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How to Pick the Perfect Sailing Destination for Your Group
As the lead charter agent at NauticEd Sailing Vacations, I get this question all the time:
“Where should we go sailing this year?”
Grant, Director of NauticEd, likes to say, “If you’re stuck between two awesome destinations, just pick one this year and pick the other next year—because if you charter each year, you’ll never run out of great places.”
And he’s right! But my usual answer is, “It depends.” Because it really does.
Your sailing destination depends on your crew’s sailing experience, the vibe you’re going for, the time of year, and even how adventurous your group feels. While there are dozens of incredible bareboat destinations, not every location is a match for every crew. Finding the right destination is one of my favorite parts of this job—and something we specialize in at NauticEd.
This quick guide highlights five of the most requested charter destinations—Croatia, Greece, the British Virgin Islands (BVI), Thailand, and Tahiti—to help you compare what each has to offer and decide what fits best for you and your crew.
A Few Things to Consider First:
Skill & Experience.
Your sailing experience and credentials play a significant role in destination choice.
- In most of the Caribbean, you don’t need a formal license (though Belize requires a temporary certificate, and some Bahamas charter companies may request certification). Instead, your sailing resume—your logged experience on the water (along with your theory knowledge)—gets reviewed.
- In contrast, the Mediterranean requires a formal license like the NauticEd SLC (plus a VHF license in many countries).
Beyond documentation, some sailing grounds are just more complex. The Cyclades and Dodecanese in Greece, for instance, can have strong meltemi winds and longer hops between isles, while the BVI (or Ionians in Greece) are perfect for line-of-sight, steady tradewind sailing—ideal for newer skippers.
Season, Location & Timing
The time of year can make or break a charter plan.
- Winter charter? Skip the Med—it’s off-season—and head to the Caribbean, Thailand, Tahiti, or the Seychelles.
- Summer charter with the kids out of school? The Med is gorgeous but busy. Consider shoulder months like June or September. The Caribbean is hot, but manageable with A/C and a generator.
Group Preferences
Is your group into beach bars or ruins? Do they want to snorkel and fish, or sip wine and wander villages?
- Prefer marine life and remote isles? Check out Tahiti, La Paz, Belize, or the Bahamas.
- Want culture and culinary experiences? Think Greece, Italy, or Croatia.
- Love lively nightlife? You’ve got Greece (Cyclades), Croatia (Central Dalmatia), or the BVI or St. Martin in the Caribbean.
Destination Snapshots
🇭🇷 Croatia – Coastal Culture
Croatia blends historic seaside towns, vibrant nightlife, and world-class food with easy island-hopping across the Adriatic.
Sailing Conditions:
Best for intermediate sailors comfortable with Mediterranean mooring and changing winds. Mostly line-of-sight navigation with a mix of anchorages, mooring balls, and marinas.
To-Do:
Explore the medieval streets of Dubrovnik, sip wine in Korčula, dive into history, and visit the Blue Cave of Biševo. Don’t miss the military history tour in Vis or the lavender fields in Hvar.
Season:
May – October. Peak season (July/August) is hot and crowded.
🇬🇷 Greece – Mythical Exploration
From the relaxed Ionian isles to the chic Cyclades, Greece has something for every kind of sailing crew—with ancient charm and history wherever you go.
Sailing Conditions:
Great for licensed bareboat skippers of all levels. The Ionians are calm and beginner-friendly. The Cyclades have stronger winds and longer passages. Dodecanese and Sporades are more remote. Expect Mediterranean mooring almost everywhere.
To-Do:
Visit car-free Hydra and hang with the donkeys. Explore ancient ruins in Rhodes, and the Mama Mia steps in the Sporades. Enjoy sunsets in Santorini, nightlife in Mykonos, and local flavor at the Fistiki Festival in Aegina (September).
Season:
May – October. Avoid peak summer if you prefer fewer crowds.
🇻🇬 British Virgin Islands (BVI) – Nature’s Sailing Playground
The BVI is the most requested destination–and for good reason. Classic Caribbean sailing—laid-back, line-of-sight, and built for fun.
Sailing Conditions:
Our number one recommended destination for those who want to experience their first bareboat charter (but who are still confident and competent). Short hops, line of sight navigation, steady trade winds, and tons of mooring balls make it stress-free.
To-Do:
Sip a Painkiller at the Soggy Dollar, jump off the Willy T, snorkel at The Indians, and explore The Baths. Visit Anegada for lobster, hike Virgin Gorda, and grab dinner at CocoMaya.
Season:
November – July.
🇹🇭 Thailand – Exotic Beauty
A stunning mix of cliffs, jungles, temples, and turquoise bays—Thailand is both exotic and welcoming.
Sailing Conditions:
Intermediate level. Mostly line-of-sight navigation, but monsoon seasons impact wind direction. Some tidal shifts. Variety of anchorages, mooring balls, and marinas.
To-Do:
Cruise Phang Nga Bay, relax on Railay Beach, kayak through limestone caves, visit floating markets, or take a longtail boat to a temple. Nightlife here includes fire shows on the beach.
Season:
November – April is best.
🇵🇫 Tahiti – Tropical Paradise
The word “paradise” doesn’t do it justice. Tahiti and the French Polyneisan islands are postcard ‘tropical paradise’, full of remote anchorages, reef adventures, and Polynesian culture.
Sailing Conditions:
Intermediate area. Consistent trade winds, longer passages, reef navigation, and anchoring are the norm.
To-Do:
Snorkel with manta rays, explore coral gardens, anchor in a Bora Bora lagoon, or hike to waterfalls. Visit Rangiroa, paddleboard at sunset, and savor fresh poisson cru under the stars.
Season:
May – October (dry season), though charters are available year-round.
These destinations are just the beginning—there are dozens more around the world. Need help narrowing it down? That’s what we’re here for.
Check out our NauticEd Destination Guides or contact us directly. Whether you’ve got a specific place in mind or you’re just getting started, we’ll help you chart the perfect course.
Your Adventure - Our Expertise
NauticEd are Yacht Charter Agents
NauticEd is your go-to resource for planning an unforgettable charter vacation, whether bareboat or captained. We don’t charge a fee – actually, we will probably save you money because of our extended search capabilities as well as our knowledge of worldwide locations (i.e., “we’ve been there”). So let us help you plan your next yacht charter vacation!
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NauticEd is a fully recognized education and certification platform for sailing students combining online and on-the-water real instruction (and now VR). NauticEd offers +24 online courses, a free sailor's toolkit that includes 2 free courses, and six ranks of certification – all integrated into NauticEd’s proprietary platform. The USCG and NASBLA recognize NauticEd as having met the established American National Standards. Learn more at www.nauticed.org.
The NauticEd Vacations team are Expert Global Yacht Charter Agents – when you book a sailing vacation or bareboat charter through NauticEd, we don’t charge you a fee – we often save you money since we can compare prices from all yacht charter companies. PLUS, we can give you advice on which destination or charter company will suit your needs best. Inquire about a Sailing Vacation or Charter.
