Yes — at the very top end of Caribbean pricing, comparable to St. Barths or Mustique. Budget options are minimal. Mid-range stays start around $400–500/night; the high-end (Cap Juluca, Four Seasons, Aurora) runs $1,500–5,000/night. Restaurants are similarly priced — dinner at Veya or Blanchards is a $200+/person evening.

December through April for the dry, cooler season. May and June are excellent shoulder months with lower rates. June–November is hurricane season with August–October peak — Anguilla was leveled by Irma in 2017 and the rebuild is complete, but most boutique hotels close from late August to late October.

Four to seven days suits the island's pace. The draw is slowing down on a different beach each day, working through the restaurant list, and not doing much else. Day trips to St. Martin and St. Barths are easy from Blowing Point ferry terminal.

Yes — one of the safest Caribbean destinations. Crime against visitors is rare; the small population and high-end visitor mix keep the island well-monitored. Standard precautions apply for unattended valuables on beaches. There is essentially no nightlife crime to speak of.

Shoal Bay East and Rendezvous Bay beaches, an exclusive high-end resort scene (Cap Juluca, Four Seasons, Aurora, Malliouhana), a serious restaurant culture for the island's size, Anguilla Day boat races, and Moonsplash music festival. The island has cultivated a deliberately low-key, low-volume tourism brand for decades.

Yes, recommended. The island is too spread out to walk between beaches and restaurants, and taxis are expensive at $25–40 per trip. A rental ($55–80/day) opens up the whole island with low traffic and easy roads. A local permit is issued at the rental desk.