Anguilla or Vieques?

Both have superb sand and warm, clear water, so the choice comes down to what is behind the beach. Anguilla's are the well-kept kind. Shoal Bay East, Meads Bay and Maundays Bay have resorts and restaurants behind them yet stay uncrowded, and boats run out to the sandbars of Sandy Island and Prickly Pear Cays.

Vieques is wilder. Sun Bay and Media Luna near Esperanza are calm and easy to reach, but the best beaches, Caracas, Pata Prieta and La Chiva inside the wildlife refuge, are at the end of dirt tracks and have no lifeguards, cafés or shade, so you bring your own. On both islands the north shore can get swell in winter while the south side stays calmer.

Anguilla is the place to eat well. Its beachfront restaurants at the west end and in Sandy Ground make dinner the main event of the evening, crayfish and grilled snapper are on most menus, and the weekend lolos add an informal local side with ribs and chicken off the grill.

Vieques is plainer: fish tacos and mofongo on Esperanza's seafront, diners and bakeries in Isabel Segunda, and fried alcapurrias from roadside kiosks. The choice is narrow and kitchens close for days out of season, so anyone renting a house should stock up on the main island before the ferry.

Neither island is a culture trip, and each can be covered in a morning or an afternoon. Vieques has slightly the stronger story. The Fortín Conde de Mirasol above Isabel Segunda covers Taíno finds, the sugar era and the decades the island served as a naval base and bombing range, a history much of the refuge land still carries.

Anguilla's sights are older and more scattered: the 18th-century Wallblake House in The Valley, the Heritage Collection Museum's account of the 1967 revolution, and the Amerindian carvings in Fountain Cavern.

Anguilla has a bit more going on. Sandy Ground's beach bars stay open late at weekends with dancing on the sand, Sunday afternoon sessions run on into the evening, and the island fills up for the reggae festival in March and carnival in August.

Vieques winds down earlier, with a few open-air bars on Esperanza's seafront and local bars in Isabel Segunda that fill up at weekends. For many visitors the only outing after dark is the kayak tour of the bioluminescent bay. Neither island has clubs.

Vieques has the better outdoors, mainly thanks to Mosquito Bay, where every paddle stroke on a dark night lights up blue-green; plan around the full moon, when the glow fades. By day the wildlife refuge offers dry forest, salt ponds and dirt tracks for cycling and birding, with semi-wild horses along the roads and easy reef snorkelling among turtles and rays.

Anguilla is flatter and drier, and almost everything it offers outdoors happens on the water: diving on reefs and wrecks in the marine parks around Prickly Pear Cays and Dog Island, and sailing and kitesurfing in the steady trade winds. On land there are cliff walks in the north and east, and little more.

Anguilla is the better base for a day away. Saint Martin is about twenty minutes by ferry from Blowing Point, with Marigot and the restaurant street of Grand Case on the French side and duty-free Philipsburg on the Dutch side. A chartered boat reaches Gustavia on St Barths in about an hour.

From Vieques the one real outing is to Culebra and Flamenco Beach, by chartered boat since there is no simple direct ferry. Old San Juan makes a long day once the crossing and the drive are added.

Both suit young children who are happy on the sand, and neither has anything built for them. Anguilla's gently shelving bays, such as Rendezvous Bay and Meads Bay, come with resorts that cater for families, and the island is short and quiet enough that every beach is close.

Vieques gives older children more to remember, with horses on the roads and the night kayak on the glowing bay. However, its beaches have no lifeguards or shade, medical care is limited, and the ferry and jeep add effort with small children.

Anguilla is far simpler. It is about 26km long, with light traffic and decent roads, so a hire car gets you to any beach quickly, and the ferry from Sint Maarten is a short hop once you have flown in.

Vieques takes planning at every stage. Ferries from Ceiba can sell out or change schedule, so many people take a small plane instead, and the refuge beaches need a jeep on rough dirt roads, booked well ahead. The shared public cars cover little beyond the run between the ferry and Esperanza.

Neither island is worth visiting for shopping. Anguilla has galleries showing local painters, resort boutiques and souvenirs such as sea salt, hot sauce and rum, with the duty-free streets of Saint Martin a ferry ride away. Vieques has a handful of galleries and craft shops in Esperanza and Isabel Segunda, and its grocery stores cost more than those on the main island.

Anguilla costs a great deal more, and the cost comes from every part of the trip. Most of the places to stay are luxury resorts and villas, restaurant bills reflect an island that imports nearly all its food, and with no buses to speak of, taxis or a hire car add to every day. Even the groceries for a villa kitchen are expensive, and winter is the dearest season of all.

Vieques runs at US prices, but the bill is easier to keep in check. The one large cost is the jeep, which the dirt tracks to the refuge beaches make unavoidable, and food in the shops and restaurants costs more because it comes over by ferry. The better villas and boutique rooms charge winter rates aimed at visitors from the US mainland, while the beaches, the main reason to come, are free.

Anguilla has more live music, though nothing formal. Reggae, soca and string bands play the beach bars around Sandy Ground, and the March reggae festival and the August Summer Festival, with calypso and boat racing, are events people travel for.

Vieques has the odd guitarist in an Esperanza bar and the yearly patron saint festivities in Isabel Segunda, with bomba, plena and salsa in the town square. For theatre or concerts you need to go to San Juan.

Both are restful islands with no high-rises or crowds, but only Anguilla has proper spas. Its luxury resorts have extensive spas with treatment rooms open to the sea breeze, so a day of treatments is easy to arrange.

Vieques offers the quiet without the luxury: yoga and massage at a few guesthouses and small studios, a pool if your villa has one, and roosters instead of nightlife.