• Substack

Anguilla Four Seasons Review: The Best Island You’ve Never Heard Of


our Seasons Anguilla is one of the most beautiful, relaxing properties we’ve visited that’s only 3.5 hours from New York City. The property and its location reminds us of a combination of Miami Beach and Mykonos. There’s the modern design, the beautiful beaches and the gorgeous 35 acre estate. The fact that Anguilla is close yet feels so far away is part of what makes it such a perfect escape from New York. Anguilla maintains its low-key vibe because there are no direct flights. You need to take a 15 minute speedboat from SXM airport to get to the island (although by 2019 there should be direct flights from MIA).

Four Seasons Anguilla Review

In 2017 the Four Seasons Anguilla acquired the Viceroy Anguilla and completely transformed the hospitality and entire vibe with a $10 million investment. We visited the Viceroy in 2014 when we got married at Ani Villas and fell in love with the modern, clean, white buildings scattered all along the beach and it wasn’t until 2019 that we finally got to come back to take in everything the property has to offer.

We came down for a quick 3 night journey and our only regret was we didn’t stay longer. I think the ideal time to stay on the property is 5 nights, because it allows you to really get into the slow pace of the island and explore all of the pools, restaurants and beaches the property and the island have to offer.

The property itself is spread over 35 acres and has 181 rooms including studio units, going all the way up to 5 bedroom villas. The villas offer the perfect group vacation setting, they come with your own butler, golf carts and plenty of space to lounge and talk by the pool, in the living room or in the kitchen. On a future trip, we’re definitely going to come back down to visit and bring a slew of friends (let us know if you want to join us).

There are four restaurants on the property, Coba, the fine-dining offer, Bamboo Bar, the casual lunch and dinner spot on Meads Bay, Half Shell, offering oysters and fresh seafood beachside and finally Sunset Lounge serving excellent beach cocktails and sushi with views of the infinity pool.

We took in the AFC Championship game at Bamboo Bar and I loved the jerk chicken and the pepper crusted skirt steak. At Half Shell, I loved the margaritas in earshot of the crashing waves. At Coba, I loved the fresh catch of the day and the complimentary bread basket. At the Sunset Lounge, I loved the sashimi and also a drink called something like the “Pirate’s Booty”, it was rum infused with smoke and served in a treasure chest. It not only looked great but hit the spot.

This normally doesn’t happen to us, but on our first night, we met a friend at Bamboo bar, and then another two friends and ended up watching the games with them, hitting a local beach bar and hanging out the rest of the trip. One of the best activities we did together was a wine and paint session. Wei’s painting looked way better than mine, but it was still a ton of fun. Nothing like swigging a rum punch and tapping into our artistic side.

I think the general vibe and welcoming nature of everyone on the property is what made making friends on the property a possibility. We can’t wait to come back to visit new friends and old friends and explore everything else the property has to offer. Thank you again to Jose, Suzanne and Amanda for making our stay amazing.

Where to eat & drink in Anguilla

Blanchard’s restaurant in West End Village is a go-to spot for anyone seeking an authentic beachside restaurant. The restaurant opened in 2011 and has been a hit ever since. It’s decidedly low-key with soups, salads, sandwiches, tacos and burgers all served from a window with outdoor seating all within reach of the ocean. Make sure you get a frozen drink with any of your orders to get that full island experience.

Elvis’ Beach Bar in Sandy Ground is a beach dive bar which couldn’t be a better possible combination of words that we love. Elvis still tends the bar and passes out shots in plastic cups. Since the hurricane in 2017, Elvis has expanded the bar into a restaurant area with cornhole, dancing and plenty of seating. Come early in the evening and order some beers, some grub and just watch the locals and tourists drink and dance the night away. The bar is a bit of a trek from the property, about a 20-30 minute drive so just plan to stay there and make that your last and final destination.

Veya restaurant in Sandy Ground has all of the flair and fine cooking you could expect from a restaurant in New York. It was our last night on the island so we went all in and got the prixe fix and wine pairing and it was fantastic. I don’t remember exactly what we ate, but I do remember that it was my first time really loving natural wine. The way they paired the food made the wine really blend perfectly and made this a spot we’re definitely coming back to visit.

When Is The Best Time to Visit Anguilla

Anguilla is located in the Caribbean and the Caribbean does indeed get hurricanes. Hurricane Irma really wholloped Anguilla in 2017 and while the majority of the island is back online, there are still people suffering and rebuilding, so when planning any trip you want to take into account hurricane season which runs from June 1 to November 30.

The best time to visit Anguilla is between May and August when the prices drop, and the weather is still beautiful. I’m always one to want to escape New York winters from December-March but that happens to be the priciest time to visit Anguilla, but if you have the budget, it’s also a great time to visit the island.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities. Lifetailored has partnered with Creditcards.com for our coverage of credit card products. Lifetailored and Creditcards.com may receive a commission from card issuers Additional Disclosure: This site has affiliate links. We may be compensated when users make a purchase or register to a third party website. For more details read our privacy policy.

More in Travel Guide