Best Time To Visit: The Caribbean offers year-round sailing. August in Anguilla is a great time for the carnival and yacht races, while in November the island comes alive with the jazz festival.

Key Cruising Areas: Anguilla is an excellent start to a Caribbean cruise – sail west to explore the diversity of the Leeward Islands or head south to the idyllic Windward Islands.

Don’t Miss: For a little local flavor, head to Gwen’s Bar and Grill on a Sunday night. Laze in a hammock in the evening warmth, sipping the famous rum punch and chatting with the locals as the scratch bands warm-up for a night of live reggae.

Best Spots for Wining and Dining: For a small island, Anguilla has an impressive selection of restaurants. With over 70 restaurants, the country is known for excellent high-end dining. One of the best luxury restaurants has to be Da’Vidas. Watch your yacht bobbing in Crocus Bay from the warm ambience of the dining room as you sample the eclectic menu. Start with the coconut-crusted scallops and a rum punch.

Best Local Dish: The cuisine of Anguilla is typically the Caribbean, filled with seafood, fresh tropical flavors, and rum! For good local food in a romantic setting, head to the waterfront at Sandy Ground and stop at Veya restaurant. The pretty lighting and treetop feel create a special ambience, while the innovative dishes will have you coming back for seconds. Try the conch fritters for an island specialty.

Local Culture: Anguillans take pride in their unique culture, which revolves around faith, family, and friends. These values are celebrated in art, dance, and music – which can be seen in the galleries around the island or the live music at most beach bars. The Carnival in July and August is a wonderful example of the Anguillan celebration.

Best Beach: With over thirty beaches on the tiny island, you will be spoilt for choice. Rendezvous Bay is claimed to be the most beautiful beach in the world, the long sandy shore overlooks the neighboring island of St Martin and is dotted with great beach shacks offering local snacks.

IYC recommends: Spend a perfect day in Shoal Bay. Anchor in the bay and spend the afternoon relaxing on the soft sand, swimming in cerulean waters, and taking the onboard toys out for a spin in the gentle waves. As the evening draws in, stop in Tropical Sunset bar to eat conch ceviche and drink rum punch, as you watch the sky turn every shade of orange in the famous Anguillan sunset.