The 8 Best Christmas & Holiday Tours in Boston

1.Cocoa and Carols Holiday Cruise

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

Join a small group of up to eight for a 90-minute evening cruise from Rowes Wharf aboard a heated, holiday-decorated New England yacht. Sip hot cocoa, listen to seasonal music, and watch Boston landmarks such as the USS Constitution and Bunker Hill Monument appear from the harbor.

“Aucune information guidée. L’heure de l’activité sur Booking inexacte. Chanteuse qui ne connaît pas les paroles des chansons de Noël et qu’on entend très peu. Excellent band. Excellent chocolat chaud. Personnel agréable.”

Check availability →Read our full review

2.Boston Holiday Cocoa Cruise

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

Cruise Boston Harbor for 90 minutes aboard a classic yacht with heated grand-salon seating, a self-serve hot cocoa bar, live holiday jazz, and views of the Seaport, USS Constitution, Charlestown Navy Yard, North End, and Old North Church. Depart from Rowes Wharf and return there.

“Such a relaxing and enjoyable experience to put you in the festive spirit for the holidays! The crew was fantastic and the boat was lovely!”

Check availability →Read our full review

3.Holiday Sights and Festive Nights Trolley Tour

★★★★★★★★★★3.9 · 79 reviews · from $37

Ride a heated double-decker trolley through Boston at night with a costumed English-speaking guide. Pass Beacon Hill, Charles Street, the North End, Faneuil Hall, Quincy Market, and the Old State House, then stop at Boston Common for photos by the Halifax Christmas tree and Frog Pond ice rink.

“Guide was nice trolley was fun - could have used more history-what was told was great. Could have seen more lights we did lots of circles”

Check availability →Read our full review

4.Boston Harbor: Winter Holiday Weekend Brunch Cruise

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

Spend two cozy hours aboard a 1920s-style yacht from Rowes Wharf. Enjoy a three-course brunch buffet, panoramic harbor views, holiday decorations, and an onboard bar. The heated cabin keeps you comfortable in cold weather, while the open deck offers fresh air and views of the USS Constitution and Boston Harbor Islands.

“Thus was a great event for Mom and me. The staff were attentive and so helpful. The food was excellent. I hope to be able to do this again in future with more members of my family.”

Check availability →Read our full review

5.Holiday Sunset Cruise in Boston Harbor

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

Board a heated 1920s-style yacht at Rowes Wharf for a two-hour holiday cruise past Fort Independence, the USS Constitution, North End, and Tobin Bridge. Enjoy sunset views, classic holiday music, and drinks available for purchase while Captain Dante and the crew may share harbor stories.

“I had a fantastic time. I will go back next year for the holiday hot chocolate cruise. The reason I gave it 4 stars is because at first we were given the seat next to the bar two steps down from the main floor where all the fun was happening. Our tRead more”

Check availability →Read our full review

6.Boston Harbor Holiday Brunch Cruise

★★★★★★★★★★5.0 · 9 reviews · from $106

Board the Northern Lights at noon from Rowes Wharf for a two-hour holiday brunch cruise. You’ll enjoy a buffet, holiday decorations, skyline views, and sights including the USS Constitution, Bunker Hill Monument, Castle Island, harbor islands, and Boston’s Seaport.

“Fantastic boat and crew! Such an enjoyable cruise….taking in the sites of Boston, seeing the harbor seals, stopping at the islands and light house…. all while listening to holiday music and enjoying a nice brunch.”

Check availability →Read our full review

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

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

Walk Salem’s historic center with a licensed guide such as Rachel or Tish, hearing ghost tales, Christmas customs, and winter solstice stories at landmarks including the Witch House, Pickering House, and Hamilton Hall. The tour stays outdoors and includes hot apple cider.

“Rachel was so sweet and so informative. Loved the walk and seeing all of the things I would have otherwise not known to look for.”

Check availability →Read our full review

8.Self-Guided Boston Christmas Tour

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

Follow a self-guided Christmas route from King’s Chapel to Commonwealth Avenue, with Santa narrating Boston’s holiday stories, Dickens connections, Beacon Hill streets, Frog Pond, and the city’s best lights. The 40 to 50 minute walk is in English and works 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.”

Check availability →Read our full review