Exclusive sailing trips in the Caribbean
Sailing at the highest level: experience the Caribbean aboard our elegant yachts — with first-class service, exquisite cuisine and a feeling of boundless freedom.
Caribbean: all sailing trips-
Modern, luxurious yachts with the highest level of comfort
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Small groups & personal atmosphere
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Private chef & experienced crew
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Sailing trips to the most beautiful bays in the Caribbean
Our sailing areas in the Caribbean
Island hopping from Antigua
Antigua is the classic among the Caribbean sailing areas and combines relaxed sailing with a remarkable density of dream beaches: the island is said to have 365 powder-white bays and wild beaches. A small paradise for every day of the year, and thanks to the short distances you will discover many of them at your ease. Combined with island hopping to Barbuda and the neighbouring islands, you can look forward to unspoilt Caribbean flair and picture-book nature. The steady trade winds and sheltered anchorages make for ideal sailing conditions.
Martinique, Guadeloupe and Dominica – Caribbean worlds full of contrast
On a sailing trip in the eastern Caribbean around Martinique, Guadeloupe and Dominica, dense rainforest, hot springs and volcanic landscapes meet a distinctly French way of life. That contrast between European influence, Caribbean ease and lush tropical nature is what makes sailing in this region so appealing, and it makes for a particularly varied time ashore and on the water. Stronger trade winds and longer legs between the islands also give the area a sportier character than many other parts of the Caribbean.
From bay to bay in the turquoise paradise of the British Virgin Islands
The British Virgin Islands (BVI) are one of the most relaxed sailing areas in the world and therefore ideal for beginners. Thanks to sheltered waters, generally calm seas and constant, moderate trade winds, you can enjoy comfortable island hopping over short distances and mostly sail within sight of land. The route passes turquoise lagoons, white sandy beaches and tropical vegetation. Shore visits to islands such as Jost Van Dyke — famous for its laid-back beach bars — or to “pirate island” Norman Island make for unique Caribbean moments.
Discovering the unspoilt Caribbean from Grenada
Genuine Caribbean feeling, quiet anchorages and particularly varied days: that is what island hopping around Grenada and the Grenadines up to St Lucia in the north-east of the island chain stands for. On a trip through the southern Windward Islands, the Caribbean shows its most authentic side. Look forward to striking volcanic landscapes, deserted beaches, spectacular snorkelling spots and colourful coral reefs in crystal-clear water. The legs are a little longer than in other areas, but the reliable trade winds make them easy to plan and guarantee intense sailing amid the singular nature of the Caribbean.
Sailing vacation and island hopping in the Caribbean
Sailing in the trade winds – under the Caribbean sun
The tropical islands of the Lesser Antilles, which stretch in a wide arc from the BVIs in the north to Grenada in the south, are among the best sailing areas in the world. Under the Caribbean sun and constant trade winds, you can experience sailing trips here with the large, elegant yachts from Sailing-Classics, which are specially designed for these conditions. With their size, our yachts offer plenty of space, comfort and freedom of movement on board – at the same time they are slim and maneuverable enough to anchor in sheltered bays. Hardly any other area offers such stable wind conditions: The trade wind blows reliably on around 9 out of 10 days and ensures real, steady sailing (we only sail in the Caribbean outside the hurricane season).
The Caribbean in all its facets
The distances between the islands are ideal for sailing trips of 4 to 6 hours. The islands themselves are extremely diverse, from steep volcanic landscapes to coral islands and reefs. What they have in common is the Caribbean vibes, the cheerfulness of the inhabitants, the omnipresent reggae and the tropical nature that often grows almost vertically up volcanoes. It is a paradise that makes many people never want to leave.
The ultimate Caribbean adventure
When sailing at sea, we can often see shoals of flying fish, frigate birds being carried upwind in front of the masts and occasionally whales such as humpback whales or sperm whales, which catapult themselves spectacularly out of the water. Turtles and many fish can often be seen at anchor (even at night with a flashlight). The starry sky at night, the short but intense downpours – all this makes a sailing vacation in the Caribbean an unforgettable experience.
Your sailing trip - optimally planned
Still not sure which sailing trip suits you best? Our experts will take time for you, answer your questions and work with you to find the perfect route. Simply arrange your personal consultation – free of charge and without obligation.
Stylish sailing for beginners and experienced sailors
Follow the call of the wind with a maximum of 26 guests, experience the beauty of sailing, anchor in idyllic bays, discover picturesque islands, explore charming harbor towns and glide through crystal-clear waters. With a bit of luck, you may even spot dolphins and whales. If possible, we sail 4-6 hours a day.
