Welcome to Serendipity Sailing Charters

Discover the world’s most breathtaking sailing destinations with expert guidance, personalized planning, and exclusive access to the top charter fleets worldwide. Whether you dream of helming your own bareboat in the Greek Isles, hiring a seasoned skipper in the Grenadines, or exploring remote anchorages in French Polynesia, Serendipity Sailing Charters makes it effortless.

With experience sailing in more than 20 iconic cruising regions—from the Mediterranean to the South Pacific, the Caribbean, Southeast Asia, and beyond—we bring insider knowledge, trusted local connections, and a passion for life under sail.

Your Adventure, Your Style

Every sailor is different. That’s why we tailor each charter to your preferred level of independence, comfort, and adventure:

Bareboat Charters

For qualified sailors who want total freedom. Choose from modern monohulls and luxury catamarans across the globe, with support at every step—from paperwork to provisioning to itinerary tips you won’t find online.

Skippered Charters

No experience? No problem. We will help you find a vetted, knowledgeable local skipper who knows the winds, the reefs, the customs, and the hidden gems that make a destination unforgettable.

Personalized Itinerary Planning

Skip the internet rabbit holes. Leverage firsthand insight from a sailor who has explored each destination personally. We’ll help you pick the right islands, anchorages, towns, restaurants, hikes, beaches, and secret spots—designed around your time frame and travel style.

The Best Boats at the Best Prices

Because we hold a boat brokerage license, we can book boats directly with the charter companies—allowing us to:

• Access their full fleet availability
• Secure promotions or negotiated pricing
• Match or beat direct-booking prices
• Earn commissions from the charter company, not from you

You get expert guidance at no extra cost, and often for less than you’d pay on your own.

Why Sail With Us?

• Global sailing experience in over 20 world-class cruising grounds
• Independent, unbiased advice—we recommend the best boat and operator, not just one brand
• Seamless planning from boat selection to itinerary design
• Support from start to finish, including pre-departure checklists and destination briefings
• A true partner in adventure, not just a booking website

Your perfect sailing vacation starts here.