3 Dreamy Islands in 1 Trip: Anguilla, St. Maarten, and St. Barth

Have you been dreaming of warm sun, crystal-clear waters, and powdery soft sand? Or is it just me? I am always seeking a tropical escape, yet my urge to see ALL the places in one trip is a real issue. Decision-making quickly becomes a feat!

A disappointing destination really hits hard when time is precious and money is hard-earned. I truly believe this 3-in-1 island itinerary is tough to beat for travelers looking to stay on multiple islands without doing a cruise. It is perfect for a family vacation, a couple’s trip, a girls’ trip, or, like me, a mother-daughter trip!

In this blog, I will tell you how easy it is to hop between three stunning tropical islands—Anguilla, St. Maarten, and St. Barth. This is a once-in-a-lifetime experience and a trip I can’t stop reminiscing about. I will forever be grateful for this amazing vacation with my mom!

---

About Anguilla, St. Maarten, and St. Barth

Anguilla

Anguilla is a British Overseas Territory and an absolute hidden jewel in the Caribbean! This 16-mile-long island is small but mighty. Boasting 33 lovely beaches, Anguilla is sure to impress even the snobbiest of beach snobs.

You can expect to enjoy pristine beaches, peaceful vibes, and world-class dining in Anguilla. Fellow foodies should know that the thought of every meal I had in Anguilla could bring me to tears of pure bliss.

English is the official language of Anguilla. The Eastern Caribbean Dollar is the official currency, with U.S. dollars being widely accepted. Travel + Leisure named Anguilla the safest Caribbean country and the #1 island in the Caribbean in 2025. It is no wonder this low-key island quickly won my heart!

St. Maarten

Our next dreamy island offers the unique opportunity to experience two culturally different areas with ease. The Dutch side is officially “Sint Maarten,” and the French side is “Saint Martin.” For simplicity, I will use St. Maarten in this blog. Mom and I stayed on the Dutch side of the island, but we definitely explored the French side too.

Some great features of the island are its 37 beaches, hundreds of restaurants, the world’s steepest zip line (the Flying Dutchman), hiking trails, and duty-free shopping! St. Maarten is also home to the internet-famous Maho Beach, where airplanes land directly overhead of beachgoers basking in the sun!

The official languages of St. Maarten are Dutch and English, and French for St. Martin. St. Maarten’s official currency is the Netherlands Antillean Guilder, and St. Martin’s is the Euro. We had no trouble using U.S. dollars; however, there was variability in accepted credit cards. We generally felt safe and walked around at night with no issues.

St. Barth

If you love parties and luxury, St. Barth (or more formally, Saint Barthélemy) just may be your new favorite paradise! This French-chic island is a total playground for wealthy travelers. Think unique beaches, luxury shopping, gourmet dining, and upscale parties. When I tell you the entire island was PRISTINE, I tell you no lies. It was immaculate!

While St. Barth’s reputation for being very expensive is absolutely true, it is possible to plan a more modestly budgeted trip. I will give you a great strategy if you are planning a vacation that doesn’t break the bank.

French is the official language of St. Barth, and once again, everyone speaks English as well. The official currency is the Euro, and you guessed it—U.S. dollars are accepted too! We felt extremely safe (and maybe a touch out of place) on the fancy-pants island of St. Barth.

Air Travel to Anguilla, St. Maarten, and St. Barth

Anguilla

There are a few airlines that offer direct flights into Anguilla’s Clayton J. Lloyd International Airport (AXA). Until December 2025, the only U.S. hub that flew to AXA was Miami (MIA) on American Airlines. Now it is also possible to fly non-stop on AnguillAir from Boston (BOS), Baltimore (BWI), and Newark (EWR) from the United States.

A common strategy for reaching Anguilla is by flying into St. Maarten’s airport (SXM), then taking a 10-minute flight or a 20-minute ferry ride (public or semi-private) to Anguilla. More details on the ports for all three islands to come.

St. Maarten

Princess Juliana International Airport (SXM) is the major airport on the Dutch side. L’Esperance Airport (SFG) is a smaller international airport on the French side.

Many airlines offer nonstop flights to SXM; however, it’s a good idea to compare flights to both airports based on your departure location

St. Barth

Gustaf III Airport (SBH) is the only airport in St. Barth. Only a handful of countries close to St. Barth offer flights to SBH. The airport can only accommodate small aircraft due to the short runway and surrounding steep hills. Watching planes land and take off is wild!

Like Anguilla, a common strategy for reaching St. Barth is to fly into St. Maarten, then take a 15-minute flight or 45-minute ferry to St. Barth.

