The Caribbean is undeniably one of the most sought-after destinations for a sailing holiday charter, and for good reason.
Its pristine white sand beaches, year-round warm weather and near-perfect sailing conditions, make it an exceptional place to explore by boat.
With over 7,000 individual islands, it's the sheer diversity that makes this tropical paradise so wonderful. Each island has its own unique charm and character, offering a blend of cultural experiences, vibrant nightlife, and secluded anchorages. From the glamorous and cosmopolitan St. Barts to the unspoilt Grenadines, there is something for everyone in this tropical paradise.
With a year-round tropical climate, warm temperatures and plenty of sunshine, the Caribbean is a perfect destination for sailing, swimming, snorkelling, and other water-based activities.
The Caribbean offers excellent sailing conditions, with consistent trade winds and year-round warm weather, making it a perfect destination for sailors whether novice or expert.
One of the highlights of a yacht charter in the Caribbean is the opportunity to visit multiple islands and explore their unique cultures, cuisines, and landscapes. Each island has its own distinct character and attractions, allowing for a diverse and enriching experience.
The Caribbean is known for its beautiful and pristine beaches, crystal-clear waters, and picturesque islands. There are numerous stunning destinations to explore, including the British Virgin Islands, St. Martin, St. Lucia, Antigua, Grenada, and many more.
Each Caribbean Island has its own unique culture, offering a vibrant mix of music, dance, and festivities. From reggae in Antigua to salsa in Cuba, you can immerse yourself in the local culture and enjoy lively nightlife experiences.
The Caribbean is famous for its delicious cuisine, influenced by African, European, and Indigenous flavours. On board your sailing holiday or on land, you can enjoy freshly prepared meals using locally sourced fresh ingredients.
The Caribbean islands boast lush, verdant landscapes with towering mountains, cascading waterfalls, and vibrant flora and fauna making it a paradise on land as well as sea.
The Caribbean is home to abundant marine life and coral reefs. Snorkelling or diving in the clear waters offers a world-class opportunity to explore nature at its most captivating.
Savour fresh seafood, tropical fruits, and local specialities. Caribbean cuisine is a vibrant and flavourful fusion of various cultural influences, reflecting the region's diverse history and bountiful natural resources.
The snorkelling and diving in the Caribbean is truly world-class, offering some of the most diverse and vibrant marine ecosystems on the planet. Explore stunning coral reefs, abundant aquatic life, and shipwrecks in locations such as the British Virgin Islands, Antigua, St. Thomas, Belize and the Bahamas.
The Caribbean is renowned for its vibrant and colourful carnivals. These festivals are deeply rooted in the region’s culture and history, often featuring elaborate costumes, lively music, dancing, and parades. Ones not to be missed include Antigua, Saint Lucia, The Bahamas and Grenada, to name but a few.
Whether you're interested in natural wonders, cultural immersion, or outdoor adventures, the Caribbean islands offer a diverse range of experiences to explore on land during your sailing holiday charter. Many islands boast lush rainforests and volcanic landscapes, all waiting to be discovered if you can tear yourself away from the haven of your sailing holiday.
If timing allows, you can watch or even participate in famous sailing events such as the Antigua Sailing Week, St. Maarten Heineken Regatta, BVI Spring Regatta or Grenada Sailing Week. These regattas attract sailors and spectators from around the world, offering a unique blend of competitive racing, stunning scenery, and vibrant Caribbean culture.
The slower pace of life in the Caribbean, often referred to as "island time," is a great encouragement to unwind and take things at a more leisurely pace. This relaxed approach will help you leave behind the stresses of daily life and when combined with the laid-back and friendly nature of the Caribbean people is just the tonic to create an unforgettable trip.
If you're looking to eat ashore in total isolation, enjoy a private beach barbecue or picnic on a secluded island, relaxing and indulging in freshly grilled seafood and a refreshing rum punch.
There's so much to explore in each sailing area of the Caribbean. Visit multiple islands on your charter, from St. Barts to St Martin, Anguilla to Antigua, or perhaps the Grenadine islands between St Vincent and Grenada, to experience different cultures, cuisines, and landscapes.
The Caribbean sailing holiday charter high season generally starts in November and lasts until April. This is typically the dry season, offering pleasant temperatures and calmer seas. It’s also worth looking outside of these times as the Caribbean enjoys a moderate climate all year round.
Monthly weather for the area *
| Avg. High Temp | Avg. Low Temp | Avg. Daily Rain (mm) | Avg. Wind Direction | |
|---|---|---|---|---|
| JAN | 25.4°C (78°F) | 24.5°C (76°F) | 0mm |  E |
| FEB | 25.5°C (78°F) | 24.7°C (76°F) | 0mm | E |
| MAR | 25.5°C (78°F) | 24.7°C (76°F) | 0.0mm | E |
| APR | 26.6°C (80°F) | 25.9°C (79°F) | 0mm | E |
| MAY | 28.0°C (82°F) | 26.9°C (80°F) | 0.0mm | ESE |
| JUN | 28.9°C (84°F) | 28.0°C (82°F) | 0.1mm | ESE |
| JUL | 29.8°C (86°F) | 29.1°C (84°F) | 0mm | E |
| AUG | 30.0°C (86°F) | 29.3°C (85°F) | 0mm | E |
| SEP | 29.9°C (86°F) | 29.0°C (84°F) | 0mm | ENE |
| OCT | 29.0°C (84°F) | 28.0°C (82°F) | 0mm | ESE |
| NOV | 27.3°C (81°F) | 26.6°C (80°F) | 0.0mm | ENE |
| DEC | 25.6°C (78°F) | 24.7°C (76°F) | 0mm | ESE |
English is widely spoken with local languages depending on the Island.
