The Best Times to Explore the Caribbean on a Charter Yacht

The Best Times of the Year to Charter a Yacht in the BVI, USVI, and SVI

Travel Tips| Private Caribbean Charters
November 11, 2025•3 min read

With its crystal blue waters and sunny skies, it seems like there’s never a bad time to charter a yacht in the Caribbean. Still, certain seasons and celebrations can make your voyage even more unforgettable—or a little more rocky.

In this blog, we’ll explore the best times to plan a vacation to the British, Spanish, and U.S. Virgin Islands based on weather, peak tourism, holiday seasons, special experiences, and more.


Benefits of visiting the BVI and USVI during Winter and Spring

Winter Season (December – February): The Sweet Spot

If there’s a “golden season” for Caribbean yacht charters, it’s right in the months of winter and spring.

While chilly winter weather grips most of the U.S., the Caribbean offers balmy days, calm seas, and postcard-perfect sunsets. The islands are alive with festivals and vibrant beach vibes, ideal for travelers seeking both relaxation and a touch of celebration.

  • Perfect for: Escaping the cold, romantic getaways, anniversaries, and New Year’s celebrations

  • What to Expect: Steady winds, dry weather, and clear skies that make for perfect sailing and snorkeling conditions

  • Pro Tip from Barefoot Cowboy: Book early. This is the start of peak season, and the islands (and our calendar) fill up fast.


Benefits of visiting the BVI and USVI in Spring and Summer time

Spring Break & Early Summer (March – July): Busy but Beautiful

Spring and summer bring warm seas, long sunny days, and that unmistakable “Caribbean energy.” Sure, the islands get busier during this time, but with the right charter company, you’ll always have space to unwind.

If you want to enjoy the tropics during your spring vacation without worrying about crowded beaches, stick to the hidden gems. Our custom itineraries let you slip away to quieter anchorages and hidden coves, the kind the big cruise ships typically avoid.

  • Perfect for: Family reunions, girls’ trips, birthdays, and multi-generational adventures

  • What to Expect: Vibrant hot spots, great swimming weather, and lively island life

  • Pro Tip from Barefoot Cowboy: Pick a charter that takes the less-traveled path so you can explore hidden gems the big yachts typically overlook.


Benefits of visiting the USVI and BVI during fall and winter

Fall & Holiday Season (November 2nd – December): Island-Style Celebrations

Want to enjoy the tropics with fewer crowds and brighter skies? Fall is your best bet.

As autumn cools things down back home, the Caribbean heats up with color, culture, and calm. This is the perfect time to gather your crew and celebrate something special, from milestone birthdays to Thanksgiving, Christmas, or even a surprise engagement.

  • Perfect for: Holiday escapes, anniversaries, or small family celebrations

  • What to Expect: Fewer crowds in early fall, followed by a festive buzz leading into the holidays.

  • Pro Tip from Barefoot Cowboy: Chartering a yacht for the holidays for no crowds, no cooking, and no stress—just turquoise waters and endless sunsets.


Hurricane season in the BVI and USVI

When Not to Travel: Late Summer to Early Fall (August – November 1), AKA Hurricane Season

Hurricane season peaks in August and September, and while not every island is affected, the weather can be unpredictable. We usually recommend planning your charter outside these months if possible. Barefoot Cowboy doesn’t even book charters during these 3 months to avoid storms.

  • Pro Tip from Barefoot Cowboy: Book for early November instead, when hurricane risks drop but crowds haven’t yet arrived. You’ll enjoy lower rates, warm seas, and plenty of sunshine.


When is the best time to travel to the Caribbean on a charter yacht

So, When’s the Best Time to Charter?

The real answer: whenever life calls for celebration (with the exception of hurricane season, of course).

Whether it’s your best friend’s birthday, a long-awaited family reunion, or just a moment to unwind, the Caribbean is always ready to welcome you aboard. There’s no better way to make special moments even better than sipping cocktails on the sandy white beaches of the Virgin Islands.

With Barefoot Cowboy, you don’t have to worry about crowds, weather, or rigid schedules. We take care of every detail so you can focus on what matters most: making memories that last a lifetime.

Ready to kick off your shoes, grab your crew, and go barefoot? Contact us today to start crafting your personalized yacht charter.

Plan your dream Caribbean vacation with Barefoot Cowboy now

Caribbean Travel TipsBVI Travel TipsUSVI Travel TipsCaribbean CharterCaribbean Hurricane SeasonBritish Virgin IslandsUS Virgin IslandsSpanish Virgin IslandsPuerto Rico Charters
Natalie is the Barefoot Cowboy's chef, boss, and happy-go-lucky lady! Natalie’s background is in the optical world, where she spent 28 years as a certified optician. She loves working with people and customizing their experience. Customer service is her forte! Natalie will tell you she has the best job in the entire world. She gets to help make sure you eat delicious food, drink the best drinks, and have the time of your life! And as an added bonus, she can adjust your sunglasses if you sit on them. Natalie’s favorite destination is Dinghy's on Water Island for Sunday Funday. She also loves Hull Bay for the local beach vibe. For drinks, she’s a sucker for Diet Coke & Cruzan Rum.

Natalie Rucker

Natalie is the Barefoot Cowboy's chef, boss, and happy-go-lucky lady! Natalie’s background is in the optical world, where she spent 28 years as a certified optician. She loves working with people and customizing their experience. Customer service is her forte! Natalie will tell you she has the best job in the entire world. She gets to help make sure you eat delicious food, drink the best drinks, and have the time of your life! And as an added bonus, she can adjust your sunglasses if you sit on them. Natalie’s favorite destination is Dinghy's on Water Island for Sunday Funday. She also loves Hull Bay for the local beach vibe. For drinks, she’s a sucker for Diet Coke & Cruzan Rum.

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