5 perfect days in Puerto Rico

If you're just looking for a beautiful beach, there are literally thousands of options around the Caribbean. But Puerto Rico gives you all the golden sand you could ever want, plus so much more. Start with Old San Juan, which has hundreds of years of culture baked into its cobblestone streets. For outdoor activities, nothing beats hiking through the rainforest of El Yunque. And for dazzling aquatic fireworks courtesy of mother nature, there’s the shimmering bioluminescent bay on the small island of Vieques. And that’s just a fraction of what’s available on Isla del Encanto (or Island of Enchantment, Puerto Rico’s apt nickname).

Whether you're a first-timer or a repeat visitor, five days is the perfect amount of time to see the highlights of Puerto Rico. Because of the island’s compact size, you can visit almost everywhere in this itinerary as a day trip from San Juan. (The one exception is Vieques, where you'll want to stay overnight to see the bio bay.) While you’re in Puerto Rico, take the advice our readers have offered over the years; we’ve included their best tips for exploring this one-of-a-kind island.

There's no better way to get to know Puerto Rico than by exploring the narrow alleys of Old San Juan. Enter the city through the old stone walls of the 16th-century Puerta de la San Juan. Standing more than 15 feet high, the imposing archway was where visiting dignitaries were once greeted. You reach the gate by strolling along the Paseo de la Princesa, a 19th-century esplanade running alongside the sun-soaked harbor. The views from here are nothing short of spectacular.

Visitors to the city 400 years ago would have entered the gate and continued along cobblestoned Calle Caleta de San Juan to the Catedral Basilica Menor de San Juan Bautista. You should follow in their footsteps to get a look inside the cathedral known for its soaring arches and beautifully decorated dome.

Follow Calle Cristo for a block or so south to reach the shopping street called Calle de La Fortaleza. It's often strung with a canopy of colorful umbrellas, making it a must for your Instagram account. Here you'll catch a glimpse of La Fortaleza, the first fortress built to defend the city against foreign invaders. It was a colossal failure, falling to attacks by the English in 1598 and the Dutch in 1625. Afterward, it was transformed into the governor's residence. It's often closed for official events, but if you find it open for tours it's worth a look.

Continue to the end of Calle Cristo, where you'll find the tiny Capilla de Santo Cristo de la Salud. Dating back to 1753, the Chapel of Christ the Savior was built when the life of a young man on horseback who tumbled over the cliff here was miraculously saved. Through the iron gate to the side is Parque de las Palomas, a lovely name that translates as the somewhat less appealing "Pigeon Park." Hundreds of the birds congregate here, waiting for someone to toss them some seeds sold by the nearby vendor.

Head east on Calle San Francisco, where you'll find the central square called the Plaza de Armas. Just beyond the park is Chocobar Cortés, which gets high marks from Tripadvisor readers. As the name suggests, there's chocolate in many of the dishes they serve, including the grilled cheese with bacon and chocolate butter. If you're just here for drinks, let us suggest the Bloody Choco-Mary, with chocolate salt on the rim.

Make your way northwest to the imposing Castillo San Felipe del Morro, started in 1539 to protect the city from attacks by sea. Better known just as El Morro, the six-level castle rises from the rocky promontory at the edge of the island. It protected the city countless times over more than 300 years, from the 1595 attack from the English to the 1898 bombardment by the U.S. Navy. There is a maze of turrets, towers, and tunnels that you're free to explore.

Head east on Calle de San Sebastián, where there are several bars where you can escape from the afternoon heat. Our top pick—as well as a favorite of Tripadvisor readers— is trendy La Factoria, a hole-in-the-wall place that often wins “best of” awards for its creative cocktails .

Several blocks farther east is the Castillo de San Cristobal, the largest Spanish fort ever built in the Americas, created to protect San Juan's eastern edge from land-based attacks. Its walls held firm until 1897, when a large segment was dynamited to allow the city to expand beyond its original footprint. It's still impressive, and has great views of the skyline from the upper level.

Earning a "best of the best" rating from Tripadvisor readers, Marmalade is the kind of place where guests go on and on about seemingly ordinary dishes like the white bean soup. (Not surprising, as here it's made with scallions, black truffle oil, and pancetta "dust.") Also getting raves is the halibut with a toasted cornbread crumble in a froth of sweet corn and jalapeños. The kitchen only offers five-course set menus, but you have several choices for each. The wine pairings bring out subtle flavors in each dish.

Didn't make a reservation for Marmalade? Tripadvisor readers say that Trois Cent Onze makes for the "perfect date night." Just about everything here—from the beef bouillabaisse with an anise-flavored sauce to the honey-roasted duck with a blood orange and wine reduction—started out as a typical French dish, but they are rethought here with creativity, originality, and island influences. Save room for the white chocolate and cardamom crème brûlée.

