Anguilla or Puerto Rico?

Both have warm, clear Caribbean water all year, but Anguilla's beaches are the more dependable. More than thirty of them ring a small, flat island, from Shoal Bay East to the sheltered curve of Maundays Bay. The sand is powdery, the water calm, and there are no high-rises and no cruise pier to bring crowds.

Puerto Rico's best beaches, Flamenco on Culebra and the quiet bays of Vieques, match anything on Anguilla, but you need a ferry or a flight to reach them. On the main island, the San Juan city beaches are handy rather than beautiful and Luquillo is the calm choice. Much of the north coast is too rough for easy swimming in winter.

Puerto Rico has more to eat. Its creole cooking of mofongo and roast pork comes with its own places to eat it, from the lechoneras of Guavate to the kiosks at Luquillo and Piñones. San Juan adds the kitchens of Santurce and the market square at La Placita.

On Anguilla the point is the dinner itself: spiny lobster and grilled snapper at polished beachfront tables on the west end and at Sandy Ground, plus weekend ribs at the roadside lolos. It is lovely for a week of long seafood evenings, but there are no markets or street food to explore, and you will have tried most of it sooner.

The gap here is wide. Old San Juan alone, with El Morro, San Cristóbal and the cobbled colonial streets inside its walls, holds more than all of Anguilla. Ponce, San Germán and the Taíno sites at Caguana and Tibes add more across the island.

On Anguilla the list is Wallblake House, the Heritage Collection Museum and the carvings in Fountain Cavern. That fills a morning or two away from the beach.

Puerto Rico wins easily, but only in San Juan. There you get weekend crowds drinking in the street at La Placita, packed bars along Calle San Sebastián and salsa and reggaeton dancing that starts late, with the Condado's lounges and casinos for a smarter night.

On Anguilla the evening is a long dinner. The beach bars at Sandy Ground and the Sunday afternoon sessions are as lively as it gets, and there are no clubs. In fact the whole island is about as quiet at night as Vieques and Culebra.

Puerto Rico has landscape that Anguilla simply lacks: the rainforest and waterfalls of El Yunque, the karst hills and Río Camuy caves near Arecibo, the coffee mountains of the Cordillera Central and bioluminescent bays to kayak through at night. In the water there is winter surf at Rincón, humpback whales passing in winter and the reef wall off La Parguera.

Anguilla is flat and dry, covered in scrub, and its outdoors is the sea: snorkelling off Little Bay, diving around Prickly Pear Cays and Dog Island, and sailing or kitesurfing in the trade winds. On land there are cliff walks and birds on the salt ponds, but no hills to climb.

Neither is a great base for outings, but Puerto Rico has more of them. You can visit Ponce and its art museum, the rum distilleries, the coffee haciendas and San Germán. Culebra and Vieques are better with a night or two of their own than as a day trip.

Anguilla's outings all mean leaving the island. Saint Martin is twenty minutes away by ferry, with Marigot, Grand Case and the duty-free streets of Philipsburg. St Barths is reachable by chartered boat as an occasional treat.

Both have calm, shallow water for small children, at Rendezvous Bay and Meads Bay on Anguilla and at Luquillo and Seven Seas in Puerto Rico. The difference is what comes after the beach. Anguilla is quiet, safe and has almost no traffic, but older children may run out of things to do within a few days.

Puerto Rico keeps them busier, with waterfall trails in El Yunque, the guided route underground at Camuy, a night paddle in a glowing bay for older children and kids' clubs at the big resorts. The cost is more time in the car, and the rough north-coast beaches are no place for young swimmers.

Both need a hire car, but Anguilla is easier to get around. It is about 26km long, traffic is light and any beach is a short drive from wherever you stay. The main hassle is getting there: a flight into Sint Maarten and then a ferry.

Puerto Rico asks more of a driver, with heavy traffic around San Juan, slow mountain roads inland and ferries to Culebra and Vieques that sell out or run late. On the plus side, you can walk Old San Juan and the Condado shore, and taxis and ride-hailing cover the capital.

Puerto Rico is the better place to shop, though it is no fashion destination. The streets around Calle Fortaleza in Old San Juan have galleries, cigar and rum shops, and the carved santos and vejigante masks worth taking home, while Hato Rey has big American malls. Anguilla has a few galleries, resort boutiques and souvenirs of sea salt, hot sauce and rum, and for any real shopping you take the ferry to Saint Martin.

Neither is cheap, but Puerto Rico is far easier on the wallet. Prices are at American levels, and San Juan's beachfront hotels are expensive in winter. Even so, roadside lechoneras, beach kiosks, cheap rum and guesthouses on the west coast and the small islands make a careful trip affordable.

Anguilla is expensive across the board, from the resorts and villas to the groceries, since the island imports nearly everything. The lolos are the only real way to save.

Puerto Rico has a musical identity of its own: salsa dance nights, bomba drumming in Loíza and Piñones, plena around La Placita and the January street festival on Calle San Sebastián. For formal performances there is the symphony orchestra at the Centro de Bellas Artes, the historic Teatro Tapia and the long-running Casals Festival.

Anguilla has reggae, soca and string bands at beach bars, best at weekends and during the March reggae festival and the August Summer Festival. There is no theatre or concert hall.

The two are close here, and both rely on resort spas rather than a bathing tradition. The difference is where you find the calm. On Anguilla the whole island is quiet, with no high-rises or cruise crowds, so rest comes easily wherever you stay.

In Puerto Rico you have to choose your base with care. San Juan is loud, but Vieques and Culebra slow almost to a stop, and Rincón has yoga and an easy surf-town pace. The old hot springs at Coamo also offer a modest soak that Anguilla has no answer to.