Caribbean – Martinique
Wohin geht’s?
Alle Segeltörns • Alle Reviere • Wann
Find sailing type
Choose a destination
Book a vacation
Sailing Trip Caribbean – Join a Sailing Adventure with sailwithus
Exotic Sailing Holiday Caribbean…
White sand, blue lagoons, vibrant coral reefs – welcome to the tropical paradise of the Caribbean! Your sailing trip is one of the most beautiful experiences ever: You snorkel in warm waters as turtles and colorful fish swim around our yacht. Discover more of it!
What our customers say
Possible Sailing Routes in the Caribbean
Cruise character
Suitable for beginners
Nature
Places of interest
Distribution port/bay
CARIBBEAN | 2025
“A dream sailing holiday in the Caribbean!” The two-week sailing holiday in the Caribbean was simply fantastic! “I thoroughly enjoyed my time onboard, especially because the group and our skipper, Dankrad, were a perfect match. It was a wonderful mix of relaxation, adventure, and fun. The planned route was diverse and well thought out, but it was great that we had the flexibility to sail to other bays if we didn’t like a particular spot. What I found especially impressive were the planned stops at local places to support the region – both through shared meals and donations for rebuilding after the hurricane. It was a great feeling to be part of this initiative. Dankrad was an outstanding skipper: responsible, competent, and always ensuring that we felt safe. At the same time, we had an incredible amount of fun onboard with him – whether through engaging conversations, shared activities, or simply enjoying the time together. I always felt well taken care of on the boat. This was already my third trip with sailwithus, and I can highly recommend it! The next trip is already booked – I’m already looking forward to it. Thank you for this unforgettable experience!”
Insight into the sailing route
The sailing trip starts in Martinique, where the crew meets and stocks up on provisions. On the second day, they sail to Marigot Bay on St. Lucia, known for its beautiful sunsets. Next, they head to Port Vieux Fort and Maria Island, before reaching the Blue Lagoon on St. Vincent on day four. The fifth day takes them to the Tobago Cays for snorkeling. After a relaxing day on Union Island, they visit Carriacou. On the eighth day, they briefly return to Martinique before heading back to the Tobago Cays. They visit the private island of Mustique and Bequia, home to a whaling museum. On St. Vincent, they explore its botany and beaches. After one last night in Martinique, the sailing trip concludes.
Possible Itinerary for the Caribbean Tour: Discover the Sailing Trip!
DAY 1 – Saturday
On Saturday afternoon, everyone will be there between 2:00 PM and 4:00 PM. A few of your fellow sailors have already arrived a day earlier. Today, you’ll prepare for your sailing holiday together. This includes grocery shopping at the supermarket. You head out with part of the crew. After 5:00 PM, you’ll board the yacht and assign the cabins. In the evening, you’ll gather for a small get-to-know dinner at a restaurant. In the Caribbean, boarding the yacht on the arrival day is possible, but the technical check-in always takes place the following morning. Therefore, departure before 12:00 PM on the next day (on our trips, Sundays) is usually not possible.
DAY 2 – Sunday
You can’t wait: “Lines loose!” to your first destination, Marigot Bay in St. Lucia. Every evening, you’ll enjoy a perfect sunset here. The location became famous through the film scenes of Dr. Dolittle in the 1960s.
DAY 3 – Monday
Every day is different. Today, the sailing route continues south to Port Vieux Fort. Here, you’ll find a unique fish market with fresh fish at great prices. If we want, we can also visit the small island of Maria Island. But be cautious, it’s a nature reserve, so we leave no traces behind.
DAY 4 – Tuesday
Sailing in the Caribbean feels amazing. As a beginner, you’re now gaining your first sailing experience with the Caribbean wind. From a distance, you can see the 1,467-meter-high volcano with its forested slopes on St. Vincent. You anchor in the Blue Lagoon, a protected and beautiful bay on the southern side of the island.
DAY 5 – Wednesday
Today, you’ll sail to the Tobago Cays archipelago. Five islands lie like green dots with white borders in the turquoise water. Everywhere you look, there are turtles and exotic fish. You anchor in the lagoon between the islands, where a coral reef blocks the waves from the Atlantic. This is one of the reasons why the lagoon is such a perfect spot for anchoring, swimming, and snorkeling.
