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You’re going to quickly realize after docking in Anguilla, that this island is in fact the most relaxing island in the Caribbean. With St. Maarten just a 20 minute boat ride away with plenty of nightclubs and casinos, visitors regularly escape the spring-break vibes to indulge in Anguilla’s serenity. With just the roar of the waves and an occasional cabana boy – Anguilla is the island of true peace and quiet.
2. Get Off the Resort
After arriving at any one of the major resorts on Anguilla, you’re never going to want to leave – but try. Although taxi prices are a major burden on such a small island, it is worth every penny to see the island – especially when you’re boating around it. Anguilla offers many private charted boat experiences…most of them STOCKED with Rum Punch (the best part). And with that private boat you can have an experience as tame or as wild as you’d like.
3. Actively Relax
I know, I know, kind of contradictory but Anguilla boasts an incredible amount of fun and (just) semi-dangerous activities. From cliff-jumping to paddle-boarding, snorkeling to tubing; when you’re immersed in the beauty of the island it somehow still feels like relaxation. The island is notoriously breezy which offers the innate opportunity to go sailing and wind-surfing almost every day. Not to mention the massive amount of islands to explore.
4. Party Like an Islander
Anguilla is not about the club-life. Instead it boasts niche bars, live-music venues and even entire islands that are unlike anything I’ve ever experienced…and girl, you know I partied A LOT in college. A bar we frequented all too often was call The Dune, a club/live music venue that can only be described as the Lost Boys treehouse from Peter Pan meets The Swiss Family Robinson…on the beach. Banky Banks: the owner, the headlining act, and the man who built the entire place by hand keeps the party going all night long. However, don’t be shocked if one of his many children (as young as 12) are behind the bar making you a cocktail.
5. Save a Cowboy, Ride a Horse (or ride both...but make the horse your priority)
This one-hour, private, sunset horseback ride was by-far the highlight of our trip. With a little bit of prior-planning I booked the trip with Seaside Stables strategically at sunset (this was the 5:00pm ride). You start wandering the streets of Anguilla before making your way down to the beach where you’re greeted with a massive sunset landscape. While you watch the sun go down, you then enter a bay where you’re free to take the horses into the ocean. In what has to be the most magical horse ride you’ll ever take in your life, you then ride back with the sun at your back just as the moon it lighting up the sky.