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Ultimate 15-Day Caribbean Adventure in Anguilla, St. Maarten & St. Martin

Ultimate 15-Day Caribbean Adventure in Anguilla, St. Maarten & St. Martin Itinerary

Last updated: 2024 Jun 14

Sun, Sea, and Sand in Anguilla

Morning
Start your Caribbean adventure with a leisurely morning at the iconic Meads Bay. After soaking in the sun and enjoying the pristine beach, head to Jacala Beach Restaurant for a delightful beachfront breakfast.
Afternoon
Explore the crystal-clear waters with the Sand Dollar Half Day Snorkel Cruise St. Martin. Immerse yourself in the vibrant marine life and enjoy a refreshing swim. After the cruise, savor a seafood lunch at the renowned Straw Hat Restaurant.
Evening
End your day with a romantic dinner at Mango's Seaside Grill, where you can enjoy fresh seafood and stunning ocean views.
Bedtime
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Meads Bay

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Sand Dollar Half Day Snorkel Cruise St. Martin

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Thrills and Chills in St. Maarten

Morning
Embark on the adrenaline-pumping St. Maarten Sentry Hill & Flying Dutchman Zipline Adventure. Enjoy the panoramic views and the thrill of ziplining through the lush landscape. Afterward, have a hearty breakfast at Tasty's Restaurant.
Afternoon
Experience the unique Philipsburg Extreme Plane Spotting at Maho Beach and watch the planes land just a few feet above you. For lunch, indulge in Caribbean flavors at Smokey's at the Cove.
Evening
Conclude your day with a relaxing Simpson Bay Bubbly Sunset Cruise with Prosecco & Snacks. Enjoy the sunset over the Caribbean Sea with a glass of bubbly in hand.
Bedtime
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St. Maarten Sentry Hill & Flying Dutchman Zipline Adventure

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Philipsburg Extreme Plane Spotting at Maho Beach

star4.66

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Simpson Bay Bubbly Sunset Cruise with Prosecco & Snacks

star4.75

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French-Inspired Delights in St. Martin

Morning
Begin your day with a visit to the charming Prickly Pear Cays. Enjoy the pristine beaches and the turquoise waters. For breakfast, savor French pastries at Veya.
Afternoon
Take a St. Martin Tango Dinner Cruise and explore the French side of the island from the water. Enjoy a gourmet lunch on board and take in the scenic views. In the afternoon, visit the Underwater Sculpture Park Snorkel Adventure for a unique underwater experience.
Evening
Dine at the elegant Barrel Stay and enjoy a fusion of French and Caribbean cuisine in a romantic setting.
Bedtime
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Prickly Pear Cays

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St. Martin Tango Dinner Cruise

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Underwater Sculpture Park Snorkel Adventure

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Relaxation and Rejuvenation in Anguilla

Morning
Indulge in a morning of relaxation at the serene Shoal Bay. Unwind on the powdery white sand beach and take a dip in the azure waters. For breakfast, enjoy a beachfront meal at Sandbar.
Afternoon
Treat yourself to a spa day at one of Anguilla's luxury resorts. Rejuvenate with a massage or a wellness treatment. For lunch, try the healthy and delicious options at Jacala Beach Restaurant.
Evening
Enjoy a sunset yoga session on the beach followed by a nutritious dinner at Tasty's Restaurant.
Bedtime
Find amazing hotels in Anguilla.
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Shoal Bay

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Island Exploration in St. Maarten

Morning
Embark on the St. Maarten Half-Day Tour of French & Dutch Sides to discover the rich history and culture of the island. Visit key landmarks and enjoy the scenic views. For breakfast, try the local specialties at Tasty's Restaurant.
Afternoon
After the tour, spend the afternoon at the vibrant Philipsburg St Maarten Beaches Tour with Transfer. Relax on the sandy shores and take a dip in the turquoise waters. For lunch, sample the fresh seafood at Smokey's at the Cove.
Evening
In the evening, take a leisurely stroll along the Sunset Beach Bar St Maarten and enjoy the lively atmosphere. Have dinner at one of the beachfront restaurants and watch the sunset.
Bedtime
Find amazing hotels in St. Maarten.
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St. Maarten Half-Day Tour of French & Dutch Sides

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Philipsburg St Maarten Beaches Tour with Transfer

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St.Maarten No1Sxm Sunset Sailing Trimaran

star4.95

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Culinary Delights in St. Martin