DAY 6 – Thursday
Union Island, the bay or harbor of Clifton, is on your itinerary. The journey takes about two and a half hours. The yacht is safely anchored. Now you can decide: a walk on the island to the viewpoint and enjoy the view over the bay, or would you rather jump into the water and then relax on deck? These are the questions you’ll be facing on your Caribbean sailing trip.
DAY 7 – Friday
Sailing in the Caribbean takes you to a different beautiful island every day. Today, you’re heading to the stunning island of Carriacou, the sister island of Grenada. This gem in the Lesser Antilles is known for its coral reefs and shallow, clear waters. Absolutely postcard-worthy! As you approach the island, you’ll quickly realize that the famous images on the postcards are no exaggeration.
DAY 8 – Saturday
Another beautiful sailing day is recorded in your logbook. On the eighth day, you’ll sail from Clifton and Union Island to the Tobago Cays. A day full of new impressions awaits you.
DAY 9 – Sunday
Once again, you sail to the paradise-like Tobago Cays. Once again, you enjoy the beautiful lagoon between the uninhabited islands, snorkel with colorful fish among the reefs, swim, daydream, and relax. Just be mindful of the current, your skipper advises. A walk on the beach? Sounds great. You’re eager to try it and experience the feeling of being on a secluded island.
DAY 10 – Monday
What a surprise! Today, your sailing trip even takes you past Mick Jagger’s house. So off you go to Mustique Island, a jet-set island of about six square kilometers. It is privately owned. Known for its luxury and seclusion, it is a favorite spot for celebrities. Besides Mick Jagger, Bryan Adams, Tommy Hilfiger, Princess Margaret, and many others have visited this island.
DAY 11 – Tuesday
Bequia, you know, the “Island of Clouds.” You anchor in Admiralty Bay, the bay in front of the capital, Port Elizabeth. Everywhere, there are sights to see. Are you in the mood to visit the whaling museum? It’s worth a visit, as Bequia was once an important whaling station. You can also head to the east side of the island to visit the “Old Hegg Turtle Sanctuary,” a turtle breeding station.
DAY 12 – Wednesday
St. Vincent offers many ways to spend your day individually. Perhaps visit the Botanical Garden in Kingstown or the Fort? Or go for a longer hike? The Vermont Nature Trail, for example, takes you through the rainforest, home to exotic birds. Or would you rather relax on the beach and enjoy the sea with a cocktail in hand from your lounge chair?
DAY 13 – Thursday
Your sailing trip shows you much of the Caribbean island world. And sailing in the Caribbean truly lives up to its name: You only need to use the engine when searching for an anchorage. This way, you can fully enjoy the journey to the sound of the waves. Today, there’s one more stop. For those who want, dive into the nightlife and experience the hot Caribbean rhythms in the bars.
DAY 14 – Friday
Your Caribbean sailing trip is coming to an end. However, you don’t let departure feelings distract you and continue to fully enjoy the stunning nature. On deck, you can hear paradise birds chirping from all sides and delight in their presence until it’s time to set sail. You head towards Martinique and make a swimming stop at lunchtime. The sun shines until late in the evening, and you watch it disappear on the horizon.
DAY 15 – Saturday
Your dream holiday in paradise, your sailing journey in the Caribbean, has come to an end: By 9:00 AM, you’ll leave the yacht and begin your journey home.
Your route
Gallery Sailing trip Caribbean
Sailing in the Caribbean – What’s Included in Your Yacht Charter:
You’re traveling with like-minded people because you all share one thing: the dream of a sailing holiday in the Mediterranean. Your crew is young and a lively mix of complete beginners and experienced sailors. What matters most to you is simple, stress-free planning and preparation.
On sailwithus sailing trips you are always traveling sustainably. We encourage our fellow sailors to do a beach clean up once on every trip so that we can do our bit to preserve the beautiful areas in which we sail. Join us and experience your dream vacation without a guilty conscience. If you want more information about sustainability with us, click here.
Especially for this sailing trip
What is not included?
Example yacht
Learn More About Sailing in the Caribbean
Arrival and departure
With a flight, you’ll go directly from the cold of Germany to paradise. Your destination airport for the Caribbean sailing trip is Martinique. From there, you’ll head to the harbor, either by taxi or minibus. The minibus is much cheaper. When you leave the airport building, be sure to ask where the minibus is heading – this way, you’ll definitely get to the harbor. Ideally, you’ll arrive at the marina between 2:00 PM and 4:00 PM, but a later arrival is also fine. Through the WhatsApp group we set up in advance, you can already get to know your fellow sailors. You’ll also receive detailed harbor information from us before your trip starts.
