Retire Early Lifestyle
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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.

The Colorful and Intriguing Streets of Sint Maarten

Billy and Akaisha Kaderli

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The mixed and controversial history of the Caribbean Islands make for many adventurous myths and story-telling.

Sint Maarten is no exception.

The colorful streets, the foods, the murals, and even names of the bars reflect bygone times of African Slavery, Indian indentured servants and famous pirates like Blackbeard, Calico Jack, and Anne Bonny - all of whom operated in this region.

Today we have duty-free shopping and international cruise ships, with tourists and vacationers all recognizing the beauty and the economic opportunities available here.

Come take a look below.

Taloula Mango’s / Blue Bitch Bar

Ok, I didn't name the place, but this reflects the brazen, in-your-face culture of previous times.

Taloula's is a popular beachfront restaurant known for its Caribbean vibe, casual dining, and stunning views of Great Bay Beach. Tourists from the cruise ships love this place for Taloula's potent rum punch (a nod to the pirates), excellent service and relaxed atmosphere.

Philipsburg Boardwalk

Today, the Philipsburg Boardwalk is a bustling 1.5-mile stretch along Great Bay Beach.

There is an assortment of beach bars, restaurants, shops, and cultural attractions, but Sint Maarten and other Caribbean islands were a hotspot for pirate activity during the Golden Age of Piracy (roughly 1650–1730). It had a strategic location, numerous coves, and the wealth flowing through the region from European colonial trade.

Sint Maarten’s role was more practical than legendary with its ports, like Philipsburg, offering pirates a place to trade stolen goods with corrupt merchants or smugglers.

This was a practice common in the region where colonial officials often turned a blind eye for profit.

St. Maarten Courthouse

This courthouse, situated on Front Street, is considered one of the most important sites on the island. The courthouse itself is even featured on the national flag of Sint Maarten.

Originally built in 1793 as the home of Captain John Philips, the founder of Philipsburg, over time, it has served as a jail, fire station, and post office before becoming the courthouse.

It also has a clock and a belfry with 25 bells.

 Philipsburg Market Place.

The Philipsburg Market Place is an open-air market.

Severely damaged in the Hurricanes Irma and Maria in 2017, the reconstruction finished in the late summer of 2024.

You can often find fresh fruits, vegetables, and spices here, as well as souvenirs and crafts.

Thoughtful mural on Sint Maarten

In the tropics, it's common to see walls painted as story-telling murals.

In this one, the coat of arms of Sint Maarten is in the upper left hand side, while themes related to freedom, struggle, hope, and the future of children fill out the rest of the wall.

Hands breaking free from chains is a clear symbol of liberation and the end of oppression that Africans lived under in earlier times.

The text on the door reads: "St. Maarten do its part in ensuring the future for our children. We have to ensure that the problems don't come." This reinforces the theme of protecting and nurturing the next generation.

These pieces of public art tell a story about Sint Maarten's history and its aspirations for the future, standing as a powerful visual narrative for both residents and visitors.

The street is part of Philipsburg’s broader cultural landscape, which includes murals organized by the ColorMeSXM project.

A monument to The Salt Pickers

Before coming to Sint Maarten, I hadn't realized that salt picking, or salt harvesting, was a cornerstone of Sint Maarten’s economy and history. It spanned from the 17th century until the mid-20th century.

The Dutch began settling Sint Maarten in 1631, drawn by the Great Salt Pond’s natural salt pans, where seawater evaporated under the sun, leaving salt crystals. Salt was a highly prized commodity - often called “white gold,” - and was used for preserving food, especially fish, in Europe and the Americas. The Dutch West India Company oversaw early salt mining operations.

By 1850, Sint Maarten exported up to 400 boatloads per year making the island a significant player in the global salt trade. This trade connected Europe, North America, and the Baltic Sea region, where salt was critical for fish preservation.

A closer look at the monument

Salt picking was labor-intensive, involving shoveling and scraping salt crystals from the pond’s surface.

The workforce included free people and enslaved individuals from both the Dutch and French sides of the island. Women were notably prominent as salt pickers, while men often fished. Enslaved workers, including women, children, and seniors, faced grueling conditions, yet the trade fostered a sense of community and identity.

The salt industry outlasted other economic ventures like sugar and cotton but declined after the 1920s due to global competition and changing economic priorities.

By 1949, the Dutch ceased salt production on the island, and tourism later replaced salt as the primary economic driver.

Back Street

In some ways, life was simple "back then."

Sint Maarten has a Front Street, a Back Street and an Old Street.

