Anguilla — A Caribbean Paradise with a Hometown Feel

Not your average Caribbean Island…

My favorite travel experiences are those where I connect with fellow travelers and/or locals in some sort of meaningful way. On this trip, the connection wheels started on the speedboat to the island as I chatted with a couple who have lived on Anguilla for 22 years. Ironically, they’re from Rochester VT, a small town about 45 minutes from where I grew up. They live on the island for 9 months and return to their VT home for the summers. We talked the entire ride over to the island – about skiing and the small mountains where locals would go (Middlebury Snow Bowl, Pico, High Pond etc.), about tight-knit communities and knowing everyone in town (for better or worse!). We talked about Hurricane Irma, the aftermath and about neighbors helping neighbors get back on their feet. Already I could tell it would be just like ‘home’ – I knew I would like it here!

So, how do you get there?


If you’re anything like me, when I’m heading to the Caribbean I think about sinking my toes in the sand, sweeping sea views, the sound of the waves, fresh seafood and of course, relaxing pool-side with a tasty cocktail! Quite honestly, I don’t want to think too much about HOW I get there, I just want to be there!

To get some Caribbean islands, there are few extra steps, but once you’re there, all that is forgotten! Non-stop options from my home town of Boston are limited to certain islands, and while that’s good (and maybe what you need) in some circumstances, you could be missing out on fabulous islands – and Anguilla is a perfect example.

From JFK, it’s an easy 4 hour flight to St. Martin. Post Hurricane Irma, the airport buildings still are under renovation and closed until later this year, but the airport itself is very much open and a busy gateway for St. Martin and nearby islands. (Also note that Anguilla is accessible via St. Barts, Antigua and Puerto Rico).

From the St. Martin airport, it’s a short plane or 30 min speedboat ride to Anguilla’s beautiful shores. This might seem like extra travel time to some, but I think it’s rather special that large planes can’t land on the island – no crushing crowds or airport noise on this island!

Four Seasons Anguilla


The Four Seasons Anguilla took over the Viceroy in 2016 and re-opened this Spring after renovations following Irma, the devastating category 5 hurricane that battered the Caribbean. Driving down the tree-lined entrance of the hotel, it’s hard to fathom that this island was pummeled by Irma – everything looks just lovely! This transformation is a credit to the people who live and work there and thrive on tourism as their primary livelihood.

As soon as I walked into the lobby,with the sea view straight ahead, I could feel myself decompressing. The outdoor spaces are stunning: wide-open, sea views at every turn, comfy gathering spots and a sprinkling of local art thoughtfully placed throughout. Think – laid-back luxury, casual yet chic – that’s the Four Seasons Anguilla.

What I especially like about Four Seasons Anguilla is the variety of accommodation options. For families and groups who perhaps need more room or privacy, there are town homes, residences and villas. These feature multiple bedrooms and baths, gourmet kitchens, laundry – and depending on your preferences, private pools, ocean and/or beach front locations. Each also has a Resident Assistant who will cater to your every whim. For those looking for a romantic spot with amazing sea views, there are the Ocean View Rooftop suites. All the accommodations are well appointed with modern amenities and beautifully decorated with earth tones fabrics and elements. The petrified wood tables, and driftwood lamps and accent pieces are not only eye catching, but tie everything together so beautifully.

That’s just a bit about the inside, so what’s on the outside?

I’m not sure there are enough adjectives to describe its location. The resort is perched on a bluff that overlooks two white powdery beaches, with Meads Bay on one side and Barnes Bay on the other. To get my bearings, I took to the beach shortly after I arrived for a walk. White powdery sand, turquoise waters, warm breezes – what more could you ask for? I strolled past Waves, the local, no-frills, laid-back beach bar as well as Straw Hat – the kind of place where you raise your flag for beach service. Now that’s island living at its finest!

Speaking of cocktails and cuisine, I’d be remiss to not mention the amazing lobster rolls and fries at Half Shell, Barnes Bay. This is the perfect place for a sundowner, and if you’re in one of the villas, this is steps away on the beach! Not to mention Omalie 365 at the Sunset Lounge. Here, right on property again, is a lively place to go after dinner for cocktails and entertainment every night of the week! And, if you need a pick-me-up in the morning, breakfast at Coba is the place to go – the detox smoothies and avocado toast were to die for!

Last, but certainly not least, after all that food and drink, it is high time to get moving! On property, you’ll find three beautiful new tennis courts as well as a state of the art fitness center that offers boot camp, yoga & cross fit. In addition, the concierge is fabulous and can provide you more daytime experiences and excursions than you could imagine. From paddle boarding to kite surfing to mermaid classes, sailing and even a Kids’ Club – no one could possibly be bored! There also are more day trips to take advantage of than you can imagine. Why not circumnavigate the island via private boat, cliff jump at Little Bay, stop by Sandy Island for a picnic or spend a day on St Barts? All these options and more are at your fingers tips.

Are you ready to go?

Just say when!   Honestly, there is no bad time to visit this Caribbean paradise EXCEPT perhaps hurricane season. Otherwise, this nearly year-round destination is simply a wonderland for couples, small or large families, friends and even corporate events.

And now to recap, just a few fast facts: Anguilla is a small island with a population of about 15,000 people and it measures 16 miles long by 3 miles wide. So… if you enjoy exploring by car, you won’t have far to drive to enjoy pristine beaches and local and upscale restaurants. (Here’s a tip: Anguilla is a British Territory, so you’ll be driving on the left! That alone can be fun, right?) — so much to do, so much to see!

Now is the perfect time for us to help YOU get there!