For departure, your yacht will return to the harbor in Martinique between 3:00 PM and 6:00 PM on Friday. Enjoy the last evening together, and then disembark the yacht by 9:00 AM on Saturday.
Sailing the Caribbean: Off to Paradise!
The island world of the Caribbean is something you should experience at least once in your life. And the best way to do so is by sailing on a yacht.
Whether it’s Martinique, Tobago, or the Caribbean dream of Saint Lucia – the sailing area with its many stunning islands is so incredible because you can sail it year-round thanks to the warm temperatures. However, the best time for sailing in the beautiful Caribbean waters is from November to April. Not least because the warm waters are home to a variety of exotic creatures. Perhaps you’ll be one of the lucky ones and encounter a sea turtle or the exotic “brain coral” while snorkeling.
Another reason for sailing in the Caribbean is the constant trade winds, which allow you to set sail whenever you want. In the Caribbean, you can truly call it sailing. You only need to use the engine when you or your crew, along with the skipper, are searching for an anchorage. This way, you can fully enjoy your journey to the sound of the waves.
Sailing Trips Caribbean – Join a Sailing Adventure with a Skipper on Board
Whether it’s your “first time” on a ship or you’re one of the “old hands” when it comes to sailing holidays in the Caribbean – it’s always a surprise to see who else is on board. You essentially live together! This means: all tasks on board are done as a team.
While sailing, everyone masters their tasks, and in the evening, you either cook together or visit a local restaurant. You won’t believe it, but cooking is especially enjoyable because the Caribbean markets offer ingredients you can’t find in Europe or anywhere else in the world. One popular item is salted fish, once a slave meal. Fish and shellfish play a major role in Caribbean cuisine. You’ll likely be surprised by the wide variety of local chili peppers, such as the very hot Habanero or the Scotch Bonnet. Common side dishes include rice, sweet potatoes, manioc, yams, as well as okra and beans. Occasionally, local wild animals like iguana or agouti are also consumed. Your island hopping in the Caribbean will surely leave you with culinary memories.
Baltic Sea, Mallorca, or Croatia? Make it easy for yourself: Welcome to the Caribbean!
Sure, Corsica, Sardinia, and Greece have it too: plenty of sun. But white, dreamy beaches with palm trees, emerald-green waters at bathwater temperatures, and a unique underwater world? Well, that’s something only the Caribbean offers. So, off you go! At sailwithus, we offer you sailing holidays like this: the trip starts from Martinique or sometimes from Guadeloupe and heads south to Grenada, exploring the beautiful Caribbean islands. As mentioned, the tropical climate is one of the main reasons to choose the Caribbean for your sailing adventure. Yacht charters are possible year-round, and at an affordable price. After all, the average annual temperature in the Caribbean is 30°C – and that guarantees you’re making the right choice for your sailing trip! The best time, however, is from November to May, outside of hurricane season. Imagine: swimming and snorkeling in the sea and a cove on a beautiful island, while at home, it’s either raining or snowing in the fall or winter. Simply unbeatable!
Sailing in the Caribbean in the Lesser Antilles – always with wind
When you book your sailing trip in winter, the trade winds blow in the Lesser Antilles. This is a very steady wind that allows you, as a crew member on a cabin charter, to set sail every day. The islands that particularly benefit from the northeast trade winds are the so-called Windward Islands. They are also known as the Islands Above the Wind, located north of Grenada. This island chain and its many islets include Antigua, Guadeloupe, Martinique, St. Lucia, Barbados, Grenada, Trinidad, and Tobago. Then, there are the Leeward Islands, including Aruba, Bonaire, Curacao, and Isla Margarita. Sailing in the Caribbean means, in addition to relaxing, enjoying culinary delights, and Caribbean music, that you’ll also gain a lot of sailing experience and nautical miles.
Climate and Geographic Information of the Caribbean
A few more important details for your week in this dream sailing destination. First, a bit about geography: The Caribbean is located in the Atlantic Ocean, north of the equator, and is part of the Central American subcontinent, consisting of the islands and island groups in and around the Caribbean Sea, along with the area between them. The island world is shaped by a tropical rainforest climate.
