7 Days in Paradise: An Itinerary for Your Puerto Rico Vacation

Palm trees on a Puerto Rico beach

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A week in Puerto Rico: sounds like a dream vacation! One week will give you the chance to see and do a lot on the island, and this itinerary is designed to help you experience the many sides of Puerto Rico. You still won't be able to see and do it all, and the two island jewels, Vieques and Culebra, didn't make the list...but that's only because there is so much to cover on the mainland.

What do you need to know before you arrive? This handy checklist covers the basics. Here are a few other tips:

  • Beachwear - An obvious one, but make sure you pack bathing suits, flip-flops, sunglasses, suntan lotion, goggles, and a nice bag to carry everything with you (you can certainly buy anything you've forgotten once you're here).
  • Dress for success - Puerto Ricans are a fashionable lot, and you'll find well-dressed people especially if you're into nightlife. Fashionable and sexy clothing will help you fit right in at the clubs, lounges, and better restaurants.
  • Pack light - There is great shopping in Puerto Rico, not just for internationally famous brands but also for local fashion, souvenirs, and other products. Make sure you have some space in your luggage!
  • Leave winter behind - Even accounting for hurricane season, it rarely gets cold in Puerto Rico. Beyond a sweater or two, you probably won't need warm clothes while you're here. Check the weather to make sure, but don't overpack for the cold.
01 of 08

Day 1: Getting Settled in San Juan

Calle San Justo (San Justo Street), Old San Juan, Puerto Rico.
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Day One is about getting to the island and settling in. Because this is a seven-day trip, I'm assuming you're flying rather than sailing into Puerto Rico. In either case, make San Juan your base. The capital has enough going on to keep you busy for the duration of your stay, but it also provides easy access to many of Puerto Rico's other destinations.

You'll fly into Luis Muñoz Marin International Airport, one of the busiest airports in the Caribbean. From here, you're only about 15-20 minutes from the heart of the city. Now, your first question will be whether or not to rent a car. For the first three days, I'd advise against it. You'll be spending your time in the city, and taxis, a good pair of shoes, and public transportation will be good enough to get you around. Traffic and parking can be a nightmare in San Juan, and many hotels charge hefty parking fees.​

As for where to stay, two of the best, most romantic, and most expensive hotels in the city are El Convento and Chateau Cervantes. If you want to stay in the Old City, these are among your best bets. Here are are a few other options:

Your first day is all about settling in and getting acquainted. If you're staying in Old San Juan, the ancient walled city on the eastern edge of San Juan, you might want to stroll its cobblestone streets and take in its romantic charm. If you're staying in the resort strip of Condado or Isla Verde, I'd suggest hitting the Condado or Isla Verde beaches.

When you're ready for dinner, head to Fortaleza Street in Old San Juan, the dining hotspot in San Juan, and check out one of these excellent restaurants:

After dinner, take a short walk in the old city, and then retire for the night. Your vacation is just getting started.

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02 of 08

Day Two: Old San Juan

La Rogativa in Old San Juan
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On your second day, head to Old San Juan and the heart of colonial Puerto Rico. Over four hundred years old, Old San Juan, or Viejo San Juan, as the locals call it, is a small, breathtaking city, bounded by walls and by the ocean. Cobblestone streets, wrought-iron balconies, and buildings painted in tropical colors greet you as you walk.

Start your first morning in Puerto Rico with a local staple for breakfast at an island institution. Head to La Bombonera, on San Francisco Street, and try out a delicious mallorca. After, take a walking tour to ensure you get the most out of your day in the old city. You can check out this suggested tour, or download a walking tour onto your iPod. Another option is to take a tour. Legends of Puerto Rico conducts both a day tour and a fantastic Night Tales in Old San Juan tour.

Along your tour, you'll come across tempting restaurants and shops. Old San Juan has excellent shopping, particularly for jewelry, local souvenirs, and clothes: feel free to indulge.

As for lunch and dinner, here are a few suggestions. For lunch, enjoy a hearty 'Rican meal at El Jibarito on Sol Street. If you crave something a little more sophisticated, head to El Picoteo in Hotel El Convento for excellent Spanish tapas.

End the afternoon at the magnificent Raíces Fountain. From here, it's a short walk to Fortaleza Street, where you can try one of the restaurants on the list for Day One, or, for a truly transporting meal, head to Panza, one of Puerto Rico's most romantic, elegant, and outstanding restaurants.

