“A day trip lets you see Anguilla. A few nights lets you feel Anguilla.”
The Dutch Side: More Energy, Entertainment and Nightlife
Cross to the Dutch side and the atmosphere changes.
Sint Maarten has more action, including restaurants, bars, casinos, shopping and the famous plane-watching experience at Maho Beach.
It’s a good fit for travelers who want their Caribbean vacation to have a little more energy after the sun goes down.
And this is exactly why choosing the right part of the island matters. Someone looking for quiet luxury on Baie Longue and someone who wants to walk to restaurants and nightlife are technically asking for the same destination, but they are asking for two completely different vacations.
That’s where knowing the island makes a difference.
Where We Love to Stay in Anguilla
There isn’t one “best” Anguilla resort because these hotels deliver very different experiences.
Cap Juluca, A Belmond Hotel sits directly on the white sand of Maundays Bay. Its distinctive architecture, beachfront rooms and suites, Guerlain spa and intimate atmosphere make it especially compelling for couples and travelers looking for classic Caribbean luxury.
Four Seasons Resort and Residences Anguilla stretches between Meads Bay and Barnes Bay and offers a much larger resort experience, with multiple pools, expansive accommodations, villas and plenty to do. It can work beautifully for couples, families and multigenerational trips when you want Anguilla’s beaches without sacrificing resort amenities.
Zemi Beach House, LXR Hotels & Resorts gives you a completely different location on spectacular Shoal Bay East. It’s a smaller luxury resort with four pools, including an adults-only infinity pool, and its Thai House Spa is housed within an original centuries-old Thai building.
Aurora Anguilla Resort & Golf Club is another excellent choice when travelers want more activities, particularly families or groups. The sprawling resort sits across Rendezvous Bay and Merrywing Bay and includes golf, a water park, pickleball, multiple restaurants and a wide range of rooms, suites, villas and estate homes.
The trick isn’t simply booking the nicest hotel.
It’s booking the one that matches the way you actually want to vacation.
Should You Visit Anguilla for the Day or Stay Overnight?
You absolutely can visit Anguilla as a day trip from St. Martin.
But if your budget and schedule allow it, we love splitting the vacation and actually staying on both islands.
A day trip lets you see Anguilla.
A few nights lets you feel Anguilla.
Once the day-trippers leave, there’s something wonderful about settling in for dinner, watching the sun disappear over the water and waking up knowing you don’t have to get back on a boat.
For the right trip, we might recommend several nights in St. Martin followed by several nights in Anguilla. For someone who prefers to unpack once, we might keep St. Martin as the home base and arrange an Anguilla day.
There isn’t one formula we use for everyone.
And Yes, You Can Add St. Barts
For travelers with enough time, this corner of the Caribbean presents one more tempting possibility: St. Barts.
That doesn’t mean we automatically recommend squeezing three islands into one vacation. More isn’t always better.
But with the right number of nights and the right traveler, St. Martin, Anguilla and St. Barts can become an incredible Caribbean itinerary combining three remarkably different experiences.
The Tropical Travelers’ Take
This is exactly the kind of Caribbean vacation where planning matters.
Where should you stay on St. Martin? French side or Dutch side? Should you spend the night in Anguilla or visit for the day? Which Anguilla resort fits you? How many nights belong on each island? Is adding St. Barts brilliant or simply too much?
Those decisions can turn the same basic itinerary into two completely different vacations.
Tell us how you like to travel, and we’ll help you build the version that makes sense for you.