December is the coldest and dullest month in many parts of the world. Luckily, this isn’t the case in the top 5 sailing destinations where sunny skies and perfect sailing conditions are year-round.
So, why not sail away to some of these tropical sailing destinations and experience the beauty of December sailing? Trade your thick winter coat for your favorite swimsuit and enjoy endless adventures as the warm breeze guides you through the most beautiful destinations in the world.
From the calm waters of the Caribbean to the balmy Florida Keys and the marvelous Hawaiian Islands, these tropical destinations ensure safe and enjoyable sailing adventures, away from the cold.
Sailing in December: Why It Is a Great Idea?
Sailing is often associated with summer; however, December is a unique chance to discover the wonders of the open sea without crowds and spending too much.
Sailing in December allows you to escape the extreme colds by setting your compass to a warm, sun-drenched location. If you’re still having doubts about visiting your dream destination in December, here are a few reasons why you shouldn’t miss out on it:
- The crowds are fewer
When you sail to popular sailing destinations in December, you’ll often experience reduced crowds which is a great opportunity to explore the area peacefully and more privately. There will be no need to struggle for space or compete for the best view spots.

- The weather is milder
Many tropical and subtropical regions offer the ideal weather conditions in December- warm but without intense heat. This ensures a more pleasant trip to some of the best sailing destinations and the most of your vacation since the extreme temperatures won’t get in your way.
- You will enjoy a unique holiday
December sailing is a spot-on choice for those looking to celebrate Christmas or New Year’s Eve in a new way. Sail away during the holidays in your private luxury yacht, away from the hustle and bustle in the city, and experience a wonderful, relaxing, and recharging celebration surrounded by your loved ones.
- You can grab special deals
December is a month of off-peak discounts and you can snag great yacht rentals at a fraction of the peak costs. In addition to the lower yacht rental prices, this period may include lower marina fees and other travel-related prices. You can redirect the budget for an even more luxurious holiday or an extended sailing adventure.
December Sailing: Must-Know Tips
If a December sailing getaway is right up your alley, prepare well to ensure the smoothest adventure possible, surrounded by the beauty of lush forests and turquoise waters.
From packing smart to booking on time, here are the must-know tips for a memorable December sailing holiday:
- Don’t forget the weather forecasts
December can be quite an unpredictable month in some regions. Therefore, before choosing a destination, check out the weather conditions. This will help you plan the perfect sailing getaway by getting the most out of an important factor: the weather!
- Be a smart packer
Even if you’re headed to a tropical sailing destination, bring enough clothes for layering to stay cozy on cooler nights. In some regions, the temperatures can drop in the evenings so the right clothes will help keep you warm and comfortable.
- Book in advance
Though December isn’t the peak season in many of these destinations, securing the best yacht and route timely ensures you get the most out of your dream yacht getaway. For a great December sailing experience, head to Book2Sail, the go-to platform for sailing enthusiasts to book luxury yachts.
- Be flexible
Sometimes, depending on the destination, December can have unexpected winds or changes in weather. If this happens on your sailing adventure, staying flexible is the key. Be open to adjusting your itinerary accordingly to continue enjoying your sailing getaway.

The Ultimate December Sailing Destinations
Now that you’ve learned about the benefits of sailing in December and the best tips for an enjoyable adventure, it’s time to reveal the ultimate December sailing destinations.
Escape December’s cold and enjoy pleasant weather without storms in some of these five breathtaking sailing destinations:
- The British Virgin Islands
Renowned for its breathtaking beaches, rich marine life, and proximity between islands for easy island hopping, the British Virgin Islands is an awesome tropical sailing destination if a Caribbean sailing adventure is on your bucket list.
The refreshing trade winds and tranquil currents create the perfect sailing conditions to enjoy your holidays.
You can explore over 50 islands and their hidden bays and azure waters, starting from the main island of Tortola. It’s also dry season there during December, so you’ll likely enjoy mostly sunny skies and minimal rainfall.

