JetSet: Puerto Rico

With winter weather setting in, we decided to head somewhere with sun, sand and surf. While all-inclusives are always fun, relaxing and easy, we wanted to try something different, so we booked a flight, hotel and car and jetted off to Puerto Rico.

If you’re like us, you don’t actually know much about this tiny Caribbean island other than that it’s where you flew into for your family cruise, so here’s a quick lesson: Puerto Rico is an “unincorporated territory of the United States“, meaning you can use American money and almost everyone speaks fluent English. It’s located in the northeastern Caribbean, east of the Dominican Republic, and the best part? You can drive from one end of the island to the other in only a few hours. 

Here are some of our favourite island hotels, restaurants and activities:

Old San Juan.

Where to stay:

We suggest starting your trip in the capital, San Juan. Old San Juan is absolutely breathtaking with colourful houses and store fronts lining the cobblestone streets. While there is no shortage of huge hotel chains, we’d suggest trying something a little different. Villa Herencia is a small, eclectic boutique hotel located half a block from the ocean in Old San Juan. If you’re looking to splurge, we suggest checking out El Convento next door, which is a converted convent complete with a rooftop pool and a beautiful courtyard. 

El Convento.

After spending a night in Old San Juan head over to La Concha Resort in Condado (also a sister hotel of El Convento). Condado is like the Miami of Puerto Rico, with luxurious hotels and restaurants lining the beach. If you’re looking for fun nightlife and a beachfront hotel, this is your place. 

Last but definitely not least, we suggest driving a couple hours west, where you’ll hit Isabela. There you’ll find Villa Montana, an idyllic little beach resort on the ocean. With old plantation-style villas and a restaurant that rivals any five-star here, Villa Montana is definitely worth checking out – we could have eaten their caramelized banana pancakes for days!

Eclipse Restaurant at Villa Montana.

Where to eat:

One of our favourite little roadside restaurants (just up the street from Villa Montana) was Ola Lola’s Garden Bar. Owned by a lovely American couple, the delicious food (insane burgers) is cooked right in the couple’s home next door. A popular “gringo” (foreigner) hang-out, the lights and open-air concept make for a pretty dreamy setting. 

Ola Lola’s Garden Bar. 
Just west of Isabela is Rincon, a haven for surfers and tourists. If you’re looking for a meal with a view, head no further. We tried Tamboo Tavern, one of many beachfront restaurants in this great little town and loved their “tostones” – essentially, plantain fries (very popular in Puerto Rico). 
Tamboo Tavern.
Back in San Juan, head to La Mallorca for delicious cafe con leche and the famous “mallorca con jamon y queso”, a pressed sandwich dusted with powdered sugar. For dinner, check out one of San Juan’s famous “OOF!” restaurants including Aguaviva,The Parrot Club, Dragon Fly, Toro Salao or Pina Colada, all great options for dinner and drinks. 
What to do:

Whether you’re into surfing, snorkeling or suntanning, Puerto Rico has something for everyone; they even have a world-famous rainforest called El Yunque, right outside of San Juan. 

El Yunque.
For great beaches and snorkeling outside of San Juan, we suggest heading to Aguadilla, Isabela or Rincon on the west coast, or heading east for a day trip to the little island of Culebra (Spanish Virgin Islands), just off of Puerto Rico, where you will find white sand and turquoise water. 

While you can definitely catch some waves in San Juan, most people head west to Aguadilla and Rincon for great surf. Adventurers will love some of the off-the-beaten-track surf beaches found there, especially because they never seem to be too crowded.

If you’ve never considered Puerto Rico for a trip, we hope we’ve highlighted some reasons you should check it out. It’s the perfect, easy way to vacation in the Caribbean.