Martha’s Vineyard half day, full day and sunset sailing charters on the famous 60’ ketch “Tandemeer”
June 20, 2026 – Sept 20, 2026: we’ll be in Vineyard Haven, Martha’s Vineyard. Keep scrolling for all charter options.
60'
Classic ocean-going ketch
50,000+
Sea miles sailed by Captain Sequoia
300+
Guest reviews on Airbnb
4
Private en-suite staterooms
Everything you need for the best day of your vacation
Largest private charter sailboat in the islands
A classic 60' ketch with room to spread out, on deck and below.
Room for your whole family or group of friends
Seating for the whole crew, bow to cockpit.
Relax and sail in spacious elegance
A large covered cockpit and sunny forward lounging area.
Big boat sailing fun in the sun (or shade)
A large, comfortable shade-covered cockpit area for everyone.
Friendly, helpful, experienced captain and crew
Decades of sailing experience, and a crew that takes care of you.
Masks, snorkels, fins and towels included
Everything you need to explore the reef is already on board.
Delicious beverages and snacks or lunch included
A spread of fresh fruit, cheese and snacks, every charter.
Sail on the big, beautiful classic ketch “Tandemeer”
Twin masts, full sail, and open water ahead.
Day sails, term charters and boat stays
New England in summer, and the Virgin Islands in winter.
Sail the islands of New England
June 20, 2026 – Sept 20, 2026: we’ll be in Vineyard Haven, Martha’s Vineyard, offering any length charter 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, Martha’s Vineyard and many beautiful ports in between, New England offers some of the best sailing, cruising and fun vacation destinations in the world.
Sail the Virgin Islands
From Dec 20 to April 30 (dates TBD), sail and swim with turtles, snorkel and dive some of the most colorful reefs in the world, and beach-hop your way around world-famous beach bars accessible only by boat. Our classic 1980 vintage 60’ ketch is the largest and most comfortable monohull doing day sails in the USVI.
The crystal-clear turquoise waters of St Thomas and St John, and the chain of islands that make up the British Virgin Islands, are unmatched for great sailing, snorkeling, beaches, diving, beach bars and dining.
Your boat day will be the best day of your vacation
However you choose to spend your day with Island Sailing Tours, you’ll love every second.
Book the best day of your vacation
Day sails, term charters and overnight boat stays aboard Island Sailing Tours’s classic 60’ ketch, Tandemeer.