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    • 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

Sunset Sail Martha's Vineyard

"A sunset is the sun's fiery kiss to the night"

Take a few hours to be fully present with nature's farewell to the day on our sunset cruise Martha's Vineyard style. This 2-hour sailing charter is our most popular. Whether you're celebrating a special occasion or just want to enjoy a leisurely evening sail, we'll make the trip one you'll always cherish.  We might be a little biased but we think ours is the best sunset cruise Martha's Vineyard has but you don't have to take our word alone - our 5-star TripAdvisor reviews agree! Read on for more.

Private Sunset Sails

Private Sunset Sails

Private Sunset Sails

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.  But wherever colors Mother Nature happens to share, a sunset cruise Martha's Vineyard style is a must! 


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 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 Martha's Vineyard Sunset Cruise

Private, Up to 6 people

$650


Bring along your favorite bottle of wine or sparkling 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.

Click the "Book Now" button below and select "Private Sail" to choose your date.

Book Now

Public Sunset Sails

Private Sunset Sails

Private Sunset Sails

A champagne toast to another beautiful sunset cruise on Martha's Vineyard

Our island is known for its beautiful coastline and a Martha’s Vineyard sunset cruise is among the "don't miss" things to do on Martha's Vineyard. Plus it's an ideal way to celebrate another day in paradise. 


Designed with you in mind, this special Martha's Vineyard sunset sail leaves no detail behind and welcomes our solo travel and couple sailors who prefer the camaraderie of others over a private sail. Not only did we make it easy and affordable for our couples and solo travelers to enjoy a Martha’s Vineyard sunset sail, we kept the group small – no crowds here! 


Enjoy a special welcome beverage as we hoist the sails and snack on a nibbles plate as we point out iconic sites. Step aboard this Martha's Vineyard boat charter with us and watch the sun’s fiery kiss to the night.

Available on Monday and Thursday evenings and created for our adult guests.*

2 Hour Sunset Sail - Public

6 guests max 

$185 per person

Click the "Book Now" link below and select "Public Sunset Sail" to choose your date.

*Guests must be 21+ years old. Youth ages 16+ are welcome if traveling with a parent or guardian 

Book Now

Best Martha's Vineyard Sunset Sail Photos

Martha's Vineyard sunset over West Chop
Sailing Vessel Phoenix under sail at sunset
Looking out at the Vineyard Haven Harbor at a sunset
The sun setting over West Tisbury on a Martha's Vineyard sunset sail.
The last bits of sunlight as the sun sets behind the trees on Martha's Vineyard island
A girl's trip to Martha's Vineyard, mother-daughter sailing excursion

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  • 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

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