New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

5-day Anguilla Adventure with Island Hopping

5-day Anguilla Adventure with Island Hopping Itinerary

Last updated: 2024 Jun 14

Historical Ruins and Beachfront Beginnings

Morning
Begin your day with a visit to the historic Wallblake House, the oldest surviving plantation house on the island. After exploring the ruins, enjoy a delightful breakfast at the charming Picante, known for its fresh and vibrant Mexican cuisine.
Afternoon
Immerse yourself in the underwater wonders of Anguilla with a morning of snorkeling at the pristine Meads Bay Beach. After working up an appetite, head to Straw Hat Restaurant for a beachfront lunch experience, featuring a fusion of international flavors.
Evening
As the sun begins to set, take a leisurely walk along the soft sands of Shoal Bay East Beach, often ranked among the world's best beaches. Conclude your evening with a sumptuous dinner at Mango's Seaside Grill, offering a perfect blend of Caribbean and international cuisine with a seaside ambiance.
Bedtime
Find amazing hotels in The Valley, Anguilla.

Island Exploration

Morning
Embark on an island tour and visit the iconic The Valley Wall. Marvel at the breathtaking views of the island from this scenic viewpoint. Afterward, satisfy your caffeine cravings at Cafe de Paris with their delicious pastries and aromatic coffee.
Afternoon
Immerse yourself in the rich history of Anguilla by visiting the Heritage Collection Museum. Learn about the island's culture, traditions, and heritage through fascinating exhibits. For a delightful lunch, head to Tasty's Restaurant and savor their mouthwatering Caribbean dishes.
Evening
Indulge in a luxurious beachfront dining experience at Hibernia Restaurant and Art Gallery. Enjoy a delectable fusion of Asian and Caribbean flavors while admiring the stunning sunset. After dinner, head to Dolce Vita for a relaxing evening of live music and cocktails.
Bedtime
Find amazing hotels in Anguilla.

Adventure and Relaxation

Morning
Get your adrenaline pumping with a thrilling jet ski tour around the island's coastline. Experience the thrill of speeding through the waves and enjoy panoramic views of Anguilla. For a quick and energizing breakfast, grab a bite at Cafe Au Lait.
Afternoon
Unwind and rejuvenate at the luxurious CuisinArt Golf Resort & Spa. Indulge in a pampering spa treatment and soak in the tranquility of the surroundings. For a leisurely lunch, head to Blanchards Restaurant and savor their delectable seafood dishes.
Evening
Treat yourself to a gourmet dinner at Veya Restaurant and savor their innovative Caribbean cuisine. Afterward, head to The Pumphouse for a lively evening of drinks, live music, and dancing.
Bedtime
Find amazing hotels in Anguilla.

Nature and Culture

Morning
Explore the natural beauty of Anguilla by visiting Crocus Hill. Take a scenic hike up the hill and enjoy panoramic views of the island. For a delightful breakfast, stop by Artisan Pizza Napoletana and indulge in their mouthwatering wood-fired pizzas.
Afternoon
Immerse yourself in the vibrant local culture by visiting The Old Factory]. Explore the local art and craft scene and shop for unique souvenirs. For a tasty lunch, head to Elvis' Beach Bar and enjoy their delicious Caribbean specialties.
Evening
Experience a true Caribbean culinary adventure at Mango's Seaside Grill. Indulge in their fresh seafood dishes and savor the flavors of the island. After dinner, relax and enjoy a cocktail at the laid-back Smokin' Barrel.
Bedtime
Find amazing hotels in Anguilla.

Beach Bliss

Morning
Spend your final day in Anguilla at the pristine Meads Bay Beach. Relax on the soft white sand, swim in the calm waters, and soak up the sun. For a delightful beachfront breakfast, head to Straw Hat Restaurant and enjoy their mouthwatering dishes.
Afternoon
Indulge in a luxurious beach club experience at Shoal Bay Beach Club. Lounge by the pool, sip on refreshing cocktails, and enjoy the beachfront ambiance. For a delicious lunch, try SandBar and their delectable Caribbean-inspired cuisine.
Evening
End your trip on a high note with a memorable dinner at the elegant Viceroy Anguilla. Indulge in their gourmet international cuisine while enjoying breathtaking views of the Caribbean Sea. After dinner, head to The Dune Preserve for a laid-back evening of live music and drinks.
Bedtime
Find amazing hotels in Anguilla.

Adjacent Cities

kayakFind the right stay during your trip.
Got a question about your trip?