Winter Sailing Holidays

Winter Sailing Holidays

Escape Winter the Sunsail Way

While others chase deadlines and grey skies, you could be crossing off a very different kind of to-do list – one that starts with sail to Norman Island and ends with catch the sunset in the British Virgin Islands. Trade routine for reef-lined anchorages and let warm breezes replace the chill back home. 

Sailing in the BVI between December and April is about slowing the pace and finding what you’ve been missing; clear turquoise water, quiet coves, and evenings that stretch out beneath star-filled skies. Whether you’resetting out on a bareboat, or choosing a skippered charter, every route reveals something worth ticking off. 

Why Sail the BVI This Winter 

BVI

Perfect Winter Conditions

Steady trade winds, calm seas, and warm temperatures make the BVI one of the most reliable sailing destinations all year. With average trade-winds around 10-15 knots and clear skies during the December–April “dry season”, you spend less time battling weather and more time sailing smoothly between islands.

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BVI

Island-Hopping Made Easy

Short passages between islands mean you can discover more each day, from The Baths on Virgin Gorda to the beach bars of Jost Van Dyke. Because the islands are close together, you’llvspend less time in the cockpit and more time exploring, snorkeling or relaxing on the beach.

explore bvi
Winter Sailing Holidays

Award-Winning Yachts

Sail on modern, fully equipped yachts, designed for comfort and effortless handling. With our world-class fleet of yachts from 32′ to 53′, you’ll enjoy well-maintained gear, up-to-date systems and a layout built for charter ease.

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Winter Sailing Holidays

Curated Itineraries

Explore our ready-made 7-day routes or plan your own, guided by our 50+ years of sailing expertise. Whether you want an easy pace for family time or a more adventurous route for seasoned sailors, our expert-designed charters give you structure without locking out spontaneity.

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All Winter Sun Destinations

Trade the winter rush for sun-drenched beaches and crystal-clear waters. A Christmas sailing holiday is the ultimate way to unwind, far from the holiday crowds. Did you know that the best time to sail the British Virgin Islands is from December through to April, making the BVI a perfect destination for sailing at Christmas?

Grenada is another popular choice in the Caribbean for winter sun packages, but the weather is likely to be better for sailing in January, so plan your trip just after Christmas into the New Year. Here, and in other Caribbean destinations like Belize, you can dine on delicious barbecued seafood, snorkel above diverse coral reefs, and soak up the sun on some of the world’s best beaches.

Want to try another winter sun destination? Book a sunshine escape to our destinations in Southeast Asia, the Indian Ocean or the South Pacific. Visit Australia’s Whitsunday Islands to marvel at turtles, manatees, and giant tropical fish gliding below a shimmering cerulean ocean.

Winter Sailing Holidays

Trusted voices from the BVI: real charterers share their Sunsail story

garypX579WD BVI

“Our family had a fantastic time in the BVI onboard our Sunsail 424 for a 5 day charter. It had been 30 years since I sailed here (in my single days) and I was excited to share the BVI adventures with my family. From arrival to departure, Sunsail’s customer service was exceptional! Of course, I knew 5 days wouldn’t be enough but my plan work, my family is hooked on sailing vacations and already talking about another Sunsail adventure next year!”

GrandTour773288 BVI

“All aspects of trip from booking, to asking questions, to checking in and checking out went very smoothly. We’ll be back before long.”

adamm805 BVI

“Fantastic in every regard. The captain they provided was just the best! A great sailor, so knowledgeable, and so much fun and friendly. (Thank you Ana!). The boat was perfect – new and everything functioned well. And the BVI’s are just the most magical place to sail. The staff at Sunsail was so helpful and friendly. Highly recommend Sunsail and the entire experience.”

