Escape to the sun-drenched islands of the French and Dutch Caribbean with a custom island-hopping journey through St. Maarten, Anguilla, and St. Barth’s.

This package is a working canvas where we’ll blend pristine beaches, chic boutiques, and laid-back beach bars into a seamless itinerary that fits your travel style. As we refine the details together, we can adjust pacing, upgrade experiences, and tailor each stop so that your time on each island feels effortless and unforgettable.

“Why Should You Island Hop Through St. Maarten, Anguilla & St. Barth's?”

1. Three islands, three distinct personalities
St. Maarten blends Dutch and French influences with lively beach bars, casinos, and great dining; Anguilla is all about low-key luxury and postcard‑perfect white‑sand beaches; St. Barts offers a chic, French‑Riviera‑in‑the‑Caribbean feel with designer boutiques and yacht‑filled harbors. Island hopping lets you experience three very different vibes in a single trip.

2. Easy, short inter‑island connections
These islands sit just a short ferry or boat ride apart, so you spend more time enjoying the destination and less time in transit. St. Maarten works as an ideal “hub” with frequent crossings to both Anguilla and St. Barts, making day trips and overnights straightforward and stress‑free.

3. World‑class beaches and water
Each island has its own signature stretch of sand: Simpson Bay and Orient Beach on St. Maarten, the powdery shores of Shoal Bay and Rendezvous Bay in Anguilla, and St. Barts’ glamorous St. Jean and Gouverneur beaches. Island hopping gives you a curated “greatest hits” tour of some of the Caribbean’s best coastline.

4. Variety of experiences in one itinerary
From Jeep and ATV adventures, ziplining, and sailing catamarans in St. Maarten, to snorkeling reefs and cruising around Anguilla’s offshore cays, to lingering at a harbor‑front café in Gustavia on St. Barts, you get a balance of adventure, relaxation, and upscale dining without having to choose just one style of vacation.

5. Excellent dining and nightlife
St. Maarten and St. Barth's are known for their cosmopolitan restaurants and wine lists, while Anguilla is famous for beach bars and grill shacks with fresh seafood and live music. An island‑hopping itinerary lets food and wine lovers' sample everything from barefoot‑casual lunches to elegant French dinners.

6. Ideal for couples, friends, or special occasions
This combination of islands works beautifully for honeymoons, milestone birthdays, and friends’ getaways because you can dial up the energy in St. Maarten, retreat to Anguilla’s serenity, and add a splash of St. Barth's glamour. It feels like several vacations in one, without the long‑haul travel between each stop.

If confirmed to participate in any trip through The Island Travel Boutique, I hereby acknowledge, and agree to, the following booking and cancellation terms and conditions: All bookings are made with Sangean Allen, a sole proprietor and the owner of all advertised trips. The deposit and payment schedule is broken down on the invoice. Review the deposit and payment schedules as well as the cancellation terms listed below, carefully.  All deposit payments are non-refundable. However, they can be transferred to another trip of your choice. This payment goes directly towards the total trip cost, confirms your trip and guarantees your spot.

You may cancel your travel arrangements at any time before the trip departure. However, note you may lose part or all of your money paid. Each trip price consists of two parts: Non-Refundable, Non-Transferable Deposit: $300 - $500 (required at booking). If a payment is made after the due date, a $100 late fee will be applied every 10 days.

If you cancel and your trip is more than 90 days away, you get a full refund (less deposit fee).

If you cancel and your trip is in less than 90 days, you have the option to transfer your payments as a credit towards a future trip with The Island Travel Boutique.

If you cancel and your trip is in less than 60 days, you have the option to transfer your payments as a credit (less 30% of trip value) towards a future trip with The Island Travel Boutique.

For any cancellations with trip date less than 30 days, the cancellation fee is equal to the full booking value.

Breakfast at the hotel.

Optional Tour: Explore Sint Maarten/St. Martin through this amazing ATV/QUAD Tour. This tour includes many stops that last between 15 and 20 minutes at the main attractions in both Dutch and French St. Maarten.

Breakfast at the hotel. Plan this day around one of your Anguilla excursions, such as the Anguilla Getaway Cruise. You will sail across from St. Maarten to enjoy Anguilla’s powdery white-sand beaches and turquoise lagoons, with ample time for swimming, snorkeling, and relaxing on deck.

Come experience a great atmosphere with a personal touch on this full day excursion to explore to beautiful island of Anguilla. Snorkel with tropical fish and turtles, enjoy an open bar with beers, rum punch and sodas and optional lunch available. This will be the most memorable Caribbean vacation.

Breakfast at the hotel. Sky Explorer and Flying Dutchman at Rainforest Adventures St. Maarten.

Breakfast at the hotel. St Barth's Daytrip from St Maarten

Spend a day experiencing the beauty of the untouched white sandy beaches and stunning snorkeling areas that St Barts has to offer! Explore the island at your own leisure, enjoying the relaxed atmosphere and gorgeous surroundings. Although small, this island has a lot to offer!

Today we say farewell to St. Maarten. Breakfast at the hotel. Checkout and transfer to the airport.