the caribbean island you never knew you needed.

Everyone knows the “typical” Caribbean islands: Jamaica, the Bahamas, Turks and Caicos. But if you’ve been there, done that – or just want a quieter, under-the-radar island to consider – Anguilla should be at the top of your list. White sandy beaches, laid-back beachfront dining, and luxury resorts dot this tiny island. Beyond the tranquil beaches, you can explore vibrant coral reefs while snorkeling or spend the day sipping rum punch and listening to live music. And while Anguilla is slower and quieter, its close proximity to the neighboring island of Saint Martin means you can easily hop over for a day trip if you need a change of scenery.

My husband, Chris, and I just returned from Anguilla where we celebrated our 10th wedding anniversary! We split our time between Cap Juluca, a Belmond Hotel, and Four Seasons Resort and Residences Anguilla. Both were wonderful, and a blog post comparing the properties is in the works. If you want to know which one I would recommend for you, let’s chat!

Scroll on for more inspiration about this tiny island, my new personal favorite Caribbean Island.

Itinerary Highlights

Getting There

Anguilla’s tranquility and serenity can be attributed to several factors, most notably its relative inaccessibility. Anguilla’s airport is small, so only large private or chartered jets can land here. That means you’re likely flying into neighboring Saint Martin’s airport (SXM) and taking the public ferry or a boat transfer over to Anguilla.

Kristen’s tips:

• Remember to bring enough cash for tipping porters, drivers, ferry captains, etc. STG provides tipping guidelines with all itineraries.
• At time of writing, SXM airport is being renovated, so I highly recommend opting for the VIP Arrival and Departure services, which allow you to skip the line for customs and immigration. This is a huge time saver!

Dining

Even though Anguilla is only 35 square miles, the island is home to over 100 restaurants. Yes, you read that right! Anguilla is the Culinary Capital of the Caribbean. They even host an annual Anguilla Culinary Experience, which is an international epicurean festival where chefs from both Anguilla and around the world meet to raise money for culinary education for the island’s next generation. With all the restaurants on the island, we couldn’t visit them all, but my personal favorites include Blanchard’s, Picante, and Cip’s.

Kristen’s tips:

• Receive a fulling dining guide with recommendations when you book your trip to Anguilla with STG.
• Go to Picante and order the steak fajitas. As my husband is prone to saying, “It’ll change your life.”

Moke rental

Renting a Moke is a fun and practical way to explore Anguilla. These open-air vehicles are perfect for navigating the island’s scenic roads, providing an enjoyable and flexible way to visit various attractions. A Moke rental offers the freedom to discover hidden gems and experience Anguilla at your own pace, making it an essential activity for any visitor. Driving in Anguilla is easy as there’s only one main road, though you will have to adjust to driving on the left side of the road!

Want more?

Want to see a full sample itinerary for 7 nights in Anguilla, including travel tips and recommendations for activities and dining? Click here. Or let’s plan your personalized itinerary to Anguilla. Let’s work together!