Been There, Chartered That? Where to Go Next This Winter

The Caribbean classics will always have their pull, but one of the best things about a yacht charter is just how much farther you can go. This winter, that could mean swapping beach clubs for rainforest in Costa Rica, heading off-grid among the islands of Raja Ampat or crossing the Indian Ocean for the Seychelles. And if the Caribbean is still calling, there are plenty of ways to experience it differently, from laid-back days off Anguilla to an island-hopping itinerary through the Grenadines.

Here are six destinations we’d have on the shortlist for the 2026/27 winter yacht charter season.

Costa Rica – For the Adventure

If your ideal charter involves doing more than moving between beaches, put Costa Rica high on the list. The country’s rugged, rainforested landscape meets a coastline that provides extensive cruising grounds, making a yacht the perfect base for exploring it all.

Days here can start early. Head ashore to explore the rainforest in search of monkeys and scarlet macaws, go surfing on the Pacific coast, dive or snorkel around Isla del Caño and the Catalina Islands, or spend the day deep-sea fishing. Corcovado National Park, on the Osa Peninsula, is one of the most biodiverse places on the planet, while time back on the water can be spent making the most of the yacht’s toys.

This is a winter yacht charter for guests who like having options. A morning exploring ashore can easily turn into an afternoon on the water toys, followed by dinner prepared by your chef and served alfresco on deck.

Yachts to Charter in Costa Rica

The 191′ (58.22m) UNBRIDLED is built with adventure in mind. The Trinity superyacht has a 5,932-nautical-mile range and an extensive collection of equipment for time on and below the water, including three tenders, four Sea-Doo Jet Skis, three SeaBobs, five kayaks, three stand-up paddleboards, fishing equipment and dive equipment. She accommodates 12 guests in six staterooms. Costa Rica is among her winter 2026/27 cruising regions.

Also heading to Costa Rica is the 164′ (50m) CHASING DAYLIGHT. Accommodating up to 12 guests in six staterooms, the Westport is particularly well set up for active days on the water, with a 37′ Everglades center console, three WaveRunners, two Lift Foil boards, kayaks, paddleboards, fishing equipment and snorkeling gear.

Panama – For the Road Less Traveled

For charter guests who have covered plenty of the Caribbean and want to shift the coordinates without giving up tropical cruising, Panama offers a different side of Central America.

Sitting between the Caribbean Sea and Pacific Ocean, Panama brings together tropical landscapes, rich marine life and some interesting cruising. The San Blas Islands are a highlight, offering natural beauty and a more remote side of the country, while time ashore can take you in a completely different direction with a day exploring Panama City, including its boutiques and restaurants.

Then, of course, there is the 50-mile-long Panama Canal, which allows yachts to cross between the Caribbean Sea and Pacific Ocean. It’s an opportunity to make the journey itself one of the most memorable parts of the charter.

For experienced charterers in particular, that’s the appeal. Panama feels like a departure from the familiar winter circuit, while offering all the freedom, warm-water adventure and outdoor living that make winter charter so good in the first place.

Yachts to Charter in Panama

UNBRIDLED brings the right adventure credentials for exploring farther afield. The 191′ (58.22m) yacht offers approximately 15,000 square feet of space from top to bottom, six staterooms and a sprawling sundeck with a 10-person Jacuzzi, full bar and exercise equipment. There is plenty to keep guests busy when anchored somewhere remote.

Anguilla – For Keeping It Easy

Going somewhere different doesn’t necessarily mean going farther. For anyone who still wants the ease of a Caribbean yacht charter but would happily trade some of the busier winter hotspots for long beaches and a slower pace, Anguilla makes a convincing case.

Part of the Leeward Islands, Anguilla is known for magnificent beaches, crystal-clear waters and a relaxed atmosphere. Drop anchor and spend the morning swimming before heading ashore, or return to the yacht, launch the water toys and make the most of the Caribbean Sea.

