Boston · EVENING EXPERIENCES

15 Evening Experiences in Boston Worth Leaving the Hotel For

39 tours  ·  from $26 a head

The better evening experiences book up early in summer and again in October. Below: the 15 to reserve first, what each includes and how they differ.

Mysteries and Murders of Salem Guided Night-Time Walking Tour - Jail stories, a church and a haunted house
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Mysteries and Murders of Salem Guided Night-Time Walking Tour

1.Mysteries and Murders of Salem Guided Night-Time Walking Tour

★★★★★★★★★★5.0 · 1,488 reviews · 1 hour 40 minutes to 2 hours (approx.) · from $36Our pick

Follow a professional guide through Salem after dark for stories of murder, mystery and alleged hauntings beyond the witch trials. Guides including Samantha, Danielle, Violet and William lead this outdoor walk from Old Town Hall to the Burying Point. Expect about 100 to 120 minutes on foot, with no entry into buildings or the cemetery.

“Our tour guide Violet was great and was super informative. Tour was a great time for me and my wife.”

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Boston: Boston Harbor Sunset Cruise - The city looks different from the water
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Boston: Boston Harbor Sunset Cruise

2.Boston Harbor Sunset Cruise

★★★★★★★★★★4.5 · 888 reviews · 1h 30m · from $31

Set out from Rowes Wharf on a 90-minute English-language cruise through Boston Harbor. Your guide points out city landmarks and shares local history, with a chance to see the USS Constitution near sunset. Indoor and outdoor seating may be available, and snacks and drinks can be bought onboard. The boat returns to its starting point.

“A great introduction to the history and sights of Boston from the water. Just enough commentary, so it wasn’t overbearing.”

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Salem Night Tour: Haunt and History Guided Night Tour - The Witch Trials Memorial and the weight of the story
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Salem Night Tour: Haunt and History Guided Night Tour

3.Salem Night Tour: Haunt and History Guided Night Tour

★★★★★★★★★★4.5 · 673 reviews · 1h 30m · from $30

Spend 90 minutes walking downtown Salem with a local historian and paranormal guide. Stops can include the Witch Trials Memorial, two cemeteries, the Old Salem Jail, and Hocus Pocus filming locations. Guides such as Penny, Bob, and Elaina mix local history with ghost stories. The route varies, and building admission is not included.

“Matty was a great guide. He was very knowledgeable and I feel like we learned a lot.”

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Boston Harbor Sunset Cruise - Choosing your seat as the light changes
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Boston Harbor Sunset Cruise

4.Boston Harbor Sunset Cruise

★★★★★★★★★★4.5 · 632 reviews · 2 hours (approx.) · from $54

Set out from Rowes Wharf for an approximately two-hour Boston Harbor cruise with open-air and heated indoor seating. The captain offers light commentary as you pass the Old North Church, Charlestown Navy Yard, USS Cassin Young, and other waterfront sights. Drinks and snacks are available to buy, and the USS Constitution’s sunset cannon may provide the evening’s most memorable sound.

“Unfortunately for us, we had a rainy sunset cruise. However, still had a wonderful time, through some mist and rain, we were still able to see the city and learn some key features. We enjoyed a light bite and enjoyed the seasonal drink menu as well.”

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Boston: Harbor Sunset Yacht Cruise - A classic yacht, not a bare-bones ferry
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Boston: Harbor Sunset Yacht Cruise

5.Harbor Sunset Yacht Cruise

★★★★★★★★★★4.6 · 570 reviews · 2 hours · from $54

Spend two hours on the 115-foot Northern Lights, a 1920s-style New England yacht, cruising Boston Harbor as daylight fades. Expect open-deck and climate-controlled seating, light commentary, music, and a sunset cannon salute from USS Constitution. Drinks and snacks cost extra, and the bar accepts credit cards only.

“The cruise is very enjoyable and interesting. If you want to sit on the top deck, you'll need to be at the dock at least 30 minutes before.”

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Sunset Cruise with Gansett Cruises in Newport, RI - From Market Square to the harbor
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Sunset Cruise with Gansett Cruises in Newport, RI

6.Sunset Cruise with Gansett Cruises in Newport, RI

★★★★★★★★★★5.0 · 538 reviews · 1 hour (approx.) · from $50

Take a one-hour sunset cruise through Newport Harbor and Narragansett Bay’s East Passage aboard a restored 50-foot lobster boat. Hear local stories from the crew, look for the Newport Bridge and a lighthouse, and enjoy a complimentary quahog stuffie and Champagne toast. Choose shaded, cushioned seating or the open upper deck; drinks from the onboard bar cost extra.

