More than almost any other island in the Caribbean except Cuba, Puerto Rico has a trove of well-preserved colonial cities. Old San Juan is the best known, and it's a must-see for anyone interested in the region's rich history. But the southern coast also has some gems, from the graceful square in Coamo to the churches of San Germán to the heady mix of neoclassical and art-deco masterpieces in Ponce.
Day 1: Old San Juan
If you truly want to experience Old San Juan, make sure you stay within the city walls. El Convento, once a Carmelite convent, is one of Old San Juan's most luxurious lodgings. Gallery Inn, whose mascot is a cockatoo named Campeche, has the most personality, while Da House is cheap and funky. After you drop off your suitcases, hit the cobblestone streets. Make sure to stroll along the city walls and visit one of the forts—most people pick Castillo San Felipe del Morro, but the nearby Castillo San Cristóbal is equally impressive. Old San Juan isn't just for historical sightseeing, though. When the sun goes down, the streets of the historic district light up, becoming one of the city's nightlife centers. For dinner head to Calle Fortaleza, where you'll find some of the city's best restaurants. Then you can while the night away at one of the happening bars or clubs.
Logistics: Believe us when we tell you that you don't want the headache of parking in Old San Juan. At San Juan's Aeropuerto Internacional Luis Muñoz Marín, take a taxi turístico (tourist taxi) to your hotel. The streets here were made for walking, and that's just what you'll do. Wait and pick up your car when you're ready to leave town for the countryside.
Day 2: Coamo
Head south from San Juan, and if you get an early enough start, take a short detour to Guayama, where you'll find the gorgeous Casa Cautiño. This 19th-century manor house, transformed into a museum, is one of Puerto Rico's most beautifully restored colonial-era structures. Continue west to Coamo, known for its thermal springs. The best place to stay is the Coamo Springs Resort, a rustic retreat with hot and cold pools. On Coamo's lovely main square is the gleaming white Iglesia Católica San Blás, one of the island's oldest churches. In terms of distance, Coamo isn't so far from San Juan—only about 60 miles (96 km)—so you don't have to leave at the crack of dawn to have most of a day to explore the town.
Logistics: Ponce is reached via Route 52, a toll road that heads south from San Juan. Exit Route 52 and follow Route 15 to Guayama. Then take Route 3 west to Santa Isabel; turn north on Route 53 for Coamo.
Day 3: Ponce
Your destination on your third day is Ponce, the "Pearl of the South." You'll know you've arrived when you drive through the massive letters spelling the name of the city. The main square, the Plaza de las Delicias, is a delight. Here you'll find the Catedral de Nuestra Señora de Guadalupe, a church dating from 1835, and the Parque de Bombas, a firehouse from 1882 that is painted in bold red-and-black stripes. There are several museums around the city, but the most interesting is the small Casa Wiechers-Villaronga, a house built in 1911. In a city filled with neoclassical confections, this is one of the most elaborate. Strolling the downtown streets, you'll also marvel at neoclassical and art-deco architecture. Don't miss the Museo de Arte de Ponce, one of the Caribbean's best art museums.
Logistics: Ponce is reached by Route 14 from Coamo. To get downtown, take Route 1.
Day 4: San Germán
Less than an hour west of Ponce is San Germán, a must-see for anyone interested in the colonial era. The best place to start a tour of San Germán is Plazuela Santo Domingo, the small park in the center of the historic district. At the eastern edge of the park is the Capilla de Porta Coeli. This chapel, at the top of some steep stone steps, is now a museum of religious art. Stroll west past the delightful assemblage of buildings of every architectural style from mission to Victorian. Make sure to see the other gorgeous church, the Iglesia de San Germán de Auxerre a few blocks north. The best lodging in the area is the simple Villa del Rey, a few miles outside of town.
Logistics: San Germán is easy to reach—simply take Route 2 west of Ponce. When you reach Route 122, head south.
Day 5: San Juan
If you have time on your way back to San Juan, stop for lunch at one of the open-air eateries near Guavate, off Route 52. You can try the famous lechón, whole pig roasted on a spit.
