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Boston Harbor

For first-time visitors

Our most recommended Boston Harbor For first-time visitors

Boston: Historical Sightseeing Cruise

1. Boston: Historical Sightseeing Cruise

Experience breathtaking views, refreshing sea breezes, and vividly told stories of Boston past and present, aboard this one-hour tour around Boston Harbor. Depart from Long Wharf, then Cruise past the USS Constitution, the oldest commissioned US Navy war ship afloat today, marvel at the Bunker Hill Monument, and catch a glimpse of the fabled Old North End Church steeple. From expert narrators, you’ll hear heroic tales and local legends from the Revolutionary War, and learn how the harbor was transformed into one of the cleanest waterways in the country. The boat is equipped to give you the best view no matter the weather, with spacious outdoor viewing decks when the weather is fine, and indoor spaces with large windows if you want to be indoors. Onboard refreshments and snacks are also available for purchase.

Boston: Harbor Sunset Yacht Cruise

2. Boston: Harbor Sunset Yacht Cruise

Embark on a sunset yacht tour of Boston Harbor. Step aboard the classic Northern Lights yacht, a coast guard certified vessel with a captain and crew. The motor yacht Northern Lights is stylized after the classic New England 1920s-style steamships. Sit back and relax in a climate-controlled (with heating and air-conditioning) cabin, or enjoy the sea breeze on the open-top deck. Be sure to visit a fully stocked bar on the main deck to purchase refreshments by credit card, to sip refreshing drinks as you cruise along the harbor. The Northern Lights yacht is one of the most comfortable and versatile cruise vessels in Boston Harbor, at 115 feet in length it features six bathrooms and provides ample seating throughout the ship for up to 149 passengers. Built for taking groups of people on spectacular sightseeing adventures, she is the perfect vessel for taking groups of friends and family out to see the harbor.

Boston: Hop-on Hop-off Old Town Trolley Tour

3. Boston: Hop-on Hop-off Old Town Trolley Tour

Enjoy a hop-on hop-off tour aboard Boston’s charming orange and green Old Town Trolley and visit more than 100 points of interest in the city at your own pace. Enjoy the freedom to hop on or off all day and discover sights like the Boston State House, Liberty Wharf, and the Charlestown Navy Yard. Take in double-decker height views while protected from the elements. The comfortable enclosed trolleys allow you to experience elevated viewing come rain, snow, or shine. Choose between 1-day and 2-day ticket options with free unlimited re-boarding. The Boston Trolley tour covers all the major areas including downtown, Beacon Hill, Back Bay, the theater district, and the waterfront. Conductors narrate the tour, offering a fun mix of trivia and humorous stories. There are 18 stops conveniently located close to over 100 points of interest in Boston, these are: • Stop 1: New England Aquarium/Faneuil Hall Marketplace • Stop 2: Historic North End • Stop 3: USS Constitution/Charlestown Navy Yard • Stop 4: North Station/TD Bank Garden • Stop 5: Old State House * Stop 6: Beacon Hill/Antique Row • Stop 7: Cheers Bar "The Original" • Stop 8: Prudential Center/Skywalk Observatory • Stop 9: Christian Science Plaza/Symphony Hall • Stop 10: Copley Place Shopping Galleries • Stop 11: Copley Square/Trinity Church • Stop 12: Old Town Trolley Welcome Center • Stop 13: Boston State House/ Boston Common/Beacon Hill • Stop 14: Boston Tea Party Ships & Museum (discounted admission included) • Stop 15: Boston Convention center - available 9:00 AM - 12:30 PM. Return shuttle leaves Stop 1 at 5:00 PM daily • Stop 16: Massport/Black Falcon Cruise Ship Terminal - this stop is part of the Seaport Loop - available 9:00 AM - 12:30 PM. Return shuttle leaves stop #1 at 5:00 PM daily • Stop 17: Boston Fish Pier - available 9:00 AM - 12:30 PM. Return shuttle leaves Stop #1 at 5:00 PM daily • Stop 18: South Station - available 9:00 AM - 12:30 PM. Return shuttle leaves Stop #1 at 5:00 PM daily

Boston: North End to Freedom Trail Food and History Tour

4. Boston: North End to Freedom Trail Food and History Tour

Learn about Boston's own Little Italy district of North End and its rich culinary scene. Also, learn about the significant role the city played during the American Revolution on a fascinating guided walking tour of Boston.  Make your way through to the heart of the North End, home to some of the city’s oldest buildings and renowned for its variety of food offerings. Try some fresh bread and Italian meats and cheeses at a hidden bakery. You will also indulge in some sweet local pastries. On the Freedom Trail, explore the Rose Kennedy Greenway, State Street, and the historic Custom House Tower. Then, head over to Old City Hall, which was the birthplace of public education in America. Don’t forget to get a picture of the bronzed Donkey outside the entrance Your tour will finish at the Boston Public Garden. Enjoy the rest of your day relaxing in the park and its beautiful surroundings. 

Boston History & Highlights Afternoon Tour

5. Boston History & Highlights Afternoon Tour

Your experience begins at the Aquarium “T” Station on the historic Long Wharf, the focus of Boston Harbor, and the economic engine of Boston for most of its history. From the harbor, continue past the Rose Kennedy Greenway, State Street and the historic Custom House Tower, the city’s first skyscraper. Then, your guide will lead you toward the famous Faneuil Hall and Quincy Market, which both boast stunning views. Moving into the heart of Downtown Boston, stop in front of the Old State House and site of the Boston Massacre. Was it really a massacre or maybe just great propaganda for the Revolution? Ask your expert guide about that one!  A short trek through Downtown Crossing brings you to Old City Hall. This beautiful building, done in French Revivalist architecture, was the seat of city government for years in Boston. It also happens to be the site of the birth of public education in America. You'll definitely want to have your guide snap your picture with the bronze donkey outside the entrance. On most weekdays, you’ll have a chance to see the government at work (or not) inside the inspiring, historic and beautiful Massachusetts State House, designed and built by famous federalist architect Charles Bulfinch in 1798. Outside the State House, take in the views of modern Boston, including the skyscrapers of Downtown, the Financial District, and the tallest building in New England: the John Hancock Tower.   Continue your journey through Beacon Hill, where you’ll have a chance to take in the quintessential architecture of Boston’s red brick row houses. Get out your cameras — this neighborhood is one of the most photogenic in the city. Finally, arrive at the beautiful Boston Public Garden, one of Boston’s favorite green spaces, where you’ll see locals walking the dogs, playing with the kids and enjoying lunch in the shade. Your guide will point you in the right direction, and will help with any and all recommendations for great things to do in Boston that evening and beyond. 

Frequently asked questions about Boston Harbor For first-time visitors

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Other Sightseeing Options in Boston Harbor

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What people are saying about Boston Harbor

As with all of these types of activities, it comes down to the quality of the tour guide. Otherwise you're just on a boat putting around for an hour looking at buildings. Good views, good pace, good length, and a fantastic guide with just enough jokes to be entertaining and not so many that he was annoying.

This sunset cruise around the harbor was very enjoyable and well worth the price. The boat and seating options are nice, as are the route and landmarks that you can see along the way. Heads up, drinks from the bar are a tad bit expensive. I would definitely recommend this sunset harbor cruise!

Janet was awesome. She had interesting stories and patiently answered questions.

Really fun way to spend some time on the harbor and learn a bit about Boston.

Excellent cruise. Unintrusive commentary and really relaxing.