Sailing Trip Around St Martin, Anguilla & St Barts
7-Day Sample Sailing Itinerary
This is a 7-day sample sailing itinerary for a Caribbean Sailing Trip around the beautiful islands of St Martin, Anguilla and St Bart’s.
Click the ‘Yachts’ Tab to see which yachts are available for a sailing holiday in this wonderful part of the Caribbean. Then get in touch and we can discuss your trip preferences during the personalised BlueFoot Travel booking process, during which we will also partner with the yacht crew to work on the best sailing holiday experience for you.
Please note that all Caribbean crewed charter sailing schedules may change due to government travel advisories and restrictions, your requests and weather conditions.
Meet your crew in Marigot, the capital of French St Martin, just 20-minutes from the International Airport. Then head out to meet your yacht anchored in the bay. Once you are settled, set sail to Anse Marcel. This lovely anchorage will be the perfect spot for a refreshing swim and then your first dinner on board.
After a sumptuous breakfast prepared by your chef on board, set sail down the Anguilla Channel and then head up to the main port of entry to the British island of Anguilla, Road Bay. Anguilla is known for its white sandy beaches, reefs and wrecks. It also has lively restaurants and bars. Road Bay has a beautiful white sandy beach where you’ll find numerous casual restaurants and bars. Laid-back is the rule on Anguilla and so drinks at Elvis’ Beach Bar are in order followed by dinner at one of the many restaurants ashore. Please note additional entry fees may apply for Anguilla.
If there is a gentle breeze then your Captain will be able to sail out to Prickly Pear Cays and enjoy the beautiful white sandy beaches and turquoise waters. Then head back to Crocus Bay for the evening. Crocus Bay is famous for its beautiful sunsets, making it a great place to anchor overnight and relax while watching the sun go down. The snorkelling is superb around Pelican Point and the beach is excellent for swimming and sunbathing. After cocktails, enjoy another delicious meal on board.
After breakfast, you can sail up to Scrub Island and then back into St Martin waters. After a quick stop for immigration, sail on to Tinatmarre, a pristine island in the heart of the nature reserve. Anchor in Baie Blanche, on the west coast facing Saint Martin, which has a delightful beach for swimming and exploring in a kayak or on SUPs. Take a wander around this now uninhabited island and you will find the remains of an airstrip, a small rail track and a cotton plantation. After you have had a chance to explore have dinner on board.
Gustavia, the main port of entry on St. Barts, is your destination today. Snug and protected, this harbour is a favourite among wealthy owners of superyachts. The red roofs of many of the buildings give Gustavia a distinct character and boutiques featuring world-famous designer wear and jewellery vie for space with superb restaurants specializing in French cuisine. There will be plenty of time to explore ashore. Wander around the high-end shops or hike up the hills to the lighthouse at Fort Gustav and climb the steps up Fort Karl for great views. Then enjoy a cocktail in one of the many bars to soak up the atmosphere. Dinner will be back on board unless you are enticed by one of the many high-end restaurants.
A few sail hops are in order. First is Anse de Colombier. This scenic and well-protected bay at the western tip of St. Barts is popular for its beauty, beach, and snorkelling. Steep hills overlook the blue waters and here we will find all manner of yachts at anchor. There is a 20-minute hiking trail, which is a great way to explore the surrounding area and build up an appetite before lunch! The next stop will be another beautiful uninhabited isle – L’Île Fourchue. Once anchored you can spend the afternoon in the beautiful surroundings of the marine and nature park. Sit back and relax onboard or head out snorkelling amongst the amazing coral reefs, spotted eagle rays, turtles and sometimes dolphins are even seen here! For those of you wanting to stretch your legs again, you can hike up to the top of the hill. It’s not too far and the views over St Barths and Sint Maarten are breathtaking. After all that activity where better to soak up the last rays of the day onboard your yacht with a sundowner or two and another delicious meal.
A week goes by fast when you are having fun! After the small hops, you will have a longer sail as you head back to St Martin. Your yacht chef will have prepared lots of delicious meals for you, but here you can enjoy some more French gastronomic delights ashore if you want to.
Want to extend this trip? Then you might want to consider including the islands of St Kitts & Nevis.
Interested in booking this trip? All your questions related to our booking process are outlined in our Crewed Yacht Charter Booking Process.
Information about airports and airlines flying into SXM can be found on the Sint Maarten and St Martin destination page. Further information relating to all Caribbean sailing trips is available on the FAQ pages.