Top Reasons to Sail the Caribbean in Winter: Sun, Celebrations & Amazing Charter Deals

WHAT APPEARS IN THIS ARTICLE?

1. Top Reasons to Sail the Caribbean in Winter: Sun, Celebrations & Amazing Charter Deals
2. Winter in the Caribbean is Special
   1. Ideal Sailing Conditions
   2. Warm Temperatures & Sunshine
   3. Warm, Inviting Waters
   4. Exciting Events
3. Winter Events in the British Virgin Islands
   1. Anegada Lobster Festival
   2. VISAR's Winter Wonderland Fundraiser at Nanny Cay Resort & Marina
   3. Christmas Tree Lighting and Concert, Lions Club of Tortola
   4. Monthly Full Moon Party at Trellis Bay
   5. Christmas in the City, Road Town, Tortola, and Christmas in Spanish Town, Virgin Gorda
   6. Holiday Season at Oil Nut Bay, Virgin Gorda
   7. Foxy’s Old Year’s Night Party at Jost Van Dyke
4. Winter Events & Highlights in the Bahamas
   1. Bahamas International Film Festival
   2. The Junkanoo Festival
5. Plan Your Award-Winning Winter Escape with Navigare Yachting
   
   

Top Reasons to Sail the Caribbean in Winter: Sun, Celebrations & Amazing Charter Deals

As winter approaches, travelers worldwide are starting to dream of sunny escapes—and there's no better place to set sail than two of the Caribbean's most iconic destinations: the award-winning British Virgin Islands (BVI) and the Bahamas. Life on these islands is flourishing from December through March, offering perfect weather, exciting events, and everything you need to leave winter blues behind. 

If you want to explore the Caribbean’s crystal-clear waters and vibrant culture, read on to discover why winter is the ultimate season to visit the BVI and Bahamas. With Tripadvisor Travelers’ Choice Awards 2024 rewarded in both of our Caribbean bases, Navigare Yachting’s unforgettable sailing charters promise well-maintained, modern, state-of-the-art catamarans and sailing yachts and top-notch service from our highly rated crew and base staff. 

With our limited-time yacht charter deals for December 2024 departures in the British Virgin Islands, it’s still not too late to book your ideal Holiday getaway. Simply contact our team of Caribbean charter experts; they’ll help you secure the best available boat of your choice. 

Winter in the Caribbean is Special

For anyone residing in a cold weather climate, winter in the Caribbean isn’t just an escape from the frigid temperatures and messy snow storms; it’s the season when these exotic islands burst into life with a warm, vibrant, and festive Caribbean spirit. Essentially a paradise on Earth, the Caribbean embraces a golden Holiday season rather than a white one. From soft cream-colored sand beaches to vibrant amber sunsets over the turquoise waves, the West Indies is the place to be during the Holiday season. 

With consistent, steady trade winds, clear skies, and warm waters, sailing in the Caribbean during winter offers the best conditions of the year. Here’s what makes it so perfect:

• Ideal Sailing Conditions: December through March marks the high season in the BVI and Bahamas and brings steady trade winds, creating optimal conditions for smooth and enjoyable sailing. Highly favorable sailing conditions give every winter yacht charter a pleasant feel, whether you’re an experienced sailor or new to yachting.
• Warm Temperatures & Sunshine: With temperatures in the upper 70s (°F), winter in the Caribbean offers warmth without extreme heat—perfect for sunbathing, swimming, and outdoor activities. Rain is rare this season, and the clear, sunny skies are ideal for island-hopping, snorkeling, and relaxing on deck.
• Warm, Inviting Waters: With gentle waves and water temperatures just right for a dip, the Caribbean Sea is a delight during winter. You’ll want to jump in at every stop, whether you’re exploring secluded coves, vibrant reefs, or snorkeling with sea turtles.
• Exciting Events: Winter in the Caribbean bursts with energy, offering unique holiday experiences like outdoor markets, ice skating, and vibrant cultural events. Each island comes alive with traditional parades and festive celebrations, giving visitors a joyful and immersive taste of the Caribbean culture.