How to Island Hop Anguilla, St. Maarten, St. Barth

Island hopping across Anguilla, St. Maarten, and St. Barth can be done in so many different ways. I will explain our exact itinerary so that you can either replicate it or use it for inspiration to customize your own multi-paradise vacation!

1) Fly into SXM and check into St. Maarten hotel for several days.

• We flew American Airlines from Asheville, NC with a short layover in Charlotte, NC.
• St. Maarten is a great base for island hopping as it offers the most flight and ferry options to other nearby islands.

2) Take ferry from Philipsburg, St. Maarten to Gustavia, St. Barth for a day trip.

• We departed from Philipsburg on Great Bay Express ferry at 9:45 AM.
• It is possible to travel round trip to St. Barth from Marigot port too.
• We enjoyed special lunch reservations, shopping, and three different beaches in a single day trip.
• Ferry tickets to St. Barth were bought online a few days in advance.

3) Take ferry from Gustavia, St. Barth back to Philipsburg, St. Maarten.

• We left St. Barth at 6:45 PM, enjoying a full day and a beautiful sunset on our ride back.

4) Take ferry from St. Martin’s Marigot to Anguilla’s Blowing Point and check into Anguilla hotel for several days.

• The ferry to Anguilla departs from the Marigot Port on the French side.
• Ferry tickets from St. Martin to Anguilla must be purchased at the port.
• Charters to Anguilla can be booked with pickup from SXM airport dock.

5) Take ferry from Anguilla’s Blowing Point and to St. Martin’s Marigot and taxi to SXM airport.

6) Fly from SXM back home to Asheville, NC.

Tips for Anguilla, St. Maarten, and St. Barth

Anguilla

Anguilla’s tranquility is wonderful, but if you desire easy access to dining and entertainment, choose larger resorts with restaurants on-site.

Some parts of Anguilla have small concentrations of walkable restaurants near hotels, such as Meads Bay or Shoal Bay, based on our experience. Other areas are more secluded and require a drive.

There is no public transportation system or rideshare services such as Uber or Lyft in Anguilla. Visitors should rent a car or rely on taxis to get around the island.

One more note for travelers, as pointed out by my mom, is that some of the beaches may pose accessibility challenges for those with limited mobility. Anguilla offers options with hotel and beach accommodations for travelers with disabilities.

St. Maarten

A mandatory Embarkation Disembarkation entry form is required to be filled out prior to traveling to Sint Maarten or Saint Martin.

St. Maarten is an island most people will want to explore rather than stay put at one hotel. It simply offers more things to do than the destinations we are discussing.

There are no ride-share services in St. Maarten or St. Martin, such as Uber or Lyft. Taxis are widely available but are very expensive. You can easily spend hundreds of dollars per day on taxi fares.

St. Maarten (the Dutch side) has an unbelievable number of casinos. Some people, including locals, find that it commercializes the island’s natural beauty. However, others might enjoy St. Maarten for its impressive gambling options while on vacation!

St. Barth

The ferry ride to St. Barth had some passengers (my mom included) calling out to God in fear. If you get seasick like I do, pre-medicate and choose an inside cabin seat in the middle of the ship.

Reservations are typically necessary in St. Barth, especially at some of the more popular restaurants. Book reservations to any special restaurants you want to try as far in advance as possible!

Renting a car in St. Barth for an entire day was cheaper than a single taxi ride. It was easy-breezy and so much fun! Our rental car (affectionately nicknamed “Skippy”) allowed us to zip around the entire island in a day!

If you want to experience St. Barth before committing to an expensive vacation, take a day trip from one of its nearby islands. This is a great way to sample St. Barth. It is also a great option for anyone who may not otherwise be able to afford a St. Barth vacation.

Hopefully, I have inspired you to plan a sunny, dreamy vacation with someone special very soon. The only negative of this trip is that it has me constantly debating between revisiting it or seeing new destinations.

Seth and I recently spent several days exploring Peru, including the Sacred Valley, Machu Picchu, and Rainbow Mountain. We battled the high altitude and won. I aim to write up my experience in a way that can do it justice very soon.

Some additional future trips in the works are Southeast Asia with two close friends, Italy with immediate family, and some beluga whale/polar bear adventures with Seth in Canada!

Okay, I know that sounds like a lot but hear me out…

I recently endured a major health scare and was blessed by God with optimal news. I feel like I have a new lease on life and will continue to be grateful for the privilege of travel.

I can’t wait to share all the beauty we discover with you all!

Thank you for joining my travels!