Tours

Sailing Martha’s Vineyard Summer 2024

June 15 2024 - Sept 20 2024: we will be in Vineyard Haven, Martha’s Vineyard offering any length charters from 2 hours to 2 weeks. Book a Day Sail, Term Charter or overnight Boat Stay from and to the Island Port of your choice this summer.

From Long Island to Nantucket, Block Island, Rhode Island, Marthas Vineyard and many beautiful ports in between, New England offers some of the best sailing, cruising and fun vacation destinations in the world.

Summer 2024 Martha’s Vineyard Charter Rates, Private Charter up to 6 People: Call for special arrangements if your group size is larger than six people.

2 Hour Tour: 550

3 Hour Tour: 750

4 Hour Tour: 900

5 Hour Tour: 1050

6 Hour Tour: 1250

8 Hour Tour: 1400

10 Hour Tour: 1650

18 Hour Tour: 2250 (All inclusive for up to six people)

24 Hour Tour: 2500 (All inclusive for up to six people)

2 Day Tour: 4500 (All inclusive for up to six people)

4 Day Tour: 6300 (All inclusive for up to six people)

6 Day Tour: 9500 (All inclusive for up to six people)

8 Day Tour: 10500 (All inclusive for up to six people)

Sailing the Virgin Islands Winter 2024-2025

The best way to enjoy the Virgin Islands is by boat. From December 20, 2024 to April 30, 2025 we will be offering day sails from two hours up to seven days on board. The crystal-clear turquoise waters of St Thomas and St John in the US Virgin Islands, and the chain of islands that make up the British Virgin Islands are unmatched for great sailing, snorkeling, beaches, diving, beach bars and dining.

Swim with turtles and spotted eagle rays, dive for spiny lobster, enjoy a stand up paddle board ride in quiet coves, swim up to world-class beach bars, or simply nap in a hammock. However you choose to spend your day with Island Sailing Tours, you will love every second.

Winter Virgin Islands Charter rates: Call for special arrangements if your group size is larger than six people.

2 Hour Tour: $450

3 Hour Tour: $550

4 Hour Tour: $650

5 Hour Tour: $800

6 Hour Tour: $950

1 Day Tour: $2500 (All inclusive for up to six people)

3 Day Tour: $4500 (All inclusive for up to six people)

5 Day Tour: $6500 (All inclusive for up to six people)

7 Day Tour: $9500 (All inclusive for up to six people)

Call +1 (203) 246-1369 or click to book

Overnight Sails with Island Sailing Tours

There’s only one thing better than a day sail in New England or the Virgin Islands, and that’s an overnight sail in New England or the Virgin Islands!

Whether you choose one night, three nights, a full week or more, an overnight charter with Island Sailing Tours allows you to take your own sweet time exploring the world’s most beautiful harbors and beaches.

This summer, Sail to Nantucket or Edgartown or Block Island, or just around the corner to the colorful fishing village of Menemsha right here on the Vineyard, to enjoy and experience relaxed cruising to other beautiful New England ports.

In winter we are based on St. John USVI and can stay in US waters for an in-depth tour of St Thomas, St John and Water Island, or Sail over to the British Virgin Islands for breathtaking snorkeling, rendezvous diving, beach bar hopping and unforgettable moonlit nights from your very own private sailboat.

We’ll design a custom sailing itinerary that ensures you’ll get the most out of your time aboard our beautiful sailing yacht. 

Do you want to learn to sail, lounge on deck or take a gourmet picnic to a secluded beach? Maybe famous beach bar party spots like the Honeymoon Beach, Maho Bay or Lovango Cay are on your list. (They certainly should be!) Or maybe you’d like a rum tour on St. Croix or a golf cart tour of Water Island. Whatever your heart desires, our captain and crew will take you there the best way possible -- aboard Tandemeer.

Private Overnight Sailing Charters

$1500 first night, $1350 each additional night (all inclusive) up to 6 people maximum

• Overnight sails on Tandemeer Include captain, crew-chef, breakfast, lunch aboard or ashore as itinerary and guest preference allows, and non-alcoholic beverages. Guests are welcome to bring alcoholic beverages aboard, or we can stock the bar with beverages of your choice for a fee. Most locations we visit have a great selection of world class dining options for dinner, or you may select an optional

  gourmet dinner aboard by arrangement for an additional fee.

• Prices include snorkel equipment, water toys, licensed captain, crew-chef, non-alcoholic beverages and snacks. Prices do not include alcoholic beverages (which can be added for a fee) special food requests or customary crew gratuity. Excursions to the British Virgin Islands (NOT Available in 2021 due to COVID-19 restrictions) require additional $70 per person customs fee. Rendezvous SCUBA dives are available by advance reservation for an additional fee.

Shared Overnight Sailing Charters

$250 per person per night, two people minimum in one private en suite two berth cabin.

• Overnight sails on Tandemeer Include captain, crew-chef, breakfast, lunch aboard or ashore as itinerary and guest preference allows, and non-alcoholic beverages. Guests are welcome to bring alcoholic beverages aboard, or we can stock the bar with beverages of your choice for a fee. Gourmet dinner aboard optional at additional fee.

• Prices include snorkel equipment, water toys, licensed captain, crew-chef, non-alcoholic beverages and snacks. Prices do not include alcoholic beverages (which can be added for a fee) special food requests or customary crew gratuity. Excursions to the British Virgin Islands require additional $70 per person customs fee. Rendezvous SCUBA dives available by advance reservation for an additional fee.

Call +1 (203) 246-1369 or click to book