boston harbor

Best Way to Spend a Day on a Tall Ship in Boston

Long before European colonization, Boston was a crucial trading center for the indigenous people of the area. Since its colonization in 1630, the city of Boston has been a major US port. In the 1800s, the US Navy built a facility there. Today, Boston Harbor is a hub for container ships, cruise ships, automobile imports, and seafood processing.

Boston is a beautiful port city with a fascinating history, and it makes a great vacation spot at any time of the year. If you’re considering a trip to Boston in the near future, you’re probably looking for some fun, family-friendly activities to fill your days. Why not try something that will give you a glimpse into Boston’s rich maritime history?

The Tall Ship Boston – An Unforgettable Dining Experience

The Tall Ship Boston is a floating restaurant built inside a 245 ft converted sailing ship. The restaurant is docked in Boston’s East Harbor and is an unforgettable experience for the whole family.

The Caledonia

Originally called The Caledonia, the ship was built in England in 1947 as a steam-powered trawler called the Akurey. For many years she was used as a research and fishing vessel before a Canadian company converted her into a sailing ship in 2002.

The Tall Ship Floating Restaurant

After sitting at the dock in Halifax for a number of years, the boat was purchased by the Navy Yard Hospitality Group and brought to Boston. She was retrofitted with an oyster shucking station in the bow and a slick bar running down her spine and is now one of Boston’s most unique dining and entertainment experiences.

The Menu

The restaurant serves shellfish and charcuterie on deck and offers beer, wine, and cocktails at the bar. There are usually food trucks parked around the area too. Food prices are comparable to other restaurants in the area.

The Venue

The pier alongside the boat has been built out into a spectacular 40,000 ft waterfront playground, featuring pop-up events, live music, retail, and food trucks. There are plenty of tall tables scattered around to stand at, or if you have a group you can rent a cabana/private lounge.

Be aware that since the venue is mostly outside, the temperature will be dependent on the weather. Summer is an excellent time to visit, but fall nights in Boston can get chilly so make sure to bring warm clothes if you plan to visit in the fall.

Hours of Operation

The hours of operation are 3 PM to 11 PM on weekdays and 2 PM to 11 PM Friday through Sunday. After 7 PM the venue is 21+.

Weekends can get very busy, and there is often a long line out front, so it pays to arrive early, or go on a weeknight instead.

The space is closed during the winter and reopens in April.


Parking around the area is notoriously difficult, and it’s usually impossible to find street parking. Valet parking is provided at a rate of $15 during the week and $25 on weekends.

Our recommendation: skip the parking and arrive by Uber or water taxi! Boston Water Taxi offers service directly to the restaurant and has many convenient places to board around the harbor.

The Liberty Fleet – Sail the Harbor on a Tall Ship

Boston is known worldwide for its fleet of historical tall ships. The Liberty Fleet is comprised of two ships, the Liberty Star and Liberty Clipper, two gaff-rigged schooners that were modeled after 19-century ships. The Liberty Fleet runs daily cruises aboard the Liberty Star.

The Liberty Star

The Liberty Star is a 67 ft sailing boat. Originally named Rachel B. Jackson, she was built in 1972 as a private sailing yacht. She has mahogany planking, oak frames, traditional fir and pine decking, and antique brass fittings.

In the mid-1980s she was purchased by a family who spent three years sailing her all the way around the world! She has also participated in the Tall Ships race, representing Boston in the races in the year 2000.

Sailing around Boston Harbor on a tall ship is a memorable, family-friendly activity. It’s a great way to step back into history and see the harbor in its former glory. Liberty Fleet offers a basic daysail, a sunset cruise, and a historical tour.


  • Basic Daysail – $39, 1.5 hours
  • Sunset Cruise – $45, 1.5 hours
  • Historical Tour – $45, 1.5 hours

Historical Tour

The historical tour introduces visitors to classic ships like the Flying Cloud and Colombia and explores how they helped shape the town’s history as a maritime hub.

Guests are invited to help the crew raise the sails while they hear the experiences of the diverse people who used to live aboard and crew the ship.

Sunset Cruise

The sunset cruise offers visitors the chance to enjoy Boston Harbor at the best time of day. Watch the sun go down with a cocktail in your hand, or help the crew raise the sails if you’re feeling ambitious!

Windjammer Bahamas Cruise

In addition to day cruises, Liberty Fleet offers more adventurous visitors the chance to participate in longer sailing expeditions.

Aboard their second ship, the Liberty Clipper, they run week-long windjammer cruises in the Bahamas. Guests have the chance to explore the remote islands of the Exumas, as well as the island of Eleuthera. The trip starts and ends in the Bahamas.

Classic Harbor Line

The company Classic Harbor Line also operates tall ship sailing cruises out of Boston Harbor aboard their schooner The Adirondack. They also provide trips aboard the motor yacht Northern Lights.

Guests have the option to take either a daysail, sunset sail, city lights nighttime sail, Boston Island picnic sail, or the special Sails and Ales tour.


  • Basic Daysail – $52/adult, $35/child, 1.5-2 hours
  • Sunset Cruise – $68, 2 hours
  • City Lights Cruise – $40, 2 hours
  • Boston Harbor Island Picnic Sail – call for prices, 3 hours
  • Sails and Ales – call for details

Sails and Ales

Sails and Ales, the sunset sail, and the city lights sail include a viewing of the USS Constitution’s nightly cannon fire to signal the Coast Guard and Navy that the sun has set. These cruises are best for adults, as child-priced tickets are not available for these trips. Alcoholic and non-alcoholic beverages are available to purchase on all sails, but no food is included. Guests are encouraged to bring their own snacks.

The Sails and Ales Autumnal Beer Tasting event is a hugely popular cruise. Classic Harbor Lines partners with local Boston brewer Harpoon Brewery to provide a full beer tasting while cruising the harbor and skirting the outer islands.

A Harpoon Brewery representative will guide the tasting and provide detailed insight into the brewing process, while the Adirondack’s knowledgeable captain answers questions about the history of the harbor. Sights include Castle Island’s Fort Independence, East Boston, the Tobin Bridge, and the USS Constitution.

The light food fare is served, but again, guests are allowed and encouraged to bring their own snacks. This cruise is 21+.

The Final Word

A tall ship cruise or visit allows you to take some time to immerse yourself in one of the city’s richest experiences. With so many incredible maritime activities to choose from, your next vacation in Boston is bound to be a good one!