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Yachts in the warm waters of the Caribbean, close to the beach and greenery-covered cliffs

Sail in the Caribbean

Tropical, untouched and unforgettable

Make holiday memories

Sailing trip in the Caribbean

Sailing in the Caribbean with a skipper is the ultimate way to enjoy the tropical island world. There’s no need for any sailing experience because a certified skipper takes care of everything from sailing to route planning. In other words, you can sit back and enjoy the many experiences of an exotic and relaxing sailing trip through one of the Caribbean’s most beautiful sailing areas.

More Sailing’s catamaran out on the tropical water
Guests sitting on the boat’s sunroof enjoying the view over the water
Beach in front of a restaurant, 8 striped parasols and a couple walking by the water.
Deluxe fruit platter with orange, melon and strawberries. Two glasses of juice to the side.

More than 15 years in the industry

Qualified Swedish skippers

Transparent, fully inclusive package

Sailing trips for all

Sail the Caribbean with a skipper and crew

Saint Vincent and the Grenadines belong to one of the world’s most beautiful sailing areas consisting of a string of islands. You’ll be met by the rhythm of reggae, swaying palms, turquoise water, sea turtles, white beaches and friendly locals. A sailing trip in the Caribbean is an extraordinary experience – a unique experience far away from mass tourism.

Our experienced skipper and host will guide you to new destinations every day, taking care of everything from sailing to planning and meals. This means you can enjoy a relaxing all-inclusive sailing holiday in the Caribbean. A skippered sailing holiday always includes breakfast and lunch, a drinks package, accommodation aboard the boat, port fees and other sailing costs.

Host cooks burgers on a griddle by the bathing platform on the yacht

Sail in the Caribbean

Your questions answered

What is included in a sailing trip?

Every sailing trip with a skipper and host includes:

  • Qualified and certified skipper with local knowledge and extensive sailing experience

  • A host who serves breakfast and lunch, including a drinks package on board the boat

  • A berth in a double cabin on the boat

  • Bed linen and towels

  • Other boat expenses such as port fees, LPG and diesel

  • Also included in our sailing trips are return flights from selected airports and return transfers from the airport to the marina

Additional costs for you as a guest are evening meals ashore and spending money for any shopping or other purchases during the trip.

What’s it like to sail with a skipper in the Caribbean?

A sailing holiday with a skipper in the Caribbean will suit you if you’re looking for a holiday that combines activity and relaxation. The skipper steers the boat, is responsible for safety, and helps to plan the route. Of course, you can take part in the sailing as much or as little as you want, and if you have any route requests, feel free to share them with us. 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.

What’s it like having a host on board?

On board the boat you are in safe hands with the crew; they take care of everything and make sure you’re having a good time. Meals on board the boat are prepared and served by the host, so you can relax and enjoy the trip. Our sailing trips always include breakfast, lunch and a drinks package (water, soft drinks, wine/beer with meals). You will eat dinner ashore in the harbour towns and villages we arrive at in the evenings, and these are at your own expense. Don’t hesitate to ask for tips on the best local restaurants – we’ll be happy to share our favourites!

What’s it like to stay on board one of our boats?

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.

What is the difference between a catamaran and a yacht?

On our sailing trips you can choose between two different types of boat – yachts (monohull boats) and catamarans. A yacht offers more of a classic feeling of sailing as the boat tilts and the sailing is generally better. A catamaran is more stable, has larger social spaces and is often better suited to larger groups or families who prioritise relaxation and socialising over sailing. Whichever boat you choose, an exciting and eventful journey awaits! Our boats accommodate between 8 and 10 guests, depending on the model.

Who are the other guests onboard the boat?

We understand that it can feel strange not knowing who the other passengers are, but there is no need to worry. Our guests are a wonderful mix of inquisitive travellers who have chosen to take a sailing trip together with other people. We welcome people of all ages on our sailing trips but we also offer specific holidays for seniors, solo travellers or with a focus on exercise – you’re sure to find the perfect trip for you.

What should I pack for a sailing trip?

