Retire Early Lifestyle
Retirement; like your parents, but way cooler

In 1991 Billy and Akaisha Kaderli retired at the age of 38. Now, into their 4th decade of this financially independent lifestyle, they invite you to take advantage of their wisdom and experience.

Port St. Maarten

Philipsburg, St. Maarten, Caribbean

Billy and Akaisha Kaderli

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Port St. Maarten is located in Philipsburg, the capital of the Dutch side of St. Maarten.

Before European arrival, the area around Simpson Bay was inhabited by the Arawak and Carib peoples, who called the island Soualiga (“Land of Salt”) due to its salt ponds, including those near Simpson Bay. These ponds later became economically significant.

Today, it's one of the busiest cruise ports in the Caribbean, handling over two million cruise passengers annually. If you have been on a cruise in the Caribbean chances are that you've been to this port.

Yachts and pleasure boats

The harbor also supports mega-yachts, sailboats, and pleasure boats, with Bobby’s Marina and other facilities nearby for smaller vessels.

The port is a gateway to both the Dutch (Sint Maarten) and French (Saint Martin) sides of the island, with no border controls due to the open border agreement.

Great Bay

This port is a major hub for cruise lines, including Carnival, Royal Caribbean, Celebrity Cruises, Holland America, Disney, Norwegian, and Princess Cruises.

It can host up to six cruise ships at once, making it a key Caribbean destination.

Great Bay is on the southern coast of Sint Maarten, the Dutch side of the island.

The port features two main piers: Pier 1, capable of accommodating four cruise ships simultaneously, and Pier 2, opened in 2009, designed to handle the world’s largest cruise ships.

It includes two screening booths for efficient passenger disembarkation. And the port has an open-air terminal with amenities like tourist information, Wi-Fi, ATMs, restrooms, shops, and kiosks.

Bobby's Marina Bridge

This pedestrian bridge crosses over the channel connecting the Great Bay to the Simpson Bay Lagoon.

This Bustling area is known for its marina, waterfront restaurants, and shops. It's a key pathway for pedestrians moving between the main Front Street area of Philipsburg and the Simpson Bay side, where Bobby's Marina is located. 

Designed in Philipsburg’s traditional architectural style, this duty-free shopping and dining area sometimes features steel pan music creating a tropical atmosphere.

While some describe it as a “tourist trap,” it’s clean and convenient. You can always take a 10-15 minute walk or water taxi ride to downtown Philipsburg for more authentic shopping and lower prices. In fact if you just go over a block or two is where the locals shop and eat.

Simpson Bay

In the 17th and 18th centuries, Simpson Bay’s proximity to the Great Salt Pond (shared with Philipsburg) tied it to Sint Maarten’s salt industry, a major export for the Dutch. Enslaved laborers worked the salt pans, and small boats in Simpson Bay transported salt to larger ships.

A key maritime area, this Bay is primarily used for yachts and sailing boats. A designated port of entry for yachts, the clearance fees run around $2USD. But there are additional bridge and anchoring fees that apply.

Water Taxis are available here and you can purchase a one-day unlimited ride ticket for about $6USD. There are also cabs and Buses with tours of the island. We mostly walked with the exception of on our last day our driver gave us a tour of the entire island including the French side.

Simpson Bay boasts a beautiful long stretch of beach, also called Simpson Bay Beach. Popular for swimming, sunbathing, and watersports, you'll find various beach bars and restaurants dotted along the sand, offering a lively atmosphere.

Boat named Black Sting Ray

The centerpiece of Simpson Bay is one of the largest inland lagoons in the Caribbean. It provides excellent shelter for yachts and boats, making it a major hub for the sailing and yachting community. 

During the 17th and 18th centuries, Simpson Bay’s secluded lagoon attracted pirates and privateers seeking to hide from colonial navies. The bay’s natural protection made it ideal for illicit trade and ship repairs, contributing to Sint Maarten’s reputation as a freewheeling trade hub.

The 1648 Treaty of Concordia, which divided the island between the Dutch and French, placed Simpson Bay firmly on the Dutch side, but its proximity to the French border (just a few miles away) facilitated smuggling and cross-border trade.

The Great Bay Express Schedule showing St Maarten to St Barth

By the 19th century, Simpson Bay was a modest fishing village.

Residents were primarily of African descent, and they relied on fishing, small-scale agriculture, and salt production.

The lagoon supported a tight-knit community with a distinct Creole culture, blending African, Dutch, and French influences.

Slavery was abolished in the Dutch Caribbean in 1863 and it led to economic shifts. Many former enslaved people in Simpson Bay turned to fishing and boat-building as livelihoods.

 Its history as a fishing village and maritime refuge contrasts with its modern role as a global sailing destination. Now it's home to events like the Heineken Regatta which has been held annually since 1980.

The bay’s cultural heritage, tied to its Afro-Caribbean roots and maritime traditions, remains a point of pride for locals.

Our Great Bay Express ticket

Our round trip tickets from St. Maarten to St. Barths for two people came to $230USD.

The Dutch side uses the Antillean Guilder and U.S. dollar, while the French side uses the Euro. 

Billy and Akaisha waiting to board the ferry

Everything was efficient, and people were friendly.

The Ferry Worker told us that the the ferry ride between St. Maarten and St. Barths would be VERY ROUGH – and it was.

It was rougher than either Billy or I had anticipated. However, we easily survived the 45 minute ride between the islands, and lived to tell the tale!

For more stories, photos and videos of Sint Maarten, click here. 

Retire Early Lifestyle appeals to a different kind of person – the person who prizes their independence, values their time, and who doesn’t want to mindlessly follow the crowd.

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