St Maarten 14-Days Yacht Itinerary

Discover the island of two souls during your 2 weeks itinerary in St Marteen.

A single island with two distinct souls, one French and one Dutch, is hidden in the corner of the Caribbean, about 250 kilometers east of Puerto Rico and south of Anguilla. This is the island of St Maarten and Saint Martin, depending on whether you pronounce it French or Dutch.

We are talking about the smallest area divided into two nations. Two different peoples and cultures have coexisted peacefully in this strip of paradise for more than 350 years.

Today, thanks to a luxuriant nature kissed by a magnificent sea, it is increasingly the leading destination in the Caribbean for lovers of pleasure boats.

VIEW YACHTS FOR CHARTER IN ST MARTIN

The legend behind the origin of coexistence

A lovely legend explains the division’s origins in two parts of the island. According to the myth, the Dutch and the French decided to divide the territory, entrusting the task to one of their soldiers. The two, drunk with red wine – the French – and the other with jenever – the Dutch – put themselves back to back and left in opposite directions along the island until they found themselves at the starting point.

The Dutchman, however, was drunker – jenever is more alcoholic – and made less progress. However, it was not a problem, as the French gained a larger territory and the Dutch became more prosperous.

Two different souls

Much time has passed since then, but something remains: the Dutch part of the island of Saint Martin is known for its lively nightlife, casinos, duty-free jewelers, and rum.

On the other hand, the French side is wilder and, if possible, more authentic: not surprisingly, there are several nudist beaches, many markets, and restaurants where you can taste the authentic local Creole cuisine. The French side is hilly, with smaller towns, and even the shopping is less hectic and compulsive than on the Dutch side.

However, an essential and characteristic aspect is the total absence of borders or barriers between the two parts. Movements from one place to another are guaranteed so much that often, you don’t even realize you have crossed to the opposite side.

14 Days Yacht Itinerary from/to St Martin

Below, we outline a possible 14-day itinerary for a boat-based sailing trip along the coasts of St Maarten and the neighboring islands. Are you ready to go?

Day 1: Arrival in St Martin

In our travel itinerary, we chose to get to St. Martin from New York, but we could also get here from Paris. Usually, the arrival time at the airport is around early afternoon. It is an excellent time to start getting to know your rental vehicle and the crew on board, settling in the cabins you have chosen, and getting used to it.

Day 2: Maho Beach, Mullet Bay, and Happy Bay Beach

Let’s start exploring this island from its most famous and photographed beach: Maho Beach. Why is she so famous? If you’ve seen photos or videos of planes practically landing a stone’s throw from the beach, this is Maho Beach.

Maho Beach is right in front of Princess Juliana International Airport, where you can see objects and people literally “flying away,” swept by the power of aircraft engines.

Subsequently, we continue along the coast to explore Mullet Bay in the Dutch part, then encroach on the French area of the Terres Basses. We continue to Friar’s Bay, but our final destination is Happy Bay.

Also reachable by a 20-minute trek from Friar’s Bay, Happy Bay is very little frequented and, therefore, considered a jewel of the island, still intimate, with a white-sand beach and palm trees for shade.

Day 3 – 4: Saba Island

The third and fourth days are dedicated to discovering an island not far from St Maarten but still not very popular with tourists: Saba.

Saba is not the typical Caribbean island because it is of volcanic origin and is practically a volcano in the middle of the ocean; it does not have many beaches but only peaks, yet it is home to exceptional marine life, a paradise for divers and snorkelers.

Although our trip is by boat, we do not believe it is a problem to land and explore the wonders of Saba. With one of the many comfortable taxis, you can reach any destination, even if the trekking reigns supreme, with trails and paths for all types of hikers, from beginners to the most experienced.

One of the most striking is the ascent to Mount Scenery, the sleeping volcano of Saba, a climb of 1064 steps.

On the way back, you can explore the tiny capital, The Bottom, and the Windward Side, with its red-roofed houses.