986NigelB BVI

“We enjoyed a fantastic 8 night bareboat sail around the BVI on a Sunsail 46 from the Sunsail/Moorings marina at Tortola. Having been used to the attention to detail of Sunsail Europe, this was sadly lacking at Tortola. There was no welcoming contact from the base in the weeks leading up to our charter. Our air con wasn’t working, there was no gas in the canister, our Wi-Fi didn’t work and multiple door handles fell off. We wasted our first morning stuck in the base while a whole host of friendly staff worked to fit the problems.
The BVI is very busy in February and on three mornings we had the 7am stress of trying to secure a Boaty Ball mooring at popular locations. These were all booked in 10 seconds! We had prebooked three marinas and all our restaurants which proved a good call.
Our boat itself was excellent with all the major features like sails, engine, generator, tender working well throughout the week. We had some great sailing in the moderate-fresh Easterly Tradewinds and also enjoyed the warm temperatures and water for swimming and snorkelling. We booked a paddleboard but didn’t get to use this due to the significant swells, even at “sheltered” anchorages.
All the Sunsail staff were friendly and helpful and with more care with the preparation and presentation of the boat, this would be a five star review.”

V6106BLlisam BVI

“My best friend and recently finished a fabulous week-long trip sailing around the BVI on a beautiful boat booked through Sunsail. Our captain, Rachel Smith, was superb. She handled the boat flawlessly, inspiring complete trust. Her knowledge of the islands led us to the best moorings, restaurants and beaches. She was unfailingly good-natured, and allowed us the time we wanted on the helm–helping us become better sailors and keeping our safety and the boat’s top of mind. Rachel’s motto is “making dreams come true.” She certainly made our vacation in the BVI a dream come true, so we highly recommend Sunsail and Captain Rachel.”

joedY4521LI BVI

“Sunsail is a large operation and has some amenities that we have not seen elsewhere. Nice showers on shore with towels. Three places to eat close by and grocery shopping including a French deli within easy walking range. Staff were friendly and helpful.
Our catamaran was pretty new, very clean, well equipped. Everything worked well. My only complaint was the minimal storage in the cabins.
We modified our itinerary a bit as we went and had a good time. Winds were good and we did most of our traveling under sail. We have some experience sailing but enjoyed experimenting with the sails.
Our only problem with crowds was at the Baths. I would avoid that in the morning when tour groups may be more likely. Didn’t see really colorful coral, etc but I did swim in the midst of 40 or 50 little yellow fish–a thrill for me. S upper at Marina Cay was nice. The Pirate’s Bight was very noisy but I enjoyed the musician and dancing.
BVI is a beautiful, beautiful place.
PS: If you fly to St. Thomas and take the ferry make reservations for the return trip. We did not and the 2 convenient ferries were sold out, though we did get another after a mad dash up the coast.”

M6303VValexc BVI

“Our charter with Sunsail in the British Virgin Islands (BVI) was an unforgettable adventure. Sunsail’s team provided exceptional service from start to finish, ensuring our catamaran was in top condition for comfort and performance. Sailing through the BVI’s stunning landscapes was breathtaking, and Sunsail’s expertise on the best spots to explore enhanced our experience.We faced a couple of technical issues along the way, but Sunsail’s prompt and efficient response ensured they were quickly resolved, allowing us to enjoy our sailing paradise without interruption. This level of attentive service made us feel highly valued and reassured us of Sunsail’s commitment to an unparalleled sailing experience.The flexibility to tailor our itinerary, combined with the beauty of the BVI and Sunsail’s outstanding service, made our trip magical. We left with memories of adventure, relaxation, and the joy of sailing, looking forward to our next journey with Sunsail.”

johnpC3691OE BVI

“We had a beautiful week sailing in the BVI. The Sunsail dock facility is beautiful and the people are great and very helpful. We booked the wrong boat, too small. But Lindsay Roberts was able to provide us with a beautiful 50′ upgrade boat and at a reasonable price. So we had all the needed equipment to enjoy our trip.”

BenA344 BVI

“Charter sailing, with any company, in the BVIs is a joy. Great, reliable winds and weather make for a sailors paradise. Sunsail / Moorings provides great boats and service and has a great facility / location.”