Sailing the Caribbean islands in December means it’s time for festivities. Enjoy lively events like their Christmas regattas and New Year’s celebrations and experience the local culture and rich cuisine while having fun!
- The US Virgin Islands
If you’re looking for a pleasant and effortless sailing destination in December, the US Virgin Islands is the place to anchor. This island chain adjacent to the British Virgin Islands is a US territory with the US dollar being the official currency is the US dollar and English as the official language.
Set sail to the main islands like Saint John, Saint Thomas, and Saint Croix, or explore more secluded islands and cays for a more serene experience. With around fifty islands and cays, the breathtaking scenery promises all-day adventures.

The December weather is perfect for sailing these islands. It’s warm with a moderate breeze and low rainfall. These conditions are ideal for snorkeling and scuba diving enthusiasts.
For a proper celebration of the holidays, enjoy some of the many festivities across the islands, from Christmas markets to beach parties for New Year’s Eve.
- Barbados
This Caribbean gem is a picture-perfect December sailing destination. Often described as paradise on earth, this once-upon-a-time English settlement is a small island country in the south-eastern Caribbean Sea visited by tourists globally, but mostly by British, American, and Canadian citizens.
As it’s yacht-friendly, Barbados is a great destination for the off-season month sailing in the Caribbean and boasts an abundance of anchoring spots and docks. You can marvel at the stunning architecture that the island is renowned for and visit historic sites like St. Nicholas Abbey.
Don’t miss out on the popular beaches like Carlisle Bay where you can go for a day of water activities or soak up the sun rays while sipping tasty rum.

Sailing there for the festive season entails vibrant Christmas markets, mouthwatering traditional Bajan cuisine, and great festivals.
- Florida Keys
The Florida Keys, a unique archipelago, is one of the most wonderful sailing destinations during December boasting warm weather, tranquil waters, vibrant marine life, and unique Christmas festivities. With temperatures ranging in the 70s and 80s, this tropical wonder is a great place to escape the cold.
The pleasant weather is a sailor’s dream as the steady breeze and calm waters ensure smooth sailing and comfortable island exploration. Some of the small islands in this chain offer some of the best tropical scenery in the US.
You can marvel at the small sandbars surrounded by reefs in azure water and occasional palm trees or have fun at the holiday festivities that capture the place’s quirky charm and laid-back vibe.

Visit the Lighted Boat Parade at Key West where decorated yachts and sailboats glide through the harbor for a memorable water spectacle. Or, visit the Historic Holiday Inn Tour in the Old Town and enjoy the decorated inns and homes.
Celebrate the holidays in style while immersing in delicious seafood and tropical cocktails while witnessing the breathtaking sunset at Mallory Square!
- Hawaiian Islands
If you sail the Pacific during December, there is no better place than Hawaii. The Hawaiian Islands are some of the best tropical sailing destinations with stunning nature, warm climate, and rich culture.
Visit the islands with active volcanoes and marvel at untouched tropical rainforests, amazing wildlife, and crystal-clear waters ideal for water adventures. If you’re curious about typhoon season sailing and avoiding dangerous weather, you can be safe as t Hawaii is mostly out of the typhoon range. So, December sailing there is much safer than heading to another warm Pacific destination.
The December weather is characterized by very little rain and mostly pleasant temperatures between 82 and 62. The consistent trade winds and tranquil waters will ensure a safe exploration of Maui, Kauai, Oahu, and the Big Island.

Hawaiian Christmas or Mele Kalikimaka celebrations are a must-visit and the Honolulu City Lights parade is a wonderful festivity with dazzling street displays. If you’re lucky, you may spot the majestic humpback whale as it migrates through Hawaiian waters.
To Conclude: Is December Sailing Worth It?
December sailing getaways are worth it! This month is the perfect time to avoid the winter blues and dive into the world of stunning tropical destinations.
Whether anchoring in the Caribbean, island-hopping in Hawaii, or enjoying the vibrant festivities in the Florida Keys, December getaways are a dream come true for sailing enthusiasts. From lower prices and fewer crowds to unforgettable underwater experiences, it’s the ideal time for sailing adventures to explore marvellous sailing destinations.

Experience the beauty of Christmas celebrations in some of the top 5 sailing destinations by booking your luxury yacht today. Book2Sail’s intuitive yacht rental platform is here to help you find the perfect vessel for your tropical getaway!
