Top Boston Cruises & Sailing

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore Boston Harbor and see the city’s historic sites while listening to live commentary on board. Pass landmarks like the Boston Tea Party ships, USS Constitution, and Boston Light—the oldest continuously manned lighthouse in the United States.

Hop into a duck boat—renovated World War II amphibious vehicle—for a comprehensive tour of Boston. Pass Boston Common, Quincy Market, and the Celtics' home turf at TD Garden. Then splashdown into the Charles River for a view of the city by boat. Learn all about Boston's history and landmarks as you go.

Explore the best that Boston has to offer on this hop-on hop-off tour of the city. See Boston’s top attractions—like the USS ‘Constitution’ and the Boston Tea Party Ships and Museum, to name a few—on the loop. Enjoy discounted admission to attractions like the Boston Tea Party Ships and Museum with the purchase of your tour. If you upgrade to the Gold or Platinum Pass, you will be given your (seasonal) Harbor Cruise ticket when you check in for the Trolley Tour. These seasonal cruises depart periodically throughout the day close to Stop 1.

Experience Boston Harbor on a sunset cruise aboard a historic tall ship. Depart from Central Wharf on the 67-foot Liberty Star or the 125-foot Liberty Clipper and enjoy views of the outer harbor, Fort Independence, East Boston, the Charlestown Navy Yard, and beyond. Relax and let the crew handle the sails or jump in the action and a grab a line on this fun and affordable outing.

Try a unique alternative to a typical night out in downtown Boston on an exciting dinner cruise along the city’s waterfront. This expedition on Boston Harbor features an all-you-can-eat buffet meal with live entertainment and dancing. Watch the sunset, then take a stroll under the stars and enjoy the view of the illuminated Boston skyline at night or head to the dance floor for music and fun inside the ship’s nightclub. Bring that special someone or a whole group of friends for a night to remember.

Enjoy views of beautiful Boston with this 90-minute sunset cruise. Watch the sun sink over the sparkling water as your guides point out the USS Constitution and other historic sights. Once the sun goes down, you’ll have a chance to see the city skyline illuminated. There is a full bar on every boat, with snacks and other beverages available for purchase.

Take an evening cruise on Boston Harbor to watch the sunset from the water. Glide out to the Old North Church and Historic Site, the Charlestown Navy Yard, Leonard P. Zakim Bunker Hill Memorial Bridge, and the USS Cassin Young. As a bonus, listen to the cannon fire of the USS Constitution, which marks the sunset each night.

Discover some of Boston’s deepest, darkest secrets on a “frightseeing” tour aboard the Trolley of the Doomed, which roams around the haunted streets and burial grounds of Boston. Your costumed host provides illuminating insights into the history of the city's spookiest sights such as Copp's Hill Burying Ground.

Relive the most important event leading up to the American Revolution on this self-guided tour of the Boston Tea Party Ships and Museum. Take a journey back in time to the famous Boston Tea Party, an incident that changed the course of American history. It’s more than a stroll through historic artifacts, though. It’s truly one of the top-rated museums in the city of Boston. Explore authentically restored tea ships and throw the fated tea into Boston Harbor.

See Boston Harbor’s sights from the water on this day sail aboard a replica of a pilot schooner. Step aboard the boat and sail off through the harbor, bound for Spectacle Island, Fort Independence, Castle Island, and Long Island. Listen to guided commentary on the harbor’s history and ecosystem while you sail, snapping photos of Boston’s coast from the water.

Enjoy Boston from the water while dining on a delicious buffet lunch on this cruise. See an array of top landmarks including Bunker Hill, the World Trade Center, and the site of the 1773 Boston Tea Party. Hear narrated commentary on the sites, and after lunch, head up to the top deck—the largest outdoor patio deck in town—where a DJ spins tunes from line dances to Top 40 hits.

Try a unique alternative to a typical night out in downtown Boston with an exciting dinner cruise along the city’s waterfront. This 3-hour expedition on Boston Harbor features a three-course meal with live entertainment and dancing. Watch the sun set, then take a stroll under the stars and enjoy the view of the illuminated Boston skyline at night or head to the dance floor for music and fun in the ship’s nightclub. Bring that special someone or a whole group of friends for a night to remember.

Cruise Boston Harbor aboard a luxury yacht, complete with superb city views and a buffet brunch featuring both breakfast and lunch offerings. For 2-hours you'll explore the waters from Rowes Wharf to the Charlestown Naval Yard and back, sailing past sights such as Castle Island and Boston Light. Spend some time enjoying the yacht's three climate-controlled decks or dancing to the sounds of a live DJ mix. There's even a glass of complimentary champagne following castoff.

