Anguilla Itinerary: Small, secluded Anguilla is still one of the more under-the-radar Caribbean destinations, which is a boon to those who visit frequently. Sandy white beaches and crystal-clear waters are the main draws of this island destination, but an array of luxury hotels, unparalleled island dining, and natural beauty make Anguilla a spot you’ll want to return to again and again.
Read on for a guide on how to spend the perfect long weekend in Anguilla.
Historically, most travelers have opted to take a commercial flight to St Maarten’s Princess Juliana International Airport and then either fly or take a ferry to Anguilla.
However, there is a better way. The easiest and most convenient option is to fly with Tradewind and take a scheduled flight directly to Anguilla from San Juan. Flights operate seasonally from December through April on Tradewind’s Pilatus PC-12 fleet, which fly directly into Anguilla’s Clayton J. Lloyd International Airport, just a quick drive from any resort on the island. For those looking for a more flexible flight option, private charters to Anguilla are available year-round.
Start your weekend with a convenient commercial flight to San Juan, Puerto Rico. Thanks to Tradewind’s interline partners, transferring from a commercial airline such as American Airlines or United Airlines to Tradewind couldn’t be easier with single-ticket booking and automatic baggage transfer. Board your Pilatus PC-12 in San Juan at 3:25 p.m. and land in Anguilla by 4:35 p.m.—Tradewind scheduled flights to Anguilla operate Friday, Saturday, and Sunday.
After landing in sunny paradise, a quick car transfer will deliver you to one of Anguilla’s top luxury resorts — Zemi Beach House, Malliouhana, and Quintessence are all excellent options on the island’s north side, and Belmond Cap Juluca is a classic choice on Maundays Bay, one of the island’s best beaches. Tradewind has a number of partner experiences with some of the top properties on the island, so be sure to explore these offers before booking your accommodations.
Opt for exploring your hotel and enjoying dinner on the property for your first night on the island—all of these hotels have top-rated restaurants.
Start your first full day on the island with some activity, whether that’s a workout at your hotel’s gym, a hike to one of the island’s popular lookout points like Windward Point Bay, or a morning spent kitesurfing or windsurfing in the cerulean waters near your hotel.
Once you’ve got your blood flowing, it’s time to spend the rest of the day enjoying the best Anguilla has to offer: its beaches. Relax on the sand near your hotel, or travel a bit further to one of the island’s 35 beach destinations. Arguably its most beautiful is Shoal Bay Beach, a two-mile strip of white sand and unbelievably clear water.
That evening, leave your hotel for dinner at one of Anguilla’s several fine dining destinations. Blanchards Restaurant on Meads Bay offers refined Caribbean cuisine and a charming open-air dining room (or equally romantic light-strung courtyard). For a more casual night, enjoy a menu that fuses flavors of Mexican fare with local Caribbean ingredients at Elvis Beach Bar which overlooks the beach and makes a perfect spot to catch a tropical sunset.
The Caribbean is beautiful from the vantage point of Anguilla’s beaches, but nothing compares to being on the water. Many offshore cays and secluded shorelines are only accessible via boat, so it’s worth chartering a sailboat for the day. Prickly Pear Cays, a pair of uninhabited islands not far from Anguilla, are a favorite destination for both snorkeling and diving. Avid anglers might prefer a deep-sea fishing charter—the waters surrounding the island are home to yellowfin tuna, wahoo, and mahi-mahi, giving you first access to the same high-quality seafood that you might find at the island’s top restaurants.
Make sure your excursion includes a stop at Sandy Island, a tiny slip of sand with a beach shack serving fresh seafood and strong frozen drinks. It’s only accessible via boat but has a designated mooring area for guests and three sea shuttles that take visitors to and from the mainland.
Start your morning with one last leisurely breakfast at your hotel, then head to the airport for the Tradewind morning scheduled flight back to San Juan and on to your final destination (or continue the trip by island-hopping from San Juan to St Barths, instead). The ease of returning home is the perfect way to cap a long weekend of island relaxation.