A private luxury yacht charter is one of the most exclusive ways to experience the world. There are no set itineraries, no crowds—just you, the sea, and the freedom to explore hidden harbors, iconic coastlines, and remote islands. And with the right timing, each season unlocks its own charter magic, whether it’s cruising the volcanic isles of the Mediterranean Sea in midsummer or whale watching in Costa Rica come spring. As someone who plans yacht charter trips for a living, here are some of my favorite places to drop anchor at every time of year.
The Winter Season
As temperatures dip in the Northern Hemisphere, yachts migrate toward warmer waters, and with them, a world of winter charter opportunities opens up.
Galápagos Islands
The Galápagos Islands are a dream destination for families and wildlife lovers. Many expedition-style yachts in this area are staffed with naturalists who guide guests through otherworldly landscapes. Days might include snorkeling with sea lions, kayaking past blue-footed boobies, and learning about endemic species over meals on deck.
Southern Caribbean
Beyond the more-touristed Leeward Islands circuit, the southern Caribbean reveals a quieter, more soulful side of island life. The Grenadines, a chain of pristine isles, are defined by their serene beaches and laid-back rhythm. The island of Bequia in particular stands out for its authenticity, where pastel-hued villages and family-run restaurants welcome travelers with genuine warmth. Nearby private island Mustique is the epitome of barefoot luxury, where evenings often end with a sundowner at the legendary Basil’s Bar. For something even more remote, head to Union Island for untamed beauty, vibrant reefs, and excellent kitesurfing.
The Spring Season
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An aerial view of Manuel Antonio National Park in Costa Rica.
Spring is the perfect time to head west—particularly to Central America’s Pacific coastlines, where the water is warm and wildlife thrives.
The Pacific Side of Costa Rica
Here, the rainforest meets the sea in a dramatic fashion. Charter guests can follow pods of dolphins, witness whale migrations, or try their hand at big-game fishing.
Nicaragua
An emerging luxury charter destination, Nicaragua’s Pacific coast offers rugged beauty, consistent surf conditions, and excellent diving. The charter fleet is small but high-quality—plan early to secure the best vessels.
The Summer Season
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Sunset on the water at the Aeolian Islands in Sicily.
While the Mediterranean Sea, with destinations like the South of France and the Amalfi Coast, is still widely considered the king of summer destinations, savvy travelers are increasingly venturing farther afield or deeper into lesser-known corners of the region.
Aeolian Islands, Italy
Dramatic, volcanic, and far less crowded than the Amalfi Coast, the Aeolian chain of Sicily is a favorite for its hiking and unique culinary scene. Salina offers panoramic trails up volcanic ridges, Panarea is effortlessly chic, and Stromboli, seen glowing gently at night or hiked at sunset, never fails to thrill.
Montenegro & Croatia
Along the Adriatic Sea, you’ll find stunning coastlines, excellent marinas, and historic, culturally rich, UNESCO-listed towns like Dubrovnik and Kotor. The beach clubs and anchorages rival those of the western Mediterranean—but without the same summer crush of crowds.
Ionian Islands, Greece
More tranquil than the Cyclades, these verdant isles offer protected sailing, historic ruins, and exceptional cuisine. There, travelers will find a unique blend of Greek, British, and Venetian cultures, as well as stunning white-sand beaches like those on the island of Lefkada.
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A Copenhagen, Denmark canal at sunrise.
Scandinavia
For something unexpected, consider cruising Norway’s fjords or Sweden’s archipelagos beneath the midnight sun. Seaplane excursions, wild landscapes, and total serenity await—but with limited yacht availability, early planning is essential.
Fall Yacht Cruises & Shoulder Season Escapes
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Exuma Islands in the Bahamas seen from a birds-eye view.
Fall is an off-season for most yachts, since many are in maintenance or repositioning after summer. This makes it the best moment to lock in top yachts for the year ahead, especially for festive holidays or next summer’s high season.
If you’re still keen to cruise, wait until Thanksgiving for a late-autumn escape.
Exumas, Bahamas
With translucent sapphire water and endless sandbars, the Exumas are the ultimate dreamy, easygoing charter destination. There, you can swim with rays and turtles, snorkel in its many blue holes, or underwater tidal caves, and even meet the island’s famous “swimming pigs.”
St. Barts
Before the winter buzz begins, St. Barts is blissfully low-key. Chic beach clubs like Nikki Beach and Shellona welcome early-season yacht travelers with laid-back luxury, and the sea is warm enough for all-day swims.
Wherever you choose to charter, letting the seasons guide your route ensures you’re always in the right place, at the right time – with the sea entirely your own.
Geoffrey Ravoire is a member of Travel + Leisure’s A-List and specializes in yacht charter trips. You can create a tailor-made itinerary with Ravoire by contacting him at geoffrey@huffmantravel.com.
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