BOSTON · MASSACHUSETTS
Boston’s best days out.
The 15 most popular evening experiences in Boston. The ones worth building a day around, with prices, run times and who runs them.
Boston Harbor Sunset Cruise: 90 minutes of guided skyline views and USS Constitution, plus an onboard bar. $31.
Most Popular“An amazing activity with a beautiful view of Boston”
2-hour Boston Harbor sunset cruise with light captain commentary, Charlestown views, and the USS Constitution cannon salute at dusk.
“We enjoyed the sunset cruise! It was relaxing and a great way to cap off our trip. The drinks were good and staff was friendly. It was nice having an outdoor and indoor/climate-controlled option for when it cooled off. The cruise went all around the harbor and was a good length of time!”
Cruise Boston Harbor on the Northern Lights for 2 hours at sunset, with light narration, music, and a cannon blast off USS Constitution.
“The Manhattan Yacht sunset cruise was amazing! Love the Christmas decor and large viewing windows on this quaint cozy boat. We also loved seeing Boston and surrounding areas from the water and the crew were super friendly and knowledgeable. Definitely recommend this winter harbor cruise.”
Boston Harbor sunset cruise from Rowes Wharf with live narration, skyline views, and a full bar. 90 minutes for about $29.
“This was a lovely way to see Boston. For the best view - get there early so you can sit on the upper deck. Doors open 30 minutes before sail.”
Sunset sailing on a Boston tall ship for $68. Two hours on the harbor with skyline views and onboard drinks for purchase.
“A really fantastic way to see Boston harbour, it’s not a tour guide type tour, which is fine by me, get a duck tour if that’s your thing, but it is a relaxed and beautiful way to get a different perspective.”
A 90-minute Boston Harbor sunset cruise with live narration, great skyline views, and the USS Constitution cannon and flag moment.
“They are not kidding when they say late arrivals will miss the boat. Boston traffic was crazy and we arrived 5 minutes just in time to wave goodbye to our friends on board leaving port. Our friends on board enjoyed the cruise but said it was crowded and there was not enough inside seating. Moral…”
Boston Harbor City Cruises narrated sunset skyline tour with USS Constitution cannon salute, views from Long Wharf, and live commentary.
“This Sunset Cruise was awesome. My mom and I were very happy with the Beautiful sunset and harbor cruise. The tour was very informational and we learned so much. The weather was perfect, but you may want to bring a light jacket as it's cool at this time of year. There was plenty of seating…”
Classic schooner sunset cruise from Rowes Wharf with real sails, Boston skyline views, and onboard drinks for about $82.
“This sunset champagne cruise was lovely! The crew was attentive and professional and the sunset views of the city were incredible. I would definitely highly recommend this activity!”
A 90-minute night walk through Boston Common, the Old State House, and historic graveyards with spooky lore and Revolutionary-era stories.
“We really enjoyed our tour with Bridget. She was very knowledgeable. The tour is the perfect length and amount of walking. It also gave us more ideas of where to visit during our time in Boston.”
A 2-hour Boston Harbor sunset sail from 60 Rowes Wharf with classic sights, friendly crew Q&A, and drinks for purchase on board.
“Amazing time. Friendly, small enough and gorgeous sunset! The staff was friendly. They were also offering drinks if you want.”
Hoist the sails and steer a classic Boston tall ship at sunset. 2-hour harbor cruise from Fan Pier with local drinks and skyline views.
“Had a great time! The captain and his crew were kind and attentive. Would recommend it to anyone!”
A 90-minute Charles River sunset cruise from Cambridge with a full bar, music, and big Boston skyline views for $36.
“Disappointing. No narrative or explanation was given of what we were seeing along.”
A 1.5-hour nighttime walk through Boston’s most famous hauntings, from the Boston Massacre site to Old North Church.
“We waited 15 minutes but no guide showed up so had to give up. Very cold to be standing around. Tried calling office but no reply and no explanation.”
Take a 1-hour Boston Harbor night cruise with blankets, warm lighting views, and stories passing USS Constitution and the Bunker Hill Monument.
“We arrived for our cruise after an evening of rain showers. It had cleared and was nice. Nearly every surface of the upper deck was wet and no attempt made by the crew to wipe anything down.”
Cozy Holiday Sunset Cruise on a 1920s yacht in Boston Harbor. Heated cabin, open deck views, Tobin Bridge, cannon fire, and city lights.
“Sunset cruise was an intimate gathering on the beautifully decorated Manhattan. The crew were very accommodating. Highly recommend!”
Every neighbourhood in the city, and every road out into New England.
