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.

Chesterfields Restaurant

Sint Maarten, Caribbean

Billy and Akaisha Kaderli

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Chesterfields Restaurant is a renowned waterfront dining destination known for its vibrant Caribbean atmosphere and stunning views of Great Bay and the marina. 

Located on the Dutch side of the island of Sint Maarten, it's the go-to spot for both locals and cruise ship visitors.

Bobby's Marina Bridge

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

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

The marina itself is a significant hub for yachts and boats, often hosting various maritime activities like the America's Cup Yacht Racing event and providing services for vessels. 

Divi Little Bay Beach Resort is the blue building in the center, on the hilltop.

Shopping and services area

The water is to the left of this photo where the boats are docked, and Chesterfields Restaurant is to the right.

The blue building in the middle left is where we purchased our ferry tickets.

The front entrance of Chesterfields

Established over 35 years ago, this nautical-themed restaurant is famous for its diverse menu featuring fresh seafood items like lobster, shrimp, scallops, mahi-mahi, and conch fritters.

But for meat lovers, there are also options such as steaks, burgers, and roast duck.

Prices are moderate with generous portions.

They also offer quality dishes like the conch cocktail and Aetna rum-raisin sundae.

Poster advertising the America's Cup Yacht Racing 12 Metre Regatta

This regatta is a unique and thrilling attraction for sailors of all ages.

This 12 metre race uses all the retired legendary sailing vessels like Stars & Stripes, Canada II, and True North IV, in a head-to-head race on a shortened America’s Cup course in Great Bay. 

 It offers participants the chance to crew authentic America’s Cup 12-metre yachts which competed in the America’s Cup until 1987. These 66-foot vessels, despite their name, are sleek, high-tech machines built for speed and agility, costing millions to develop.

Participants are divided into crews of 4–18, with no prior sailing experience required. You can take active roles like grinding winches, trimming sails, or timing maneuvers, or simply enjoy the ride. 

The race lasts about 2–3 hours with a post-race rum punch party at Chesterfields.

Open to ages 6 and up. People say it's a bucket-list experience, and up to four regattas run daily.

Various sailor knots

You have heard of sailor knots, right? These are important for securing the boat to a pier, attaching sheets to sails and securing a boat to the mooring. They also make sure the rope doesn't slip or jam up.

This case shows a bowline knot, a figure eight, a cleat hitch and a square knot to name a few.

Indoor open-air seating

The restaurant has an inviting ambiance with both indoor and outdoor seating. It's ideal for enjoying tropical cocktails, local beers, or wines while watching sunsets.

Live music nights and happy hour specials add to the island vibe.

Humorous sign

Chesterfields is known for the humor that servers show and for the comfortable setting to watch the sun set over turquoise waters.

Large yachts enjoy the bay

With the prestige Port St. Maarten holds as a major hub for cruise lines, this key Caribbean destination is attractive for yachts and cruise ships from all over the world.

The front of Chesterfields

Casual and comfortable, this wide open view of the sea is perfect for daydreaming as well as watching the amazing sunsets of the Caribbean.

Charter boats available

Tour boats are available for touring the island or for making a visit to the French side for lunch.

Our bill for 2

Our bill for 2 double espressos and pastries cam to $42.30 Dutch Guilders, or $23.50USD.

Captain "Tony" of Caribbean fame

This is a portrait of the infamous Captain "Tony" Tarracino, a legendary figure in Key West, Florida.

He was immortalized by Jimmy Buffett in the song "Last Mango in Paris" from the 1985 album of the same name.

Tarracino was a charismatic charter boat captain, bar owner, gambler, and former mayor of Key West. He owned Captain Tony’s Saloon at 428 Greene Street, a historic bar where Buffett performed in the early 1970s, often paid in tequila. The saloon, a Key West institution, hosted celebrities like Ernest Hemingway and Truman Capote, with barstools painted with their names.

Captain Tony led a colorful life which included running guns for Cuban mercenaries during the Bay of Pigs invasion, marrying four times, and fathering 13 children.

His adventurous exploits and larger-than-life personality inspired Buffett’s lyrics, and he remained a beloved figure until his death at 92, with his legacy preserved in Key West’s lore and in Buffett’s music.

Chesterfields is the perfect place for Tony's portrait.

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Chesterfields

Jauncho Yuausquin Blvd

Point Blanche, St. Maarten

Tele 1. 721. 542. 3484

Open daily from 7:30 AM to 10:00 PM

Breakfast, lunch, dinner, caters to tourists and locals alike

Tele: +1 721-542-3484

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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