what the forecast is for that day. If small craft advisories or worse are in effect at the start of the rental, the rental may be postponed, canceled, or otherwise restricted at the discretion of the management. In that case, the rental can be re-booked at no additional cost. In low wind situations, you will need to plan your sail so that you can be back at the dock on time.

Cancellations

Rental reservations are charged at the time of booking. Rescheduling within three calendar days of the originally scheduled start of the reservation will result in a $50 rescheduling fee per occurrence. Cancellations made within two calendar days of the scheduled day of the reservation will receive no refund. Refunds are not available for lack of wind.

The boats are covered by insurance. Please inform management of any damage that occurred during the rental. The Lessee has no liability for repairs. However, Annapolis Sailing School is not responsible for personal injury or damage to other boats. You should check your own insurance coverage before sailing.

Other Restrictions

• Children on board must be at least 5 years old
• No alcohol allowed on boats
• No pets allowed on boats
• No swimming off the boats allowed
• No anchoring
• Boats are not permitted to dock at other marinas or facilities other than Annapolis Sailing School

Want to stay in the know about Annapolis Sailing School? Sign up for our new monthly newsletter here to receive information on classes, events, schedules and more!

No thanks, I’m not interested!

Picture Perfect Sailing

• Meet your Skipper

Sail in Annapolis, Book a Sailing Cruise Today

Enjoy quality time with family and friends sailing out of Annapolis. You'll fall in love with the Chesapeake Bay. Your sailing charter awaits. 

CHOOSE YOUR SAILING ADVENTURE

Sailing options.

With Picture Perfect Sailing, the options are virtually endless!

Your skipper will take you for a day sail in Annapolis for a few hours towards St Thomas Point Lighthouse or the Chesapeake Bay Bridge, or perhaps around Annapolis harbor. For a longer sailing charter, choose our all-day sailing experience or overnight. You'll find yourself sailing to Baltimore or Saint Michaels. Book a sailing cruise now, make the memories of a lifetime with your family and friends!

Day Sail: come sailing for a few hours

Duration: 3 hours (leaves and returns to Annapolis)

Starting at $650 for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

Sunset Sails: come sailing as the sun goes down

Duration: 2.5 hours (leaves and returns to Annapolis)

Starting at $650 weekdays for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

All Day of Sailing: come sailing on the Chesapeake Bay all day!

Duration: 6 hours (leaves and returns to Annapolis)

Starting at $1,550 weekdays for 2 guests. Your sailing charter includes: skipper, crew member, snacks, lunch & beverages. Please check rates and book a sailing cruise by clicking the button below.

Overnight Sailing: experience sailing and sleeping aboard!

Choose one or two overnights: (leaves and returns to Annapolis)

Single (one) overnight: typically departs at 10am, one overnight in Baltimore or St Michaels, with disembarkation at 5pm the next day. Variations upon request. Starting at $2,450 weekdays for 2 guests. Your sailing charter includes: skipper, hostess, lunches x 2, snacks, breakfast x 1 & beverages. 

Double (two) overnights: typically departs at 9am,  one overnight in Baltimore or St Michaels, second overnight at the dock back in Annapolis and disembarkation at 9am the next morning. Starting at $3,900 for 2 guests.  Your sailing charter includes: skipper, hostess, snacks, breakfast, lunch x 2 & beverages.

The prices displayed in the booking schedule include yacht fuel, dock fees, water, propane for cooking, yacht insurance, cabin linens & bath towels. 

What’s not included: water activities off the boat (due to insurance limitations) such as swimming, paddle boarding or dinghy use; dinners (plan dinners on shore); crew gratuity.

How to book a sailing cruise with an overnight? Contact us for availability and custom pricing.

*Rates vary by season. Holiday rates upon request. Special pricing for Navy families, veterans, and first responders.  Contact Picture Perfect Sailing for more information and to book a sailing cruise today!

The Sailboat

You'll sail aboard a Beneteau Oceanis 45, with extensive cockpit protected by canvas and well-appointed to accommodate up to 3 couple for overnight sailing in maximum comfort; a head (bathroom) with shower, a full galley (kitchen) and comfortable salon. Arguably the nicest charter boat to sail in Annapolis. Let the sailing adventures begin, book a sailing cruise now.

With Picture Perfect Sailing, your designated skipper (and mate, depending on your sailing option!) will lead the sailing charter: maneuver the boat, guide your visit of the Annapolis area on the water, and ensure the fun & safety of all! 

Meet your skipper .

Let's Connect

Inquire now about rates & availability.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Picture Perfect Sailing, Annapolis sail charters.

Join my mailing list.

Be the first to hear about early-bird specials and travel tips to Annapolis.

Copyright © 2023 Picture Perfect Sailing

All Rights Reserved.