Morning
Explore the local markets and sample the fresh produce at the Marigot Market. Immerse yourself in the vibrant colors and flavors of the Caribbean. For breakfast, try the traditional pastries at Veya.
Afternoon
Take a St. Martin Full-Day Catamaran Sail to Prickly Pear Cays and enjoy a day of sailing, snorkeling, and beach hopping. Indulge in a gourmet lunch on board. In the afternoon, visit the Loterie Farm Fly Zone Treetop Zip-Line Adventure for an adrenaline-filled experience.
Evening
Dine at the acclaimed Jacala Beach Restaurant and savor the fresh seafood and Creole dishes in a beachfront setting.
Bedtime
Find amazing hotels in St. Martin.
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Simpson Bay Lambada Sunset Cruise of Sint Maarten

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St. Maarten Full-Day Catamaran Sail to Prickly Pear Cays

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Loterie Farm Fly Zone Treetop Zip-Line Adventure

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Beach Bliss in Anguilla

Morning
Spend a relaxing morning at the secluded Cove Bay. Enjoy the tranquility of the beach and take a leisurely swim in the calm waters. For breakfast, have a beachfront meal at Sandbar.
Afternoon
Afterward, head to the Sandy Island for a true castaway experience. Relax on the pristine sands, snorkel in the clear waters, and enjoy a barbecue lunch. In the afternoon, take a Sandy Island Day Trip and enjoy the stunning views of the surrounding islands.
Evening
For dinner, dine under the stars at the romantic Jacala Beach Restaurant and savor the fresh seafood and French-Caribbean cuisine.
Bedtime
Find amazing hotels in Anguilla.
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Los Cabos Sunset Fajitas Dinner Cruise on Cabo Escape

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St. Martin Tango Dinner Cruise

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St. Martin Tango Dinner Cruise

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Adventure and Relaxation in St. Maarten

Morning
Start your day with an St Maarten Atv island highlights tour and explore the island's hidden gems. After the tour, have a hearty breakfast at Tasty's Restaurant.
Afternoon
Spend the afternoon at the St. Maarten Orient and Maho Beaches Half-Day Tour. Relax on the pristine beaches, swim in the turquoise waters, and witness the planes landing at Maho Beach. For lunch, enjoy the beachfront dining at Smokey's at the Cove.
Evening
Unwind with a Simpson Bay Lambada Sunset Cruise of Sint Maarten. Enjoy the sea breeze, the stunning views, and a glass of champagne as you watch the sunset.
Bedtime
Find amazing hotels in St. Maarten.
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St Maarten Atv island highlights tour

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St. Maarten Orient and Maho Beaches Half-Day Tour

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Simpson Bay Lambada Sunset Cruise of Sint Maarten

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Nature and Adventure in St. Martin

Morning
Explore the lush landscapes of St. Martin with a St Maartin Sky Explorer and Flying Dutchman Entry Ticket. Enjoy the panoramic views and the thrill of the Flying Dutchman. For breakfast, try the French pastries at Veya.
Afternoon
Visit the St. Martin 3-Hour Rhino Safari Excursion for a unique off-road adventure. Explore the hidden gems of the island and enjoy a barbecue lunch in the wilderness. In the afternoon, take a St. Martin Half-Day Tour of French & Dutch Sides to discover the highlights of the island.
Evening
Dine at the elegant Barrel Stay and enjoy a fusion of French and Caribbean cuisine in a romantic setting.
Bedtime
Find amazing hotels in St. Martin.
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St Maartin Sky Explorer and Flying Dutchman Entry Ticket

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St. Martin 3-Hour Rhino Safari Excursion

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St. Maarten Half-Day Tour of French & Dutch Sides

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Serene Retreat in Anguilla

Morning
Indulge in a morning of relaxation at the serene Shoal Bay. Unwind on the powdery white sand beach and take a dip in the azure waters. For breakfast, enjoy a beachfront meal at Sandbar.
Afternoon
Treat yourself to a spa day at one of Anguilla's luxury resorts. Rejuvenate with a massage or a wellness treatment. For lunch, try the healthy and delicious options at Jacala Beach Restaurant.
Evening
Enjoy a sunset yoga session on the beach followed by a nutritious dinner at Tasty's Restaurant.
Bedtime
Find amazing hotels in Anguilla.
Popular
activity-image

Shoal Bay

star4.78

click to access prices

Island Exploration in St. Maarten

Morning
Embark on the St. Maarten Half-Day Tour of French & Dutch Sides to discover the rich history and culture of the island. Visit key landmarks and enjoy the scenic views. For breakfast, try the local specialties at Tasty's Restaurant.
Afternoon
After the tour, spend the afternoon at the vibrant Philipsburg St Maarten Beaches Tour with Transfer. Relax on the sandy shores and take a dip in the turquoise waters. For lunch, sample the fresh seafood at Smokey's at the Cove.
Evening
In the evening, take a leisurely stroll along the Sunset Beach Bar St Maarten and enjoy the lively atmosphere. Have dinner at one of the beachfront restaurants and watch the sunset.
Bedtime
Find amazing hotels in St. Maarten.
Popular
activity-image

