If you’re looking for a Caribbean destination with beautiful beaches, authentic Caribbean food, vibrant nightlife, island-hopping opportunities, and plenty of ways to use points and miles, St. Martin/Sint Maarten should be at the top of your list.

I recently spent six days and five nights exploring the island, celebrating my birthday, beach-hopping, dining at local restaurants, and taking a day trip to Anguilla. In this guide, I’m sharing everything I learned, including where to stay, how to get around, what to pack, how much it costs, and a complete 5-day itinerary based on my actual trip.

Where Is St. Martin/Sint Maarten?

St. Martin/Sint Maarten is located in the northeastern Caribbean and is one of the most unique islands in the region because it is shared by two countries.

• The northern side, Saint-Martin, is French.
• The southern side, Sint Maarten, is Dutch.

Although the names are spelled differently, both are pronounced “Saint Martin.” Locals will quickly point out the distinction, and it is one of those fun facts many first-time visitors learn shortly after arriving.

Despite being divided between two countries, there are no border checkpoints between the French and Dutch sides, making it easy to explore the entire island during one trip.

St. Martin vs. St. Maarten: What’s the Difference?

Saint-Martin: The French Side

The French side is known for its laid-back atmosphere, beautiful beaches, beach clubs, and incredible dining.

Official language: French
Currency: Euro
Popular areas: Grand Case, Orient Bay, Marigot
Best for: Dining, beach clubs, relaxation, French-Caribbean culture

Sint Maarten: The Dutch Side

The Dutch side is known for resorts, nightlife, casinos, shopping, and the famous Maho Beach plane landings.

Official language: Dutch, although English is widely spoken
Currency: Netherlands Antillean Guilder, though U.S. dollars are widely accepted
Popular areas: Philipsburg, Simpson Bay, Maho Beach
Best for: Nightlife, shopping, resorts, casinos, beach bars, plane spotting

The best part is that you do not have to choose one side. With a rental car, you can easily experience both during your trip.

How I Booked This Trip Using Points & Miles

One of my favorite things about this trip is that it was booked almost entirely using points and miles.

Flights

I flew from Chicago (ORD) to St. Maarten (SXM) with a layover in Charlotte using American Airlines miles.

• 20,000 American Airlines AAdvantage miles
• Approximately $104 in taxes and fees

Hotel

We stayed at Port de Plaisance Resort, a Trademark Collection by Wyndham property, located near Simpson Bay and just minutes from Princess Juliana International Airport (SXM).

The stay was booked using 67,500 Wyndham Rewards points for a spacious two-bedroom, two-bathroom suite. One of the biggest reasons I loved this property was the amount of space. Unlike a traditional hotel room, our suite included a full kitchen, dining area, living room, multiple balconies, and separate bedrooms.

Having a full kitchen made a huge difference throughout our stay. We were able to store drinks, snacks, leftovers from restaurants, and even prepare quick meals when we didn’t feel like dining out. It also helped us save money on food while still enjoying some of the island’s best restaurants.

Why I recommend it:

• 10 minutes from the airport
• Spacious suites
• Full kitchen
• Great home base for exploring both the French and Dutch sides
• Excellent value when booked with Wyndham Rewards points

Want the full breakdown? I’ll be sharing a complete review of Port de Plaisance Resort, including room photos, amenities, location, and whether I’d stay there again.

New to Points & Miles?

If you’ve been collecting points but aren’t sure how to use them—or you’re ready to start traveling for nearly free—check out my Beginner’s Guide to Points & Miles.

Inside, I’ll show you how I use credit card points, airline miles, and hotel rewards to book trips like this one for a fraction of the cost.

Grab your copy here!

Getting Around the Island

My biggest recommendation is to rent a car.

We rented through Avis and found it gave us the flexibility to explore both sides of the island at our own pace. The cost for our stay was just $262, with the rental car deposit being approximately $500.

However, several travelers recommended local companies with little to no security deposit requirements, such as:

• Hardee Car Rental
• Exclusive Car Rental

While some larger rental companies may hold as much as $1,000. Shop around and compare options before booking.

