Boston Cruises & Sailing Tours tours

Boston Cruises & Sailing Tours

7 experiences to discover

Day & Sunset CruisesDinner CruisesSailing Trips

Explore the best cruises & sailing tours tours and activities in Boston. Our unbiased ratings help you find the perfect experiences for your trip.

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Boston Tall Ship Sunset Harbor Cruise
4.5Rating:

Boston Tall Ship Sunset Harbor Cruise

$60-$68

Hoist the sails and steer the ship

2-hour sunset sail along Boston Harbor

Boston Harbor Sunset Cruise
4.45Rating:

Boston Harbor Sunset Cruise

$70-$73

Sail aboard a classic yacht at sunset

Cruise on classic yacht

Boston Harbor Sailing Cruise
4.42Rating:

Boston Harbor Sailing Cruise

From $67

Sail past Boston's iconic skyline

1.5 or 2-hour cruise

Boston Harbor Brunch Cruise
3.86Rating:

Boston Harbor Brunch Cruise

$94-$106

Savor a gourmet brunch buffet

Narrated tour of Boston and the harbor

Boston Harbor Brunch or Dinner Cruise
3.82Rating:

Boston Harbor Brunch or Dinner Cruise

$79-$86

Savor gourmet brunch or dinner

Cruise aboard the Odyssey

Boston Tall Ship Harbor Sail with Brunch Option
3.41Rating:

Boston Tall Ship Harbor Sail with Brunch Option

From $35

Relax on a classic tall ship

Admission and sailing

Boston Harbor Sunset Sightseeing Cruise
3.16Rating:

Boston Harbor Sunset Sightseeing Cruise

$49-$52

Admire the stunning Boston skyline at sunset

90-minute narrated Boston Harbor sunset cruise