caribbean sailing Archives - Venturesail Holidays

One of the many joys of a Caribbean sailing holiday is the opportunity to visit unspoiled, authentic destinations away from the tourist hustle and bustle. Our voyages to the Caribbean aim to visit new anchorages nearly every day, providing fantastic opportunities to experience the islands like never before. Where you anchor can make all the difference to your holiday, and our experienced skippers and crew know the best secret Caribbean anchorages, ensuring you the most enjoyment both from the boat and ashore.

Discover deserted islands lined with rainforests, sail through volcanic bays in the wake of pirates, and dive right off the boat into pristine waters filled with magnificent coral reefs. Although sailing with the wind means no anchorage can ever be guaranteed, we’ve compiled our top ten Caribbean anchorages, beaches, and bays below.
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Les Saintes Bay, Guadeloupe

Eye of the Wind Les Saintes Caribbean — Les Saintes Bay

Les Saintes Bay, named by UNESCO as one of the world’s most beautiful bays, is located in the volcanic island chain of Îles des Saintes, in Guadeloupe. Flanked by 18th century forts, this Caribbean anchorage provides a blend of old world historical charm with quintessential tropical scenes, where coconut trees and white sands abound. The area is renowned for its historical usage by pirates and buccaneers. This is easy to imagine when aboard the traditional windjammer Eye of the Wind, who often finds herself at this picture perfect Caribbean anchorage.
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Loubiere, Dominica

A small bay on the island of Dominica, Loubiere offers easy access to all the main attractions of the island. Anchor close to the shore, where the sounds of Dominican music and singing in the streets will drift across to the boat, tempting you to shore. The bay is a short distance to the main port city of Roseau. Here you can immerse yourself in the colourful local culture, and experience the delights of the local markets.

Aerial view of Roseau, Dominica — Roseau, Dominica

Another highlight of Dominica is the renowned Champagne Reef, a natural wonder sure to leave you speechless. As you snorkel through beautifully coloured coral and fish, bubbling waters erupt from volcanic thermal springs on the ocean floor. When the bright Caribbean sun hits the microscopic bubbles, they crackle and explode in the water like tiny diamonds, hence the name Champagne reef. If you’re looking for a Caribbean anchorage with easy access to snorkelling, local markets, and culture, Loubiere is sure to delight.

Dominica is a potential Caribbean anchorage for luxury classic yachts Rhea and Chronos on their voyages surrounding the islands of Antigua, Dominica and Guadeloupe.
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Tyrell Bay, Carriacou, Grenada

Beach on the island of Carriacou, Caribbean

View of Tyrell Bay, Carriacou, Caribbean

Tyrell Bay lies on the small island of Carriacou, forming part of the country of Grenada. Named the ‘Gateway to the Grenadines’, it’s a popular Caribbean anchorage for our voyages with historic brigantine Florette. Set off from the boat and make use of the onboard kayaks to explore inlets filled with mangrove trees, with oysters living in the dense protective branches. If island exploration is on the cards for the day, hop ashore to journey around the island of Carriacou, perhaps stopping off in some of the infamous local rum bars!
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St George’s Harbour, Grenada

Grenada is home to so many of our favourite Caribbean anchorages that we simply couldn’t resist adding it to the list twice!

Located on the southern end of the island, many consider St George’s Harbour to be the most picturesque Caribbean anchorage and it’s easy to see why. Awaken at sunrise to take in the scenery surrounding the boat, with the island’s rolling green hills dotted with splashes of brightly coloured villages and settlements. Spend the day exploring the island further, swimming in waterfalls, trekking around crater lakes and sampling the local rum. St George’s Bay is a frequent starting point for our Caribbean voyages, and we truly believe there’s no better place to start your sailing adventure in Grenada!
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Pitons Bay, St Lucia

