If you’ve never heard much about Anguilla, that’s kind of the point. It’s a tiny, flat sliver of an island (about 16 miles end to end) at the top of the Leeward Islands, just a few miles north of St. Martin, and it’s a British Overseas Territory. So you’ll see the Queen’s-English spellings and they drive on the left, but they use the Eastern Caribbean dollar (US dollars are accepted pretty much everywhere).

Anguilla is a special place for my family. We first came over 20 years ago on a day trip from St. Martin and always hoped we’d make it back one day. Since then we’ve been back twice: once as a whole family for my sister’s 40th, and once just as a couple. Whenever I’m craving that real, relaxed Caribbean feeling, this island hits the spot every time.

What to expect: no cruise ships, no high-rises, no casinos, and no real “scene” in the Vegas sense. What you get instead is some of the most beautiful beaches in the Caribbean (there are 30-plus of them), really good food for an island this small, and a pace that forces you to slow down. It’s quietly luxurious. People come here to do nothing, beautifully.

Getting There (Easier Than You Think)

Anguilla has a reputation for being hard to get to. It’s easier than it sounds, and you’ve got two good options.

Fly direct from Miami (my pick). American Airlines flies nonstop from Miami to Anguilla in about 3 hours, and if you can make it work, this is the way to go. No connection, no ferry, no hauling luggage (or a toddler) across a dock. You land and you’re at your hotel in minutes. The catch is that the schedule changes with the season. For fall it’s currently Wednesdays and Saturdays, starting October 7, 2026, and in peak winter (roughly mid-December through March) American usually steps it up to daily service. Always double-check before building your trip around it.

Fly into St. Maarten and take the ferry. If the Miami flight doesn’t line up with your dates, fly into Princess Juliana Airport (SXM), which has lots of nonstop flights from the U.S., and take a boat over. The cheapest option is the public ferry from Marigot on the French side, about a 10–15 minute taxi from the airport. It’s around US$30 per adult, runs several times a day, and the crossing is only 20–25 minutes. You’ll land at Blowing Point Ferry Terminal and clear customs there. Heads up: there’s a departure tax (roughly US$28–36 per adult) on top of your ferry fare.

Where to Stay

Aurora Anguilla Resort & Golf Club: We stayed during our fam trip at Aurora on Rendezvous Bay. They built a splash pad with slides for the kids, and there’s an 18-hole golf course if that’s your thing. There’s plenty of space to spread out and a long, calm stretch of beach. You don’t have to leave the property to eat well either. There are a few restaurants on-site, from Japanese at Tokyo Bay to ribs and lobster on the sand. But one of my favorite things about staying here is that you can walk along the beach to a couple of great local spots: Sunshine Shack in one direction and Bankie Banx’s Dune Preserve, the legendary reggae beach bar, in the other.

(I’ll post a full review on this hotel soon)

Belmond Cap Juluca. The iconic whitewashed domes on Maundays Bay. I’ve written a full review of my stay, including what I loved and what I didn’t, so I’ll let that do the talking: read my Belmond Cap Juluca review.

Four Seasons Resort and Residences Anguilla. We didn’t stay here, but we went for sunset drinks and it looked amazing. It sits on a bluff between Barnes Bay and Meads Bay, so the views are unreal, and the design is sleek and modern. It’s family-friendly luxe, and it’s probably where I’d stay if I came back with my toddler.

What to Do (Mostly, Nothing)

Honestly? Relax and enjoy. That’s the main activity here, and I mean that as the highest compliment. But a few things are absolutely worth doing.

Rent a car if you can. Anguilla is small, but the best beaches and restaurants are spread out and taxis add up fast. Having your own wheels means you can beach-hop and go to dinner on your own schedule. Just know they drive on the left, so that takes some getting used to. Your rental company will sort out the temporary local driving permit you’ll need.

Spend a day at Shoal Bay East, my favorite beach of all time. I don’t say that lightly. It’s laid back, the water is every shade of clear blue, and the sand is the softest, whitest sand I have ever felt, like powdered sugar. It’s easy, too: parking is simple, and you can rent beach chairs from the restaurants along the sand when you arrive. Grab a rum punch, listen to some reggae, dig your toes into that soft sand, and have an iconic day.

Take a boat day. Charter a boat to snorkel and hop between the little offshore cays. Sandy Island is a tiny speck of sand with a beach bar. Prickly Pear Cays has gorgeous water, great snorkeling, and a lunch spot right with the best rum punch around on the beach.

Where We Ate

Anguilla has a pretty good food scene. Here’s where I’d send you.

Blanchard’s (Meads Bay). This place is so cute: colorful, cozy and charming, right on the sand. Go for sunset, because the sunsets here are unreal. It’s the kind of dinner you’ll still be talking about on the flight home.

Sunshine Shack (Rendezvous Bay). If you eat meat, don’t miss this. It’s a casual, barefoot beach shack known for its barbecue ribs and chicken, and it’s exactly what you want after a morning in the water.

Savi Beach Club (Meads Bay). Come here for a vibe. It’s a stylish, design-forward beach club with daybeds, a sushi kitchen and a boutique. Go for a long lunch or sunset, dress up a little, and listen to music beachfront.

Four Seasons, for sunset. Even if you’re not staying there, go for a sunset drink. The views over the water are amazing, and it’s the perfect way to start an evening.

Nightlife (Yes, There’s Some)

Anguilla isn’t known for nightlife, and that’s part of its charm. But if you want a night out, you’ve got options.

Savi Beach Club is the most “scene” you’ll find on the island: stylish, buzzy, and great for drinks that turn into a late dinner. The Four Seasons sunset bar is the place to start your evening with a cocktail and those big views. And Sandy Ground is a small stretch of beach lined with a few bars, the closest thing Anguilla has to a nightlife strip. Elvis’ Beach Bar, where the bar is built out of a boat, is the classic, with rum punch, music and a fun crowd. Wander between the spots along the sand and see where the night takes you.

Make It a Two-Island Trip

Since Anguilla is so close to its neighbors, it’s easy to pair with another island. I’ve done it both ways.

Anguilla + St. Maarten. On one trip I combined Anguilla with St. Maarten, which makes a lot of sense if you’re flying into SXM anyway. The easy option is to spend a few nights there on either end. Belmond La Samanna, on Baie Longue on the French side, has been on my list forever. I haven’t stayed yet, but it’s the one I’d book for the St. Maarten half of this trip.

Anguilla + St. Barths. For my sister’s 40th, we paired Anguilla with St. Barths. We took the ferry back to St. Maarten, then hopped on a puddle jumper to St. Barths for a short, very scenic flight. It’s a little more work logistically, but it’s 100% worth it. You get Anguilla’s laid-back beach days followed by St. Barths’ chic, buzzy energy, and the two feel like the perfect contrast.

The Bottom Line

Quick take:

• Getting there: fly nonstop from Miami if the days line up; otherwise fly into St. Maarten and take the 20-minute ferry.
• Where to stay: Aurora for families, Belmond Cap Juluca for iconic luxury, and the Four Seasons for family-friendly luxe.
• Don’t miss: a full day on Shoal Bay East, a boat day to Sandy Island and Prickly Pear, and sunset at Blanchard’s.
• Good to know: they drive on the left, and a rental car is worth it.
• Best for: travelers who want a real, relaxed Caribbean vacation, not a party island.

Anguilla isn’t the island for nightlife or nonstop excursions. It’s for soft sand, clear water, long lunches and even longer sunsets. Rent a car (and remember to stay left!), spend at least one full day on Shoal Bay, and eat very, very well. It’s one of those places that feels like a real vacation, and it’s on my list to come back to again and again.