Almost 90% of all yacht vacations take place in the Virgin Islands. There is a reason for this…. They are the easiest to get to, easiest to sail, and beautiful, making it ideal for yacht charter vacations of all kinds. But, after you have been on a couple of yacht charters in the BVI, where should you go next? I’d say, all things considered, the Cyclades in Greece, Croatia’s coast, the Grenadines and St. Maarten would make up the next best locations, with St. Maarten being the best of those choices for a sailing tour.
Below is a sample itinerary for the greater St. Maarten area for your next Caribbean Sailing Vacation. The island of St. Maarten ( which is ½ French and ½ Dutch) is pretty much a round island, so, depending on the weather, you might start your vacation from any point on the island. So, don’t focus on the numbered “days” on this itinerary, as they might come to you in any order. Also, you can do any kind of yacht vacation in St. Maartin – bareboat, crewed all-inclusive, captain only, or crewed ½ board. For me, while all options are great, the crewed ½ board option is superior, because a large part of these island’s fun is in exploring the culinary treats the islands have to offer.
Day 1
After landing at Princess Julianna Airport, get your Caribbean sailing adventure started with a 10 minute taxi drive through busy Simpson Bay, past literally 100s of restaurants and bars, to the Simpson Bay Yacht Club where you will meet your charter yacht.
After a welcome drink, take a walk down Simpson Bay, explore the beach and/or the bars.
My favorite, and a great way to start your trip, is Roxxy’s Beach Bar.
Day 2
Exit the draw bridge and sail west, a very short ways to Mullet Bay beach, and beach bar. This is a great snorkel spot, a wonderful beach and a funky little beach bar.
After lunch, continue on to Grand Case, on the French side of the island. Grand Case is the Caribbean capital of fine French cuisine… and home to another one of my favorite island bars, Rainbow Cafe.
Day 3
Anguilla is a short 5-mile sail to the north. If you have been to the BVI, and to Anegada, the beaches in Anguilla are even better!
Anguilla is a great island to rent a car or scooter and explore. You can easily go all the way around the island, stopping at beautiful beaches and cool bars in one day, but make sure you do not miss Blanchard’s Bar and Bankie Banx Dune Retreat Bar. Bankie is to this part of the Caribbean, what Foxy is to the BVI.
Day 4
Just north of Anguilla are two amazing islands that will remind of you of Sandy Key, and Sandy Spit in the BVI.. but much, much better.
Take your pick for the morning, lunch and early afternoon at either Prickly Pear Island or Sandy Island.
Take a late afternoon sail from here to Tintamarre Island, a national park, for more snorkeling and a quiet dinner.
Day 5
Continue your sailboat trip, with a very short sail, less than 3 miles, takes you to Pinel Island, where you can spend your day snorkeling, kayaking and exploring.
On weekends, this is St. Maarten’s version of the Soggy Dollar Bar, but with a European cool vibe. You might also elect to do a day trip from here, to Loterie Farm in the St. Maarten rain forest, where you can rent a cabana, zip line, play a little golf or just relax.
Day 6
The biggest sail so far, you have about 20 miles to sail to amazing St. Barth’s. St. Barth’s is an island where you could literally spend days, but if you only have one day to spare, you can’t miss Nikki Beach. Dubbed the sexiest place on earth, this amazing beach and bar scene will blow you away.
Day 7
Another longer sail back to St. Maarten, but you have choices today.
You can sail to Philipsburg, a quaint Dutch town full of shopping and history, or sail back to Simpson Bay and to yet another amazing beach and beach bar scene, Karakter Beach Bar.
This amazing place is built out of a restored touring bus and makes an amazing final afternoon on this amazing island.
Either way, you are a very short distance for your final morning ride back to the St. Maarten airport.