Disembark your ship and take a short walk from Cruiseport Boston to explore the best the city has to offer—a hop-on hop-off tour of Beantown. Visit Boston’s top attractions on a loop around town. Get to know the city, on your own, with live onboard commentary from a professional tour conductor.

Discover the best of Boston and see the sights that interest you most on this half-day tour. Board your private vehicle along with your group and explore key landmarks in the comfort of an air-conditioned vehicle. See Harvard University, Fenway Park, the Boston Public Library, Beacon Hill, and much more while listening to commentary from your driver about Boston’s history.

Enjoy a gourmet brunch on this scenic cruise of the Boston Harbor. Set sail aboard the Northern Lights at Rowes Wharf and settle in for a buffet filled with quiche, waffles, bacon, fresh fruit, and more. View popular Boston highlights such as Bunker Hill Monument, the USS Constitution, Old North Church, and Sea Castle Island. This brunch cruise offers a great overview of Boston and a lovely morning on the water.

Get a comprehensive overview of Boston’s key landmarks during this half-day tour of the city. Combine a walking tour with a driving tour to cover more ground than you would if you just did one. See important sights like the USS Constitution, Old North Church, and the Paul Revere House and learn about the city’s history from your tour guide.

We are a veteran owned coach service that offers an intimate experience with live guide to Kennebunkport from Boston. This breathtaking tour has many unique stops along the coast of New Hampshire and Maine for stunning pictures, snacks and shopping. We ride New Hampshire's coastline to the picturesque town of Portsmouth, NH for a one hour break. From here, we continue up the coast of Maine to the Nubble Lighthouse. Once in Kennebunkport, enjoy exploring the town on your own or add in a 1.25 hour lobster tour with our affiliated partners. Spend an unforgettable day with us, the tour professionals who maximize your travel experience the right way. Want to customize your experience? Group outings and military discounts available. Add an award winning lobster tour to your day. Visit Walkers Point where former President Bush vacations, learn history and view sea-life. Please book well in advance, lobster tour sells out quickly. Tours are limited to; Tues & Thurs ONLY June 1th-Sept 23th

Make this holiday season one to remember with this cocoa and carols holiday cruise on Boston Harbor. With dates offered throughout November and December, you can add a magical touch to your holiday, and easily find a date that works for you. Plus, you’ll cruise the harbor aboard a 1920s-style yacht with live music and a complimentary cup of cocoa to sip on as you take in beautiful views of Boston.

This tour will begin at your home, hotel or cruise ship and take you past the most interesting places in Boston including the Paul Revere House, the USS Constitution, the Bunker Hill Battle Monument, Copley Square and Fenway Park. Along the way you’ll see the historic homes and churches of the Back Bay, the South End, and Beacon Hill. You’ll hear the stories behind Paul Revere’s ride, the Boston Massacre and the Boston Tea Party. You’ll see Boston’s most prominent buildings and neighborhoods as well as some lesser-known points of interest. This is the best way to see as much of Boston as possible in a brief time and do so at a pace you will enjoy.

Grab a drink and settle into the heated, main observation cabin to enjoy a 90-minute experience on this beautiful 1920s-style yacht. *Please note that this event includes a 15 minute pre-boarding, followed by a 90-minute cruise to allow guests time to settle in before the cruising portion commences. During the cruise, grab a hot cocoa or festive libation from the bar and take in the sights as the boat cruises around Boston's waterfront neighborhoods, such as North End. Enjoy cruising under the Tobin Bridge for a unique perspective of this iconic landmark. The Captain will provide light commentary of Boston Harbor's sightseeing highlights in conjunction with enjoyable music throughout the trip. Watch the sky as it changes from blues to oranges behind the outline of Boston's city skyline.

Combine an indulgent brunch with a sightseeing boat tour on this two-in-one festive outing. Meet at Rowes Wharf, and hop aboard the Northern Lights: a 1920s-style yacht. Over the course of several hours, you’ll see landmarks ranging from the Seaport District and USS Constitution to Sea Castle Island and beyond. You’ll also enjoy a 3-course holiday brunch menu and can even warm up courtesy of the onboard hot chocolate bar.

See all Boston's most important sights in a six hours, private, guided city tour, in a comfortable luxury vehicle. If you value, time, privacy, comfort and would like to have a good overview of the city of Boston, Lexington and Concord at your own convenience and pace, we are the right choice for you. We will drive by or stop and wait at the sights you are most interested in. Our tour is totally customizable and our priority is to please you, not keep a schedule.

Whether you’re looking for something to do solo or have a big group to entertain this holiday season, this Irish holiday caroling cruise in Boston Harbor is just the thing to get everyone in the Christmas spirit. Along with a live Irish band playing Christmas songs and a 1920’s-styled motor yacht decked out in decorations, you’ll also catch views of some of Boston’s most memorable landmarks from the water.