There's no more sophisticated place to enjoy a craft cocktail than at the pretty Princesa, an open-air establishment back on the Paseo de la Princesa. It claims to serve just about every type of rum made in Puerto Rico.

OLD SAN JUAN AREA TOUR OPTIONS

Spend the morning across the harbor from Old San Juan touring one of the city's pair of well-established rum distilleries. The two could hardly be more different. Casa Barcardí is a slick operation, just as you'd expect for a distillery that produces 150,000 liters of spirits each day. Everything here is on a massive scale, so the tours start with a trolley ride to the visitor center. From there, visitors head out on several different tours according to their interests. Some learn about the flavors of different types of rum, while others focus on how to mix them in cocktails. If you're a rum aficionado, splurge on the Founder's Experience, which takes you on a behind-the-scenes tour of the facility, including a look at the unique aging process. Casa Bacardí is in Cataño, a quick ferry ride from Pier 2 in Old San Juan.

At the historic Hacienda Santa Ana, the Ron del Barrilito Visitor Center, on the other hand, is a much more intimate affair. This craft distillery sees far fewer visitors, which means that the tours feel much more personalized. You have plenty of time to ask questions of the remarkably well-versed guides. The facility is in the community of Bayamón, about a 15-minute drive from Casa Bacardí.

Which facility should you visit? Tripadvisor readers give a Travelers' Choice Award to both Casa Bacardí and the Ron del Barrilito Visitor Center, so you can’t go wrong with whichever you choose.

When you're ready for lunch, head to the upscale beachfront community of Condado. Many of the city's lavish resort hotels are here, steps from the shore. Just off the major thoroughfare of Ashford Avenue is Cocina Abierta, one of the area's most adventurous restaurants. Argentine Chef Martín Louzao has put together different five-course tasting menus for vegetarians, pescatarians, carnivores, and those who will eat just about anything.

To stretch your legs afterward, take a stroll along tree-lined Ashford Avenue to see many of the city's most beautiful boutiques. Even if you only plan on window shopping, you'll probably spot one or two items you have to take home. For the most stylish women's resort wear, head to the fashionista favorite Nativa. A duo of local designers creates men's fashions that blend urban shapes and tropical colors at hip and happening Roots.

A 15-minute walk south takes you to the Museo de Arte de Puerto Rico, a gorgeous gallery focusing on artists from Puerto Rico and the Caribbean. The collection spans the centuries, with masterworks from the 16th century to the present. Don't miss the sculpture garden in the rear, which winds through a flower-filled garden.

You've just crossed into Santurce, San Juan's capital of cool. Not familiar with this neighborhood? San Juan's biggest barrio, Santurce has a reputation for being the city's hipster hangout. It has an artsy vibe, thanks to the colorful murals along Calle Loiza (the neighborhood's main drag), Calle Cerra, and Avenida Juan Ponce de León.

Your first stop should be Lote 23, an open-air food court with food trucks ranging from Mexican flautas (stuffed tortillas rolled into a cigar shape) to Caribbean tostones (deep-fried medallions of plantains). There are also kiosks selling fine wines and craft beers. If you need to take a break from all that walking, this is the place.

After strolling through the neighborhood, enjoying a coffee from one of the many cafes or ducking into a gallery or two, head to the Plaza del Mercado. It's a fairly small farmer's market during the day, but after 6 pm the market and the surrounding neighborhood transforms into a street party called La Placita de Santurce. There's always something happening here, but the crowds are biggest from Thursday to Sunday, when food vendors set up in the alleys and strolling musicians get the crowds dancing. Make sure to look up, because a lot of the celebrating takes place at rooftop bars and restaurants.

Where to start on your exploration of La Placita? If you want cheap, tasty comida crillo (Puerto Rico's version of comfort food), head to La Alcapurria Quema. Everything on the menu is made to order, so it all comes to your table piping hot. Grab a seat on the patio so you can watch the fancy footwork of the salsa dancers.

If you're looking for a more refined restaurant, consider the top-rated Santaella. The kitchen takes traditional dishes like quesadillas and transforms them by filling them with goat cheese, honey, and white truffle oil. If we had to choose an entrée, it would probably be the deep-fried red snapper that seems to be leaping off the plate. Music blares out of several nearby establishments, but you can't hear any of it from the sophisticated dining room.

SANTURCE AREA TOUR OPTIONS

Get an early start to El Yunque National Forest, a 45-minute drive east of San Juan. Trust us, you'll want to get here as soon as they open the gates at 7:30 a.m. Not only will you beat the crowds, you'll avoid the hottest part of the day. You'll also have a better chance of missing the rain showers that fall several times a day. (This is a tropical rainforest, after all.) Bring a rain poncho and hiking boots, just in case.