Beginning with Philipsburg Boardwalk, Front Street is next, then Back Street.

Old Street runs perpendicular to these, where various local shops and cafes stand, offering tourists refreshments or a meal.

African Market

The African Market in Philipsburg, Sint Maarten, is a shopping destination offering a unique selection of handmade African-inspired goods.

It's in the heart of Philipsburg, the capital of the Dutch side of Sint Maarten, and this market specializes in authentic artwork, jewelry, and clothing directly sourced from Africa.

You can find handcrafted artwork such as paintings and carvings, jewelry like beaded necklaces and earrings, and clothing inspired by African designs.

It's not a big store, as you can see, and they are used to bargaining, so don’t hesitate to negotiate for better deals.

Bring cash (U.S. dollars are widely accepted) as not all vendors on the island take credit cards

Back "in the day" both Dutch and French powers relied heavily on enslaved Africans to work on sugar, cotton, and salt plantations.

The British Slavery Abolition Act of 1833 didn’t directly apply to Dutch or French territories, but it influenced the region.

The French abolished slavery in 1848, freeing enslaved people on Saint Martin. The Dutch lagged behind, only abolishing slavery in Sint Maarten in 1863, with a 10-year “transition” period that forced formerly enslaved people to continue working for their former enslavers until 1873.

Methodist Church in Philipsburg, Sint Maarten.

The Methodist Church in Philipsburg was founded in 1851, making it one of the oldest religious institutions on Sint Maarten.

Established by John Hodge, an enslaved African from Anguilla, introduced Methodism to the island in 1817. His efforts laid the groundwork for the church’s formation, initially through services held in homes.

The current stone structure, built in 1851, was reconstructed in 1976 and has since been a central place of worship.

The church is located on Front Street near key landmarks like the Philipsburg Courthouse and the Salt Pickers Monument.

Early members, including John Hodge, are buried here in the cemetery.

A non-working but pretty clock

This clock, as pretty as it is, isn't giving the correct time.

However, it's fashioned in the European style and adds character to the street.

A local woman and Akaisha

During our stay on the island there were several celebrations and costume-wearing events.

This young woman said she wanted to be a "Jewish Princess" so in her mind, she dressed as one for the parade.

Personally, I look as though I stuck my finger in a light socket, with my hair so wild and without shape, but hey, it's the tropics!

Maybe I'm in costume too!

The quiet road leading to the Courthouse

With the shaped and cleaned palm trees, this road gives a stately look to approaching the Courthouse.

The pastel-colored buildings of "Little Europe"

A prime shopping area, you can see signs for luxury brands like "Dior," "Hermes," and "Zenith."

This small shopping area is located on Front Street in Philipsburg, which is famous for its duty-free shopping.

As an aside, during the Pirate's hey day, Sint Maarten's reputation for lawlessness attracted a mix of settlers, including former pirates turned “legitimate” traders.

Smuggling thrived well into the 18th century, as Sint Maarten’s duty-free status - which is still a draw today - made it a hub for illicit trade.

Greenhouse Restaurant

The Greenhouse Restaurant is located on Front Street, in the heart of the city.

It has a casual yet vibrant atmosphere, offering a mix of Caribbean, American, and international cuisine. 

There is a happy hour and live music at night.

Robbie’s Lottery

Robbie’s Lottery is a well-known lottery operator in Sint Maarten

Gambling is a notable part of the island’s tourist-driven nightlife, reflecting its reputation as a Caribbean "Sin City."

Sint Maarten has 13 casinos overall, with several concentrated in Philipsburg, the capital. The gambling scene here caters primarily to tourists, especially cruise ship passengers.

Gambling in Sint Maarten is technically unregulated, operating in a legal gray area. There’s no formal gambling legislation.

Small outlets such as Robbie's often serve as social hubs where locals gather, play, and chat, while also attracting tourists with the promise of quick wins.

Plaza Oliva

Plaza Oliva is located on Back Street which is known for affordable fashion, electronics, and everyday items. You'll find a mix of retail stores, boutiques, or local vendors.

Front Street has more luxury brands.

This Plaza is a 10-15 minute walk from the cruise port.

Old Street

Old Street is a short, "cobblestone" alley running off Front Street, and stretches just one city block. 

The street is lined with buildings that date back to this period, originally homes that have been converted into shops, galleries, and cafés. These structures feature traditional Caribbean and colonial architecture, with colorful facades—often painted in bright hues like yellow, pink, and blue—adding to the street’s vibrant, picture-perfect appeal.

