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, but an array of luxury hotels, unparalleled island dining, natural beauty, and easy flights to Anguilla make it a spot you’ll want to return to again and again. New developments underway in 2025 include two luxury marinas, several resorts and upscale residences, and an expanded airport with a new passenger terminal.
Read on for an Anguilla travel guide on how to spend the perfect long weekend on this friendly island.
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 sea shuttle 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, St Barths or Antigua. Flights to Anguilla operate seasonally from December through April from San Juan, and January to April from St Barths and Antigua. Scheduled flights offer an elevated travel experience 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 from throughout the Eastern Caribbean or from the mainland US through Tradewind’s network of trusted partners.
Friday
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, United Airlines, and JetBlue Airways to Tradewind couldn’t be easier with single-ticket booking and automatic luggage transfer. For transfers through Antigua, enjoy single-ticket booking with British Airways. Board your Pilatus PC-12 in San Juan in the late morning or afternoon and land in sunny paradise just an hour later.
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, Neveah Villa Anguilla is considered “heaven on Earth” nestled on the far end of Long Bay beach, and Cap Juluca, a Belmond Hotel is a classic choice on Maundays Bay. 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 property for your first night on the island—all of these hotels have top-rated restaurants.
Saturday
Start your first full day on the island with some activity, perhaps a workout or yoga session at your hotel’s fitness center. Other things to do in Anguilla include a hike to one of the island’s popular lookout points like Windward Point Bay, cycling along the coast, seaside golf, 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 farther to one of the island’s 35 beach destinations. Each has its own personality. Cove Bay on the south coast is calm and wide, making it perfect for horseback riding on the beach. Arguably Anguilla’s most beautiful beach is Shoal Bay East, a two-mile strip of white sand and unbelievably clear water that’s ideal for swimming, snorkeling, and kayaking. Rent a lounger, sip a rum punch, and enjoy a leisurely lunch of grilled lobster or Anguillian-style snapper at one of the open-air beachfront spots like Madeariman Bar & Restaurant or Tropical Sunset Restaurant & Bar.
That evening, leave your hotel for one of the tastiest attractions in Anguilla: dinner at one of its many fine dining destinations. Anguilla has a notable culinary scene, with a high concentration of gourmet restaurants and talented chefs, including the annual five-day epicurean festival, the Anguilla Culinary Experience. You’ll find delicious barbecues, seafood, and gourmet fare that’s a fusion of flavors reflecting Anguilla’s cultural diversity. Jacala Beach Restaurant is open seasonally and serves French classics with a Caribbean twist. Don’t miss the freshly-caught crayfish, a local delicacy. Blanchards Restaurant, also on Meads Bay, offers refined Caribbean cuisine and a charming open-air dining room (or equally romantic light-strung courtyard). Their signature dessert is the Cracked Coconut, an artful concoction of coconut ice cream and Baileys Irish Cream in a coconut-dusted chocolate shell. 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 harbor and makes a perfect spot to catch a tropical sunset. For a lively atmosphere, head to the open-air Picante, a Caribbean taqueria, for a mango or guava margarita, seafood enchiladas, and tableside guacamole.
Sunday
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 cocktails. It’s only accessible via boat but has a designated mooring area for guests and four sea shuttles named Happiness, Bliss, Joy, and Euphoria that take visitors to and from the mainland.
Monday
Start your morning with one last leisurely breakfast at your hotel, then head to the airport for one of Tradewindʻs scheduled flights back to San Juan and onto your final destination. Or continue the trip by island-hopping directly from Anguilla to St Barths or Antigua. The ease of returning home is the perfect way to cap a long weekend of island relaxation.
To learn more about Tradewind’s private charter and scheduled flights to Anguilla and booking your vacation, please visit our website. To receive a private charter quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-203-267-3305 option 2. For questions regarding scheduled flights, contact our scheduled service team at scheduledservice@flytradewind.com or 1-203-267-3305 option 1.