Massachusetts
Sunset Tours

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Our most recommended Massachusetts Sunset Tours

Martha's Vineyard: All Island Tour

1. Martha's Vineyard: All Island Tour

Sit right back and enjoy the most unique tour on Martha's Vineyard. Hop on an exciting fun-filled bus and hear about the fascinating history of the area narrated by 3rd and 7th generation islanders. Start at the amazing town of Oak Bluffs (once known as Cottage City) where you will learn about the Methodist Campgrounds and their history of bringing tourism to MV.  Next, travel through Vineyard Haven (also known as Tisbury), the oldest port of 200 years and hear about the hardships of living on an island devastated by fire in 1888 and ransacked by General Grey in 1778. See the beautiful vistas of rolling hills and ancient stone walls as you make your way to the western side. Learn about the af/am heritage and how the island became a stop on the underground railroad. Hear about the indigenous peoples of Martha's Vineyard and how Thomas Mayhew converted the Native Americans to Christianity. After this, the south shore and two sounds blanket the island and have a gorgeous chain of islands called the Elizabeth Islands that have an amazing history of their own. Watch a screen that shows what certain sites looked like in the 1800s to get a better view of how we have evolved. Don't forget the movie JAWS, there will be many sites to see where all the scenes from the movie were filmed. End the tour with a gift bag including maps, guides, coupons, and handmade trinkets. There are plenty of opportunities for photos and much more.

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: Sunset Tall Ship Harbor Cruise

3. Boston: Sunset Tall Ship Harbor Cruise

Set sail onboard a genuine tall ship such as the 125' Schooner Liberty Clipper or the 67' Liberty Star and be transported back in time. See the Boston skyline, its harbor, and the different neighborhoods from the water during this sunset cruise. While breezes keep you cool you are welcome to help the crew hoist the sails the old-fashioned way (use those muscles) or just relax, enjoy a drink, and watch as others haul sails. Take a turn at the helm (steering wheel). Both ships offer both alcoholic and non-alcoholic beverages for sale. Do you think you might get hungry while you are onboard? Bring your favorite take-out and make it a picnic (sorry, no coolers or BYOB permitted). Choose between a 1.5-hour cruise on the 67" Liberty Star or a 2-hour cruise on the 125" Liberty Clipper.

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

4. Boston: Harbor Champagne Sunset Sail from Rowes Wharf

Embark on a sightseeing sunset cruise on Boston harbor and soak up the views of the famous skyline. Admire city highlights, including the Inner Harbor Islands and the Boston Fish Pier.    Board an elegant sailing yacht, the ' Adirondack III.' Travel in style on a classic 80 foot pilot schooner that is comfortable and spacious. Glide smoothly over the water and have the option of purchasing a refreshing drink at the onboard bar. Admire views of the historic scenery of Boston Harbor as you pass by the Boston Fish Pier and the Moakley Federal Courthouse at Fan Pier. Capture pictures of Castle Island and the Donald McKay monument. Cruise through the Inner Harbor Islands. Step back in time as you cruise by the historic Charleston Navy Yard. Go by the lush greenery of the Waterfront Park and take in the modern architecture of buildings like the New England Aquarium. Take a selfie in front of the Boston skyline. Have your questions about the sights and history of Boston Harbor and its surrounding areas answered by the attentive crew. Hear facinating facts and old-time legends about the maritime world of Boston. Return to your meeting point at the end of the tour.

Boston: Sunset Cruise

5. Boston: Sunset Cruise

Meet at Rowes Wharf and set off on a guided boat tour. This sunset cruise will give you unparalleled views of Boston's famous landmarks. Escape the heat and admire Boston’s beautiful skyline and the historic USS Constitution as the sun sets behind the city. Your expert guide will be able to tell you about some of the city's landmarks and history. As evening sets in, the sunset cruise will highlight popular and famous scenes set at Boston Harbor from both past and present. Snacks and cold beverages including water, juice and soda; as well as a full bar, are available on every boat.

