San Juan was founded in 1521, which makes it the oldest continuously inhabited European-established settlement under the United States flag. The Spanish spent the next two and a half centuries fortifying it: El Morro on the headland, San Cristóbal covering the landward approach, and a wall around the old town that still stands. The whole complex is a UNESCO World Heritage site.
The practical consequence for anyone travelling from the United States is unusual. Puerto Rico is a US territory, so there is no passport requirement for US citizens, the currency is the dollar, and domestic mobile plans work. You get a five-hundred-year-old walled Spanish city, a rainforest and bioluminescent water without an international departure.
The island is bigger than the beach strip
Puerto Rico is about 160 kilometres long and the north coast resort strip is a small part of it.
Old San Juan is the walled city: blue cobblestones, painted façades, the forts and the best restaurants on the island. It is compact and entirely walkable.
Condado and Isla Verde, minutes east, are the beachfront hotel districts — Condado more residential and design-led, Isla Verde nearer the airport with the bigger resorts.
Dorado and Río Grande, thirty to forty-five minutes either side, hold the large resort estates with golf.
El Yunque, inland from Río Grande, is the only tropical rainforest in the United States National Forest system, with waterfalls and trails an hour from the capital.
Vieques and Culebra, small islands off the east coast reached by ferry or a short flight, have the emptiest beaches. Mosquito Bay on Vieques is the brightest recorded bioluminescent bay in the world — dinoflagellates that light up when the water is disturbed, best on a moonless night.
Rincón, in the west, is the surf coast and where the whales pass in winter.
One honest note: Hurricane Maria in 2017 caused severe damage and recovery across the island has been uneven and long. Most of the hotel stock reopened years ago and tourism infrastructure is in good shape, but if you are booking somewhere small or off the main coasts it is worth confirming current status directly.
The nine below are grouped by area.
Old San Juan
Inside the walls.
Hotel El Convento occupies a Carmelite convent built in 1651, with a courtyard, a plunge pool on the roof and the cathedral across the street. It is the oldest building operating as a hotel in the Americas and it is the way to stay in the old city.
Hotel El Convento
Old San Juan · 4★ · $$$
A 1651 Carmelite convent across from the cathedral
Check availabilityPalacio Provincial sits in a restored nineteenth-century government building nearby with a small room count, a rooftop and a more contemporary interior.
Palacio Provincial
Old San Juan · 5★ · $$$$
A restored government building with a rooftop and few rooms
Check availabilityCondado and Isla Verde
The beachfront districts, minutes from the old town.
Condado Vanderbilt Hotel occupies a restored 1919 landmark on the Condado beachfront with two pools, a spa and the most formal service on the island.
Condado Vanderbilt Hotel
Condado · 5★ · $$$$
A restored 1919 landmark with two pools and a spa
Check availabilityFairmont El San Juan Hotel sits on Isla Verde in a 1958 building with a domed lobby, a large pool complex and the best beach of the city hotels.
Fairmont El San Juan Hotel
Isla Verde · 5★ · $$$$
A 1958 domed lobby above the best city beach
Check availabilityLa Concha Resort occupies a beachfront position in Condado with a rooftop pool, a livelier tone and rates below the landmarks.
La Concha Resort
Condado beachfront · 4★ · $$$
Rooftop pool and a livelier tone below landmark rates
Check availabilityO:live Boutique Hotel sits a street back from the Condado beach in a small design-led property with a rooftop and a good restaurant.
O:live Boutique Hotel
Condado · 4★ · $$$
A small design-led house with a rooftop and a strong kitchen
Check availabilityDorado and Río Grande
The resort estates, either side of the capital.
Dorado Beach, a Ritz-Carlton Reserve occupies a former Rockefeller estate on the north coast with five kilometres of private beach, several golf courses and a spa built along a river. It is the most complete resort in the Caribbean.
Dorado Beach, a Ritz-Carlton Reserve
Dorado · 5★ · $$$$
A former Rockefeller estate with five kilometres of private beach
The St. Regis Bahia Beach Resort sits on a beach at Río Grande between the Atlantic and El Yunque, with a golf course, a spa and the rainforest twenty minutes inland.
The St. Regis Bahia Beach Resort
Río Grande · 5★ · $$$$
Golf and beach with El Yunque twenty minutes inland
Check availabilityVieques
By ferry or a short flight, for the empty beaches and the bay.
El Blok occupies a low concrete and wood building on the Vieques coast with a rooftop, a small room count and the bioluminescent bay a short drive away.
El Blok
Esperanza, Vieques · 4★ · $$$
A concrete and wood rooftop near the bioluminescent bay
Check availabilityWhat we have left off
The paradores, the island's network of small family-run country inns, are excluded. They are a genuine Puerto Rican institution, they are inexpensive, and they are guest houses rather than hotels.
What to do
Walk Old San Juan early, when the blue cobbles are empty and the light is on the façades, and do El Morro before the cruise passengers land.
Go to Mosquito Bay on Vieques on a moonless night with a kayak operator. Swimming in it is prohibited to protect the organisms, and the trip is still the best thing on the island.
Hike El Yunque, booking the timed entry in advance, and go to La Mina or the Angelito trail rather than only the roadside towers.
Eat mofongo, lechón from the roadside pork highway at Guavate on a Sunday, and drink the rum, which is made here in quantity.
Surf or watch whales at Rincón between January and March.
Practical notes
San Juan's airport is the main Caribbean hub with heavy US traffic and no passport requirement for US citizens. Vieques and Culebra are reached by ferry from Ceiba or by a ten-minute flight.
December to April is the dry season and peak. Hurricane season runs June to November with the peak from August to October. Summer is hot, wet and much cheaper.
A car is useful for El Yunque and the west; the old town and the beach districts do not need one.
Every hotel bookable in Puerto Rico
Questions people actually ask
Do US citizens need a passport?
No. It is a US territory, with the dollar and domestic phone plans.
Where is the bioluminescent bay?
Mosquito Bay on Vieques is the brightest recorded anywhere. Go on a moonless night with a licensed operator.
Old San Juan or the beach?
Old San Juan for the walled city and the food, Condado or Isla Verde for the sand. Ten minutes apart.
How many nights?
Six. Two in the old town, three on a beach and one for El Yunque or Vieques.