St. Maarten Half-Day Tour of French & Dutch Sides

star4.50

click to access prices

Popular
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Philipsburg St Maarten Beaches Tour with Transfer

star4.47

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Popular
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St.Maarten No1Sxm Sunset Sailing Trimaran

star4.95

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Culinary Delights in St. Martin

Morning
Explore the local markets and sample the fresh produce at the Marigot Market. Immerse yourself in the vibrant colors and flavors of the Caribbean. For breakfast, try the traditional pastries at Veya.
Afternoon
Take a St. Martin Full-Day Catamaran Sail to Prickly Pear Cays and enjoy a day of sailing, snorkeling, and beach hopping. Indulge in a gourmet lunch on board. In the afternoon, visit the Loterie Farm Fly Zone Treetop Zip-Line Adventure for an adrenaline-filled experience.
Evening
Dine at the acclaimed Jacala Beach Restaurant and savor the fresh seafood and Creole dishes in a beachfront setting.
Bedtime
Find amazing hotels in St. Martin.
Popular
activity-image

Simpson Bay Lambada Sunset Cruise of Sint Maarten

star4.75

click to access prices

Popular
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St. Maarten Full-Day Catamaran Sail to Prickly Pear Cays

star4.60

click to access prices

Popular
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Loterie Farm Fly Zone Treetop Zip-Line Adventure

star4.00

click to access prices

Beach Bliss in Anguilla

Morning
Spend a relaxing morning at the secluded Cove Bay. Enjoy the tranquility of the beach and take a leisurely swim in the calm waters. For breakfast, have a beachfront meal at Sandbar.
Afternoon
Afterward, head to the Sandy Island for a true castaway experience. Relax on the pristine sands, snorkel in the clear waters, and enjoy a barbecue lunch. In the afternoon, take a Sandy Island Day Trip and enjoy the stunning views of the surrounding islands.
Evening
For dinner, dine under the stars at the romantic Jacala Beach Restaurant and savor the fresh seafood and French-Caribbean cuisine.
Bedtime
Find amazing hotels in Anguilla.
Popular
activity-image

Los Cabos Sunset Fajitas Dinner Cruise on Cabo Escape

star4.19

click to access prices

Popular
activity-image

St. Martin Tango Dinner Cruise

star4.71

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Popular
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St. Martin Tango Dinner Cruise

star4.71

click to access prices

Adventure and Relaxation in St. Maarten

Morning
Start your day with an St Maarten Atv island highlights tour and explore the island's hidden gems. After the tour, have a hearty breakfast at Tasty's Restaurant.
Afternoon
Spend the afternoon at the St. Maarten Orient and Maho Beaches Half-Day Tour. Relax on the pristine beaches, swim in the turquoise waters, and witness the planes landing at Maho Beach. For lunch, enjoy the beachfront dining at Smokey's at the Cove.
Evening
Unwind with a Simpson Bay Lambada Sunset Cruise of Sint Maarten. Enjoy the sea breeze, the stunning views, and a glass of champagne as you watch the sunset.
Bedtime
Find amazing hotels in St. Maarten.
Popular
activity-image

St Maarten Atv island highlights tour

star5.00

click to access prices

Popular
activity-image

St. Maarten Orient and Maho Beaches Half-Day Tour

star4.36

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Popular
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Simpson Bay Lambada Sunset Cruise of Sint Maarten

star4.75

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Farewell to the Caribbean

Morning
On your last day, take a moment to enjoy the beauty of the Caribbean. Spend the morning at Shoal Bay and savor the final moments on the pristine beach. For breakfast, have a beachfront meal at Sandbar.
Afternoon
Relax and reflect on your journey with a spa treatment at one of Anguilla's luxury resorts. Indulge in a massage or a wellness therapy. For lunch, enjoy the healthy and delicious options at Jacala Beach Restaurant.
Evening
Conclude your Caribbean adventure with a sunset cocktail at a beachfront bar, watching the colors of the sky change as the sun dips below the horizon.
Bedtime
Find amazing hotels in Anguilla.
Popular
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Shoal Bay

star4.78

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Top Anguilla Travel Videos

Adjacent Cities

St. MaartenSt. Martin

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