Powered by GoDaddy

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

Grant Boost for Brendan Sailing: Opening Doors for Young Sailors

Annapolis, MD – Brendan Sailing Program has recently announced the reception of a significant grant from The Kahlert Foundation, a move that promises to substantially enhance the scholarship opportunities for young sailors. This funding is a critical step in ensuring that financial barriers do not prevent children from accessing the organization’s unique sailing and educational programs.

In recent years, the demand for scholarships has seen a dramatic 42% increase, with over 60% of participants requiring financial assistance. Brendan Sailing, known for its commitment to inclusivity, has consistently worked to ensure that no child is turned away due to financial limitations. The backing from The Kahlert Foundation is seen as a continuation of the support that has been pivotal in offering hundreds of young individuals the chance to develop self-confidence, independence, and vital life skills through sailing.

James P. Muldoon, the Founder and Chairman of Brendan Sailing, expressed his gratitude towards The Kahlert Foundation for their sustained support. “At Brendan Sailing, we never turn down a child for financial reasons. It is important that these children have the same opportunities to build social skills and teamwork, regardless of their financial position,” Muldoon stated, underscoring the foundation’s crucial role in supporting Brendan’s mission.

The partnership with The Kahlert Foundation has not only enabled Brendan Sailing to provide scholarships but also to continue enriching its program offerings. This summer, the program is set to take place at its Annapolis location and St Mary’s College of Maryland, featuring a curriculum designed to accommodate diverse learning styles. With a focus on hands-on learning and confidence-building, the courses will be led by US Sailing certified instructors.

Jane Millman, the Executive Director of Brendan Sailing, highlighted the impact of The Kahlert Foundation’s support, “This generous gift will enable us to continue creating successes for youth in our programs this summer and beyond.” The grant will allow Brendan Sailing to expand its reach and continue its mission of providing tailored experiential learning opportunities for children with learning differences.

The Brendan Corporation, established in 1987, and The Kahlert Foundation, founded in 1991 by William “Bill” E. Kahlert, have both played instrumental roles in supporting youth development through various programs. The Kahlert Foundation, in particular, focuses on initiatives across Maryland and Utah that promote positive outcomes in health care, education, youth programs, veteran organizations, and human services.

For more information about Brendan Sailing’s summer programs or to make a donation, interested individuals can visit www.brendansailing.org . Similarly, to learn more about The Kahlert Foundation and its mission, visit www.kahlertfoundation.org .

Download The Free 2024 Visitor Guide

This handy resource includes a complete listing of accommodations, restaurants, shopping destinations, and more in Annapolis and Anne Arundel County!

Sign Up For Our E-Newsletter

Sign up today and we'll keep you in the loop on upcoming deals, specials, and happenings in and around Annapolis.

STOP BY OUR VISITORS CENTER

26 west street annapolis, md 21401, [email protected], phone: 410-280-0445, fax: 410-263-9591.

Annapolis Discovered

Access annapolis.

• Privacy Policy

©2024 VISIT ANNAPOLIS. ALL RIGHTS RESERVED.

This website uses cookies to enhance user experience on our website. Learn more.

Download our 2024 Visitor Guide!

Plan your stay in Annapolis & Anne Arundel County

Sailing Club Holds Membership Drive

The NIH & NOAA Sailing Association (NIHSA) is a Recreation and Welfare Association activity club. Membership is open to NIH and NOAA (National Oceanic and Atmospheric Administration) employees, fellows, contractors and their families, and NIH patients.

The club’s main activity is sailing five Flying Scots, owned by the club and maintained in slips south of Annapolis, Md., on the South River. Club meetings are held each month and are open to all members. Yearly membership dues vary according to the level of participation. Members qualify to charter club boats by completing the NIHSA basic training course or by demonstrating competence in a comprehensive checkout sail.

NIHSA provides many opportunities for club members to get together and share time on the Chesapeake Bay. Check out the website for more details: www.nihsail.org .

Brown University Athletics

Brown University

Graham Hall Team Race Interconference

Sailing Prepares for Four Event Weekend

3/15/2024 5:39:00 PM | Women's Sailing, Coed Sailing

BROWN UNIVERSITY SPORTS FOUNDATION The Brown University Sports Foundation (BUSF) is the lifeblood of the athletics program and exists to enhance the student-athlete experience through philanthropic support from alumni, parents, fans, and friends. A gift through the Sports Foundation makes an immediate impact on today's Brown Bears and helps them to be their best in the classroom, in competition and most importantly in the community. To learn more about supporting the Bears, please click  here . FOLLOW US ON SOCIAL For the latest on Brown Athletics, please follow  @BrownU_Bears  on Twitter,  @BrownU_Bears  on Instagram, like   BrownUBears  on Facebook, and subscribe to the  BrownAthletics  YouTube channel.