Summary
I visited Anguilla (3 nights) in May 2014 for a babymoon with my wife and one of our close couple friends. We love going to the Caribbean in April or May because the crowds tend to be less yet the weather is still great. Anguilla is one of the lesser developed Caribbean Islands, which was a welcome change from some of the more commercialized island destinations we have been to. The island also has very high-end accommodations, nice local restaurants and great beaches / waters – making this a very memorable and relaxing trip.
Accommodations
We stayed at the Viceroy Anguilla (now converted to the Four Seasons Anguilla). This hotel is a fabulous destination for relaxation by/in the pool(s), long walks / lounging on a pristine beach, spacious rooms and a lively bar area in the evenings. The local staff in the hotel is also extremely welcoming and helpful. From the US, you will likely fly into St. Maarten so the hotel can help organize your full-service transfer – including customs, immigration, boat trips and ground transportation.
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Activities
The most fun we had was relaxing in and around the Four Seasons’ pool areas, the neighboring beach and the pristine waters. We enjoyed the Fitness Facilities and Tennis Courts at the hotel, in addition to a fun day of golf at the Cuisinart Resort’s Golf Course. Other great destinations for relaxation and live music include the popular Cove Bay Beach with live music (and lunch) at Smokey’s or the pristine Shoal Bay
Dining
Most of the destinations we visited and enjoyed tended to be casual and lively (and thus less formal). For a nice, casual breakfast we enjoyed Straw Hat and for casual lunch we liked Blanchard’s Beach Shack – both of which are a beach walk from the Four Seasons. We also enjoyed the views and light lunch at the Four Seasons’ Bamboo Bar & Grill amidst the pool areas. For dinners, we enjoyed taking a trip to the Sandy Ground neighborhood which is more lively – our favorites included Pumphouse for American fare & great live music and Dolce Vita for Italian and great views. We also enjoyed a casual dinner and drinks in the Sunset Lounge of the Four Seasons. Our favorite meal was one we stumbled into – dinner at Picante for Mexican. The Four Seasons hotel’s golf cart (if it is still running) can take you within steps of the restaurant.
Recommendation
I would definitely recommend Anguilla as a nice (albeit a bit pricey for accommodations) getaway destination in the Caribbean for a restful, relaxing and rejuvenating retreat. Try to make sure wherever you stay has a lot of activities that you might be interested in because you will likely spend much of your visit there. The Viceroy / Four Season resort and Anguilla the island itself was a perfect babymoon destination for us and we look forward to a future trip in the years to come. Enjoy!