“I was definitely pleasantly surprised! I have gone to Newport in the past and went to other sunset cruises, but this one was small but intimate, great communication and friendly staff. It was such an enjoyable experience, would recommend to all my friends and family.”

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Narrated Sunset Cruise of Boston Harbor - Watching the skyline change at twilight
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Narrated Sunset Cruise of Boston Harbor

7.Narrated Sunset Cruise of Boston Harbor

★★★★★★★★★★4.0 · 532 reviews · 1 hour 30 minutes (approx.) · from $29Best value

Depart Rowes Wharf for a 90-minute Boston Harbor cruise with live English narration. Pass Fish Pier, Logan Airport, East Boston, Charlestown, and the USS Constitution as the light changes over the skyline. A full bar and snacks are available to buy. Arrive early if you want a seat on the upper deck.

“The trip was awesome, very little noise from the engine, the narration was a nice touch, drinks were good. No music or dancing, a bit quite.”

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Sunset Sailing Cruise on a Tall Ship in Boston Harbor - Sunset, Breeze, and the Onboard Bar
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Sunset Sailing Cruise on a Tall Ship in Boston Harbor

8.Sunset Sailing Cruise on a Tall Ship in Boston Harbor

★★★★★★★★★★4.5 · 414 reviews · 2 hours (approx.) · from $68

Spend about two hours sailing Boston Harbor aboard a traditional tall ship, with the city skyline and harbor islands as your backdrop. The crew handles the sailing and may invite you to help with the sails. Drinks and snacks are available for purchase. Crew members have included Captain Fredo, Jess, and Max, though the team can vary.

“Weather was great, but conversations with crew was the most enjoyable. They were very welcoming and knowledgeable and seemed to love what they do.”

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City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise - Old Ironsides and the cannon at day’s end
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City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

9.City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

★★★★★★★★★★4.5 · 411 reviews · 1 hour 30 minutes (approx.) · from $56

Cruise Boston’s inner and outer harbors for 90 minutes, with live English commentary, skyline views at sunset, and a look at the restored Boston Tea Party ships and USS Constitution. The Constitution’s cannon and flag lowering mark the day’s end. Depart from Long Wharf, May through October. Food and drinks are sold on board.

“The boat tour was great. Great views & the tour guide made it very enjoyable & funny. Only bad part was the annoying family that was being very loud & listening to music the whole time on their phone. Would have liked to throw them overboard. Would still highly recommend though!”

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Boston: City Cruises Sunset Skyline Cruise with Commentary - Castle Island, Logan Airport, and East Boston
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Boston: City Cruises Sunset Skyline Cruise with Commentary

10.City Cruises Sunset Skyline Cruise with Commentary

★★★★★★★★★★4.6 · 381 reviews · 1h 30m · from $55

Cruise Boston Harbor for 90 minutes with an English-speaking guide, passing Castle Island, Logan Airport, the North End, and more. The sunset trip includes commentary and a view of the USS Constitution’s traditional cannon salute. Guides have included David Coffin and Kevin, though your narrator may differ.

“Great view of the city and lots of good info about the city of Boston even though I have lived here my whole life.”

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Black Cat Ghostly Night Tour in Salem - Starting by the Bewitched statue
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Black Cat Ghostly Night Tour in Salem

11.Black Cat Ghostly Night Tour in Salem

★★★★★★★★★★5.0 · 344 reviews · 1 hour 45 minutes (approx.) · from $30

Meet your guide by the Bewitched statue, check in at the Black Cat Curiosity Shoppe, then spend about 1 hour 45 minutes walking among Salem’s haunted sites and hearing ghost stories alongside local history. Guides such as Vin, Zach, David, and Daniel have earned praise for lively storytelling. The route returns to the starting point.

“Vin was very knowledgeable about Salem facts and the surrounding area. He was loud enough for all to hear, and was very easy to understand with good diction. Finally, he was entertaining and kept the crowd engaged for the entire duration of the tour. He is highly recommended.”

