Thank you for purchasing your Groupon with Liberty Fleet! We are excited to have you aboard. Follow these easy steps to redeem your voucher online:

  1.  Select "Redeem Groupon Voucher" and choose the tour you would like to redeem your Groupon for. 
  2.  Select your cruise date on the calendar.
  3.  Select the number of passengers you are booking. Each Groupon code is redeemable for a single individual. 
  4.  Enter your Groupon voucher code in the indicated field during checkout. 
  5.  Enjoy your sailing!

Thank You!

Your private charter inquiry has been successfully submitted and one of our charter coordinators will be in touch soon.


Boston Sailing Charters
& Special Events

If you’re hosting a Boston special event for your company, friends, family, clients, or employees, you want it to be memorable. We can’t think of a better way to wow your guests than by bringing them sailing on board one of our magnificent tall ships for a Boston private sailing charter on Boston Harbor. With several catering and bar options, we are able to customize each occasion to fit your needs. Whether a Boston corporate mixer, a Boston wedding, or a Boston private party, come aboard with us for an unforgettable sailing experience!

Boston Private Sailing Charters aboard Schooner Liberty Clipper and Schooner Liberty Star

Meet Our Fleet

Get to know our two beautiful 18th century replica vessels available for Boston private sailing charters in Boston Harbor: the schooners LIBERTY CLIPPER and LIBERTY STAR!



Host Corporate Events, and Company Outings on a Private Boat Charter Sailing Boston Harbor

Boston Corporate Events

We specialize in hosting Boston summer company outings on a fun and fantastic Boston Harbor sailing cruise!

  • Client Receptions
  • Employee Recognition
  • Summer Mixers
  • Goal Achievement Celebrations
  • Team Appreciation Outings


Boston Wedding Boat Charters on a tall ship cruise sailing Boston Harbor.

Boston Tall Ship Weddings

Imagine your elegant Boston wedding on deck of a magnificent tall ship while sailing through beautiful Boston Harbor. Make your special day truly unique with a venue like no other aboard a sailing ship in Boston!



Boston special events on a Boston sailing ship cruise in Boston Harbor.

Boston Private Celebrations

Sailing on a tall ship in Boston Harbor is a fun and memorable way to celebrate in style. Bring your friends and family out for a Boston private boat charter.

  • Anniversaries
  • Birthdays
  • Graduation
  • Milestone Celebrations
  • Family Reunions


Boston team building charters are a unique way to bring your group together on a sailing ship!

Boston Team Building Charters

Need a break from the office but still want to keep juices flowing? Our Team Building charters take corporate and college-level groups out into Boston Harbor to participate and compete in various seamanship tasks while learning transferrable skills.



Boston tall ship sailing and leadership programs for companies, schools, churches, boy scouts and youth groups. Sail training and leadership development while sailing Boston Harbor with the Liberty Classroom.

Liberty Classroom

Enrich your summer camp, youth group, or scout troupe experience with a Boston Harbor sailing field trip! With programs customizable to specific age groups, we love to bring young people on board to help them learn and become passionate about sailing.



Boston Sailing Charters and Boston Private Boat Cruises Catering and Bar Options

Catering & Bar Options

A great celebration needs great food and drink! Check out our caterers and view our bar packages for your private Boston Harbor charter.



Boston Sailing Charters, Boston Boat Charters, Boston Harbor Charters FAQ

Liberty Fleet Charter FAQ

Have a question about a Boston Sailing Charter with us? Check here for frequently asked questions!


Catering & Beverage Options

Put the finishing touches on your private Boston sailing charter with great food and drink!

Catering and Beverage Options on your Boston Tall Ship Private Charter

 All beverages are provided on board by the Liberty Fleet. If you would like to have your event catered, we work with two excellent caterers that have a great selection to fit your dietary and budgetary needs. Please see below for our bar package options, as well as some brief information about each caterer. If you book a charter with us, you will work directly with the caterer to customize your own menu for your event.


Bar Packages

Full Open Bar

Beer & Wine Bar

Drink Tickets

Consumption Bar

Cash Bar

A list of our stocked beverages is available upon request, and we can accommodate most special orders if you prefer specific selections.



Because catering on a tall ship requires special equipment and training, we ask that you utilize one of our recommended caterers. However you are more than welcome to bring your own catering on board or arrange a ‘drop’ at the ships by another vendor. Sample menus are available on request.

The Silent Chef

113 Front Street • P.O. Box 535 • Scituate • Massachusetts • 02066
(781)545-6665 • (781)544-3415 fax

The Liberty Fleet has been working with The Silent Chef for over 20 years! The Silent Chef offers fresh, high-quality ingredients and is the caterer we recommend if you are really looking to impress important clients or guests. Their options include a large hors d’Oeuvres spread, a buffet, bar-be-que, and even a clambake! If you are hosting a special event and are looking to serve your guests a full meal on board, consider The Silent Chef.