The Caribbean sailing area is divided into two regions: First, the Greater Antilles, which include the Bahamas, Cuba, Jamaica, Haiti, the Dominican Republic, and Puerto Rico. These large islands are part of the Greater Antilles. Then, there are the Lesser Antilles, the island chain in the eastern Caribbean, which sailors from all over the world love to visit to experience the unique Caribbean island charm.
In addition to traditional fishing villages, the active experience is completed by a pristine rainforest on Dominica, as well as stunning beaches and bays like those in the Tobago Cays, which belong to St. Vincent and the Grenadines, or in Antigua. And of course, it’s convenient that on the French Antilles, you can pay with the Euro due to their status as part of the European Union.
Sailing in the Caribbean – Relaxing sailing holiday for beginners and advanced sailors.
You just want to relax and enjoy the day, but also stay active, maybe even rack up some sailing miles, or simply try out what the often-mentioned fascination with sailing is all about? The price is right! Send your email inquiry and secure your spot on a sailing yacht with double cabins to the Caribbean! If you think this is only for experienced sailors, you’re mistaken. No prior knowledge is needed for the charter. On board, you can learn everything you need to know. The yachts are operated by an experienced skipper, who has plenty of tips for sailing in the Caribbean and is happy to share them. However, where you go is up to you and your crew. Overnight stays in a marina are just as possible as stays in a secluded bay, where you can jump straight from the yacht into the water and enjoy the holiday feeling. The individual marinas and anchorages are not far apart. So, you’ll decide with the skipper and crew whether you want to sail for just a few hours and take a shore excursion or if you want to embark on a longer journey that day. Your sailing trip in the Caribbean includes many days filled with unforgettable moments at a beautiful marina or bay or simply enjoying a cocktail or smoking a cigar at a Caribbean beach bar. Payments are made from the onboard cash fund.
Adventure Dream Vacation: Bequia – the largest island of the Grenadines.
Here you go: Maybe you’ll decide at the last minute to visit Bequia during your sailing holiday with your fellow sailors. The island is only 18 square kilometers in size but is one of the largest in the Vincentian part of the Grenadine Islands. How about a scooter tour around the island with a quick detour to the Old Hegg Turtle Sanctuary? Or you might wonder, as you encounter some of the elegant catamarans in the Lesser Antilles, whether that might also be an adventure worth trying. Every day sailing over the turquoise waters is full of highlights. Then, the anchor drops, and you decide whether you’d rather swim at a reef or go on an exploration tour.
Even on a sailing holiday in Thailand, you can fully take advantage of the benefits of sailing. Small island groups that are only accessible by boat, secluded bays, and spectacular sunrises define your overseas sailing experience. Get to know the most beautiful corners of Thailand and discover for yourself that the sailing trip in Thailand is truly unique!
Your Most Frequently Asked Questions
No, you don’t need any prior experience. Our sailing trips are for everyone – whether you’re completely new to sailing or already have some experience. Throughout the week, our skippers will teach you everything you need to know and make sure you’re always safe and well taken care of.
That depends on the type of trip you book. On our Youngline trip, your fellow sailors will be between 18 and 39 years old. On our Forever Young trip, they are between 40 and 59 years old. For our themed and training trips (Green Ahoi, Yoga, SKS), there is no age limit.
All crew members meet on Saturday between 2 and 4 p.m. at the marina. Around 5 p.m., you’ll board the yacht, and after a detailed safety briefing the next morning, you’ll set sail. A later arrival on Saturday evening is theoretically possible, but we don’t recommend it – please coordinate with your fellow crew members via WhatsApp in advance!
Our fellow sailors and skippers come from the DACH region (Germany, Austria, and Switzerland), so the main language on board will be German. However, all skippers speak English, and international sailors are very welcome.
On the first day of the sailing trip, cabins will be assigned. The crew and skippers can choose their cabins based on their preferences and needs. Generally, cabins are assigned with gender separation. If you would like to stay with a specific person or prefer not to share a cabin with someone of a different gender, feel free to mention this during booking. We will take your preferences into account.
We sail on modern yachts of various sizes: 3-cabin, 4-cabin, 5-cabin, and 6-cabin yachts. Accordingly, there are between 5 and 12 fellow sailors on board.
