Ranked #1 on TripAdvisor and 2022 Traveler's Choice Award Recipient

(508) 923-7177

  • Home
  • Our Services
    • Vineyard Day Sails
    • Special Events
    • Off The Vineyard
  • Book Now
  • About Us
  • Photo Gallery
  • Directions
  • Contact Us
  • The Vineyard
  • Policies & FAQ
  • News & Updates
  • More
    • Home
    • Our Services
      • Vineyard Day Sails
      • Special Events
      • Off The Vineyard
    • Book Now
    • About Us
    • Photo Gallery
    • Directions
    • Contact Us
    • The Vineyard
    • Policies & FAQ
    • News & Updates
  • Home
  • Our Services
    • Vineyard Day Sails
    • Special Events
    • Off The Vineyard
  • Book Now
  • About Us
  • Photo Gallery
  • Directions
  • Contact Us
  • The Vineyard
  • Policies & FAQ
  • News & Updates
Book Now

Sailing Excursion Options

2-Hour Harbor Day Sails

Sunsets & Special Occasions

2-Hour Harbor Day Sails

Experience the beauty of Martha's Vineyard island as you explore the inner harbor of Vineyard Haven. Relax and bask in the sun or take a more active role and help with the activities of sailing.  


2-hour charters may be scheduled 

any time of day.


2 Hour Charters

Up to 6 People

$550


 In compliance with U.S. Coast Guard CFR Subchapter C, we carry a maximum of 6 guests, but have options for larger groups. 

See below for details. 


Requests are considered, however, for your safety and enjoyment, the Captain will determine the best route for your sail based on current, tide, and wind conditions on the day and time of your sail.

Book Now

3- or 4-Hour Day Sails

Sunsets & Special Occasions

2-Hour Harbor Day Sails

Venture outside the Vineyard Haven harbor with us and enjoy sailing more of the Martha's Vineyard coastline. Bring your own prepared foods, utensils & alcoholic beverages, or ask about catering for a picnic underway.


3 Hour Charters

Up to 6 People

$700

4 Hour Charters

Up to 6 People

$850


 In compliance with U.S. Coast Guard CFR Subchapter C, we carry a maximum of 6 guests, but have options for larger groups. 

See below for details. 


Requests are considered, however, for your safety and enjoyment, the Captain will determine the best route based on tide, current and wind conditions on the day and time of your sail.

Book Now

Sunsets & Special Occasions

Sunsets & Special Occasions

Sunsets & Special Occasions

Make a toast to another perfect day in paradise with a sunset sail around the  harbor. Sunsets are always special on Martha's Vineyard, but from the water aboard a sailing vessel they take on a magical quality.  Celebrating a birthday, anniversary or proposal?  Sunset sails are the perfect venue for your special evening.


2 Hour Charters

Up to 6 people

$575


 In compliance with U.S. Coast Guard CFR Subchapter C, we carry a maximum of 6 guests, but have options for larger groups. 

See below for details. 


Requests are considered, however, for your safety and enjoyment, the Captain will determine the best route based on tide, current and wind conditions on the day and time of your sail.

Book Now

Add On Catering Options

Gourmet Hors d'oeuvre Platters

Gourmet Hors d'oeuvre Platters

Gourmet Hors d'oeuvre Platters

Leave the snacks to us! 


Not only do we include soda & snacks on all our charters, we offer delicious platters with a variety of cheeses, fruits, charcuterie and crackers. They're complimentary on our 4-hour sails, but you can add them on shorter sails.  Interested in something more filling? Ask about our other catering options.

From $100

Dessert Platters

Gourmet Hors d'oeuvre Platters

Gourmet Hors d'oeuvre Platters

Everyone knows salty & sweet go together perfectly!  


If the salt air gives you a sweet tooth, we've got you covered.  Add a gourmet dessert platter with a variety of local fudge, cookies, and other sweets to any sail.


$100

Need to accommodate a large group?

The Vineyard's Hottest New Sailing Option - Perfect for 7-12 people

The race is on!  With half your group on each boat, Phoenix goes head-to-head against your friends aboard another vessel in an informal sailboat race. Grind the winches and tack the boat to sail past your friends on our sister ship - or let the crew do it for you! 


Not up for racing? No problem - we can do a more leisurely tandem sail that allows for great photos ops!

Available in 2- or 4-hour tours  ~  From $1100

Call to reserve your 2- or 4-hour group sail

Copyright © 2018 Sail The Vineyard - All Rights Reserved.

  • Book Now
  • Contact Us

We sailed south for the winter

We'll reopen on May 26, 2023. Use our "Book Now" button to reserve your sail for our 2023 sailing season.

Book Now