A New World of Holiday Sailing
From Chesapeake Bay in the north to Costa Verde in the south, a wide range of American sailboat charter locations await. From ports of call as diverse as urban Annapolis, remote and spectacular desert island landscapes in the Gulf of Cortez, idylic western Caribbean cays along the world's second largest barrier reef, and the Atlantic rainforest of Serra da Bocaina National Park, there are plenty of safe, secure and reliable offerings for avid sailors to seek out adventure on bareboat and crewed charters in North, Central and South America.
Year-Round Sailing, with Two Continents to Choose from
The Best in American Charter Sailing Destinations
For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...
Latest Blog Posts
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Sailing Between US VI, British VI and Spanish VI
Step-by-step guide to current regulations for sailing between the British Virgin Islands and US Virgin Islands, and the US Virgin Islands and Spanish Virgin Islands.
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A Short History of Chartering in Bay of Islands, NZ
Once home to over 40 bareboat charter yachts, the Bay of Islands stood proudly among the world’s sailing destinations. Kiwis and visitors alike could explore this subtropical paradise aboard locally managed fleets. Times have changed.
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Getting to Vava'u, Tonga for your Sailing Holiday (2025)
Your 2025 guide to getting to Tonga—international flights, Fiji to Vava‘u direct service, domestic Saab 340B airlink from Tongatapu and ferry option via Haʻapai.
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Why a Lot of Itinerary Advice Misses the Mark for Sailing Holidays
Learn why many bareboat sailing itineraries found online can be misleading, and how first-hand advice makes all the difference.
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Modern Consumer Tech on Sailing Charter: do we really need it?
When thinking about a sailing holiday, it’s natural to wonder whether to bring our modern gadgets along for the ride - or leave them behind entirely. Technology is so deeply woven into the fabric of our daily routines. So should we pack our tablets and smartphones or is a sailing charter the perfect opportunity to fully disconnect and reset?
The Sail Connections Guarantee
One contact - every option - advice you can trust.
- Matching any competitive offer
- Sourcing boats with discounts available
- Personalising our proposal just for you
- Qualifying the operator as well as the boat
- Advising without bias based on 25+ years of experience
- We do more than just book yachts!
We will match any discount website offer on charter boat price, and still provide our customary high level of service.
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