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Best results for

Sailing in Mattapoisett, MA

Showing 1-24 of 26 results
2-Hour Private Sailing Charter in Newport

2-Hour Private Sailing Charter in Newport

Sail Narragansett Bay on a private 36-foot sloop with your captain

5.0 • 210 reviews
$419
Private Friendship Sloop Sailing Charter in Newport

Private Friendship Sloop Sailing Charter in Newport

Private Ladybird sail with crew, music, and room for your own drinks and snacks

5.0 • 46 reviews
$1,002& up
5-Day Marine Systems Class in Barrington

5-Day Marine Systems Class in Barrington

Build practical confidence diagnosing and maintaining your boat’s essential systems

4.9 • 82 reviews
$1,420/ person
Shared Buzzards Bay Sailing Trip from New Bedford

Shared Buzzards Bay Sailing Trip from New Bedford

Catch the bay breeze past New Bedford's working waterfront

4.8 • 24 reviews
$80/ person
Private Vineyard Sound Sailing Charter

Private Vineyard Sound Sailing Charter

Feel the power of sailing on Martha's Vineyard waters

$1,268
Private 3.5-Hour Sailing Cruise in Newport

Private 3.5-Hour Sailing Cruise in Newport

Sail Narragansett Bay on a private 3.5-hour cruise aboard the 36' sloop Hurrah

5.0 • 210 reviews
$843
Private Friendship Sloop Sailing Charter in Newport

Private Friendship Sloop Sailing Charter in Newport

Private sailing with room to swim, picnic, and explore Newport’s coast

5.0 • 46 reviews
$1,463& up
Private Sailing Charter in New Bedford Harbor & Buzzards Bay

Private Sailing Charter in New Bedford Harbor & Buzzards Bay

Sail New Bedford Harbor and Buzzards Bay on a private charter

4.8 • 24 reviews
$466& up
3-Hour Vineyard Sound Sailing Charter

3-Hour Vineyard Sound Sailing Charter

Sail Vineyard Sound with lighthouse views and secluded swim options

$2,113
Newport Sunset Sailing Cruise

Newport Sunset Sailing Cruise

A private harbor sail with landmark views as daylight fades

5.0 • 210 reviews
$419
Mattapoisett Harbor Private Sailing Charter

Mattapoisett Harbor Private Sailing Charter

Sail close to the water on an interactive harbor charter

4.8 • 24 reviews
$371& up
Sunset Sail Charter on Martha's Vineyard

Sunset Sail Charter on Martha's Vineyard

Relax on deck as the sun sets over the water

$3,169
Sailing Refresher Lesson in Mattapoisett

Sailing Refresher Lesson in Mattapoisett

Tailor a hands-on sail to the skills you want to sharpen

4.8 • 24 reviews
$371/ boat
Sunset Sail in Vineyard Haven

Sunset Sail in Vineyard Haven

Sail Martha's Vineyard aboard a historic 1926 schooner

4.8 • 86 reviews
$128/ person
Morning Harbor Sailing Cruise in Newport

Morning Harbor Sailing Cruise in Newport

Sail Newport Harbor and Narragansett Bay on a quick, family-friendly morning cruise

5.0 • 210 reviews
$294
Private Morning Sailing Charter in Newport

Private Morning Sailing Charter in Newport

Sail Newport’s coast from Fort Adams to Brenton Point

5.0 • 67 reviews
$1,251
2-Day Sailing Cruise From Barrington

2-Day Sailing Cruise From Barrington

Sail beyond Narragansett Bay as an active crewmember

4.9 • 82 reviews
$1,150/ cabin
Private Sailing Charter in Martha's Vineyard

Private Sailing Charter in Martha's Vineyard

Set sail on a private classic sloop tailored to your group

4.9 • 32 reviews
$731& up
Afternoon Sailing Charter in Newport

Afternoon Sailing Charter in Newport

Private sailing with shaded lounging, hidden-cove swims and Newport coastal views

5.0 • 67 reviews
$1,251
4-Hour Sailing Lesson on Narragansett Bay

4-Hour Sailing Lesson on Narragansett Bay

Practice sailing skills with an instructor on Narragansett Bay

4.9 • 82 reviews
$201/ person
Martha's Vineyard Sunset Sail

Martha's Vineyard Sunset Sail

Share an evening harbor sail as the light shifts over the water

4.9 • 32 reviews
$217/ person
Martha's Vineyard Historic Schooner Sailing Cruise

Martha's Vineyard Historic Schooner Sailing Cruise

Raise the sails or take the wheel on Martha's Vineyard waters

4.8 • 86 reviews
$107/ person
Newport Sunset Sailing Charter

Newport Sunset Sailing Charter

Private golden-hour sailing with room to relax, dine, and swim

5.0 • 67 reviews
$901
2-Hour Private Sunset Sailing Cruise in Narragansett Bay

2-Hour Private Sunset Sailing Cruise in Narragansett Bay

Private sunset sail for up to 4 on Narragansett Bay

4.9 • 82 reviews
$159
12
Mattapoisett Things To Do
SailingBike Rentals57Kayaking Tours22Boat Tours15Paddleboarding13
More
  • Stand Up Paddle Boarding11
  • Fishing Charters10
  • Trolley Tours8
  • Yacht Charters8
  • Axe Throwing6
  • Bike Tours6
  • Boat Rentals6
Bus Van and Limo Tours5
  • Parasailing4
  • Sunrise and Sunset Tours4
  • Ghost and Haunted3
  • Museum Tours3
  • Tubing3