Popular Charter Destinations
Sail the World with Serendipity Sailing Charters
From sun-drenched Caribbean anchorages to cliff-lined Mediterranean harbors and remote Pacific atolls, Serendipity Sailing Charters connects you with the world’s most iconic sailing grounds.
Your broker isn’t just reading from a brochure—he’s sailed in more than 20 of these destinations himself. That means you get recommendations based on real-world experience: which islands are worth an extra day, which marinas are best avoided on a Friday, and where the truly special anchorages are hiding.
How It Works
- Tell us when and where you’re thinking of traveling.
- We’ll recommend destinations that match your season, budget, and experience level.
- We’ll suggest specific charter bases, boat types, and routes tailored to your group.
- We’ll handle the boat booking and help you shape a day-by-day itinerary.
You’re never choosing from a generic list—every trip is custom.
Featured Regions:
The Caribbean
Warm trade winds, line-of-sight sailing, and relaxed island culture make the Caribbean perfect for both first-time and experienced charterers.
- British Virgin Islands (BVI) – The classic “easy mode” charter: short hops, protected waters, beach bars, mooring balls, fun for families and new sailors.
- Grenadines & St. Vincent – A bit more adventurous: longer passages, steady tradewinds, and wild, unspoiled anchorages like Tobago Cays.
- Antigua, St. Martin, Guadeloupe & beyond – Mix of French flair, colonial history, and excellent sailing.
Best for:
Families, first-time bareboat charterers, winter and early-spring escapes, relaxed island-hopping.
The Mediterranean
History, food, culture, and lively harbors—plus reliably sunny summers.
- Greece (Ionian, Cyclades, Saronic Gulf, Dodecanese) – From calm, green Ionian bays to the windier Cyclades, we’ll help you match the region to your comfort level.
- Croatia & Montenegro – Medieval towns, crystal-clear water, wine regions, and island chains that are tailor-made for one-week or 10-day itineraries.
- Italy, Balearic Islands, French Riviera & more – Chic ports, fantastic cuisine, and a great blend of sailing and shore excursions.
Best for:
Food and wine lovers, couples’ trips, groups who enjoy harborside dining and exploring historic towns.
Asia and South Pacific
South Pacific & Indian Ocean
For sailors looking for something more remote and spectacular.
- French Polynesia (Tahiti, Raiatea, Bora Bora) – Clear lagoons, reef passes, and postcard-perfect scenery.
- Thailand - breathtaking scenery, friendly locals, inexpensive food and Thai massages.
- Seychelles – Granite islands, white sand beaches, and unique wildlife
Best for:
Bucket-list trips, honeymoons, experienced sailors, and travelers who want to feel truly “away from it all.”
Europe & North Atlantic
December 2024 - $1,750
- Canary Islands – Excellent winter conditions, longer legs, and a taste of Atlantic sailing.
- Scotland, Norway, Sweden & Northern Europe – For those who prefer dramatic landscapes, fewer crowds, and cooler climates.
Best for:
Adventurous crews, shoulder- or off-season sailing, and those who prioritize scenery over suntans.
Not Sure Where to Go?
You don’t have to know your destination yet—that’s what we’re here for.
Tell us:
- When you can travel
- How much time you have
- Your sailing experience
- What kind of trip you’re imagining (family vacation, friends’ adventure, romantic escape, “sail hard / play hard,” ultra-relaxed)
We’ll recommend the best destination, boat, and route—and then book it for you at the same or lower price than going direct.
Ready to Start Planning?
Share your dates, group size, and any destinations you’re considering, and we’ll send you a few tailored options.
For more ideas, you can also look at some of the past "by the cabin" trips offered by Serendipity Travel here: Past Trips