Logistics: From San Germán, take Route 2 until you reach Ponce. Exit onto Route 52; a toll road takes you all the way to San Juan.
If you have a week for your trip, this itinerary will give you a taste of each of eastern Puerto Rico's highlights. However, if you are short on time, Puerto Rico is still the perfect destination. Nonstop flights from many U.S. cities mean that even a long weekend is a possibility, though after you see the beaches, you may not want to limit yourself to just a night or two on Vieques or Culebra.
Day 1: El Yunque
East of San Juan is El Yunque, the undulating rain forest that covers much of the eastern edge of the island. It's a highlight of any trip to Puerto Rico, and you can still have a memorable time if you have only one day to spend there. Several of the trails can be done in an hour or less, including one leading to the spectacular waterfalls called the Cascada La Mina. Spend the night in Río Grande; our favorite hotel along this stretch of shoreline is the luxurious St. Regis Bahia Beach Resort, known for its Robert Trent Jones golf course, beautiful private beach, and first-rate service.
Logistics: Take Route 3 east of San Juan; then head south on Route 191, which leads through El Yunque.
Day 2: Reserva Natural Las Cabezas de San Juan
Head to Fajardo, on the northeastern tip of the island. Drop your stuff off at your hotel—we prefer the smaller ones like the Fajardo Inn —and then head out for a prearranged tour of the mangrove forests of the Reserva Natural Las Cabezas de San Juan. However, exploring this area isn't just a daytime experience. You may also want to head out at night to get a very different view of Las Cabezas; you can paddle through the bioluminescent bay here in a kayak. Companies offer the trips nightly, though your experience will be heightened if there is no moon. In the afternoon, take a boat excursion from Fajardo to the Islas Palominos.
Logistics: Take Route 3, which leads all the way to Fajardo, from where Route 987 leads to Cabezas de San Juan.
Days 3 and 4: Culebra
Culebra has some of the most beautiful, powdery soft beaches that you'll find in all of Puerto Rico. It's a small, quiet island, so you won't find much to do except relax. But then, that's the draw. There are no big hotels or fancy restaurants, only small guesthouses and some villas. If this sounds like too much of a get-away-from-it-all experience for your tastes, then skip Culebra and spend more time on Vieques, which has more resorts and better restaurants, and plenty of eco-focused activities. If you want to visit both islands, you can fly between Culebra and Vieques, but note that there's no ferry link.
Logistics: Drop off your rental car in Fajardo (or in Ceiba if you're flying)—you'll want to rent a sturdier four-wheel-drive vehicle once you get to Culebra. Take a 90-minute ferry trip from Fajardo or 10-minute puddle-jumper flight to the island from Ceiba. We recommend taking the plane, as the views are spectacular.
Days 5 and 6: Vieques
Close—both in terms of atmosphere and geography—to the U.S. Virgin Islands, Vieques has an entirely different feel from the rest of Puerto Rico. If you've never been to Vieques, we strongly recommend you spend at least one night there. The beaches are endless, the snorkeling is remarkable, and the Puerto Mosquito Bioluminescent Bay is one of nature's best shows. A great way to explore the island is on a bicycle tour arranged by a local operator.
Logistics: You'll want to fly between Culebra and Vieques—there are scheduled direct flights between the islands. Otherwise you'll need to return to Fajardo and take a ferry to Vieques.
Day 7: San Juan
From Vieques, take a puddle-jumper flight back to San Juan (or to Ceiba's airport to pick up your rental car). If you want to spend a day in Old San Juan, take a flight into Aeropuerto Fernando L. Ribas Dominicci, which is a short taxi ride from San Juan's colonial heart. If you are connecting to a flight back home, then all you have to do is switch planes and you'll be on your way.
Logistics: If you are connecting to a flight back home, make sure your flight to San Juan is headed to Aeropuerto Internacional Luis Muñoz Marín. If it is going to San Juan's regional airport, Aeropuerto Fernando L. Ribas Dominicci, you'll have to shuttle between the airports.
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