No better way exists to visit several destinations on one single trip than by chartering a yacht. Whether sailing through the crystal-clear waters of the Caribbean, Mediterranean, or South Pacific, a multi-destination sailing charter provides the ultimate freedom, adventure, and luxury.
You can opt for a bareboat or a skippered charter, and no matter your choice, island-hopping aboard a catamaran or sailboat enables you to experience various cultures, secluded coves, and stunning scenery — all at your own leisure.
Why a Multi-Destination Yacht Charter?
- Unparalleled Flexibility – Unlike cruise ships or set itineraries, a yacht charter allows you to personalize your trip according to your desires.
- Private Access – Much of the world’s most beautiful locations are accessible only by sea.
- True Experiences – Stay as long as you wish in each location, immersing yourself in the local way of life and cuisine.
- Privacy & Comfort – Whether you charter a luxury catamaran or a classic sailboat, you’ll have an intimate, private experience with family and friends.
Top Destinations for Multi-Stop Yacht Charters
The Caribbean
The Caribbean is one of the world’s best destinations for island-hopping by yacht. With its calm trade winds, turquoise waters, and countless islands, it offers something for every type of sailor.
Best Time to Sail: December through April, when the weather is dry and trade winds are consistent.
The popular destinations you must include in your Caribbean sailing itinerary:
- British Virgin Islands (BVI): Known as the “Sailing Capital of the World,” BVI provides a combination of secluded bays, lively beach bars, and world-class snorkeling locations. Popular ports of call are Tortola, Jost Van Dyke, and Virgin Gorda.
Anchorage & Mooring Fees: Buoys to moor cost $30-$50 per night, with anchoring free in most places.
- The Grenadines: Renting a yacht here means you can visit Bequia, Mustique, and the Tobago Cays, all of which have untouched beaches and vibrant sea life.
Anchorage & Mooring Fees: You will pay approximately $10-$20 per night in marine parks and mooring areas.
- Bahamas: Home to more than 700 islands and cays, Exumas, Abacos, and Eleuthera are ideal for a sailing holiday to remember.
Anchorage & Mooring Fees: Fees for mooring are $20-$40/night, whereas anchoring is free in all but a few places.
The Mediterranean
For those interested in a blend of cultural past and blue water, the Mediterranean is an exceptional sailing destination.
Best Time to Sail: May to October, with peak season in July and August.
- Greek Islands: From Athens to Mykonos, Santorini, and Crete, explore ancient ruins, taste delicious Mediterranean food, and visit iconic whitewashed villages.
Anchorage & Mooring Fees: Mooring in marinas can cost from €20-€100 per night, but anchoring in bays is usually free.
- Croatian Coast: The Dalmatian Coast provides historic cities such as Dubrovnik and Split, in addition to secluded islands like Vis and Hvar.
Anchorage & Mooring Fees: Mooring buoys are €20-€50 per night, with anchoring fees in certain national parks.
- Amalfi Coast & Sicily: Sail by Positano and Capri before reaching the Aeolian Islands for volcanic scenery and crystal waters.
Anchorage & Mooring Fees: Marina fees may be steep in high season, between €50-€200 per night.
The South Pacific
Adventure-seekers seeking to experience unspoiled waters find the South Pacific paradise.
Best Time to Sail: April to November, skirting the cyclone season.
- French Polynesia: Tahiti, Bora Bora, and the Tuamotu Atolls are famous for amazing snorkeling, tropical landscapes, and a relaxed vibe.
Anchorage & Mooring Fees: Mooring rates are approximately $10-$30 per night, though anchoring in lagoons is sometimes free.
- Fiji: Famous for being welcoming to locals, with white-sand beaches and top-class diving sites.
Anchorage & Mooring Fees: Mooring rates are from $5-$25 per night, with free anchorage in most places.
- Whitsundays, Australia: Situated close to the Great Barrier Reef, there are pristine beaches and amazing sea life.
Anchorage & Mooring Charges: Mooring charges between $20-$50 per night, anchoring is allowed in most bays.
Selecting the Right Charter for Your Trip
Bareboat vs. Skipper Charters
- Bareboat Charter: Best suited for experienced sailors, this chapter provides you with a complete command of the course and itinerary.
- Skippered Charter: Best for those who wish to unwind while an experienced captain navigates and has local expertise.
Catamaran vs. Sailboat
- Catamarans: Provide greater stability, room, and shallow draft for anchoring near shore.
- Sailboats: Deliver a classic sailing experience with improved wind efficiency and handling.
Tips for an Unforgettable Sailing Experience
- Plan Your Route in Advance – Study weather patterns, anchorages, and local regulations.
- Stock Up on Supplies – Provisioning facilities are often limited in out-of-the-way islands.
- Be Flexible – Weather conditions may necessitate changes in the itinerary.
- Respect Local Cultures – Engage with local communities and practice responsible tourism.
- Assure Safety – Bring appropriate navigation equipment, communication tools, and emergency supplies.
Conclusion
Hiring a yacht for a multi-destination sailing vacation is the best means of discovering the world’s most beautiful waterscapes. Whether sailing the Caribbean, Mediterranean, or South Pacific, with the liberty of sailing, you can find hidden treasures, have memories that last a lifetime, and have unforgettable experiences.