- Exclusive atmosphere & conviviality in a small group
- Fantastic sailing areas with unique harbors & bays
- Classic yachts with high comfort & premium service
Best time for a Caribbean sailing trip
Lots of sun, little rain and pleasant winds: the months of December to April are ideal for sailing in the Caribbean. This is the dry season and paradise welcomes you with low humidity and pleasant daytime temperatures between 25 °C and 29 °C.
In May, it becomes more humid, the winds weaken and become more irregular and the rainy season announces itself, which makes sailing in this month a little more challenging. In June, the hurricane season begins in the Caribbean, so Sailing-Classics does not offer any sailing trips during this time until the end of November.
| Month | Air temperature | Water temperature | Rainy days | Wind |
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| December | 26–28 °C | 27 °C | 8–10 | 15–20 kn |
| January | 25–27 °C | 26–27 °C | 5–8 | 15–25 kn |
| February | 25–27 °C | 26 °C | 5–7 | 15–25 kn |
| March | 26–28 °C | 26–27 °C | 4–6 | 15–25 kn |
| April | 27–29 °C | 27–28 °C | 4–6 | 12–20 kn |
Escape the European winter and discover the beauty of the Caribbean at the best time to travel – exactly when the sailing experience is particularly pleasant.
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Caribbean sailing in December
- December is suitable for all those who want to soak up the sun in winter and enjoy good, stabilizing wind conditions (“Christmas winds“) want to start the sailing season. At the end of the year, the Caribbean ports are bustling with activity as many sailors arrive after crossing. Our Christmas and New Year’s Eve voyages are very popular with our guests.
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Sailing trips in January and February
- January and February are perfect for Caribbean sailors who want maximum reliability: constant, gradually freshening trade winds, very little rain and optimal conditions for classic sailing trips. In February, visibility is particularly clear, so there is plenty to discover underwater during our mostly daily swimming and snorkeling stops.
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To the Caribbean in March and April
- March probably offers the best combination of stable winds, sun and pleasantly warm temperatures – ideal for sailing enthusiasts who want to get the most out of their Caribbean vacation. In April, at the end of the main season, it gets a little warmer & calmer. This time suits guests who want to enjoy relaxed sailing with a little less wind and more serenity.
Which Caribbean destination suits you?
The Caribbean has a very special magic, which makes choosing the right sailing trip not so easy. The good news is that there is no wrong decision. Which sailing area suits you best depends on your personal preferences.
If you want to combine classic sailing with maritime history and beautiful beaches, you are in the best of hands in and around Antigua. You can experience the most pristine side of the Caribbean along the Grenadines with their partly untouched nature. If you want to sail off the beaten track, this is the place for you.
The area around Martinique will delight anyone who wants to combine French culture, Creole cuisine and varied sailing. And the British Virgin Islands are ideal for beginners who appreciate calm waters and relaxed island hopping.
What you can expect on a Caribbean sailing trip with Sailing-Classics
A Caribbean sailing trip is much more than just a vacation, but an intense travel experience where deceleration, comfort and a wonderfully free feeling at sea come together.
Your day in Caribbean waters begins with breakfast on the spacious teak deck with a view of the endless turquoise blue expanse. Freshly fortified, you then sail for a few hours. Keep an eye out for animal companions such as frigate birds, turtles or even humpback whales along the way before you head for a new bay to anchor for a swim break after a light lunch or delve deeper into Caribbean life on a shore excursion.
For dinner, it’s back on board, where Caribbean-inspired delicacies are freshly prepared for you. Sample a three-course menu and look forward to freshly caught fish and creative fusion cuisine that combines Mediterranean lightness and Caribbean sophistication. When the endless starry sky stretches over your yacht after dinner, the Caribbean will begin to cast its spell over you.
With a maximum of 26 guests, who often become friends, and an attentive crew of 10, a very personal atmosphere is created on board. Traveling under sail is a sustainable and natural way to discover the Caribbean. The wind is the most important driving force, and when anchoring, great importance is attached to the respectful treatment of sensitive ecosystems such as coral reefs.
Journey to the Caribbean
The Caribbean is easily accessible from Germany, Austria and Switzerland. Depending on the destination, with a transfer or, in some cases, directly. For sailing trips from Antigua, there are seasonal direct connections from Frankfurt. Martinique is particularly easy to reach via Paris, from where there are several non-stop connections to Fort-de-France.
There are currently no direct flights from Europe to the British Virgin Islands. Connections via San Juan (Puerto Rico), St. Martin or Antigua have proved successful; from there, a regional flight continues to the BVIs.