Your first stop, especially if you have kids in tow, should be the El Portal Visitor Center, which has displays about the park's wildlife and screens an interesting film about the endangered Puerto Rican parrot. There's also a pleasant café and clean restrooms. (You'll definitely want to take advantage of these.)

It's possible to do a driving tour of El Yunque, stopping along the way at scenic overlooks like the Yokahú Observation Tower. But the best way to experience the park is by lacing up your boots and hiking one or two of the trails through the rain forest. One of the easiest is the Angelito Trail, a 20-minute there-and-back trail that takes you to a tranquil spot on the Mameyes River where you can take a dip. Bring along a swimsuit and a towel if you plan to go in the water. Even more spectacular is the Mount Britton Trail, a moderately challenging trail that takes about an hour. At the top is an observation tower and some sweeping views of the rainforest.

After heading out the main gate at El Yunque, make a right toward the seaside community of Luquillo. You'll soon run across a long line of brightly colored kioskos along the beachfront. Some of these "kiosks" are simple takeaway stands, while others have expanded over the years into full-fledged restaurants. Simply wander down the sidewalk, stopping wherever something catches your eye.

One place almost guaranteed to have a crowd is Ely's Place, at Kiosk #10. The menu has dozens of different dishes, but you can't go wrong with Puerto Rican favorites like alcapurrias (cylinders of deep-fried dough) and piononos (edible cups made from fried plantains) stuffed with conch, octopus, or other types of seafood. Grab a table in the back where you can enjoy your food while gazing at the ocean. The beautifully present entrees at Terruño, at Kiosk #20, would look right at home at any of the high-end eateries in Old San Juan. No wonder it gets a "best of the best" designation from Tripadvisor readers.

When you've had your fill at the kiosks, head to nearby Playa Luquillo. It's a beautiful crescent of white sand backed by palm trees — and that's the whole reason you came to Puerto Rico, right? There's a convenient parking lot and rentals for lounge chairs and umbrellas. The beach is often crowded on the weekends, but during the week you might have it to yourself.

From the nearby town of Fajardo, you can board a catamaran bound for an uninhabited island called Cayo Icacos. You definitely won't be alone here, as dozens of other boats blaring dance music deposit their passengers on the pristine white sand. If you're looking for a beach party—or, as one Tripadvisor reader put it, a "beer commercial" vibe—Cayo Icacos is hopping from early morning to late afternoon. If not, you can wander down the shore to a quieter spot or go snorkeling in the turquoise waters.

Ready for one of your most memorable meals in Puerto Rico? On your way back to San Juan, stop for dinner at Piñones, a seaside community where you'll find dozens of no-frills eateries. Called chinchorros, these food stalls are an important part of Puerto Rican culture. Groups of friends or family members come to this and other communities to move from one eatery to the next, sharing dishes that are only found on the island.

Do as the locals do, sampling pickled conch at one eatery and codfish pancakes at another. Start out at El Nuevo Acuario, where the kitchen turns out impressive dishes like lobster empanadas with cheese and guava or grouper with a pineapple-habanero aioli. The open and airy dining room will make you want to linger. For a nightcap, head to the nearby La Casita Amarilla. You can enjoy a beer and a breeze on the dock leading into the lagoon.

EL YUNQUE AREA TOUR OPTIONS

Nicknamed the "Pearl of the South," Ponce, on Puerto Rico’s southern coast, couldn't be more different from Old San Juan. Puerto Rico's second largest city saw an economic boom that began at the end of the 19th century, and its downtown blends Art Nouveau, Art Deco, and other early 20th century styles into a style of its own called Ponce Creole. Wandering the streets here is the best way to spend your time.

To get your bearings, start off at Plaza las Delicias, the tree-shaded square that serves as the heart of the historic district. The handsome Fuente de Los Leones, or the Fountain of the Lions, sits near the center of the park. Even though it's still early in the day, do as the locals do and enjoy a cone from the adjacent King's Cream. No matter when you visit, there's sure to be a line out the door.

You can't miss the park's most unusual feature, a red-and-black wooden building called the Parque de Bombas. Built to house a volunteer firefighter's brigade, it has stood on this spot since 1882. Inside you'll find some antique firefighting equipment, but the exterior is the big draw here.

A few blocks east is the Museo de la Historia de Ponce, located inside an historic building that combines the usual Ponce Creole style with Moorish flourishes. The museum is fairly small, but still manages to tell the story of Ponce in surprising detail. It's worth it so see the interior of the historic Casa Salazar-Candal house.

One of the best downtown restaurants is Lola, in a handsome building on the northwestern corner Plaza las Delicias. The interior is strikingly modern, but also calls to mind the Ponce of its early 20th century heyday. The menu takes inspiration from around the globe, and a popular appetizer is naan bread with goat cheese, fig jam, and pear slices, while the hanger steak entrée is rubbed with coffee and served with passion fruit butter.