Above and Beyond

42 A Plympton Street • Boston • Massachusetts • 02118
(617)426-5999 • (617)422-0758 fax

Above and Beyond is local – right here in Boston! – and offers several budget-friendly options as well as high-end spreads, including an outstanding raw bar for cocktail parties. If you’re looking to serve a more casual lunch or dinner on board, Above and Beyond offers lunch and dinner “drops” – they’ll set up the food on deck before your event, but no servers will be present on board. Similarly, if you’re wanting a quick ‘grab and go’ lunch aboard for a shorter sail, consider their boxed and bagged lunch options!


Photo credit: Carly Michelle.

Liberty Fleet Private Charters FAQ

Frequently Asked Questions for chartering with the Liberty Fleet

Have a question? Check here to see some of our most frequently asked questions. If you don’t see your answer on the list, please contact us by phone (617.724.0333) or email ( and we’ll be happy to help!

Sail on the Liberty Clipper

What happens if it rains on the day of my charter?

We sail rain or shine!  Both the LIBERTY CLIPPER and the LIBERTY STAR have awnings that cover the majority of their decks to keep you out of the rain. 

We will not sail in dangerous weather (thunder/lightning), and will do our best to work with you to reschedule your charter should it thunderstorm on the day of your charter.

If you would like to play it safe, we offer (and recommend) weather insurance.

Will I or any of my guests get seasick?

We sail within the safety of Boston Harbor, which is a large protected area with very calm water.  The most motion you might feel while on board may be from the brief wake of a passing boat.

No passengers have become seasick during our harbor cruises in the last several years.

How much does it cost?

Charter costs include but are not limited to: hourly rate, crew gratuity, and bar options (as desired).  A mandatory 5% convention center fund (CCF) tax will be calculated from the hourly charter rate and added to the total.  Each quote is custom tailored to each charterer, so please request a quote for your outing!

How do you determine hourly rate?

Charter rates depend on a variety of factors, including the time of day (morning/afternoon/evening) and the date (weekday vs. weekend and June/July/August/September).  Keep in mind that certain time periods may be subject to a premium rate.  Actual rate will be provided in a quote.

Is there a minimum length of time for a charter?

We have a minimum of 2 hours for a charter.

When are charter fees due?

We require a 50% deposit once the charter contract has been signed to hold your date and time.  The remaining balance is due 60 days prior to your charter date.  If you book a charter within 60 days of your sail, we require the full amount due up front.

How can I pay?

Checks and credit cards are accepted.  Credit cards will be subject to a 3% transaction fee.

Can I bring my own beer/wine/liquor on board?

In compliance with Massachusetts state law, we cannot allow passengers to bring their own alcohol on board.  However, we work with several large suppliers and will be happy to special order particular selections and bring them on board for you.

Liberty Classroom Sail Training

Tall ship sailing & educational field trips in Boston Harbor

Come learn the basics of traditional sailing on board an authentic tall ship!

Sailing aboard a tall ship offers an enriching opportunity for learning. Our fleet offers a rare chance to sail the waters of Boston Harbor while learning seamanship skills on a traditional tall ship. Work side-by-side with your students, raising sails and coiling down lines.

The program is designed for elementary, middle, and high school age groups. Optimal group size is 50-80 participants with a student/chaperone ratio of 1:10. Field trips are available Monday – Thursday in the months of June, July, August, and September.

Spending the day sailing on a Boston Harbor cruise makes an excellent summer outing for summer camps, boy scout and girl scout troupes, youth groups, and more!

Read on below to learn more about our on board sailing education program.



Sail Training

You and your students will be split into groups that will rotate between stations, mastering new skills and assisting team members.

Training Areas

Safety: Groups will learn about ship safety equipment, lifesaving equipment and safety drills.  Our crew will provide instruction and training.  Your group will then select a group-leader and assign tasks to members of the group who will then successfully perform a safety drill based upon the information they have learned.

Seamanship: Groups will be provided instruction in a small selection of knots and splicing.  Participants will help one another learn the material and successfully complete the following: square knot, bowline knot, clove hitch, becket bend, and a short splice or an eye splice.  (Liberty will provide both rope and instruction sheets)

Sail handling: Throughout the charter, groups will be asked to help handle the sails. As the ship is constantly moving, this will occur throughout the trip including setting sail at the beginning of the charter, sail handling throughout and striking sail at the end of the charter.

Ship handling: All trainees will have an opportunity to pilot (“drive”) the ship during their charter.  After each participant has piloted the ship, that participant will then provide the instruction, supervision and debriefing to the next trainee under careful supervision of our Coast Guard Licensed Captain.