If there is still time, you can head to one of the island’s two tiny coves, where you can snorkel. One is right under the airport: Cove Bay.

Day 5 – 6: St Barths

We leave Saba to explore the magnificent and chic St. Barth for the next two days.

St. Barth is a dream island, a favorite destination for VIPs and the international jet set.

With its small, luxurious hotels and elegant, refined style, St Barths enjoys the reputation as an island for the rich, and indeed, it is enough to look around to see large megayachts anchored in its waters or at the port of Gustavia, the capital.

However, the beaches are all accessible, public, and free, and we know we will find some genuinely breathtaking ones to relax in: Anse de Colombier and Anse des Flamands are just two of St. Barth’s jewels. Another famous beach is also Anse de Grande Saline, and of course, with our charter boat, we can choose which ones to visit.

Day 7 – 8: back to St Maarten

Since we haven’t had enough trekking back on our home island, we dedicate the next two days to exploring the hinterland. The first stop may be the highest point in St. Martin, aka Pic Paradis.

Sure to take in beautiful views, if you feel in the mood for adventure, you can visit Loterie Farm, where you can fly through the trees on a zip line.

You cannot miss visiting Fort Louis, the ruins of a fortress overlooking Marigot, from which you can admire a magnificent coast view. The view will certainly repay the effort of the climb.

Finally, for dinner, we recommend Grand Case, which is not by chance nicknamed the “gastronomic capital of the Caribbean.”

Day 9: Ilet Pinel

Today is a relaxing day at one of St Maarten’s pearls: Ilet Pinel.

Located along the northeast coast, Ilet Pinel is a small uninhabited island, as it is part of the Sint Maarten Marine Park.

It can be reached by boat and, from our experience, if you have to choose a time to visit, it is better in the afternoon, as its most beautiful beach faces west. A slice of heavenly beach, the privilege of the few visitors.

A sportier alternative to lounging on the beach is to circumnavigate the island by kayak in search of your deserted beach.

Not-to-be-missed: How much does a St Barts yacht charter vacation cost?

Day 10: Prickly Pear Cays

The day begins with a navigation towards the last leg of our journey, Anguilla. However, before heading to the island, we make a slight detour to the northwest and reach the Prickly Pear Cays.

Two small uninhabited islands are located about six miles north of Road Bay, Anguilla. The two coral islets are divided by a narrow channel named Prickly Pear East and Prickly Pear West. The westernmost of the two is mainly coral rock and shrubs, making access particularly difficult. A white sand beach characterizes the eastern one on the north side.

Day 11 – 13: Anguilla

Anguilla boasts some of the most beautiful beaches in the world. It is not for nothing that Rendez-vous Bay and Shoal Bay East have long been in the top 3 of the Tripadvisor ranking.

Perfectly located to touch the crystal-clear sea typical of the Caribbean, Anguilla is also part of the “English Caribbean.” Its position between North and South America makes it within the United Kingdom’s scope.

There are several attractions in Anguilla, each different at different times of year. The best times to visit this paradise location are between December and April.

In Anguilla, it is possible, if not obligatory, to snorkel, go hiking, and take relaxing walks along the seafront.

Inevitably, visit The Valley, the capital of Anguilla, which is home to many residents. The clubs in the city are ideal for aperitifs and after dinner.

Another destination is Wallblake House, the perfect place to learn about the typical colonial style that has historically shaped the island. A dip into the past is ideal for discovering the place’s history.

On the other hand, Anguilla is a small island to the east of the mother island: you usually go there for a day trip. Equally suggestive but less accessible is “Dog Island,” an uninhabited islet accessible only with a reservation: a romantic destination much appreciated by couples.

Day 14: Back to St Maarten

Here is your last day of yacht charter in St Maarten. You can dedicate the morning to the last baths before saying goodbye to the crew and our splendid boat, heading to St. Martin airport, where the return flight awaits you.