Day One and Two covered the old city; on Day Three, you'll see the rest of Puerto Rico's capital.

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03 of 08

Day Three: Touring San Juan

Beach at Ritz Carlton, Isla Verde.
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On Day Three, it's time to go beyond the old city and into the rest of San Juan. Since the beach is a big reason to come to Puerto Rico, it makes sense that you devote the morning to lying on one of San Juan's glittering stretches of sand. Where you lay down your blanket will depend on what you want:

  • Isla Verde and Condado Beaches are the ritzy resort strips where people go to see and be seen.
  • El Escambrón, in the Puerta de Tierra neighborhood, is popular with the locals and is a "Blue Flag" beach (a designation given to clean, well-maintained beaches).
  • Ocean Park Beach has a more laid-back vibe.

Where you spend the morning will also dictate where you eat lunch. Here is one suggestion for each beach:

  • Isla Verde and Condadao - check out Ceviche House for a fresh, light departure from local cuisine.
  • El Escambrón - that's an easy one. There's an excellent Puerto Rican restaurant by the same name right on the premises.
  • Ocean Park - head to Pinky's on Maria Moczo Street for healthy burritos, wraps and excellent smoothies.

The afternoon can be spent in several ways, depending on your tastes. Here are five suggestions:

  1. Museum lovers must visit the inspiring Puerto Rican Museum of Art in Santurce. (A worthy second stop is the Museum of Contemporary Art.)
  2. Nature lovers should check out the sprawling Botanical Garden in Hato Rey
  3. Shopaholics will want to hit the fashionable boutiques on Ashford Avenue in Condado.
  4. Gamblers should head to one of these hotels to try their luck.
  5. Bacardi fans should visit the Bacardi Distillery, one of the best free activities on the island.
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04 of 08

Day Three (Continued): Enjoying the San Juan Nightlife

People sitting in front of a cafe at the Old Town in the evening, Calle de Christo, San Juan, Puerto Rico, Carribean, America
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After a busy day, return to your hotel and relax until dinner. When you're ready to head out for the night, pick from the following itineraries, sorted by neighborhood:

Old San Juan

  1. Bodega Chic (Calle Cristo 51), Barú (creative Puerto Rican) and Dragonfly (Latin-Asian fusion) all have the advantage of serving excellent food and converting into hip lounges later at night.
  2. After dinner, you can also head to the Nuyorican Café for a night of sultry salsa dancing and live bands.
  3. End your night at one of Old San Juan's late-night bars, like El Burénor at Club Lazer, where the party doesn't stop until dawn.

Isla Verde

The hotels are where it's at here:

  1. Destination: The Water & Beach Club. For dinner, try Tangerine, a sexy restaurant with a naughty menu, then head upstairs to Wet, the hotel's awesome open-air rooftop lounge.
  2. Destination: El San Juan Hotel & Casino. Start with dinner at the excellent Italian La Piccola Fontana, and then migrate to the best casino in San Juan. Also at the hotel is one of the city's best clubs in Club Brava.

Miramar and Puerta de Tierra

  1. For fine dining in a lovely setting, check out Delirio or Chayote, in Miramar. Both are the restaurants of local celebrity chef Alfredo Ayala.
  2. From either restaurant, you're just a short ride away from the stylish N Lounge at the Hotel Normandie.

Ocean Park and Santurce

  • Dinner at the eclectic and excellent Pamela's is a must for Ocean Park denizens.
  • If it's the weekend, the place to be after dinner is La Placita in Santurce, an open-air block party where the locals gather for cheap drinks and a festive atmosphere. You can also check out Dunabars in Ocean Park, where live bands and a laid-back vibe will welcome you.
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05 of 08

Day 4: Excursion to Two Landmark Puerto Rico Attractions

Camuy Caves
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You have an option today of renting a car for the remainder of your trip or taking a guided tour to two of Puerto Rico attractions that are not only unique but in their own way, wondrous. If you want someone else to drive, call ahead and reserve a tour to the Arecibo Telescope and the Camuy Caves.

There are several tour companies that offer this package. Try Countryside Tours. Several hotels also offer the tour, so you might want to check with the front desk before making a call.

Of course, you can also opt to drive yourself. Most of the major car rental companies are represented on the island. The observatory is about 1.5 hours west of San Juan. It's mostly a straight shot on Route 22 until you reach the town of Arecibo. Then head south on Route 10 for about 20 miles and then follow the signs to the observatory. From here, take Route 129 southwest for roughly 12 miles to the entrance of the Camuy Caves.

