Boston Harbor Sailing Cruises aboard our classic Schooners! Discover Boston Harbor cruises on a Boston Tall Ship Sail.
From June through September, we offer the finest Boston harbor cruise sailing trips in Boston Harbor aboard our fleet of tall ships. Come take the helm and see Boston's skyline and Boston harbor islands on a Boston Harbor cruise sail. Choose your Boston Sailing Experience:
Boston Day Sails
While sailing Boston on a tall ship harbor cruise, you'll be welcome to take help hoist the sails, take the helm, enjoy a drink from the ships bar or just relax and enjoy Boston Harbor on a Boston Tall Ship Sail.
Join us on a Boston Sailing Cruise for Boston private events, Boston Schooner Sails, Boston boat tours and Boston Tall Ships. We are Boston's only Fleet of Tall Ships where you can extend your sail and stay overnight on our Boston Tall Ship Waterfront Bed and Breakfast.
All-inclusive Windjammer Cruises and Overnight Tall Ship Sailing Vacations aboard our fleet of Classic Tall Ships.
We offer tall ship Windjammer Cruises in New England, the Chesapeake Bay and the Caribbean Islands aboard our historic replica windjammers. Enjoy a Virgin Islands Windjammer Cruise or a Bahamas Windjammer Cruise. Discover your tall ship sailing vacation:
Our all-inclusive vacation cruises offer the perfect mix of activity and tranquility. You can relax all day or help the crew sail our ship. Our cook will keep you happy and you are free to set your own pace - rediscover life on a Liberty Windjammer Cruise!
Come experience the romance of a traditional sailing ship while enjoying modern comforts and amenities on a windjammer cruise sailing vacation. Our chef prepares your meals with fresh local ingredients daily.
Watch dolphins jump in our wake, enjoy moonlit evenings at anchor or explore the coastal towns and villages we will visit. With a maximum of 24 guests aboard, you can always find a quiet place to yourself on our sailing vacations. For the adventurous type, you can join in hoisting the sails, or just sit back and relax as our professional crew will ensure your safety and comfort on our sailing cruises.
Experience something better on your next tall ship cruise, experience a sailing vacation with the Liberty Fleet aboard one of our classic Windjammers. On your sailing vacation you will experience peaceful mornings, fun days and beautiful evenings. Relax and have fun on a tall ship cruise!