Philipsburg, founded in 1733 by John Philips, was established between Great Bay and the Great Salt Pond to facilitate the salt trade. The town is a narrow strip, only four streets deep and one mile long, with Front Street, Back Street, and the Boardwalk being the primary arteries. Old Street, as one of the oldest streets in Philipsburg, connects these areas and offers a glimpse into the town’s colonial history.

Another colorful mural

There is a guided mural tour in Sint Maarten, where you can see this mural in person.

Tropical flowers, a local woman, a cruise ship, palm trees and the sea.

Another mural organized by the ColorMeSXM project.

Diamonds International

Diamonds International is part of a larger chain that began in St. Thomas over 30 years ago and has since expanded to over 100 locations across the Caribbean, Mexico, Central America, and Alaska, with its headquarters in New York City. 

This one is located on Front street which is lined with duty-free stores.

It is one of the Caribbean’s most recommended jewelers offering a wide selection of luxury jewelry.

When you complete a purchase, DI has been known  to offer champagne to celebrate.

Bargaining is part of the Caribbean culture, and you can haggle for better deals, especially on larger purchases like engagement rings or watches.

Diamonds Be Dazzled

This shop focuses on a curated selection of jewelry, including diamonds, gemstones and locally inspired pieces like Caribbean charm bracelets or larimar jewelry, which are common in Sint Maarten.

If you’re seeking a unique piece with a local flair, visit early in the day to chat with staff and explore their offerings.

Again, bargaining is common in Philipsburg, so don’t hesitate to negotiate.

Billy and Akaisha in front of the Courthouse

The heart of downtown is very clean.

You won't see trash lying about nor will you encounter graffiti.

It's a respectful sort of place with friendly people showing Northern European manners.

Local tailor

When you travel as much as we do, from time to time, there is bound to be a need for a repair.

Billy's bag zipper went pffffffttt! and this local tailor from Jamaica charged him $10USD to fix his bag.

We paid him cash.

Google Fashion?

Fashion retail is common on Sint Maarten but this storefront is likely using the "Google" branding without authorization.

It's an obvious business move to leverage the name for visibility. 

This shop sells casual clothing and has many sales signs.

Sint Maarten’s duty-free status means no taxes are added, so some items can be up to 50% cheaper than in other countries.

Akaisha purchasing bottled drinking water

The sun and its heat are exceptional on these Caribbean islands.

One must hydrate themselves often or you could find yourself rather faint.

I am purchasing some bottled water here at a local store for $1USD.

A poster advertising the famous Maho Beach

Maho Beach, located on the Dutch side of St. Maarten, is a famous beach known for its proximity to the Princess Juliana International Airport, where planes land and take off just a few meters above the beach  

This unique feature makes it a popular spot for tourists and aviation enthusiasts.

The beach itself is small and sometimes crowded, with waves that can be high.

We saw the real deal here watching the planes land when we were catching our flight to Nevis, West Indies.

We certainly recommend this experience.

Billy and a sweet young girl

Billy's here at the grocery store speaking with a local.

The islanders are very friendly.

Caribbean Rotis

Here's an interesting story for you.

 Following the abolition of slavery on the island, plantation owners across the Caribbean faced labor shortages as freed Africans often refused low-wage plantation work.

Indian indentured labor in the Caribbean emerged as a replacement for that enslaved labor, and they they worked on sugar plantations and elsewhere under five-year contracts.

These contracts typically promised wages, housing, and a return passage after five years, but conditions were often harsh.

There were long hours, inadequate food, and limited medical care.

Many laborers were misled about the work or destination, and the system has been criticized as a “new form of slavery” due to the exploitative nature of these indentured servants.

Well, the Indians brought with them the delicious comfort food called Roti.

It's now a very popular dish made as a a flatbread wrap (like a burrito for easy eating) from a simple dough of flour, water, salt, and sometimes oil or baking powder.

The dough is rolled out into a thin, round shape, cooked on a flat griddle (tawa), and often lightly brushed with oil or butter for a soft, slightly flaky texture.

It's a portable meal with fillings like curry or stew, reflecting the Indian influence but adapted with local Caribbean flavors.

There are chicken curry rotis, goat rotis, beef, shrimp and vegetable rotis.

It's a balance of savory and spicy, and Caribbean roti fillings often feature a mix of Indian spices with local additions like thyme, allspice, and fiery Scotch bonnet peppers. Some places might add a touch of sweetness with ingredients like coconut milk.

Roti in Sint Maarten reflects the island’s multicultural heritage, blending Indian, African, and Caribbean influences.

Have you ever had one?

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