One of the most iconic anchorages in the Caribbean, and a favourite of luxury yachts Chronos and Rhea on their Caribbean sailing holidays. Anchor beneath the ancient volcanic wonders known as the pitons, which dominate the island’s skyline. The bay is part of a protected region that has been designated by UNESCO as a World Heritage Site. As a result, the area is teeming with vibrant marine life, from parrotfish and angelfish to some of the rarest turtles in the world. Soufrière, a laidback, idyllic town with authentic Caribbean charm and appeal, is easily accessible from the mooring.
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English Harbour, Antigua

A natural harbour, with a long naval history as a strategic port, English Harbour lies on the southernmost tip of Antigua. Along with a thriving international boating community, the area is also home to a wide variety of local cafes and restaurants, ready and waiting to tempt you to shore. If relaxation is on the agenda for the day, the plentiful beaches surrounding the harbour make for a great visit. Unwind on the soft white sand as turquoise water laps at your feet, looking out over the lush green mountains that dominate the landscape. Falmouth Harbour is within walking distance and often a starting point for Caribbean voyages with luxury yachts Rhea and Chronos.
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Colombier, St Barthélemy

Only accessible by boat or on foot, the secluded and coveted beach of Colombier is a popular anchorage on our voyages around the island of St Barths. Utter bliss and calm, rugged beauty reigns supreme in this quiet corner of the island. Although there aren’t as many amenities as other anchorages, this simply highlights the varied nature of sailing in the Caribbean. From one day to the next you could be celebrating in busy beachside bars, or unwinding on a seemingly private beach with nothing but the waves crashing at the shore. Due to the island’s volcanic origins, there is an abundance of unique wildlife, as well as many shallow reefs ideal for snorkelling.
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Road Town, Tortola, BVI

Road Town, a bustling harbour and the main hub of the island of Tortola, is a frequent Caribbean anchorage for traditional tall ship Eye of the Wind and historic brigantine Florette. Views of the luxuriantly green surroundings will greet you as you anchor here, and the streets are lined with vibrant restaurants and shops. Enjoy the relaxed atmosphere of the beach during the day, perhaps taking part in some of the water sports available on shore such as snorkeling and scuba diving. As night falls, head to the neighbourhood bars and restaurants, where locals congregate for live music and dancing.
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Cumberland Bay, St Vincent

One of the lesser-known bays in the Caribbean, Cumberland Bay is a popular anchorage for luxury yachts Chronos and Rhea. Situated on the verdant island of St Vincent, this anchorage showcases the very best of the island. A tranquil bay, surrounded by a luscious forest of coconut palms, it is the ideal location to decompress and enjoy the water sports available on Chronos and Rhea. A wonderful spot for swimming in protected waters after jumping off the bowsprit!
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Anse Noire, Martinique

If you’ve seen enough crystal clear waters and white sand beaches, head to Anse Noire on the island of Martinique for a change of scenery. Jade green waters and black volcanic sand make for an anchorage straight out of a dream. A small, secluded cove lined with palm trees, it is a place of reflection and tranquility. Head underwater to get up close with the local marine life, including sea turtles that often visit to rest on the seagrass that lines the bay. A possible stop off the boat for many of our Caribbean voyages, Anse Noir is a must see if the winds allow!
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Find out more about sailing in the Caribbean

If any of theses anchorages have tempted you, find out more about sailing holiday charters in the Caribbean with our extensive fleet. Whether it’s luxury classic yachts Chronos and Rhea, windjammer Eye of the Wind or historic Florette, there’s a Caribbean adventure to suit all!

The Caribbean is regarded by many as the Best Place in the World to holiday. Home to thousands of islands and perfect sailing winds (out of hurricane season of course!) we would have to agree with this… Forget the all inclusive Caribbean resorts and head for an authentic Caribbean adventure on an all inclusive sailing holiday! Sailing trips to the Caribbean should be on everyone’s bucket list, and if you’re still not convinced then here are our top ten reasons for choosing a sailing holiday in the Caribbean!

