Tours
Any length charter from 2 hours to 2 weeks, in Martha’s Vineyard every summer and the Virgin Islands every winter, aboard the classic 60’ ketch Tandemeer.
Sailing Martha’s Vineyard Summer 2026
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 Martha’s Vineyard Charter Rates, Private Charter up to 6 People: Call for special arrangements if your group size is larger than six people.
$650
$850
$1,000
$1,150
$1,300
$1,600
$2,000
$2,250
All inclusive for up to six people
$2,500
All inclusive for up to six people
$4,500
All inclusive for up to six people
$6,300
All inclusive for up to six people
$9,500
All inclusive for up to six people
$10,500
All inclusive for up to six people
Optional One Way Fees
After you book a charter, these optional one way fees may apply:
- Vineyard Haven to/from Edgartown - $150
- Vineyard Haven to/from Menemsha - $200
- Vineyard Haven to/from Woods Hole - $200
- Vineyard Haven to/from Oak Bluffs - $100
- Vineyard Haven to/from Nantucket - $600
Sailing the Virgin Islands Winter 20XX
The best way to enjoy the Virgin Islands is by boat. From December 20, 20XX to April 30, 20XX 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, Private Charter up to 6 People: Call for special arrangements if your group size is larger than six people.
$450
$550
$650
$800
$950
$2,500
All inclusive for up to six people
$4,500
All inclusive for up to six people
$6,500
All inclusive for up to six people
$9,500
All inclusive for up to six people
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
$1,500 first night, $1,350 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.
Cancellation policy
5 days in advance: 100% refund
4 days in advance: 75% refund
3 days in advance: 50% refund
2 days in advance: 25% refund
24 hours or less in advance: 0% refund.
Paid in full charters may be rescheduled at any time up to two days before trip date for any available date and time within the following 13 months with no penalty.
Ready to pick your dates?
Call, email or book online for a day sail, term charter or overnight boat stay aboard Tandemeer.