Beaches and Culture in the Caribbean: Puerto Rico

After arriving at San Juan airport, grab a rental car if you are more of an explorer type (there's lots to see on this island!), or breeze through to your pre-arranged transport through the hotel.

The O:LV Fifty Five Hotel is just a short drive away, set on the edge of Old San Juan in an area called Condado Beach which has a very similar vibe to Miami. The boutique hotel is chic and luxurious, and a perfectly located base for your adventures.

If you have the energy, head out on the Condado Lagoon on a kayak or paddle board arranged through the hotel, or relax in the stunning rooftop pool. The bar here, Arya, is a fantastic place to watch the sunset on your first night in Caribbean paradise.

After a sunset cocktail, head to a relaxing dinner at SOCIAL, located in the Condado Beach Hotel, a short walking distance away with a gorgeous ocean view.

Or if you are looking for something more lively, hop in a quick Uber over to Santaella, a buzzy hotspot serving modern Puerto Rican fare in a sexy setting.

One theme you are going to quickly notice in Puerto Rico is a heavy dose of fried food, so balance that with some of the fresh offerings here, including the excellent Pinchos de Atún. Make sure you have a reservation in advance.

For an evening cocktail before or after dinner, head across the street to the adorable JungleBird bar with strong tiki bar vibes. Grab a seat in the backyard patio and choose from one of many gorgeous drinks.

Now that you've settled in, you're going to want to spend a day exploring colorful Old San Juan. Store your luggage and head into town to enjoy a fantastic brunch at tiny La Madre, serving delicious Mexican fare (don't forget the margaritas!).

From here it's an easy stroll to the northwestern tip of town where you can visit the stunning Castillo San Felipe del Morro, a citadel built by the Spanish between the 16th and 18th centuries. You are free to roam the grounds including a gorgeous oceanfront walkway with views of the crystal blue sea. Your ticket also gives you access to Castillo San Cristóbal to the east.

Afterward, spend some time exploring the narrow streets of town, visiting shops and art galleries.

Once you have your fill, grab your bags because it's time to head to the beach. Dorado Beach, a Ritz-Carlton Reserve, and St. Regis Bahia Beach are both excellent options for luxurious relaxation. If you choose the St. Regis, you can close out your evening with dinner in the sophisticated Paros dining room, serving excellent Greek cuisine. Request a table by the window for ocean views.

If you want some adventure with your beach, the St. Regis is closer to El Yunque National Forest, a mountainous rainforest where you can hike and play in waterfalls. Be sure to book a reservation in advance to gain full access to the park.

In nearby Loquillo Beach, you can visit one of the many casual dining kiosks including Terruño. This is your opportunity to try mofongo, a tasty traditional Puerto Rican dish featuring mashed green plantains.

Back at the hotel, there are plenty of options for entertainment, including the Boat House where you can paddle board, fish, or jump on the inflatable water playground. Definitely spend plenty of time by the expansive pool, or on the beach, walking to the east (the west direction is under construction).

Later, have the hotel arrange a golf cart to take you to the nearby Beach Club to enjoy a casual dinner outside on the oceanfront patio.

Rest up and enjoy, departing the beach the next morning at your leisure.