St. Maarten & Surrounding Islands: Relaxed & Retired

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Jenna Stickel
Curated By

Jenna Stickel

  • St. Martin

  • Beaches

  • Tropical Vacations

  • Food & Wine

  • Outdoors & Nature

  • Relaxation

Advisor - St. Maarten & Surrounding Islands: Relaxed & Retired
Curator’s statement

Three passport stamps in one trip is the best way to spend a week away. In this guide, we will go through relaxing recommendations as well as fun trips and sights for people of all ages to enjoy. With St. Maarten being your home base, get ready to experience the beach trip of your dreams.

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Where to stay in St. Maarten and beyond

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Things to do in St. Maarten and beyond

View of Eden Rock from Nikki Beach in St. Barths

Toppers Rum Distillery

Rum in the Caribbean is like baguettes in France: a must.

At Toppers, not only will you get hands-on experience on how rum is made, but you will get over 20 samples and rum-infused food tastings.

Three different tour options give you the best insight into this family-operated distillery.

They also have over 15 different flavored rum options for you to purchase and bring home.

Day trip to St. Barths

Passport required. Feel free to extend your trip utilizing the hotels mentioned above.

To get to this luxurious island, the Great Bay Express is a direct ferry that leaves out of Philipsburg, St. Maarten and drops you off in Gustavia, St. Barths.

Once in St. Barths after customs, Le Petit Deauville is a great spot for a small breakfast croissant and coffee before you start your day.

For the luxury shoppers: Gustavia is the place to be. Stroll Rue De La République for high-end shops such as Prada, Dior, Louis Vuitton, etc.

For the the beach clubbers: Take an Uber (around $50 one way) to Nikki Beach (secure a reservation for a day bed in advance). There you will be able to relax and enjoy the crystal clear blue water, while relaxing on your day bed and having drinks and food brought out to you as you wish.

If you wish to venture out a little for lunch, right next door is Eden Rock, one of the island’s most famous hotels and perfect for lunch.

Day trip to Anguilla

Passport required. Feel free to extend your trip utilizing the hotels mentioned above.

There are a few different options for getting to Anguilla: Marigot Ferry, charter boat, and private catamarans ($60-$150).

Once in Anguilla after customs, an Uber to Shoal Bay East is a must for the most gorgeous beach in the Caribbean.

Ray will meet you where you can rent beach chairs and an umbrella for $15 for the day.

There are multiple beach bars to choose from where you can get lunch and drinks while you enjoy the view.

Catamaran tours

There are many different tour options ranging from $50 to $160 depending on what is included

Tours differ by length, activity (snorkeling, beach hopping, private charters to Anguilla, etc.), if food is included, sunset or day cruises, etc.

Maho Beach plane spotting

Lay on the beach and watch planes land directly over your head. Best time to view is 12 p.m.–3 p.m.

Enjoy lunch at Sunset Bar & Grille.

Shopping in Marigot (French side) & Philipsburg (Dutch side)

Marigot: High-end boutiques and a market with arts, spices, and rum. Best days are Wednesday and Saturday mornings.

Philipsburg: Check out Front Street for jewelry and watches, and Back Street for deals on clothes.

Places to eat & drink in St. Maarten and beyond

Lunch at Ocean Lounge, Holland House

  • Ocean 82: Reservation required. The best spot on the French side for amazing food and even better views. Their fresh lobster makes for a top-tier lobster bisque.

  • Roma Restaurant Cucina Italiana: Reservation required. From the burrata to the chicken parm and of course, crème brulee—what more do you need?

  • Jax Steakhouse: Reservation required. Located in the Maho Market area, Jax is known as St. Maarten’s number one steakhouse for a reason. Tomahawk steak, filet mignon, ribeye, and not to mention the delicious cocktails will have you wanting to dine here daily.

  • Ocean Lounge: This beachfront restaurant is great for breakfast, lunch, or dinner on your trip.

  • Sunset Beach Bar: Perfect for a quick beach-front bite while watching the planes land in St. Maarten or enjoying a sunset view.

  • Coffee Lounge: Walk up a flight of stairs to access the entrance. A great spot in Philipsburg to grab an amazing coffee and a croissant before spending the day at the beach or shopping.

Need to know

  • Take the earliest boat departure to St. Barths and Anguilla so you get the most for your money on these islands.

  • If you are staying on the Dutch side (Philipsburg, where the cruise port is in St. Maarten) check the cruise schedule and schedule your day trips during this time to avoid crowds.

  • If you get motion sickness on boats, take Dramamine before heading on any day trip or catamaran excursion (especially the boat to St. Barths).

  • Sunday is known as a day of rest here, so a lot of shops and restaurants are closed.

Jenna Stickel

Travel Advisor

Jenna Stickel

Advisor - Jenna Stickel

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For more inspiration and insider recommendations, visit our St. Martin page.