Ranked #1 on TripAdvisor 5 years in a row

(508) 493-8767

  • Home
  • Sailing Tours
    • Sailing Charters
    • Private Sails
    • Public Sails
    • Sunset Sails
    • JAWS Martha's Vineyard
    • Fireworks Sails
    • Sips & Sails Jazz Cruise
    • Weddings & Vow Renewals
    • Destination Sailing
    • Learn to Sail
    • Catering Options
  • Book Now
  • Directions
  • About Us
  • Contact Us
  • Things To Do
  • Policies & FAQ
  • News & Updates
  • Job Opportunities
  • More
    • Home
    • Sailing Tours
      • Sailing Charters
      • Private Sails
      • Public Sails
      • Sunset Sails
      • JAWS Martha's Vineyard
      • Fireworks Sails
      • Sips & Sails Jazz Cruise
      • Weddings & Vow Renewals
      • Destination Sailing
      • Learn to Sail
      • Catering Options
    • Book Now
    • Directions
    • About Us
    • Contact Us
    • Things To Do
    • Policies & FAQ
    • News & Updates
    • Job Opportunities
  • Home
  • Sailing Tours
    • Sailing Charters
    • Private Sails
    • Public Sails
    • Sunset Sails
    • JAWS Martha's Vineyard
    • Fireworks Sails
    • Sips & Sails Jazz Cruise
    • Weddings & Vow Renewals
    • Destination Sailing
    • Learn to Sail
    • Catering Options
  • Book Now
  • Directions
  • About Us
  • Contact Us
  • Things To Do
  • Policies & FAQ
  • News & Updates
  • Job Opportunities

Private Sailing Charters on Martha's Vineyard Island: "Just You & Me & The Sea"

Since we began sailing Martha’s Vineyard and sharing our sailing charters with guests in 2018, we've focused on luxurious exclusivity with our private day sails. Enjoy our topside decks and cockpit; play Captain or Pirate for the day! Our private days sails are tailored just for you and only for you and whoever you choose to bring aboard with you (up to a maximum of 6 people.) 

Private Day Sail and Sunset Sail Options

Vineyard Haven Harbor 2-Hour Sails

Martha’s Vineyard Sunset Sails & Special Occasions

Martha's Vineyard 3- or 4+ Hour Day Sails

Family on a private day sail with Sail The Vineyard in Vineyard Sound, Martha's Vineyard

 Experience the beauty of Martha's Vineyard island on one of our sailing charters and explore the inner harbor of Vineyard Haven. Our expansive harbor is a sailor's playground. Generally well-protected and calm, this harbor tour is a fantastic way for "first-timers" to sail Martha’s Vineyard. Plus it’s a fantastic opportunity to enjoy just enough of an escape from the crowds of land life. Learn about the history of the island and Vineyard Haven with a quick circle through the inner harbor if you like. Relax and bask in the sun or take a more active role and help with the activities of sailing. Offered daily, this is our most popular sail. 


2-hour charters may be scheduled 

any time of day.


2 Hour Charters

Private, Up to 6 People

$625


Don' forget the ship's rations! Gourmet hors d'oeuvre or dessert platters are available as purchase add-ons for our 2-hour sails.  You'll be able to add them to your cart during the reservations process.

Book Now

Martha's Vineyard 3- or 4+ Hour Day Sails

Martha’s Vineyard Sunset Sails & Special Occasions

Martha's Vineyard 3- or 4+ Hour Day Sails

A sailing girls trip with Sail The Vineyard aboard Phoenix, Vineyard Haven Harbor, Martha's Vineyard

Sometimes you just need a happy medium! For those who feel like a 2-hour Martha's Vineyard sailing charter is too short but 4 just might be too much for unseasoned sea legs, our 3-hour sailing trip takes us beyond the harbor. Venture out into Vineyard Sound with us and enjoy sailing a little more of the Martha's Vineyard island coastline.


3 Hour Charters

Private, Up to 6 People

$775


If you just live to be on the water like we do, a Martha's Vineyard boat charter of only 2 or 3 hours just isn't enough! Hoist the sails with us and let's set sail for far away shores - or at least one outside the harbor. With 4 hours we can sail Martha’s Vineyard Sound; a bit longer and we can make a full day destination sail to the Elizabeth Islands, Lambert’s Cove, Menemsha or other exciting locations.


4 Hour Charters

Private, Up to 6 People

$900

Sailing trips from 5-8 hours are also available.  Call for details and pricing.

  

Don' forget the ship's rations! Gourmet hors d'oeuvre or dessert platters are just the beginning. Let us pamper you with a fabulous sandwich platter or a full picnic aboard. Call for pricing and details. 

*Hors d’oeuvre platters are included on sails of 4+ hours and can be added to your cart for any sail of 2-4 hours..

Book Now

Martha’s Vineyard Sunset Sails & Special Occasions

Martha’s Vineyard Sunset Sails & Special Occasions

Martha’s Vineyard Sunset Sails & Special Occasions

Sailing Vessel Phoenix during a private sunset sail in Vineyard Haven Harbor, Martha's Vineyard

  Have you ever noticed that sunsets are different from one place to another? You may notice more red and orange hues in the Caribbean, perhaps more lavender and violet or even brilliant blue around Cape Cod. 


From the water, there is a decidedly magical quality; a Martha's Vineyard sunset sail takes the magic to another level. Designed to be a more low-key, relaxing and leisurely sail, our sunset sails ae perfect for those seeking romance, too. Celebrating a Cape Cod elopement, Martha’s Vineyard wedding, birthday, anniversary or marriage proposal? A sunset sail Martha’s Vineyard style is the perfect venue for your special evening.


2 Hour Charters

Private, Up to 6 people

$650

Traveling solo or want the camaraderie of fellow travelers? Click here to learn more about our 

Public "By The Ticket" Sailing Options


Bring along your favorite bottle of white or sparkling white wine and add on our famous gourmet hors d'oeuvre platter to compliment your perfect evening on the water.  You'll be able to add it to your cart during the reservation process.

Book Now

Call us: 508.493.8767

Copyright © 2025 Sail The Vineyard - All Rights Reserved.

Click here to review our Privacy Policy

Powered by

  • Sailing Charters
  • Private Sails
  • Public Sails
  • Sunset Sails
  • JAWS Martha's Vineyard
  • Fireworks Sails
  • Sips & Sails Jazz Cruise
  • Weddings & Vow Renewals
  • Destination Sailing
  • Learn to Sail
  • Book Now
  • Contact Us
  • Policies & FAQ
  • Job Opportunities

New Themed Public Sails

 Stellar sailing. Unrivaled live entertainment. Brunch. It’s easy – like a Sunday morning.

Swoon to the talented tunes of the island's own guitar artist Rich Giaimo while you sample sweet and savory brunch hors d'oeuvres along with a liquid treat. 

Sundays starting June 15.

Click to reserve your sail

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

DeclineAccept