Anguilla

December to April is the dry, breezy peak — clearest water, calmest seas, and the festive fortnight booking further ahead than any other week of the year. May and June are the connoisseur's window: still dry, still calm, noticeably quieter and better value. The Atlantic hurricane season runs June to November, with the risk concentrated from August into October, and a good part of the island's hotel and restaurant trade closes for part of that stretch. The reopening weeks in November are among the best-kept secrets here.

Five to seven nights suits it. Anguilla is a one-resort island rather than a touring one, and the rhythm is a beach, a boat day to the offshore cays, and dinner somewhere on the sand. Anything shorter and the Sint Maarten connection eats too much of the trip. Many clients pair it with a few nights in St Barths or Sint Maarten, and we sequence the crossings so the joins stay short.

Two ways, and the choice matters more than people expect. Most travellers fly into Sint Maarten and cross the channel by boat — either the public ferry from Marigot, which is cheap, slow and ends in an immigration queue at Blowing Point, or a private charter from the airport dock, which is the upgrade worth taking. Anguilla also has its own airport, Clayton J. Lloyd International, served by regional carriers and by a small number of direct flights. We book the crossing at the same time as the flights, because arranging it on arrival is how a good first day gets lost.

Four Seasons Resort and Residences Anguilla, on the West End between Meads Bay and Barnes Bay. It opened as a Four Seasons in October 2016, with interiors by Kelly Wearstler and resort architecture by Wimberly Allison Tong & Goo, and it holds one hundred and twenty guest rooms and suites alongside villas, townhomes and residences. The two-storey beachfront spa runs to thirteen treatment rooms over Meads Bay, and dining spans modern Caribbean at SALT, coastal Mexican at Lima-Limon and beach classics at Bamboo Bar & Grill.

You pay the same rate as booking direct and gain preferred-partner benefits — breakfast, upgrades when available, and a resort credit — with the occasion flagged so the resort prepares a welcome. The larger value on this island is the logistics: the Sint Maarten crossing booked with the flights rather than improvised on arrival, the right room category requested early, the boat day out to the cays, and tables at the beach restaurants that fill weeks ahead in high season.