Is Driving Difficult?

You’ll often hear people say driving on the island is “crazy.”

Honestly, I think that depends on what you’re used to! As someone from Chicago who regularly drives in a major city, I found it manageable.

Traffic can build around rush hour and airport arrival times, but outside of that, it was fairly straightforward. We also didn’t have issues with parking.

Money, Credit Cards & Cash

You should bring both credit cards and cash.

During my trip:

• Visa was widely accepted
• Mastercard was widely accepted
• Tap-to-pay (digital wallets) worked in many places
• American Express was accepted at some larger establishments
• Smaller local businesses often did not accept American Express

For example:

American Express worked at some beach clubs and larger restaurants. Local favorites like Captain’s Rib Shack did not accept American Express.

Best Credit Cards for Travel

Want to know which travel credit card I actually use?

One of my go-to cards is the Chase Sapphire Preferred® because it earns flexible points that can be transferred to airline and hotel partners, offers primary rental car insurance, has no foreign transaction fees, and earns bonus points on travel and dining purchases.

For a trip like St. Maarten, those benefits can add up quickly. Between renting a car, dining out across both the French and Dutch sides of the island, and earning points toward future travel, it’s one of the cards I keep in my wallet.

If you’re considering applying for the Chase Sapphire Preferred® or want a deeper look at the card’s benefits, travel protections, earning potential, and how I use it to book trips like this one, check out my complete review below.

Chase Sapphire Preferred Review: Still the Best Starter Travel Card?

Disclosure: If you apply through my link, I may earn a commission at no additional cost to you. Thank you for supporting Journey With Reese J.

What to Pack

The Caribbean sun is no joke.

• Swimsuits (bring several)
• Coverups
• Lightweight dresses
• Linen sets
• Breathable clothing
• Comfortable sandals
• Dinner outfits
• Light rain jacket

Beach Essentials

• Beach bag
• Sunglasses
• Sun hat
• Reef-safe sunscreen
• Facial sunscreen
• Scalp sunscreen
• Beach towel
• Swim shoes

If you wear braids, locs, twists, or protective styles, do not forget scalp sunscreen! I’ve learned that lesson the hard way. One of my favorites to use is Coola. You can find it here!

Travel Essentials

• Passport
• Portable charger
• Car charger
• Reusable water bottle or Stanley
• Packing cubes
• Medications
• Waterproof phone pouch

You shop my Amazon Travel Essentials and more here!

Content Creator Essentials

As a content creator, I also packed:

• Camera
• Drone
• Tripod
• SD cards
• Extra batteries
• Portable power bank

You shop my Amazon Content Creator Must-Haves here

Drone Restrictions

As an FAA Part 107 drone pilot, I always travel with my drone when permissible.

However, many areas around St. Maarten fall within restricted airspace due to Princess Juliana International Airport.

I was unable to fly in areas such as:

• Kalatua Beach Club
• Maho Beach area
• Balaou Floating Bar

I was able to get footage in portions of Philipsburg and other approved areas. Always check airspace restrictions before flying.

Best Beaches in St. Martin

Mullet Bay Beach (My Favorite)

If I could only recommend one beach, this would be it.

Why I loved it:

• Crystal-clear water
• Soft sand
• Beautiful shades of blue
• Great atmosphere

Orient Bay

Located on the French side.

Known for:

• Beach clubs
• Restaurants
• Water sports
• Stunning views

Grand Case Beach

Perfect for relaxing and catching sunset after dinner.

Maho Beach

• Plane watching

Things to Do in St. Martin

• Visit Maho Beach (watch planes land overhead)
• Jet Cars Experience
• Kalatua Beach Club
• Da Waterhole
• Topper’s Rum Distillery Tour
• Balaou Floating Bar
• Island hopping (easy day trips to Anguilla and St. Barths)
• Shopping in Philipsburg
• Ziplining at Rainforest Adventures
• Beach hopping
• Massages overlooking the ocean

One of my favorite last-minute experiences was a cliffside massage before heading to the airport.