Grenada is well connected from Europe, especially via London; there are seasonal connections several times a week with a short stopover in Barbados. Depending on the departure point and destination, you should generally allow around 11 to 16 hours (including transfers) for the journey. In the British Virgin Islands, the onward journey may be slightly longer due to additional island transfers.
When planning your trip, also bear in mind the time difference. Depending on the time of year, the Caribbean is five to six hours behind Central European Time.
What our guests say
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Every wish read from the eyes
5 stars +
The crew really read every wish from our eyes. The food was excellent... If I had to award stars for cuisine and service, it would be 5+. .. We had a lot of fun!!!
Read the full review
Isabella after the Christmas and New Year's Eve cruise on the CHRONOS in the GrenadinesIsabella -
Wonderful and full of experiences
A great pleasure
I would like to express my great pleasure at having taken part as a passenger in the wonderful, eventful and indeed exhilarating voyage with the RHEA on the occasion of the Antigua Classic Yacht Regatta 2025. Even a few days later, it was a trip that I will remember for a very, very long time.
Read the full reviewMatthias after the Antigua cruise on board the RHEA -
I have rarely eaten so well on board
A new, very enjoyable and luxurious sailing experience
As a long-time sailor and skipper on self-chartered yachts, I wanted to get to know a larger sailing yacht and not have to take care of everything myself.
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It was a wonderful trip of around 200 NM from Martinique via Domenica, Les Saintes, Guadeloupe to Antigua. A varied trip in all weathers with gusts and rain showers, a short night trip but also lots of sunshine and occasionally in the company of curious dolphins circling around the bow. In between, there were various shore excursions and an interesting bus trip across the island of Domenica, including a visit to a waterfall and getting to know the local cuisine. Of course, there was also enough time to swim in the wonderfully turquoise blue, clear but warm sea water before breakfast or to go to a bay to snorkel extensively and admire the still quite intact underwater world. In particular a giant tortoise and, among other things, a wonderfully turquoise-colored parrotfish.
The international crew of ten looked after the ship and us as guests in a relaxed and friendly manner. I have rarely eaten so well on board. The chef not only provided a delicious lunch every day, but also a varied 4-course menu for lunch. It was unbelievable what he conjured up in his kitchen.
The first officer offered to answer any questions we had. Occasionally, under his guidance, we were also able to operate the winch to hoist or lower the sails. Of course, we were also lucky that there were only 13 guests on the ship, so we had plenty of space above and below deck.
All in all, a new, very enjoyable and luxurious sailing experience.Kai after his journey from Martinique to Antigua
Experience Caribbean joie de vivre under white sails
Discover our sailing trips through the Caribbean – stylish, authentic, unforgettable
We have the answers for you
Important information
You don’t need any sailing experience for a Caribbean cruise, as there is always an experienced crew on board. However, if you would like to join in as an experienced sailor, you are very welcome to do so.
Sailing-Classics offers various sailing trips, which usually last between 7 and 10 days, occasionally longer. Various sailing trips are offered from December to April. Simply choose the date and route that suits you best.
A Caribbean trip on one of our yachts is very suitable for solo travelers. Thanks to the personal atmosphere on board with a maximum of 26 guests and shared moments such as sundowners or dinner in the evening, there is plenty of opportunity to get in touch with fellow travelers.
The cabins on board the yachts from Sailing-Classics are luxuriously furnished and combine classic yacht style with modern comfort. On the CHRONOS, KAIRÓS and RHEA you can expect spacious double cabins with en-suite bathrooms.
All cabins have individually adjustable air conditioning, shower and WC, closet, hand and bath towels, hairdryer and 230-volt sockets. Depending on the category, the beds can be used flexibly as double or single beds. Daylight enters the cabins through portholes, which serve as comfortable retreats after a day at sea.
The price of a sailing trip with Sailing-Classics includes the sailing experience with flexible shore excursions depending on the weather, as well as a large part of the experience on board. This includes accommodation in your booked cabin, support from the experienced crew and daily catering with freshly prepared meals on board. Water, tea and filter coffee are also included, while other drinks (such as alcoholic beverages) are charged separately.
Not included in the tour price are arrival and departure, transfers and personal expenses on land. A detailed overview of services can be found on the respective tour pages.
Sailing-Classics takes you to the Caribbean beaches at the best time of year. Sailing trips in the Caribbean take place between December and April, when the temperatures are pleasantly warm, there is less rain, the air is less humid and the wind is particularly stable.
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