1. Warm Weather
Temperatures in the Caribbean sit between 23ºC to 30ºC all year long both day and night – so you can ditch those woolly jumpers but don’t forget the suncream! Whilst there’s plenty of time to be spent ashore sunbathing on the beach, one of the best things about yachting in the Caribbean is the gentle ocean breeze as you relax on the deck of the boat.

2. Perfect Sailing Winds
We obviously make sure that our holidays occur outside of the hurricane season! The Caribbean has constant trade winds, averagely blowing at about 15 – 25 knots from the East, most of the year. Dream sailing conditions making island hopping a dream to navigate for our skippers on Eye of the Wind, Chronos, Rhea, and Florette. So whether you’re joining us on a 5* luxury yacht, or on a traditional tall ship, the warm winds make sailing a breeze..

3. Beautiful Beaches
We have all seen the photos of the pure white beaches hugging the islands providing the perfect holiday backdrop. Whilst typical Caribbean beach resorts are brimming with tourist hustle and bustle, our boats can take you to so many “off the beaten track” beaches you won’t know where to look! So whether it’s beaches overlooked by the volcanic mountains of St Lucia, or tropical beach destinations hidden along the shores of Antigua, find your favourite hidden gem beach in the Caribbean (and be sure to let us know!).

4. Wonderful Wildlife
From flamingoes to Sea Turtles, Marmut Monkeys to rare butterflies, the Caribbean is home to a rich and diverse abundance of fascinating wildlife and rare species. One of the benefits of a sailing holiday in the Caribbean is the proximity to marine wildlife. From our boats, you can swim with dolphins and sea turtles, snorkel with tropical fish in beautiful coral bays or even rent a diving suit at a local village and explore the shipwrecks. Whatever island you visit, rest assured you won’t be short of wildlife spotting opportunities.

5. Crystal Clear Waters
Low water density and lack of industry make for fantastically clear waters so swimming and snorkelling are top of the list for activities! And not only are they crystal clear but the average water temperature is also 27ºC – it’s like swimming in a lovely bath! Many of our voyages are able to take in the world class snorkelling destinations in the Caribbean, including the reef-lined Bequia Island or the under-water world of Tobago Cays.

6. Thousands of Islands
The Caribbean is made up of thousands of islands and with so much to explore, you’ll be longing to return for more from the moment you arrive. A skippered sailing holiday is the best way to experience as many islands as possible, with each mainland wonderfully culturally different from the next.

7. Fabulous Food
Traditional Caribbean food is a fabulous fusion between African, European, East Indian and Chinese cuisine. Your all inclusive Caribbean vacation starts with our on board chefs, who will certainly make sure that they are hopping ashore to grab the local delicacies to cook up a feast for your dinner. The seafood is especially fresh and the spices available will be like nothing you have tasted before. And of course, you must try the Caribbean rum!

8. Colourful Caribbean Culture
From the beautiful timber buildings to the local festivals to the wildlife, there are so many ways in which the Caribbean is full of colour. It would be impossible to choose the best Caribbean islands to visit, with each having its own unique community and culture. A sailing holiday in the Caribbean allows you to soak in as much culture as possible on your tropical vacation! The festivals reflect the rich and cultural diversity of the islands and if you catch one, you will be in for a once in a lifetime experience!

Tobago Cays Caribbean unsplash — Sea turtle

underwater sculpture Caribbean — Sea turtle

9. Interesting History
The Caribbean is steeped in colonial history with each island seemingly worlds apart from the next. The BVI is home to many pirate stories and shipwrecks while the Dominican Republic, Antigua and Barbuda are full of historical and archaeological places of interest for those who love to sniff out a bit of history. A skippered sailing holiday to the Caribbean means you have built in tour guides in the form of our experienced crew who will be more than happy to make recommendations on all the top sights and hidden gems.

10. The Caribbean People
Whatever island you visit, you will find the (majority!) of locals to be friendly, happy-go-lucky and amazingly laid back. As you anchor from one port to the next be sure to befriend the locals, as they know all the best hidden gems of the area. They really do make your Caribbean sailing holiday experience a relaxed one!