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1692 Salem Night Walking Tour - A history walk, not a ghost tour
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1692 Salem Night Walking Tour

12.1692 Salem Night Walking Tour

★★★★★★★★★★5.0 · 333 reviews · 2 hours (approx.) · from $35

Walk downtown Salem from Essex Street to the Witch Trial Memorial with a local guide. Over about two hours, hear how the 1692 panic began, who was accused and judged, and how the trials ended. The route passes the Witch House and other historic sites. Guides have included Jeff and Jeremiah; expect an outdoor, family-friendly walk in any weather.

“Great tour with local recommendations and tons of political knowledge about the history of witch trials.”

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Boston: Harbor Champagne Sunset Sail from Rowes Wharf - The Fish Pier and Fan Pier bring the working waterfront into view
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Boston: Harbor Champagne Sunset Sail from Rowes Wharf

13.Harbor Champagne Sunset Sail from Rowes Wharf

★★★★★★★★★★4.8 · 299 reviews · 2 hours · from $82

Spend two hours sailing Boston Harbor aboard Schooner Adirondack III or IV, passing the Fish Pier, Inner Harbor Islands, Navy Yard, and city waterfront. The crew answers questions about local sights and maritime history. Beer, wine, champagne, and soft drinks are available for purchase by credit card; bring a picnic and a warm layer.

“We enjoyed our 4th of July sail. The crew did a great job catering to us all. My 11 year old son really enjoyed the sailing talk the crew gave. It was so fun!”

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Ghosts of Boston Night-Time Walking Tour - King’s Chapel Burying Ground from outside the gates
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Ghosts of Boston Night-Time Walking Tour

14.Ghosts of Boston Night-Time Walking Tour

★★★★★★★★★★4.5 · 267 reviews · 1 hour 30 minutes (approx.)

At 8 pm, join a guided 90-minute walk from 58 Tremont St to hear ghost lore and Revolutionary-era history at Boston Common, the Old State House, King’s Chapel Burying Ground, and Granary Burying Ground. The cemeteries are viewed from outside their gates. Guides have included Kimmy, Justin, Beth, and Harlan; your guide will vary.

“Fun and informative and the city at night beautiful. Our guide was fun and full of energy and knowledge”

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Newport, RI: Evening Cocktail Cruise of Narragansett Bay - A Complimentary Cocktail and a Cash Bar
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Newport, RI: Evening Cocktail Cruise of Narragansett Bay

15.Evening Cocktail Cruise of Narragansett Bay

★★★★★★★★★★4.6 · 219 reviews · from $45

Board the Coastal Queen at Bowen’s Landing for a 75-minute evening cruise past Newport Harbor, Rose Island, Jamestown, historic forts, and the Newport Pell Bridge. Your ticket includes one drink for ages 21 and up. Choose the main salon or open-air upper deck, and bring cash if you want anything from the onboard bar.

“Great and very friendly staff Very accommodating to the disabled”

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New in Evening Experiences

★ 4.5Newport Scenic Sunset Cruise on Classic Boat Rum Runner IIFrom $5013 reviews
★ 5.0America’s Cup Evening Sailing Adventure Newport, RIFrom $4010 reviews
★ 5.0Golden Hour Escape: Private Sunset Sail in Coastal Maine20 reviews
★ 5.0Private Guided Night Photography Tours on Cape Cod (for one photographer.)From $42538 reviews
★ 5.0Cape Cod Sunset Kayak TourFrom $809 reviews
★ 4.0Boston Premium Night Tour With View Boston Observation DeckFrom $1348 reviews
★ 5.0Holiday Sunset Cruise in Boston HarborFrom $7011 reviews
★ 4.5Boston Harbor Night CruiseFrom $4513 reviews
★ 5.0Back Bay Evening Chocolate TourFrom $604 reviews
★ 4.4Ultimate Dead of Night Walking Ghost TourFrom $2626 reviews
★ 4.9Newport Sunset Sail on Schooner AdirondackFrom $6715 reviews
★ 4.9Sunset Sail on Schooner MadeleineFrom $6734 reviews
★ 4.7Sunset Cocktail CruiseFrom $5022 reviews
★ 4.8Evening Cruise on Newport HarborFrom $4812 reviews
★ 4.4Margarita Sunset Cruise in Hyannis HarborFrom $325 reviews

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After dark

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