Sailing Trips in the Caribbean

Sailing Trips in the Caribbean with a Skipper and Crew

Joining a sailing trip in the Caribbean with an experienced skipper is one of the best ways to explore this tropical island paradise. No sailing experience is required — a certified skipper takes care of navigation, route planning, and the daily logistics of life on board.

This allows you to fully relax and enjoy the journey while discovering secluded beaches, vibrant island culture, and breathtaking turquoise bays. Sailing trips in the Caribbean offer the perfect blend of adventure and relaxation as you island-hop through one of the world’s most beautiful sailing regions.

Sail the Caribbean with a skipper and crew

The islands of Saint Vincent and the Grenadines form one of the world’s most spectacular sailing regions. This chain of tropical islands is known for its laid-back Caribbean rhythm, swaying palm trees, turquoise waters, and white sandy beaches. Along the way you may spot sea turtles, explore small island villages, and experience the warm hospitality of the local culture. Sailing trips in the Caribbean offer a unique way to discover these islands far from the crowds of large resorts.

With an experienced skipper and welcoming host on board, your Caribbean sailing trip becomes a relaxed and all-inclusive experience. The crew takes care of navigation, route planning, and meals while guiding you to new islands and beautiful anchorages each day. Your sailing holiday includes breakfast and lunch prepared on board, a drinks package, accommodation on the yacht, port fees, and other sailing-related costs — allowing you to simply unwind and enjoy the magic of the Caribbean at sea.

What does a typical day on board look like?

MORNING

Waking up on a yacht during a sailing trip in Greece is a peaceful way to begin the day. Start with a refreshing morning swim in the clear Mediterranean water or enjoy a quiet cup of coffee on deck as the harbor slowly comes to life. Soon after, a generous breakfast is served on board and shared together in the cockpit — the perfect start before another day of sailing and island exploration.

MID-MORNING

After breakfast, the skipper gathers everyone briefly to outline the day’s sailing route and highlights along the way. Then it’s time to set sail. If you’re curious about sailing, you’re welcome to get involved — from helping raise the sails to learning a bit about navigation — while those who prefer can simply relax on deck and enjoy the sunshine. As the yacht glides between islands, there’s plenty of time to unwind and take in the beauty of the Greek sea.

LUNCHTIME

As lunch approaches, we stop in a quiet, peaceful bay where we put down anchor for a few hours and enjoy a lunch prepared with local ingredients. There will also be plenty of time for sunbathing, swimming and enjoying your surroundings. Perhaps you’ll take the dinghy out to explore the nearest beach?

AFTERNOON

After lunch, we sail on to one of Greece’s beautiful harbours, towns or villages, where you will spend the night. Some light snacks are served on arrival and the skipper will tell you more about the day’s destination.

Our Destinations

Join our sailing trips in some of the world’s most beautiful cruising regions. During the summer season, explore iconic Mediterranean and Baltic destinations such as Croatia, Greece, Italy, and Sweden. When autumn and winter arrive in Europe, our sailing journeys continue in the warm waters of the Caribbean.

Whichever destination you choose, the experience remains the same — a carefully designed, all-inclusive sailing trip where the crew takes care of the sailing, planning, and onboard hospitality. All you need to do is relax, enjoy the journey, and discover new places at sea.

Your questions answered

Our sailing trips are designed to be simple and mostly all-inclusive, allowing you to relax and fully enjoy the experience at sea. Each sailing trip with a professional skipper and host includes:

A qualified and certified skipper with strong local knowledge and extensive sailing experience
A dedicated host who prepares breakfast and lunch on board, along with a drinks package during the trip
Accommodation in a double cabin on the yacht
Bed linen and towels
Boat-related costs such as port fees, LPG, and diesel

The only additional costs during the trip are typically evening meals ashore and any personal spending for shopping or other purchases during the journey.

Staying on a boat isn’t so different from being at home – the main difference is that there is limited space, water and electricity on board. That’s why it’s a good idea to think about saving water and take shorter showers, especially when you are moored to a buoy or at anchor.

You will stay in a private cabin aboard a catamaran or yacht, depending on which trip you book. Each cabin sleeps two people, so if you’re travelling alone, you will share a cabin with another guest. Depending on the boat model, guests will sleep in either double beds or bunk beds.

All our boats have comfortable beds, a kitchen (galley), showers and toilets, as well as areas for socialising including the cockpit, parts of the foredeck and the saloon inside the boat.

Whilst sailing, you can charge your phone via a 12V power socket. When moored in a marina with access to shore-side electricity, you can charge via a 220V power socket.
Some of our boats have generators – when the generator is running you can use the 220V power socket without being connected to shore-side electricity.
Harbours often have showers and toilets you can use, depending on the destination.

During your sailing trip, the crew ensures everything runs smoothly so you can fully relax and enjoy the experience at sea. The host takes care of meals on board, preparing and serving breakfast and lunch while creating a welcoming and social atmosphere for everyone on board.

Our sailing trips include breakfast, lunch, and a drinks package with water, soft drinks, and wine or beer served with meals. In the evenings, the yacht typically docks in a harbor town or island village where guests enjoy dinner ashore and explore the local restaurants and cafés.

Your host and skipper are always happy to share their favorite recommendations, helping you discover the best places to dine and experience authentic local cuisine along the way.

