Planning for a quick jaunt to the island

There’s no doubt about it, three days in Anguilla is a quick trip to the island. There are typically two types of guests that fall into this category: folks from Miami or NY hopping down for a quickie Caribbean getaway (with direct flights to SXM, it’s a fairly easy trip) or guests who do a St. Martin/Anguilla or St. Barths/Anguilla combo trip. We see the latter a fair amount; guests want a taste of two distinctly different islands and pop on over to see the tranquility of Anguilla while getting the nightlife of St. Martin or the glitz of St. Barths on the front or back end of their trip.

If you’re planning on spending a few short days on the island, here are a few ways to get the most out of your time here:

Rent a car.

Yes, Anguilla is small, but it’s not walkable unless you want to stay on one beach for the extent of your stay (which some people happily opt to do). If you want to get out and explore — or even leave your home base for dinner — the easiest, most cost-effective way is to rent a car. Car rentals will cost you $40+ per day plus a one time temporary license fee of $20. Considering taxi costs, rentals are a worthy investment.

Explore other beaches.

Anguilla is famous for its 33 extraordinary beaches and each one has its own unique character and charm. If you’re staying at the Frangipani on Meads Bay, you’ll have access to one of the island’s best beaches, but you’ll probably want to scope out some other views as well. Head down to gorgeous Rendezvous Bay for a long stretch of sand or venture down to the East End’s secluded Savannah Bay for pinky-golden sands and a beach all to yourself.

My choices for three days of exploration? Meads Bay, Rendezvous Bay, Savannah Bay and Shoal Bay.

Book your dinners in advance.

Besides beaches, one of Anguilla’s top draws is its culinary scene. Frequently touted as the culinary capital of the Caribbean, the island has a shocking number of fantastic high-end eateries with a few mid-priced gems mixed in. If you’re coming during high season, play it safe and make reservations in advance. Most of the big name spots (Dolce Vita, Straw Hat, Veya, Picante and others) will be too jammed to accept walk-ins (especially with groups larger than two). Want some eatery ideas? Check out our restaurant spotlights.

My personal choices for three nights in Anguilla? Picante, Straw Hat and Dolce Vita.

Tip: Plan your lunches strategically and see different sides of the island over a mid-day meal. da’Vida, Smokey’s, Gwen’s and Scilly Cay offer awesome — and totally different — lunch experiences.

Experience the nightlife.

You’re not going to experience the same nightlife as St. Maarten (no clubs and casinos here), but Anguilla’s late night scene is charmingly Caribbean and extraordinarily memorable. Head down to Elvis’ Beach Bar in Sandy Ground for a toes-in-the-sand experience or make your way to Elvis’ neighbor, the Pumphouse, for live music in a historic Anguillan building. If you’re here on a Thursday, be prepared for a buzzing late night scene in Sandy Ground!

Charter a boat.

When it comes to exploring the nooks and crannies of an island, what better way is there than by boat? If you’re staying at the Frangipani, you can charter our 34′ boat, Relentless, for a half day or full day, depending on what you’re looking to do. You can also jump on board for a cocktail cruise or a snorkeling trip to Little Bay! Looking for other charter options? Try Calypso, Funtime or Gotcha! for different offerings and availability.

Want something more classically West Indian? Check out the newest addition to charter options, Tradition. Tradition is a 50′ Carricou wooden sloop built in 1978 that offers day trips, snorkeling trips, lobster lunch cruises and custom charters.

Now we need fellow Anguilla lovers to chime in! If you have just three days to spend in Anguilla, what’s on your to-do list? Leave your thoughts in the comments below for future visitors to the island!