Quest774772 BVI

“This was our 2nd nine-day cruise around the BVI with Sunsail/The Moorings. Each time we’ve hired a Captain. Our 1st time the Captain was just “Ok”, this trip our Captain, “Rico” was awesome. Rico is engaging, knowledgeable, helpful, and a pleasure to have on the boat. If you need to hire a Captain, we highly recommend you request Hendrico Vivier [Rico] you won’t be sorry 😊”

Types of Winter Sun Holidays

We offer sailing holidays for sailors of all abilities and experience levels. Whichever destination you choose for your winter sun or Christmas sailing trip, you’ll have great options for charter types and extras.

Winter Bareboat Charter Holidays

Take charge on a bareboat charter holiday. You’ll have the freedom to sail at your own pace and explore as much or as little of your chosen destination as you like, calling at quiet bays and bustling towns or simply enjoying the sensation of the ocean slipping away beneath your keel. A bareboat charter holiday is just you, a beautiful yacht, and the boundless ocean to explore.

Winter Flotilla Holidays

Sail with like-minded adventurers on a flotilla holiday in the Caribbean, where each day is a perfect mix of independent sailing and lively social gatherings. Explore the paradise islands of the BVI with a group of fellow flotilla adventurers, sailing alone or in groups by day and meeting up for fun social activities by night. Flotilla sailing holidays are perfect for families and groups, giving you the chance to improve your sailing skills and make new friends in the beautiful Caribbean sunshine – discover some of our top winter sun sailing destinations for families.

Winter Skippered Charter Holidays

On a skippered charter holiday, you can relax and let an experienced skipper take the helm while you soak in the beauty of your surroundings. From hidden anchorages to off-the-beaten-path island gems, your sailing adventure is in expert hands. Improve your sailing skills with the help of an expert skipper, ready to take the helm when you need a rest and happy to step back and show you the ropes. You’ll benefit from local insights and advice, heading off the tourist trail to discover your destination’s hidden gems.

Embark on a Winter Sailing Adventure

Benefits of Winter Sun Holidays

Make cold days and dark nights a world away by travelling to one of our warm winter destinations in December, January or February. Make it your New Year’s resolution to take some ‘you time’ to top up your tan and thaw off, and feel the warmth of the sun on your skin as you cruise some of the world’s most exotic sailing destinations.

A winter sun holiday is the perfect escape, offering a dose of vitamin D, brighter moods, and a chance to explore new destinations. Enjoy fewer crowds, lower off-season prices, and the opportunity to stay active with activities like swimming and water sports. Plus, it is the ideal time to relax, make memories, and soak up the warmth while leaving the cold behind.

Things to Do on a Winter Sun Holiday

A sailing winter sun holiday is the ultimate way to escape the chill and immerse yourself in tropical paradise. Swim in warm, turquoise waters or snorkel over vibrant coral reefs teeming with colourful marine life. For diving enthusiasts, many destinations offer world-class dive sites where you can explore underwater caves, shipwrecks, and abundant sea creatures. Each day brings the chance to anchor near secluded beaches, perfect for relaxing on soft sands or enjoying a private picnic.

Food lovers will relish the opportunity to savour fresh, locally prepared dishes. Whether it is a seafood feast at a beachfront restaurant or cooking on board with ingredients sourced from bustling local markets, the flavours of the region will enhance your journey. With every new island or coastal stop, you will discover breathtaking scenery, peaceful bays, and a variety of activities that make your sailing winter sun holiday unforgettable.

Winter Sun Holiday FAQ

 Are winter sun yacht holidays family-friendly?

Yes, yachts can be equipped with family-friendly amenities, and destinations often include safe swimming spots and fun activities for children.

What activities can I enjoy on a winter yacht holiday?

Snorkelling, diving, paddleboarding, swimming, beach picnics, and exploring local towns are all highlights of a yacht holiday. The winter season is a good time for adventurous holidays packed with activities.

What should I pack for a winter sun yacht holiday?

Pack light, with swimwear, sun-protective clothing, non-slip shoes, sunscreen, a hat, and evening layers. Don’t forget water-resistant bags and your travel documents. Be sure to have a read of our packing list for a sailing holiday blog for more details.

Plan Your Dream Vacation