Packing for a sailing trip is much like packing for any other holiday in the sun. Keep in mind that sunlight reflects off the water around the boat, so it’s a good idea to bring extra sun cream or a shirt/sarong and good sunglasses. Make sure you also pack a soft bag you can easily fold up and put away on the boat; hard cases take up a lot of space in the cabins.

Good to have with you:

Sunglasses
High SPF sun cream
Hat or cap
Swim shoes or sandals
Shoes for wearing on board the boat should only have light-coloured or white soles, though it’s always best to go barefoot
Insect repellent
A few swimming costumes
Books and games
Snorkelling equipment
Seasickness tablets (if you tend to get seasick)
Light raincoat or windbreaker
Spare beach towel (one towel per person is provided. Sheets and pillowcases are also included)


Psst: It’s a good idea to pack a change of clothes in your cabin bag in the unlikely event that your checked luggage is delayed. It may be useful to have a few clothes, swimsuits and a toothbrush in your cabin bag.

Do I need to be able to sail before I go?

No, you don’t need any previous sailing experience to join our sailing trips. We welcome everyone – regardless of your previous experience – and we make sure that you feel safe on board our boats. An experienced skipper is responsible for sailing the boat and, as a guest, you can participate as much or as little as you want. Take the opportunity to learn more about navigation, hoist the sails and practice tying knots – or enjoy the surroundings on the foredeck, with a good book and pleasant company.

What about insurance and cancellation if something happens?

You can find more information about insurance and what happens in the event of cancellation in our travel terms and conditions.

Can I hire a stand-up paddle board (SUP)?

If you want to, you can hire a SUP for your boat. Let us know and we’ll see what’s available!

Do I need to carry cash when travelling to the Caribbean?

When travelling to the Caribbean, it’s a good idea to bring some cash to pay in restaurants etc. Where we sail, the official currency is the East Caribbean Dollar (EC$). It is possible to withdraw cash at the destinations, but it will probably be cheaper to exchange currency before departure.

What’s sailing in the Caribbean like?

Sailing in the Caribbean is something special. Sail around tropical islands, swim with turtles and enjoy the wonderful warm breeze and delicious food. It’s an adventure like no other. It’s a great choice for everyone, from families with children to groups of friends.

Life on board

What does a typical day on board look like?

When is the best time to go sailing in the Caribbean?

Sailing season in the Caribbean runs from December to April when the weather is sunny and pleasant and the winds are stable. We sail in the St Vincent and the Grenadines area, an island realm which offers a varied sailing experience in a tropical climate. The period between December and April is called the dry season with sun and pleasant tropical temperatures (approx. 24–29°C). During this period there is less risk of rain and hurricanes – but it’s good to be prepared for short showers even at this time of year.

  • Temperature

    Between 24°C – 29°C+ during December to April

  • Season

    December to April

  • Wind

    Stable prevailing winds Dec – April Hurricane season June – Nov

Average temperatures in the Caribbean

7 people with pirate hats and eye patches

“I was surprised that it was so untouched and unexplored! It felt like Thailand in the 90s.”

The boats we sail in the Caribbean

Luxurious 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.

Aura 51, luxurious catamaran with large spaces. Two women sitting comfortably on the foredeck.

Which routes do we sail in the Caribbean?

Our sailing trips depart from the lush island of Grenada, also known as “The Spice Island”. Grenada boasts tropical rainforests, white sandy beaches, rum distilleries and refreshing waterfalls. From here we sail north through one of the Caribbean’s most beautiful sailing areas – the Grenadines. During the weeks we adapt the route to the weather but we are happy to listen to your thoughts and wishes. Examples of islands we often visit are Carriacou, Mayreau, Bequia and Tobago Cays.

What our guests say

Would you rather be at the helm yourself?

Hire a yacht in the Caribbean

Would you prefer to book a bareboat charter and discover the Caribbean for yourself? Here at More Sailing we hire out monohull boats and catamarans in two of the Caribbean’s most attractive sailing areas – Saint Vincent and the Grenadines and the British Virgin Islands.

Catamaran moored in turquoise waters
Choose from More Sailing’s selected boats

No Caribbean trips available – see our other destinations!

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