Day 1 | Arrive and explore the quaint town of Marigot, St. Martin

Your sailboat will be waiting for your arrival in the French capital of St. Martin – Marigot.  After getting settled in on Oryxx your Caribbean sailing party can wander the streets of Marigot. Marigot is a quaint town dotted with multiple shopping boutiques and delicious French cuisine. Explore the 18th century Fort Louis, which is situated on top of a hill in Marigot with views stretching as far as Anguilla island.

Day 2 | Your pick of snorkeling, paddleboarding, or kayaking in Anguilla

Day 2 of your Caribbean sailing vacation we’ll sail to the British island of Anguilla and the stunning Crocus Bay. Enjoy snorkeling and cliff jumping in this pristine spot or a casual paddleboard/kayak through its serene blue waters. We provide snorkel gear, kayaks, and paddleboards so you have quick and easy access to the Caribbean Sea!

A short dinghy ride offers the solitary Sandy Island for the quintessential Caribbean experience. Another short ride gets you to Shoal Bay, the world famous white sand beach that has been listed as a “Top 5 Beaches in The World” numerous times. This beach will have you feeling relaxed and in vacation mode in no time! Nearby, the town of Sandy Ground has many great beachside restaurants and casual Caribbean nightlife.

Day 3 | Savor the tranquillity on Anguilla’s surrounding islets

Depending on the weather on Day 3, we’ll set sail for one of the uninhabited islands surrounding Anguilla on your charter. Dog, Prickly Pear, and Scrub Island are all beautiful island paradises, where there’s no lack of sun, sand, or water activities. The best part they are free of cruise ships and overcrowded tourism – SCORE!

Anguilla hosts seven wreck dives around the island. If you’re a scuba diver wanting to venture into some of these wrecks on your charter, this is your spot to find a myriad of tropical sea fish, sea fans, and coral! Once the day is coming to an end we’ll head back to Crocus Bay to anchor for the night.

Day 4 | Snorkel with turtles in St. Barts

For the longest sail of your Caribbean sailing charter, we’ll leave early on Day 4 and arrive in Gustavia, St. Barts, three hours later. The gorgeous French colonial town is the jewel of this part of the Caribbean with its red roof houses. With amazing restaurants to high-end duty-free shops, it has it all. You can explore the town or even jump on a scooter or ATV to explore the island to its fullest.

We’ll cruise the sailboat around to drop anchor at Anse de Colombier. This horseshoe-shaped bay provides you with one of the best snorkeling spots in St. Barth's. Its steep hills which overlook the Caribbean Sea also host scenic hiking trails with views stretching all the way to Ile Fourche.

Day 5 | Escape light pollution and spot the Milky Way bright as day over Ile Fourche

Day 5 of your Caribbean sailing vacation we’ll set sail to the nearby island of Ile Fourchue. This uninhabited island has incredible snorkeling. Part of St. Barts marine reserve, this island’s water houses an abundance of Caribbean reef and nurse sharks, barracudas, stingrays, sea turtle, and lobster galore. Take a shot at navigating your way to the rock buttes of Ile Fourchue if you’re looking to get in a little day hike. You’ll reach the top to the panoramic view of St. Barts and St. Martin.

Watch as the Milky Way starts to appear right before your eyes at night. Due to this island's zero light pollution, the starry sky of Ile Fourche will give you another level of Caribbean tranquility.

Day 6 | Enjoy local cuisine and the pristine waters in Orient Bay

A couple hour sail from Ile Fourchue brings us back to St. Martin. We’ll anchor in the windward side off Orient Bay. This 2-mile long white velvet beach hosts multiple beach clubs, watersports, kiteboarding, jet skiing, and more. Pop into the open-air eateries located near Orient for some delicious French cuisine.

Located in the heart of the marine park nearby, you can visit the little sandy island of Pinel, an alternate option for a day on the beach and a local lunch. Another great place to snorkel, Pinel offers a variety of marine life in the area, and this protected bay is great for a kayak and paddleboard! This little island is a local favorite and one of St. Martin’s best kept secrets.

Day 7 | Snorkel, cocktails, tapas, repeat in Grand Case

On day 7 of your Caribbean sailing vacation, we’ll take a short sail to Tintamarre. This flat island was used as a secret submarine base in World War II. This island now is your host for a perfect beach day and natural mud cliffs that when mixed with water, leaves your skin feeling soft as a baby!

Later in the day, we’ll continue down the coast to Grand Case. You can enjoy a snorkel at Creole Rock, where you might see the elusive and beautiful Eagle Ray! End the day with one of the most idyllic places for a sunset stroll and enjoy one of Grand Case’s famous eateries on the beach – our favorite La Villa or Spiga

Day 8 | Get your last Caribbean fix & souvenirs and hope for a plane delay on your final day!

Wake up to your last day with a delicious breakfast in Grand Case. We’ll then sail the final hour back to Marigot and prepare for your departure.


This Leeward Island sailing charter itinerary is only a sample to what these idyllic islands have to offer. Remember that all sailing charters are fully personalized to your schedule, desired activities and destinations. Contact us today to talk about ideas of what your next sailing charter could look like in the Caribbean.