Recently, I had the chance to visit Anguilla. This was not a rewards-fueled trip, but I still wanted to share my thoughts in this destination as a Caribbean travel enthusiast.
In case you’re unaware, Anguilla is a small British territory off the coast of St. Maarten. It’s known for its upscale hotels and resorts and, of course, it’s absolutely obscene white sand beaches. Anguilla is also known as a culinary destination, and one where tourists are welcomed with open arms.
Anguilla did sustain some damage from the hurricane, but they have rebuilt enough that it’s hardly noticeable for visitors. Several hotels and restaurants are still under construction, but the entire place should be 100% operational soon.
Anguilla Beaches
While there is a lot to do in Anguilla, this island is really all about the beaches. While they’re all beautiful in their own way, my favorite was easily Rendezvous Bay. This beach is home to the famous Sunshine Shack Bar, along with amazing views of neighboring St. Maarten. The scenery on this beach was so gorgeous that it too my breath away. Pictures don’t even do it justice.
My second favorite beach on the island was probably Shoal Bay, which featured the whitest and softest sand I’ve ever seen along with crazy-turquoise (and warm!) waters. Finally, we loved Little Bay, which is another gorgeous white sand beach you can only access via boat unless you want to climb down a cliff using a rope. It was beautiful there!
We also took a day trip to Sandy Island, which is a small, private island off the shores of Sandy Ground in Anguilla. This island has nothing on it but a restaurant, a bar, and some beach chairs, but it is pure paradise! If you want to get away from it all and have a giant lobster lunch, this is the place to go.
Where We Stayed
My husband and I split our stay across two hotels, which we often do since I love staying in more than one place. First, my husband and I stayed in a small boutique hotel called Mead’s Bay Beach Villas. This beachfront property has only four beachfront villas, each with their own private plunge pool, two bedrooms, and 2.5 baths. This property isn’t cheap at $550 per night during low season, but it’s pretty reasonable if you split your two-bedroom villa with another couple and pay $275 per night each. Obviously, you have a private beach, private villa, and private pool for that price! Our villa was extremely nice and comfortable, and on Mead’s Bay, one of the most gorgeous beaches on the island.
We also spent two nights at Zemi Beach House, which is a truly unique family-friendly hotel. This property can cost as little as $350 per night, which is a lot, but it is a five-star luxury resort. At Zemi Beach House, we enjoyed the free breakfast, the amazing pool, and Shoal Bay, which is consistently rated one of the world’s most beautiful beaches. Our room was also huge, with a giant balcony, a comfy king bed, and a suite bathroom with a separate soaking tub.
Paying for a Trip to Anguilla
While Anguilla is easily one of the more expensive Caribbean islands, I didn’t think prices were that bad. Food at the grocery store was probably on par with prices in Grand Cayman. We went to the store one day to buy snacks for our villa and spent around $45.00 for food that would likely cost around $35-$40 in the U.S. On another trip, two Gatorades and a big pack of razors cost $8. Not too bad. Like many of the other smaller islands, they have to import all their food and have higher prices due to the added expense.
Restaurant prices were similar to Aruba, but there were plenty of cheap roadside places to get a bite to eat for cheap. We stopped at a bar near the Four Seasons Anguilla called Waves that had $7 drinks and $8 appetizers, for example. There’s also a strip of outdoor lunch stands in The Valley, the capital city of Anguilla. Here, you can find cheap fish tacos, Johnny Cakes, and other local delicacies. Like anywhere else, there are cheap places to eat if you look.
In terms of hotels, the island doesn’t offer any big chains that have their own rewards programs (other than the Four Seasons). However, you can pay for a hotel with a flexible travel credit card like the Capital One Venture. The island offers many condo-like accommodations in the $200 – $300 per night range, so prices aren’t that over-the-top despite the island’s beauty and reputation.
In terms of flying to Anguilla with airline miles, this is absolutely possible. Most people fly into St. Maarten’s Airport (SXM), which is fully operational in working out of temporary buildings as they rebuild their main airport after the hurricanes. You can get from U.S. airports to SXM for as little as 25,000 American AAdvantage miles off-peak, or even less if you book the same flights with British Airway Avios. You can also fly round-trip for 35,000 United miles round-trip plus taxes and fees. There are plenty of other options, but the best deal for you depends on where you’re coming from, award availability, and the type of frequent flyer miles you collect.
Once you get the SXM, you’ll need to take a taxi to the ferry terminal that will take you to Anguilla. The least expensive round-trip ferry is $60 per-person. In addition, you’ll pay a $23 per person departure tax when you leave Anguilla, and this tax can only be paid in cash.
The Bottom Line
While Anguilla may require more cash and a few more steps to visit, I think it’s worth it. Some of the most beautiful beaches on the island rival the scenery in Bora Bora, and that says a lot. Plus, the people are friendly and the food is amazing. It’s also extremely safe to rent a rental car and explore.
We loved the island so much that we’ll be going back next June. But next time, we’re taking our kids.
Have you ever been to Anguilla? Why or why not?


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