Better still, it doesn’t need to stand alone. The wider Leeward Islands cruising grounds include St. Maarten, St. Barths, Antigua, St. Kitts and Nevis, making it easy to build Anguilla into a broader itinerary. For guests who love the Caribbean but want to change up the itinerary, sometimes that’s all it takes.

Search yachts available for charter in Anguilla and the Leeward Islands.

The Grenadines – For Island Hopping

St. Vincent and the Grenadines comprise 32 islands and cays strung across 60 miles of sea, with each island a relatively short hop from the next. Start around St. Vincent before moving through a chain of islands that each bring their own personality. Bequia is one of the more developed islands in the archipelago. Mustique offers a more glamorous and sophisticated retreat, while the Tobago Cays comprise five uninhabited islands and offer a wildlife reserve and marine park, with opportunities for swimming, snorkeling and diving.

The short distances between islands are part of what makes a Grenadines yacht charter work so well. Breakfast can be served in one anchorage, lunch somewhere completely different and dinner under the stars off another island entirely.

For charter guests who have already explored the northern Caribbean, the Grenadines offer a reason to head south. The wider Windward Islands are known for lush landscapes, volcanic peaks, beautiful beaches and a year-round tropical climate, with winter bringing warm, sun-filled days.

Search yachts available for charter in the Grenadines and Windward Islands.

Raja Ampat – For Going Properly Off-Grid

Raja Ampat is a secluded archipelago within Indonesia, a country with more than 17,000 islands stretching across more than 3,000 miles. It is a destination where the journey is dictated less by restaurants and beach clubs and more by what’s happening in the water, on the reef or beyond the next island.

For divers and snorkelers, that is a major part of the appeal. Indonesia’s waters are rich with marine life, while its cruising grounds combine secluded coves, tropical rainforests and abundant underwater life. Raja Ampat sits among Indonesia’s most remote cruising options alongside destinations such as Komodo National Park and the Banda Sea.

When you’re not underwater, days can be spent kayaking through quiet bays, heading ashore into tropical landscapes or anchoring somewhere that feels completely removed from the rest of the world.

For charter guests who have already covered the Caribbean and Mediterranean and are ready to push much farther beyond the familiar, a Raja Ampat yacht charter is a very different proposition. Remote, adventurous and centered almost entirely around the natural world, this is winter charter at its most exploratory.

Seychelles – For the Long-Haul Escape

If you’re going to fly farther for winter sun, make it count. Scattered across the Indian Ocean off East Africa, the Seychelles comprise 115 islands and are among the world’s most isolated archipelagos. The landscape is characterized by tropical vegetation, granite rock formations and white-sand beaches.

A yacht opens up much more than the best-known beaches. Charter itineraries can move from Mahé through islands including Praslin and La Digue, with opportunities for snorkeling, watersports and exploring ashore along the way.

There is plenty worth going ashore for, too. Praslin is home to the Vallée de Mai Nature Reserve, a UNESCO World Heritage Site, while La Digue offers nine miles of coastline and can be explored by bicycle. The archipelago’s waters add another dimension, with diving, snorkeling and wildlife encounters throughout an itinerary.

Yachts to Charter in the Seychelles

Fresh from a 2026 refit, the 204’4″ (62.3m) Oceanco LUDZIE will cruise the Seychelles for the 2026/27 winter season.

With a 4,500-nautical-mile range, five staterooms and 1,166GT of volume, she has the scale for a proper Indian Ocean escape. Her amenities include a beach club, Jacuzzi, gym, beauty room and steam room, while her toy collection features a water slide, WaveRunners, SeaBobs, an eFoil, electric surfboard, kayaks, paddleboards and multiple towables.

So, Where Next?

A winter yacht charter can still mean white sand, warm water and long lunches on deck. But it doesn’t have to mean going back to exactly the same place. That’s the advantage of charter: the yacht, itinerary and destination can all be shaped around how you want to spend your time.

UNBRIDLED, CHASING DAYLIGHT and LUDZIE will be among the yachts cruising these regions during the 2026/27 winter season. Explore the yachts or speak with a Northrop & Johnson charter expert to start planning your winter escape.