Around the corner on Calle Reina Isabel is Casa Wiechers-Villaronga, a wedding cake of a building that epitomizes the elegance of Ponce Creole style. There are so many homes on this and nearby streets, many of them waiting to be restored, that you can spend hours exploring the neighborhood.

The crown jewel of Ponce is Castillo Serrallés, in the hills above the city. A Spanish Revival masterpiece, it's known as "the house that rum built." It was constructed for the son of the founder of Destilería Serrallés, the distillery that makes Don Q rum. These days the mansion is a museum that tells the story of the rum and sugar cane industries and how they turned Ponce into a very wealthy city.

On your drive back to San Juan, stop in the community of Guavate, Central Puerto Rico's most famous carretera del lechón, or "pork highway." On a winding mountain road, you'll encounter dozens of eateries selling meat carved from whole roasted pigs turning on spits. This is one of the culinary treats of Puerto Rico, and Guavate is where they do it best. The Lechonera de Mojito is one of the first eateries you'll encounter, and it has many aficionados, but continue up the road and stop wherever there's a crowd. Many stands close at 7 or 8, so don't arrive too late.

PONCE AREA TOUR OPTIONS

To make the most of your time, take a small plane to the offshore island of Vieques. The hop takes less than a half hour, and the sight of this impossibly green island in the middle of the Caribbean is nothing short of spectacular. (Alternatively, a ferry from Fajardo, about an hour from San Juan, to Vieques takes about 90 minutes.)

What makes Vieques so special is that more than 60% of the island is protected as part of the Vieques National Wildlife Refuge. The reserve's 17,771 acres (14,671 acres in the east and 3,100 acres in the west) cover a wide swath of the island, so hop in the four-wheel-drive vehicle you've rented from one of the local agencies and begin exploring. You're sure to see some of the wild horses that roam the island.

Inside the refuge, the beaches on the island's southern shore are well worth seeking out. If you have time for just one, head to Playa La Chiva, which means Goat Beach. It's a long crescent of powdery white sand wrapping around an impossibly blue bay. There's great snorkeling at either end, where the water is calm and clear. Don't be surprised to see manta rays floating across the ocean floor. The only amenities here are some covered pavilions where you can escape from the sun.

Two other nearby beaches are just as beautiful. To the west is Playa Caracas, which is usually a little more crowded. There's barely a ripple in the water, making this a perfect beach for families with young children. Playa La Plata, to the east of Playa La Chiva, is by far the quietest of the three. You won't have to go far to find a spot all to yourself.

If you're wondering how the owners came up with the name for Tin Box, all you have to do is drive past the metal-covered exterior. Step inside and you will likely be enchanted by the open-air dining room and its views over the bird-filled treetops. Barbecued meats—think cubes of smoked pork and piles of spare ribs—are the most popular items on the menu, but there's something here for everyone. It's located smack in the middle of the island, so it's never too far out of your way.

On the island's southeastern coast is Playa Negra, a beautiful black sand beach. The richly colored sand is washed down a stream from volcanic rocks at nearby Monte Pirata. A short walk through a forest leads down to the shore, which you'll probably have to yourself. The crashing waves are lovely to look at, but mean this isn't the best beach for swimming.

Head into the quaint town of Esperanza, a short drive to the east. The waterfront walk, known as the Malecón, is a great spot for a stroll.

On either side of the Old Sugar Cane Pier, Playa Esperanza is a fine place to wade in the water. But the most beautiful beach within walking distance of town is two-mile-long Balneario Sun Bay, a gently curving stretch of golden sand. It costs a few bucks to get in, but in return you get access to restrooms, shower areas, and a little eatery.

Under some graceful arches, El Quenepo is the loveliest restaurant you'll find in Vieques. Tripadvisor readers agree that the grilled pear salad with candied pecans is the way to start your meal, followed by the pan-seared duck with a crispy fontina risotto cake or the braised pork with an apple-tamarind glaze. The tile-floored dining room is lovely, and there's also a second floor terrace with views of the ocean. For a drink afterward, nearby Bar La Nasa has delicious cocktails and a beach party atmosphere.

The reason you came all this way to Vieques is probably to take a kayak trip out to Mosquito Bay, Puerto Rico's brightest bioluminescent bay. It glows on moonless nights thanks to millions of microorganisms known as dinoflagellates. When the water is disturbed, like when your paddle dips below the surface, they seem to sparkle. It's magical when you trail your fingers through the water and it begins to shimmer. The darker the night, the more you will see. Tripadvisor readers give it a Travelers' Choice Award.

VIEQUES AREA TOUR OPTIONS