Winter Events in the British Virgin Islands

The British Virgin Islands light up like a Christmas tree during the Holiday Season, featuring a series of can’t-miss celebrations that showcase the islands' lively culture, delicious food, and festive spirit. Here are some of the highlights to look forward to this winter season:

• Anegada Lobster Festival (Nov 29 - Dec 1, 2024)
  Kicking off the season, this festival celebrates Anegada’s culinary specialty—lobster. Savor fresh lobster dishes, enjoy live music, and meet friendly locals and fellow travelers at this foodie paradise.
• VISAR's Winter Wonderland Fundraiser at Nanny Cay Resort & Marina (from Nov 29, 2024)
  Known for its unique ice-skating rink, this event brings the winter holiday experience to the tropics. Families and friends gather to skate, mingle, and support a good cause—an unusual and memorable event in the Caribbean! 
  The skating rink is not made out of real ice, but rather a technology-based synthetic compound that works just as well for ice skating, without requiring cold temperatures. And the best part? It’s right by Navigare’s award-winning BVI yacht charter base!
• Christmas Tree Lighting and Concert, Lions Club of Tortola (Dec 7, 2024)
  This annual tradition brings people together for an enchanting evening of music and lights, marking the beginning of the holiday season with community and celebration.
• Monthly Full Moon Party at Trellis Bay (Dec 15, 2024)
  Every full moon, Trellis Bay hosts a magical night with fire dancing, live music, and traditional island BBQ food, cooked right on the beach. In December 2024, this celebration will fall on the night of December 15. It’s an unforgettable experience to enjoy under the shimmering Caribbean moonlight and a favorite among our yacht charter guests and boat owners!
• Christmas in the City, Road Town, Tortola, and Christmas in Spanish Town, Virgin Gorda
  These holiday markets are infused with local traditions, delicious foods, and live music. Both towns come alive with the spirit of the season, offering a rich cultural experience. Visitors can sample traditional food, admire work by local artists, shop for handmade gifts, or simply wander the local markets while basking in the traditional Caribbean holiday spirit. Stay tuned for dates.
• Holiday Season at Oil Nut Bay, Virgin Gorda
  Embrace a combination of relaxation and fitness with holiday events at the luxurious Oil Nut Bay resort. Dine at the top-rated restaurant, relax by the pool, or recharge with a day at the spa. During the holiday season, guests can also participate in activities like pickleball tournaments, paddle races, and wellness sessions while soaking in the holiday cheer. It’s the perfect stop on your BVI December yacht charter with Navigare Yachting.
• Foxy’s Old Year’s Night Party at Jost Van Dyke (Dec 31, 2024)
  What better way to end the year than by celebrating in style at one of the most legendary New Year’s Eve parties in the Caribbean? Foxy’s Bar hosts this famous celebration, featuring live music and the one-of-a-kind “Old Year’s Walk” parade on the beach. Foxy’s beach bar is conveniently located on the shores of Jost van Dyke, which makes it a perfect stop on your yacht charter. Just moor the yacht, take the dinghy to the shores, and get ready to ring in the new year with a beach party like you’ve never seen before. 

Winter Events & Highlights in the Bahamas

In the Bahamas, winter celebrations bring people together through lively parades, unique festivals, and colorful displays of Bahamian culture. Here are a couple of winter events that will make your winter visit to the Bahamas memorable:

• Bahamas International Film Festival (November 18-22, Nassau, Rock Sound, Harbour Island): For movie lovers, this annual film festival is a chance to experience the glamour of international cinema right in paradise. The event takes place on three different islands, traveling from Nassau, to Rock Sound, to Harbour Island throughout the week, while filling all of the Bahamas with an artistic flair. Filmmakers, actors, cinematographers, and movie lovers gather making this a unique addition to any Bahamas winter itinerary.
• The Junkanoo Festival (Dec 26 and Jan 1): This must-see vibrant street parade is one of the most famous traditions on the Caribbean calendar, and showcases Bahamian culture through elaborate costumes, rhythmic music, and exuberant dancing. Held on Boxing Day and New Year’s Day, the largest parade takes place in Nassau, but celebrations are planned on several other islands to bring visitors up close to this lively tradition no matter their location. The Abacos hosts an incredible Junkanoo Festival in the historic town of New Plymouth on Green Turtle Cay on New Year’s Day. It’s a must-see experience on your Bahamas winter yacht charter with Navigare Yachting. 

Plan Your Award-Winning Winter Escape with Navigare Yachting

With winter delivering the best Caribbean sailing weather, an array of exciting events, and exclusive discounts, this season is the perfect opportunity to plan a winter yacht charter. Navigare Yachting’s booking deals offer up to 20% off yacht charters departing in December 2024, allowing you to experience our award-winning destinations in the British Virgin Islands and the Bahamas at the height of the peak season at an unbeatable price. Reach out to our dedicated in-house team for assistance booking your discounted winter getaway today!

Navigare Yachting is a five-time 2024 Tripadvisor Travelers’ Choice Award winner. Since 2001, over 400,000+ charter guests have set sail with Navigare - it’s safe to say that your yachting adventure will be in capable hands. With 12 exotic locations worldwide, the possibilities are endless! Whether you're an experienced sailor or a first-time adventurer, Navigare Yachting opens up a world of exploration, discovery, and sailing that comes with complete peace of mind.