8-Day St. Maarten, Anguilla & St. Barth Island-Hopping Escape

Arrive at Princess Juliana International Airport (SXM), where you will be welcomed and transferred to your accommodation in St. Maarten. After check-in, enjoy some time to settle in and recover from your journey. Depending on your arrival time, begin exploring the island with a relaxed visit to Philipsburg, the Dutch capital. Walk along Front Street, browse Caribbean shops and discover the colorful waterfront surroundings. Continue to Great Bay Beach, where you can enjoy the warm Caribbean water and views of the cruise harbor. Spend the evening enjoying dinner at your leisure and preparing for the island adventures ahead.

After breakfast, begin a guided sightseeing experience around the Dutch side of St. Maarten. Explore Philipsburg’s historic center, including its colonial-era architecture, waterfront promenade and local shopping streets. Continue towards Fort Amsterdam, a historic defensive site offering panoramic views over Great Bay and the surrounding coastline. Learn about the island’s colonial history and the historical importance of its strategic harbor. Later, travel through the Simpson Bay area and enjoy views of the marina, lagoon and coastal neighborhoods. Depending on the day’s conditions, finish with beach relaxation at Mullet Bay, known for its beautiful sandy shoreline and clear water. Return to your accommodation in the late afternoon.

After breakfast, cross to the French side of the island for a cultural and coastal discovery tour. Begin in Marigot, exploring its waterfront, local market area and French Caribbean architecture. Continue to Fort Louis, where the elevated viewpoint offers sweeping views of Marigot Bay, neighboring islands and the Caribbean Sea. After the historical visit, travel towards Grand Case, a coastal village recognized for its French Caribbean food culture and traditional atmosphere. Enjoy free time to explore the village and experience local cuisine at your own expense. In the afternoon, continue towards Orient Bay for beach relaxation, swimming and optional watersports available locally. Return to your St. Maarten accommodation in the evening.

Enjoy breakfast before checking out and traveling to Marigot Ferry Terminal on the French side of St. Martin. Complete the necessary departure formalities before boarding the scheduled ferry to Blowing Point in Anguilla. The crossing typically takes approximately 20 minutes, subject to weather and operational conditions. On arrival, meet your local transfer representative and begin discovering Anguilla’s relaxed island atmosphere. Travel through the island’s coastal communities before heading to Shoal Bay East, one of Anguilla’s best-known beaches. Spend the afternoon enjoying the soft white sand, turquoise water and peaceful beach environment. Guests can swim, relax, take photographs or enjoy optional water activities. Later, transfer to your selected accommodation and enjoy a relaxed evening.

Following breakfast, dedicate the day to discovering more of Anguilla’s coastline. Begin with a scenic drive through the island’s western communities, stopping around Meads Bay to appreciate its long sandy shoreline and calm Caribbean atmosphere. Continue towards the West End, where guests can explore the coastal scenery and enjoy photography opportunities. Depending on sea conditions and the selected boat operator, embark on an optional or pre-arranged marine excursion towards Anguilla’s surrounding cays, such as Prickly Pear Cays. Enjoy time on the water, with opportunities for swimming and snorkeling where conditions permit. Return to the main island in the afternoon and spend additional time relaxing at the beach. The evening is free for dining and leisure.

After breakfast, check out and transfer to Blowing Point Ferry Terminal for the return crossing to Marigot. Complete departure formalities and board the scheduled ferry to French St. Martin. Upon arrival, continue by private or pre-arranged ground transfer to your accommodation on the Dutch side of St. Maarten. The remainder of the day is reserved for relaxation after the Anguilla experience. Guests may explore Simpson Bay, enjoy the island’s marina atmosphere, visit nearby beaches or spend time shopping for Caribbean souvenirs. This overnight stop also provides a practical buffer before the next international island crossing.

Enjoy breakfast before transferring to the designated ferry departure point in St. Maarten. Board a scheduled ferry to Gustavia, the capital of St. Barth, allowing sufficient time for passenger check-in and border formalities. On arrival, explore Gustavia’s picturesque harbor, where yachts, waterfront buildings and hillside scenery create a distinctive Caribbean setting. Continue with a guided island discovery drive towards St. Jean, an attractive coastal area known for its beach and scenic surroundings. Enjoy free time for swimming, photography and relaxation. Later, visit Shell Beach, a beautiful coastal location near Gustavia known for its shell-covered shoreline. Guests can enjoy the beach atmosphere before checking in to their selected St. Barth accommodation. Spend the evening exploring Gustavia or enjoying French Caribbean dining at your leisure.

Enjoy breakfast and some final leisure time in St. Barth, depending on the ferry departure schedule. Guests may take a short walk around Gustavia, enjoy the harbor scenery or purchase souvenirs before checking out. Transfer to the designated ferry terminal and board the scheduled return service to Philipsburg, St. Maarten. On arrival, continue to Princess Juliana International Airport or another agreed departure point for your onward journey. This concludes your eight-day Caribbean island-hopping experience across St. Maarten, Anguilla and St. Barth.