Boston Cruises & Sailing Tours

32 experiences to discover

Day & Sunset Cruises Dinner Cruises Sailing 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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4.62

Boston Harbor Sunset Cruise

$70-$82

2 providers combined

Sail aboard a classic yacht at sunset

1.5-hour holiday cruise on classic yacht

4.57

Boston Dinner Cruise with Buffet and Live Music 3 hr

From $450

1 provider live

Sip cocktails in the topside lounge

Three-course buffet dinner

4.57

Boston Yacht Tour Aboard the Trilogy 2 hr

From $2500

1 provider live

Sail the largest private yacht in New England

103' M/Y Broward yacht

4.57

Boston Dinner Cruise on Mother's Day

From $186

1 provider live

Savor a delicious plated dinner

Unlimited coffee, hot tea, and iced tea

4.57

Boston Full Moon Cruise

From $35

1 provider live

Relax under the full moon

Restroom on board

4.56

Boston Harbor Tropical Boat Cruise

From $61

1 provider live

Experience a tropical escape in Boston Harbor

90-minute harbor cruise

4.55

Boston Harbor Alive After Five Cruise

From $56

1 provider live

Cruise through Boston Harbor

Light snacks available for purchase

4.55

Boston Charles Riverboat Cruise with Cookies & Carols 1 hr

From $30

1 provider live

Enjoy festive holiday music

Cruise

4.55

Boston Harbor Private Sunset Cruise

From $1200

1 provider live

Witness the Boston skyline at sunset

Water and soft drinks provided free of charge

4.54

Boston Doggy Costume Party Cruise 2 hr

From $31

1 provider live

Dance with your furry friends

DJ and raffle prizes

4.54

Boston Harbor and Charles River Architecture Boat Tour

From $47

1 provider live

Take in Boston's iconic landmarks

Boston Harbor and Charles River cruise

4.53

Boston Harbor Full Moon Cruise

From $31

1 provider live

Cruise Boston Harbor under a full moon

2-hour cruise with 30-minute boarding time