For just $50 for 30 minutes, it was one of the most peaceful moments of the entire trip. Don’t skip it and book in advance!

Day Trips from St. Maarten

One of the biggest advantages of staying in St. Maarten is its location. It’s very easy to island-hop. You can be on another island in less than 30 minutes via the public ferry or in less than 10 minutes by plane!

Anguilla

If you’ve followed me for any amount of time, you already know that Anguilla is my happy place. In fact, it’s one of my favorite islands in the Caribbean.

The ferry ride takes about 25 minutes, making it easy to spend a full day exploring before returning to St. Martin in the evening.

Although Anguilla is a relatively small island, there’s no shortage of things to do. Some of my favorite stops include:

• Sunshine Shack or Straw Hat for authentic Caribbean food
• Savi Beach Club (trust me, don’t skip this one)
• Shoal Bay Beach
• Meads Bay

If you plan to visit Savi Beach Club, I highly recommend making reservations in advance. One of the best parts is that you can reserve a beach bed without a minimum spend, making it one of the best beach club experiences in the Caribbean.

I also recommend renting a car. We paid approximately $70 for the day, including the temporary driver’s permit. Keep in mind that Anguilla drives on the left side of the road, so remember: stay left!

If you’re looking for a luxury experience, several resorts offer day passes, including Four Seasons Anguilla and Zemi Beach House. Families traveling with children may also enjoy Aurora Anguilla, which features a water park and family-friendly activities.

The island’s relaxed atmosphere, crystal-clear water, and stunning beaches are exactly why I keep returning. If you have an extra day during your St. Maarten vacation, don’t skip Anguilla! And yes, you’ll be getting an additional passport stamp!

Want all the details? I’ll be sharing a complete guide to visiting Anguilla from St. Maarten/St. Martin, including ferry information, costs, where to eat, and the perfect one-day itinerary.

St. Barths

Another popular day trip option from St. Martin is St. Barths (Saint Barthélemy), a French Caribbean island known for luxury resorts, designer shopping, celebrity sightings, and some of the Caribbean’s most famous beach clubs.

Visitors can reach St. Barths via ferry or a short regional flight from St. Martin.

The island is home to luxury boutiques including Louis Vuitton, Hermès, Dior, Cartier, and other high-end brands, making it a favorite destination for luxury travelers and yacht enthusiasts.

St. Barths is also known for iconic beach clubs and restaurants such as La Guérite, Nikki Beach, and Gyp Sea Beach Club, which attract celebrities, influencers, and travelers from around the world.

We ultimately decided to save St. Barths for another visit. After our ferry ride back from Anguilla, my friend wasn’t particularly excited about hopping on another potentially choppy boat ride, and so we decided to spend more time enjoying St. Maarten and St.Martin itself.

One thing to keep in mind is that many shops and businesses close on Sundays, so if luxury shopping is on your itinerary, you’ll want to plan your visit accordingly.

If designer boutiques, beach clubs, yachts, and glamorous French-Caribbean vibes are your thing, St. Barths is absolutely worth adding to your Caribbean bucket list.

One of the things I love most about using St. Maarten as a home base is that it makes island hopping very easy. By adding day trips to Anguilla and St. Barths, this itinerary gives you the opportunity to visit four different countries/territories during a single vacation—Saint-Martin (French side), Sint Maarten (Dutch side), Anguilla, and St. Barths—while collecting up to three passport stamps along the way.

Nightlife

If you’re looking for nightlife, St. Maarten has plenty of options. One thing I loved was that many of the popular bars, lounges, and clubs are located near one another, making it easy to park and club/bar-hop throughout the night.

Most venues feature a mix of Caribbean music, hip-hop, R&B, Afrobeats, and dance music, so the biggest difference comes down to the atmosphere you’re looking for.

Some of the nightlife spots we visited included:

Nowhere Special

A fun open-air venue with great energy and a relaxed atmosphere. It’s a great place to start your evening, grab a drink, and enjoy live music or entertainment before heading to other spots nearby.

