After being recently let down by Four Seasons in Bora Bora my wife and I decided to give them another go for an extended vacation. Let me clarify too that we were simply let down by the standard Four Seasons has set for themselves.
Anguilla was absolutely amazing. We would recommend flying into St. Maarten, spending the night there and then coming to Anguilla by boat. The airport in Anguilla is very small, plus St Maarten and Anguilla are very different despite being 10 miles apart so it was nice to experience both. If you are looking for an island to go and party hard Anguilla isnt for you. It is one of the most relaxing place I've ever been and the four seasons there was absolutely flawless. And I mean flawless. The concierge helped us with every aspect of our stay before we even got there, the sunset lounge is breathtaking, the adults only pool was great, the beach that is about a 1 mile walk to the end was beautiful, our room was amazing and the staff was absolutely first rate and wonderfully friendly.
I unequivocally recommend this hotel above any of the others, we visited them all and not one held a candle to the four seasons, believe me. There are some amazing restaurants on this island that we would recommend too as we tried a different one every night. Mango's, straw hat, Pimms, dolce vita, Veya are all worth trying.
A few last points. Bring cash, most places prefer cash including the touristy stuff like snorkeling, ATVs, etc. Not all places take amex, so bring visa as well. ATV rental for the day was a great way to explore the whole island, private boat tour around the island with snorkeling, day trip to St. Barths, hitting the various beaches away from your hotel, lunch on one of the small offshore Cays, and relaxing by the stunning adult pool at the four seasons.
This property seriously has no competitors on the island. It is the most expensive but the property, rooms, and service are second to none among five star hotels we've visited around the world. Anguilla is absolutely amazing, if you are looking for a place to unwind and relax this is it. St. Maarten and St Barth's are a short boat ride or flight away (we flew to St. Barth's) if you want a little hustle and bustle, and great shopping to go with your relaxation (grand case district in st. Maarten was amazing as well for dinner. Lastly, if you choose Anguilla, don't bother looking at any other hotels, the four seasons is the only choice for the discerning traveller and it blew away our already lofty expectations.