So, why are you making this trip? Simply put, you're visiting two sites that are unique in the world. The Arecibo Telescope is the world's largest radio telescope, a remarkable feat of engineering, and the site of the climactic last scene in the Bond movie "GoldenEye" (for all the 007 fans).

The Camuy Caves are among the largest subterranean cave systems in the world, and the only one of its size to boast an underground river. Visitors travel in open-air trolleys and then take a 45-minute walk through the caves, admiring the stalactites, stalagmites, and natural vegetation that flourishes in the system.

This is an all-day trip. Fortunately, you'll be rewarded in the evening with a culinary excursion into Puerto Rican fine dining. After a rest in your hotel, head to Ajili Mójili and enjoy some of the best local cuisine on the island.

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06 of 08

Day 5: Visiting El Yunque

High angle view of El Yunque Rainforest from the Yokahu Tower, El Yunque, Puerto Rico
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If you didn't rent a car yesterday, you'll definitely need it today, because it's the best way to visit Puerto Rico's natural treasure and cultural icon: El Yunque National Forest.

Rather than stop for lunch, take a picnic lunch that you can enjoy deep in the rainforest after a good hike. Fortunately, on the way to El Yunque along Route 3, you'll find one of Puerto Rico's better panaderías, or bakeries (but really, they're much more than just bakeries). Panadería Don Nico serves up a mean menu of sandwiches and local pastries...just what you need for your trip.

After the rainforest, continue along Route 3, heading east, and look out for signs for Luquillo Beach. A pleasant, beautifully kept and fully serviced public beach, Luquillo is wildly popular with Puerto Ricans, and it will make for a complete change from the rainforest.

For dinner, drive back along Route 3 until you find a string of roadside eateries. There are the famous kiosks of Luquillo, home to dozens of small shacks and tiny restaurants that serve up a blend of local specialties, finger foods, greasy snacks, and cheap drinks. It's a complete departure from yesterday's fine restaurant. The kiosks are rustic Puerto Rico at its best.

After dinner, most people will want to head home. The truly intrepid, however, might want to head east, to Fajardo. Call ahead at Yokahú Kayak Trips (787-604-7375), who will take you out into Fajardo's biobay where you can take a glow-in-the-dark nighttime swim. It's an eerie but fantastic experience if you're up for a late night out.

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07 of 08

Day 6: Choose Your Adventure in Puerto Rico (Or Lack Thereof)

Silhouette of divers and angelfish
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On your last full day, you might be raring to kick your vacation up a notch, or you might be ready to relax and take it easy. For the former, try the following three options:

  1. Aventura Tierra Adentro: This tour company is designed to feed your adrenaline. With canyoning, rappelling, free-jumping, caving, and a host of other dangerous-sounding activities on its menu, it's guaranteed to end your Puerto Rico trip on an exhilarating note.
  2. Sailing & Snorkeling: Fajardo is the sailing capital of Puerto Rico, and you're much better off by driving to the eastern coast and hopping aboard the Erin Go Bragh for a day sail to one of the many islets around the mainland.
  3. Diving: If you want to dive (Puerto Rico has excellent dive sites), you'll want to switch this day's activities with Day 5, to give you an extra day until your flight out. You'll also want to contact Ocean Sports in Isla Verde, who will be happy to introduce you to Puerto Rico's underwater kingdom.

However, if you want to take it easy you might want to check Day 3's itinerary and follow one of the activities you missed out on. There's always shopping, the beach, the casino, and the old city to keep you entertained. You can also take a leisurely day trip out to Piñones, a nearby beachfront community that makes for a pleasant rustic retreat.

If you're sticking around the city, you must visit La Casita Blanca for lunch. Tucked away in Santurce, this small, unpretentious spot is Puerto Rican home-cooking at its best, as its legions of fans will readily attest.

For dinner, you might want to veer away from the heavy local diet, especially if you ate at La Casita Blanca. If so, try one of these interesting international choices. But if you've saved up for a special last meal, head to the Puerto Rican Museum of Art and Pikayo where the line between food and art get happily blurred.

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08 of 08

Day 7: Leaving Puerto Rico

Straw hats for sale, Old San Juan, San Juan, Puerto Rico, December 2009
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On your last day, relax and enjoy what's left of your vacation in San Juan. The beach might call, you may have souvenirs to buy, or you may just want a last look at Viejo San Juan. Day 7 is not about saying "goodbye," but rather, "see you soon."