Recent Searches
Clear

Top Massachusetts Sailing

Saved to wishlist!
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Massachusetts. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials
Select Dates
Dates
On the Water
Water Tours
Extreme
Cruises & Sailing
Nature and Wildlife
Motor Sports
Half-day Tours
Sightseeing Tours
Private Sightseeing Tours
Sporting Events
Sightseeing Cruises
Historical Tours
Sunset Cruises
Day Trips
Day Cruises
4WD Tours
Private and Luxury
Art & Culture
Outdoor Activities
Tickets & Passes
Sort by:Featured

Harbor Cruise & Sail On Our 125 Foot Tall Ship Liberty Clipper in Boston

Harbor Cruise & Sail On Our 125 Foot Tall Ship Liberty Clipper in Boston

star-4.5
32
Explore Boston by boat with this cruise on the Liberty Clipper. Help the crew hoist the sails or simply find a spot on deck to enjoy the views. Your captain creates a route depending on wind direction, heading toward the outer harbor for a glimpse of Fort Independence, or sailing toward East Boston for views of the Charlestown Navy Yard, home to the USS Constitution.
More
  • 2 hours
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

star-4.5
71
Experience Boston Harbor on a sunset cruise aboard a historic tall ship. Depart from Central Wharf on the 67-foot Liberty Star or the 125-foot Liberty Clipper and enjoy views of the outer harbor, Fort Independence, East Boston, the Charlestown Navy Yard, and beyond. Relax and let the crew handle the sails or jump in the action and a grab a line on this fun and affordable outing.
More
  • 2 hours
  • Taking safety measures
From
$48.00
From
$48.00
Taking safety measures

Sightseeing Day Sail around Boston Harbor
Likely to Sell OutLikely to Sell Out

Sightseeing Day Sail around Boston Harbor

star-4.5
31
See Boston Harbor’s sights from the water on this day sail aboard a replica of a pilot schooner. Step aboard the boat and sail off through the harbor, bound for Spectacle Island, Fort Independence, Castle Island, and Long Island. Listen to guided commentary on the harbor’s history and ecosystem while you sail, snapping photos of Boston’s coast from the water.
More
  • 1 hour 30 minutes to 2 hours
  • Taking safety measures
From
$55.47
From
$55.47
Taking safety measures

6 Hour Sailing Tour of Vineyard Haven Harbor and Sound

6 Hour Sailing Tour of Vineyard Haven Harbor and Sound

Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard Sound. Tandemeer is a big beautiful 1980 classic 60' ketch made famous in the 1982 hit movie "Trading Places" with Eddie Murphy, Dan Akroyd and Jamie Lee Curtis. Fun in the Sun in Style.
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$1,250.00
per group
From
$1,250.00
per group
Taking safety measures

4 Hour Sailing Tour of Vineyard Haven Harbor and Sound

4 Hour Sailing Tour of Vineyard Haven Harbor and Sound

Sailing is the best way to see and experience Vineyard Haven Harbor, Nantucket Sound and Vineyard Sound. Tandemeer is a big beautiful 1980 classic 60' ketch made famous in the 1982 hit movie "Trading Places" with Eddie Murphy, Dan Akroyd and Jamie Lee Curtis. Fun in the Sun in Style.
More
  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$650.00
per group
From
$650.00
per group
Taking safety measures

Privateer Schooner Sailing Tour in Salem Sound

Privateer Schooner Sailing Tour in Salem Sound

star-5
218
Embark on an interactive sailing excursion off the coast of Salem on a replica historic privateer schooner. Great for families and anyone who gets bored easily, this adventure keeps you engaged by offering opportunities to help with tasks such as raising the sails and steering the boat. Plus, the crew shares stories about the history of Salem and the role played by privateers.
More
  • 1 hour 45 minutes
  • Free Cancellation
  • Taking safety measures
From
$44.00
From
$44.00
Taking safety measures

Filters

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Sailing in Massachusetts?
Q:
What Sailing in Massachusetts are taking additional safety precautions?
Q:
What Sailing in Massachusetts are good for avoiding crowds?