Most of the countries in the Caribbean have their own currency but also US dollars are widely accepted along with major credit cards.
All Caribbean countries appreciate a tip for work well done
You can't beat a monohull charter from Caribbean on a sailing holiday for an authentic sailing experience and connection with the wind and water. Whether you're looking for a bareboat, skippered or fully crewed charter where you can sit back and relax, we've got all the bases covered.
Discover natural beauty in diverse cruising grounds, and soak up the local atmosphere in a wide variety of anchorages. We‘ll handpick a selection of yachts to suit your needs, so you can start planning a journey to remember.
A catamaran charter from Caribbean on a sailing holiday is all about comfort, luxury and convenience, with their twin hulls making them extremely stable. Expansive open decks allow for spacious seating, socialising and sunbathing, while below deck each hull typically contains its own cabins, complete with ensuite bathroom.
This layout is particularly good for couples or families travelling together as it offers more personal space. Our catamarans are available as either bareboat or skippered charters, with a host or hostess if needed, or fully crewed.
A luxury yacht charter on a sailing holiday from Caribbean is the epitome of opulence and comfort. Our boats have beautifully designed interiors and state-of-the-art facilities, ensuring a supremely relaxing and luxurious experience.
Customise your itinerary according to the destinations, activities, and experiences you desire; your crew will be on hand to ensure a fully tailored and unique trip. Whether you're looking for gourmet meals prepared by a private chef, wildlife spotting around remote islands, glamorous nightlife, or swimming in secluded coves, contact one of our experts today to create a unique and unforgettable trip.
A sailing holiday allows you to experience the sea, wind, and sky up close, not to mention the chance to spot dolphins or other marine life native to your cruising area.
Looking for a total break from your everyday routine? A sailing holiday provides a truly different experience. Being rocked gently by the sea while surrounded by stunning nature is guaranteed to lower your stress levels.
Your boat serves as both transportation and lodging, offering a total change from the everyday - and a fantastic way to explore a variety of locations.
Whether you're a first-time sailor or an old hand, your skipper will be happy to give tips on sailing techniques and nautical knowledge. Or feel free to sit back, relax and simply enjoy being on board.
On a sailing holiday you can reach tucked away coves, quiet beaches, and small islands which are inaccessible to land-based tourists.
The nature of sailing together means you tend to foster deeper connections with travel companions in a close, shared environment. Special memories are guaranteed.
The weather doesn’t always do what you want, but with a boat charter you can easily adjust your plans based on weather, preferences, or unexpected discoveries.
On a sailing holiday you have the freedom to plan your own itinerary and visit multiple destinations, with the journeys between them being part of the fun.
A bareboat sailing holiday with Pure Yachting gives you the freedom to create your own itinerary and explore Caribbean and beyond at your own pace. Tailor your trip to match your preferences, and if you need advice or inspiration our charter experts will always be on hand to suggest areas to explore.
We select our sailing holiday fleet from trusted operators, chosen by us for the quality of their boats and the fact they offer a high level of service. To charter on a sailing holiday you'll typically need a qualification such as the RYA Day Skipper, the AS104 Bareboat Cruising, ICC certification or be able to demonstrate relevant experience.
With a professional skipper at the helm to confidently navigate around Caribbean and beyond, you’re free to relax and enjoy every moment. The skipper's expertise ensures smooth sailing, allowing you to immerse yourself in the beautiful surroundings.
However, if you fancy getting more involved, our fully qualified skippers will be more than happy to show you the basics, or help you brush up your sailing skills.
On skippered sailing holiday, there's also the opportunity to add a host or hostess who can prepare meals and help with tasks such as childcare, concierge services and housekeeping.
A crewed sailing holiday from Caribbean comes in many shapes and sizes, ranging from sleek superyachts to luxury catamarans, contemporary motor yachts to classic yachts and more, all with crews who are committed to ensuring your comfort, safety and enjoyment.
Each trip offers the opportunity to create a unique journey and our charter experts will guide you through choosing the perfect boat and customising the itinerary to your specification. Whatever your preferences, we take care of all the details, ensuring you and your party have a unique and unforgettable holiday.
Whether snorkelling in crystal-clear waters, coming face-to-face with abundant marine life, hiking through lush rainforests, or exploring the Caribbean's extensive cruising grounds, there are endless opportunities for adventure and exploration.
The beauty of cruising through the Caribbean on a sailing holiday charter is the freedom to discover hidden gems and secluded spots that are inaccessible to larger boats or cruise ships.
Another reason we love the Caribbean is the famously welcoming and hospitable culture. If you like to connect, the locals are friendly and always ready to share their knowledge and stories. From sampling flavourful Caribbean cuisine to dancing to calypso or reggae music, immersing yourself in the local culture adds an extra layer of richness to your sailing holiday charter experience.
For those seeking relaxation and pampering, the Caribbean offers myriad luxurious resorts, spas, restaurants and beach clubs. After a day of exploring or lounging on your sailing holiday, you can indulge in a rejuvenating spa treatment, dine in gourmet restaurants, or sip a refreshing cocktail while watching the sun set over the horizon.
Last but not least, the Caribbean offers excellent sailing conditions. The steady trade winds and often line-of-sight navigation make it an ideal destination for sailors of all levels. Whether you want to embark on a thrilling sailing adventure or enjoy a leisurely cruise from one idyllic island to another, the Caribbean caters to all levels of expertise.
Exploring this tropical paradise on a sailing holiday charter allows you to create unforgettable memories and experience the ultimate holiday in a truly extraordinary destination.
If you are doing a bareboat charter, you need to consider if you have the relevant sailing licences. If you are on a skippered or crewed charter, it's good to understand the weather conditions for the trip so you can bring the appropriate clothing and think about which locations you would like to visit so as you can let the skipper know.