Top 8 Boston Holiday Tours, Priced and Timed

1.Cocoa and Carols Holiday Cruise

★★★★★★★★★★4.7 · 97 reviews · 1h 30m · from $65Our pick

Board a 1920s-style New England yacht at Rowes Wharf for a 90-minute evening cruise. You’ll relax in a heated salon, listen to holiday music, and see Boston landmarks such as the Bunker Hill Monument and USS Constitution from the harbor. The crew can answer questions, and drinks and light snacks are available to buy onboard.

“bellissima la vista e il panorama della città illuminata vista dal mare, splendida la barca con addobbi natalizi e musica live natalizia x tutta la crociera”

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2.Boston Holiday Cocoa Cruise

★★★★★★★★★★4.5 · 85 reviews · 1 hour 30 minutes (approx.) · from $82

Set out from Rowes Wharf for a 90-minute Boston Harbor cruise aboard a classic yacht. You’ll pass the Seaport, USS Constitution, and North End while a live jazz band plays holiday music. Choose a departure time, settle into an assigned table in the heated salon, or step onto the open bow for views. Food and drink costs need checking before you book.

“Comfortable and scenic ride in the harbor. We wouldn’t have minded another half hour but overall, great atmosphere with the live band and the refreshments. Mostly kid friendly and smooth sailing!”

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3.Holiday Sights and Festive Nights Trolley Tour

★★★★★★★★★★3.9 · 79 reviews · from $37

This 90-minute evening ride pairs a costumed guide’s stories of Boston holidays with views of Beacon Hill, Charles Street, Faneuil Hall, the Old State House, and the North End. You stay aboard for most of the route, with one short photo stop at Boston Common beside Frog Pond’s ice rink and the Halifax Christmas tree.

“Tour Guide was full of energy and lively. Really enjoy this tour. Weather was cold but hey it was Christmas time. Learned some amazing history as well.”

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4.Boston Harbor: Winter Holiday Weekend Brunch Cruise

★★★★★★★★★★4.6 · 24 reviews · from $106

Cruise Boston Harbor for two hours aboard a 1920s-style yacht dressed for the winter holidays. A three-course brunch buffet is included, while drinks are available to buy at the onboard bar. Look for views of the Harbor Islands and USS Constitution from the heated cabin or open deck.

“A wonderful, entertaining and relaxing experience. The atmosphere of the boat and Boston Harbor, the food, as well as a running commentary of Boston's sites made for a great experience. The food was delicious and the crew provided a great experience.”

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5.Holiday Sunset Cruise in Boston Harbor

★★★★★★★★★★5.0 · 11 reviews · from $70Top rated

Spend about two hours on a holiday sunset cruise from Rowes Wharf aboard a 1920s-style yacht. Watch the city lights come on, pass the North End and USS Constitution, and cruise beneath the Tobin Bridge. There is a heated cabin and open deck, holiday music, and a bar selling drinks. Captain Dante has led the harbor commentary on some sailings.

“Sunset cruise was an intimate gathering on the beautifully decorated Manhattan. The crew were very accommodating. Highly recommend!”

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6.Boston Harbor Holiday Brunch Cruise

★★★★★★★★★★5.0 · 9 reviews · from $106

Board the 1920s-style yacht Northern Lights at Rowes Wharf for a two-hour holiday brunch cruise. You’ll eat a buffet meal, view Boston Harbor from the observation cabin or open top deck, and pass sights including the Bunker Hill Monument, USS Constitution, Castle Island, and the Seaport. Drinks cost extra, and tables may be shared.

“We enjoyed the views, the holiday decor and delicious food! There was so much food! The small boat allowed for an intimate cruise.”

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7.Ghosts of Christmas Past a Haunted Holiday Stroll in Salem

★★★★★★★★★★5.0 · 6 reviews · 2 hours (approx.) · from $35

Join Witch City Walking Tours for a two-hour holiday stroll through Salem, starting and ending at Old Town Hall. A licensed English-speaking guide, including Rachel or Tish, leads stories at landmarks such as the Witch House, Ropes Mansion, and Pickering House. Expect Christmas customs, ghost tales, winter-solstice lore, and hot apple cider. Stops are outdoors; you do not enter the Witch House.

“The guide was a lot of fun. She knew so much. Made it a great experience for me. Felt very comfortable.”

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8.Self-Guided Boston Christmas Tour

★★★★★★★★★★5.0 · 3 reviews · 40 to 50 minutes (approx.) · from $9Best value

This private, self-guided Boston walk runs from King’s Chapel to the Alexander Hamilton statue on Commonwealth Avenue, with Santa narrating stops tied to Christmas traditions, Charles Dickens, authors, and holiday lights. It takes about 40 to 50 minutes, costs $9.75 per person, and one tour can be used on up to four phones.

“We had a great time on the Christmas walk. Enjoyed learning the history and the humor sprinkled through it added to the enjoyment.”

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