A sailing trip with a skipper is the perfect holiday if you want to relax and enjoy, but also take an active part in sailing and other fun experiences. The skipper steers the boat, is responsible for safety, and helps to plan the route. Our skippers are not only professionals, they also know where to find the best islands, restaurants and bays for swimming. The skipper sleeps on board the boat but always has their own cabin, and is available whenever needed.

In addition to extensive sailing experience, our skippers hold certifications such as the Coastal Skipper Examination, Boat Skipper licence C and Short Range Certificate (SRC) licence. All our staff undergo thorough training arranged by More Sailing in Sweden and Croatia.

When Is the Best Time to Go Sailing in The Caribbean?

The sailing season in the Caribbean typically runs from December to April, when the weather is sunny, the trade winds are steady, and conditions are ideal for exploring the islands by yacht. Our sailing trips take place in the beautiful waters of Saint Vincent and the Grenadines, a tropical sailing region known for its turquoise bays, palm-fringed islands, and relaxed island atmosphere.

This time of year is considered the dry season, with warm tropical temperatures usually ranging between 24–29°C and plenty of sunshine. Rainfall is generally light and brief, and the risk of hurricanes is very low. These stable weather conditions make December through April one of the best times to enjoy sailing trips in the Caribbean and experience the islands at their most vibrant.

We sail with these yachts

Aura 51

Experience the Caribbean island realm onboard the 50-foot catamaran Aura 51. The yacht is designed for sailing performance with high comfort and boasts large social spaces that simply has to be experienced. The catamaran is equipped with AC in the saloon and cabins as well as a generator which allows you to stay cool even when the boat is at sea.

Number of guests
Six spacious cabins with twelve berths (double beds) for guests along with two skipper’s cabins for the crew. Six shared bathrooms with shower and toilet.

Highlights
Aura 51 is one of the largest boats in our fleet with the highest possible standard.

Which routes do we sail in the Caribbean?

Our sailing trips depart from the lush island of Grenada, often called the “Spice Island” thanks to its fragrant nutmeg plantations and tropical landscapes. Grenada offers a beautiful mix of rainforest-covered hills, white-sand beaches, historic rum distilleries, and refreshing waterfalls.

From here we sail north through one of the Caribbean’s most spectacular cruising grounds – the Grenadines. Throughout the week we adapt the route to the weather and sailing conditions, while always taking your preferences into account.

Along the way we typically explore idyllic islands such as Carriacou, Mayreau, Bequia, and the breathtaking marine paradise of the Tobago Cays.

5-star experiences

"Boon was incredible to work with. I used them to broker a yacht in the Philippines and it was one of the best trips of my life….and I am a frequent traveler with high expectations. Polina is a seasoned professional and responded to all of my requests and questions in lightning speed. The contracting process was painless. It’s rare to receive this level of concierge service these days. HIGHLY RECOMMEND!"

Amber Z.

"Kaarel and Polina were incredibly helpful throughout the whole process. I would definitely book a charter yacht through them again."

Sophie D.

"We had the most amazing experience! Everything went perfectly smoothly from start to finish. The team was incredibly helpful, kind, and genuinely on our side — something that’s rare to find, especially when dealing with the often tricky world of boat rentals. Thanks to Boon Yacht OÜ, we enjoyed the most beautiful trip on a yacht in Croatia, completely stress-free. Their professionalism and personal touch made all the difference. We can’t wait to book our next adventure through them again — highly recommended! ⛵✨"

Epp S.

"We had an amazing experience with Kaarel and Polina providing great ideas and support for our charter"

Meelis K.

"A fantastic sailing trip in Greece with knowledgeable and caring staff. We visited both quiet bays and picturesque small towns. The food on board was very good and varied."

Anna A.

"We just got back from a fantastic week in Croatia with Noah as skipper and Filippa as host.
A truly wonderful experience with fantastic food and beautiful islands.
We have already booked next summer to Croatia again.
"

Niklas T.

"What a fantastic week on the beautiful sailing boat Astrid in Greece.
A trip where we were all completely new to each other but that changed quickly, we have had so much fun and cozy the whole week and Filippa our host and our skipper Håkan contributed with safe sailing, fantastic good food and lots of fun to it. THANK YOU for this super wonderful experience!
"

Astrid T.

"Experienced a wonderful week in the Greek islands with a great crew and great experiences. 😎"

Thomas P.

"The trip to Greece was very successful. Fantastic crew who did everything they could to make sure we had a great time."

James K.

"We are seven friends who had a fantastic trip with a catamaran Excess 11 in Croatia in September 2025. Professional and pleasant Olivia and Emil made sure to exceed our expectations every day. Top-class meals both in terms of flavors and beautiful arrangements. Fantastic views and changing nature, shore excursions. Every day was a new adventure and we could just follow the journey and enjoy. The fact that the weather was also perfect was an extra bonus. A memory for life!"

Margareth T.

"We sailed around the Croatian archipelago on Do-Re-Mi. Sailing interspersed with incredibly good food, drinks, swimming stops, jumps and play. Old and new acquaintances framed the journey to perfection. Last but not least our hosts, Captain Gösta and Linus raised the experience to world class. 5 sails out of 5 possible."

Carl S.

Sailing Trips in the Caribbean

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