Boston: Summer Nights Sunset Trolley Tour

6. Boston: Summer Nights Sunset Trolley Tour

Discover Boston’s illustrious story aboard Old Town Trolley on this exciting new sunset tour. Watch the city skyline fade into the night over the Charles River. See the moonlight light up Boston’s cobblestone streets and colonial architecture as guides show you the city’s most iconic locations. Take in all the picturesque scenery as you pass by iconic locations such as the North End, Boston Harbor, the Boston Commons, the Massachusetts State House, Boston Public Library, the Bunker Hill Bridge, TD Garden, the Museum of Science, Trinity Church, John Hancock Tower, and Cambridge. Discover the rich history of America’s Cradle of Liberty on this 90-minute tour. Witness history come to life as soft music and lively narration set the stage for a beautiful sunset over the Charles River.

Boston Harbor: Full Moon Cruise

7. Boston Harbor: Full Moon Cruise

The cruise will start from Rowes Wharf and head out towards the fish pier and logan airport. Boarding begins 30 minutes prior to departure. During the cruise, you will be right under the flight path of Boston Logan Airport and hear the engines roar as the planes land and take off. We will head towards the Boston Harbor Islands and then back to the dock along the East Boston and Charlestown waterfronts. View the USS Constitution, the United States Navy's oldest commissioned ship, in all its splendor under the moonlight. There is a full service bar and light snacks available for sale during your cruise. You can also select an option to have a glass of prosecco included in your ticket.

Boston: Guided Night Tour with Sunset Cruise

8. Boston: Guided Night Tour with Sunset Cruise

Step back into the American Revolution and view the very best sites and attractions of Boston on a guided sunset cruise and nighttime walking tour. Join a local expert guide and uncover the story of Boston with historic highlights and personalized recommendations. Begin your tour of Boston with a pickup from your hotel in the downtown area. Kick off your night in Boston with a scenic sunset cruise on Boston Harbor. Relax and take in the breathtaking panoramic views of the city skyline illuminated at night. Next, back on land, your local guide will take you on a narrated walking tour of the North End neighborhood. Stop outside the famous Skinny House, the narrowest house in Boston. See the historic Old North Church, the George Robert Fountain, and the Paul Revere House. You will have the opportunity to grab a quick pastry from Mike's Pastry at the end of your tour. Finally, be returned to your hotel in Boston so you can enjoy the rest of the night.

Frequently asked questions about Massachusetts Sunset Tours

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Other Sightseeing Options in Massachusetts

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What people are saying about Massachusetts

Overall rating

4.3 / 5

based on 44 reviews

Was contacted by owner of tour group that morning to verify I was coming and pickup location. That was great! However, during my ferry ride over, she notified me that our pickup was changed to the other dick on Martha's Vineyard since ferries were being diverted due to wind. My ferry was not diverted which caused me just a few minutes of anxiety as I had never been there before and wasn't sure how to the other place; but before I could figure it out, she called back and said a taxi was on its way and were to meet him! That was going out of her way to help! I very much appreciated this! Taxi driver was great too. Devin the guide was very knowledgeable and personable. Only 5 in our group and he accommodated us very well. Highly recommend Homegrown Tours!

The sunset cruise was a beautiful way to see the Boston skyline. There’s a lot of space and seating. The cruise also makes sure to stop and let passangers see the USS Constitution shoot it’s evening cannon. Great experience for the price!

Our cruise was fabulous! The boat exceeded our expectations- no metal benches!- the interior was gorgeous!! Even though it was rainy, we had a lovely time. Service and atmosphere were spectacular! 10/10 recommend!

It was a pleasant experience, the staff was very helpful, and made it very easy when boarding the yacht. I would definitely book one again and recommend it to my friends!

It was absolutely lovely. Very chilled out. Lots of space on upper deck. Great bar. Lovely vibe. LOVED EVERY MOMENT.