As a beach bum and island lover, I’m always looking for an escape to some sun, sand, and water. Last month, I got to experience all that Anguilla has to offer by spending a total of 4 days/3 nights exploring, and I quickly fell in love with everything about the island (especially a favorite local bite – Johnny cakes!). It was such a fun experience that I can’t wait to return with my family in the future.
Tucked away in the northern Caribbean in the British West Indies, Anguilla is one heck of a gem of an island (with a population of 15,000 and a total of only 6 stoplights, FWIW) that’s just 16 miles long by 3 miles wide of tranquil beauty and pristine white-sand beaches. 
The most popular way to get to Anguilla from the United States is by flying into St. Maarten (SXM) and then taking a short 30-minute boat ride or ferry to Anguilla. Another gateway to Anguilla is via San Juan, PR (SJU).
Sometimes there are great fare sales to St. Maarten, but during peak-season, prices can skyrocket, so it’s not a bad idea to consider using miles. United, American, Delta, and Jet Blue all service SXM.
- United has nonstop flights to SXM from Newark, Chicago, Washington DC. The cost in miles is 17.5k each way, or when booking a round trip award, you might be able to still add in a free domestic one way.
- Delta has nonstop flights from New York and Atlanta for 30,000 SkyMiles roundtrip at level 1 coach.
- JetBlue flies from New York and Boston. Like Southwest, JetBlue’s award program is variable and the price in points is determined by the price of the fare.
- American has nonstop flights to St. Maarten from New York, Philadelphia, Charlotte, and Miami for 17.5k miles each way. A better option would be to use 10,000 British Airways Avios + $5.60 for those same flights.
Once I landed in St. Maarten, I hopped on a charter boat to Anguilla. There are many transfer options from a variety of companies catering to different needs. I personally used GB Ferries (the price for the transfer is $120 round trip). The boat was very nice and carried only 8 or so passengers. Overall experience was extremely pleasant, on-time, and seamless (bumpy ride though, but I loved every second of it!). Of course there are cheaper options including a general ferry for $20.
Where to Stay
Unfortunately for us points and miles enthusiasts, there are virtually no major hotel chain options (sorry, no Diamond breakfasts!); however, I did have the chance to stay at two different properties during my stay as well as visit several other properties. The majority of the accommodations available are apartment-style villas, perfect for family travel.
I spent my first night at the Carimar Beach Club, which is located right on the beautiful Mead’s Bay beach. Average nightly rates range from$230-$675, depending on the season and type of villa. The property features 24 fully-furnished villas, all with large spacious balconies and great views. It was refreshing to stay in a place that required me to open the door using a “real key” in place of key card, and I loved how homey and cozy it was. The beach itself was simply amazing, and one of the best I’ve experienced in the Caribbean.
My next two nights were spent at the Shoal Bay Villas, located right on Shoal Bay, which was recently voted as one of the best beaches in the world by the Travel Channel. Rates range between $275-$580 depending on the season and type of villa. The villas were cute and “islandy”. My favorite thing about this resort was stepping out and having the beautiful Shoal Bay beach as my “backyard” (here’s a video of that on my Instagram account).
To appeal to the luxury seekers, we visited 3 other resorts on the island:Viceroy Anguilla (wow!), Cap Juluca, and the Cusinart, where we were able to spend the day as we wished.
The Viceroy Anguilla is simply stunning to say the least, but it’s a steep investment at $500 (resort view room) to $3,600 per night (for a 5 bedroom beachfront villa).
I also really loved spending time at the beautiful Cap Juluca hotel, and was even able to go horseback riding on the beach during my visit to this property! This property also is a bit pricey, with rooms in the $600-$1,100 nightly range, but the resort is surely stunning.
I also had a chance to visit the CuisinArt Golf & Spa resort located on Rendez-vous Bay beach. The beach vibe here is a bit more “happening” and great for water sports. The CuisinArt is also the only resort on the island that has an 18-hole golf course (I naturally opted to check out the spa instead, and genuinely had one of the greatest massages of my life – ask for Ishalyn, and thank me later).
The entire trip was a blast, and there was never a dull moment. There are activities and things to do that appeal to everyone, and it’s safe to say I’d return to Anguilla in a heartbeat. The only bump I encountered was forgetting that theres a $28 departure tax, that’s payable with cash only. Of course I am always so concerned with earning points that I forgot to bring the cash (#amateurhour). As an unfavorable alternative, the immigrations gift shop will “spot you” the cash by tacking on a 20% surcharge (!!!) when using your credit card in the shop.
Stay tuned for my next post about where to eat and some fun excursions to consider.
Have you visited Anguilla before? What were your impressions? Feel free to discuss your experience!
*This post is written in partnership with the Anguilla Tourism Board. All opinions and stories are my own, of course. I owe them a world of thanks for showing me all that the island has to offer.
Hey Angelina…..Did your kids go…If not dont you miss them and they miss you. You were just in Europe too… Not judging..just jealous!!. Would love to do getaways like that with my points but being away for a while I would feel like a shitty dad.
Hi Richie, my kids did not come on this trip, but I would take them here in a heartbeat! Of course I miss them and they miss me. We stay in touch multiple times a day. Kids come on 80% of my trips, but I do believe a few days alone doing things that make me happy is healthy and makes me a better parent.