Avantika & Amore

Located next to one another and directly across from Lotus Nightclub, Avantika and Amore offer a more lounge-like atmosphere with music, cocktails, hookah, and a social crowd. We enjoyed the mix of Caribbean music, hip-hop, and R&B, and it was easy to move between venues throughout the night.

Lotus Nightclub

If you’re looking for a true nightclub experience, Lotus is one of the most popular options on the island.

Expect:

• DJs
• Dancing
• VIP sections and bottle service
• A larger late-night crowd

We were told by locals and staff that the venue tends to get busier later in the evening, especially on weekends and when certain DJs are scheduled to perform, so keep that in mind.

District 721

District 721 was the perfect way to end my birthday trip.

We visited on a weeknight, so it wasn’t overly crowded, but the atmosphere was very nice. Between the stylish décor, live DJ, craft cocktails, and overall vibe, it’s easy to see why this spot is so popular.

If you’re celebrating a birthday, girls’ trip, or special occasion, I’d definitely add District 721 to your list—especially on a weekend or one of their busier nights.

Safety

As two women traveling together, safety is always a priority. Throughout our trip, we felt comfortable and welcomed.

At Port de Plaisance:

• Staff were attentive
• Security was visible
• Golf carts transported guests throughout the property
• We felt comfortable returning to our suite at night

As always:

• Lock your vehicle
• Use your hotel safe
• Stay aware of your surroundings
• Don’t leave valuables visible

How Much Did This Trip Cost?

Because I used points and miles, my total out-of-pocket expenses came to approximately:

Had I paid cash for flights and accommodations, this trip would have easily cost over $3,000.

Best Time to Visit St. Martin

December–April

• Best weather
• Peak season
• Higher prices
• Most popular time to visit

May–June

• Fewer crowds
• Great weather
• Better hotel rates

July–November

• Lowest prices
• Hurricane season
• More rain
• Great for budget travelers

My 5-Day St. Maarten Itinerary

Here’s a quick overview of how I spent six days and five nights exploring St. Martin, St. Maarten, and Anguilla:

Day 1: Fly from Chicago to St. Maarten, pick up a rental car, check into Port de Plaisance Resort, and enjoy dinner at Captain’s Rib Shack.

Day 2: Relax at Kalatua Beach Club, experience the Jet Cars near Philipsburg, enjoy dinner at Bamboo House, and explore the nightlife scene at Nowhere Special, Avantika, and Amore.

Day 3: Take a day trip to Anguilla, visit Sunshine Shack and Savi Beach Club, explore the island’s beautiful beaches, and return to St. Martin in the evening.

Day 4: Start the day with breakfast at Mr. Papaya, spend the afternoon at Balaou Floating Bar on the French side, and celebrate with a birthday dinner at JAX Steakhouse.

Day 5: Enjoy brunch at Baraite, tour Topper’s Rum Distillery, have dinner at Palapa Grill & Hidden Oasis, and end the evening with cocktails, music, and great vibes at District 721.

Departure Day: Squeeze in one last island breakfast, enjoy a relaxing cliffside massage overlooking the ocean, and head to the airport refreshed and already planning your next trip back.

This itinerary provided the perfect balance of beach clubs, local food, nightlife, island hopping, relaxation, and cultural experiences without feeling rushed.

Final Thoughts

St. Maarten and St. Martin offer something for every type of traveler. Whether you’re looking for crystal-clear beaches, authentic Caribbean food, vibrant nightlife, luxury beach clubs, or the opportunity to explore neighboring islands like Anguilla and St. Barths, you’ll find it here.

What I loved most about this destination is its versatility. One moment you’re relaxing on a beautiful beach, the next you’re enjoying a beachfront lunch, exploring a different side of the island, or planning a quick ferry ride to another Caribbean destination.

Whether you’re traveling on points and miles, planning a girls’ getaway, celebrating a birthday, or simply looking for a Caribbean destination with a little bit of everything, St. Maarten delivers.

And if you’re anything like me, you’ll be checking flight prices and planning your next visit before you’ve even unpacked your suitcase.