Puerto Rico wasn’t even on my radar until I met my friend Jessica of Dining Traveler (thank you for all of the local tips!) over a year ago. I found myself following a month long adventure she was on all over the island via social media and knew I soon had to explore it first-hand.

An island so close and so easy to access, and yet a world away from the busy and sprawling U.S. cities many of us are accustomed to, this place has real charm. Upon commencement of my first visit to the island, I left with a nice lay of the land. From San Juan to the Southwestern side receiving a beautiful introduction to the U.S. territory.

From the white sand beaches of the south side to Old San Juan, here are some of my favorite experiences that I would recommend if you’re heading there for the first time too.




Vibrant hues of lime green, bright blue and pinks adorn the sides of the blue glazed cobbled side-streets. With this framing, it’s impossible to prevent yourself from wanting to capture every detail of the city’s atmosphere in your photos. The National Parks Service fort, Castillo San Cristobal, is loaded with views from every angle so that you can capture the best of the city and take home your most beautiful memories.

Views of Old San Juan


If you’re looking to stay at a beachfront luxury hotel in San Juan, the newly renovated and upscale Vanderbilt Hotel is the spot. A modern contrast to the unique historical heritage of the old city, the Vanderbilt nails it with details. A glass of champagne during check-in, turndown service, and even a personalized wake-up call make you realize how necessary some luxuries can be. Not to mention, each room also has an abundance of the most conveniently located outlets (all with USB plugs!) and a free minibar, in case you worked up an appetite in one of the four hotel pools - a traveler’s dream!

The Vanderbilt Condado, Best Hotels Condado Puerto Rico, Luxury Hotels Condado Puerto Rico

There are many options for dinner in the Condado. I loved my experience at Cocina Abierta. They also have a brand new cooking school tucked away down the hall, just beyond the kitchen. Madelines and 1919 are two others restaurants in the Condado worth dining at - they even source their greens from a local aquaponic farm.

Before you leave San Juan, make sure to check ‘a stroll down Calle Loiza’ off your bucket list. With vintage boutiques like Len.T.Juela (I discovered Lattuga Organics made-in-Puerto Rico coffee scrub here-- and I’m obsessed!), and stops for sweets (order an assortment macarons and fresh squeezed lemonade at Double Cake cafe), you’ll stay entertained - and full - for hours.


To the east, Humacao is only a short distance from the capital and is home to some of the island’s best beaches. We spent an entire week staying in the neighborhood of Punta Santiago in Humacao, just across the way from Monkey Island.

Luquillo Beach in Puerto Rico

If you’re in this area, it really doesn’t get more local than a nice dinner at Kiosko El Limon. Another lively local family friendly dining area is just up the road 5 minutes alongside Playa La Fanduca.

The El Yunque National Forest is a great day trip from Humacao. The tropical rainforest provides an opportunity for all ages to explore short hikes, massive waterfalls, and vast views atop the Yokahu Tower.

El Yunque National Forest in Puerto Rico - Waterfall


On the west coast, you’ll find the laid back surf town of Rincon. For a locally-owned, family friendly hotel, check in at the Rincon Beach Resort. It is in an ideal location along the waterfront, with a long stretch of sand to walk at sunset or sunrise.

Rincon Hotel in Rincon, Puerto Rico

If surfing isn’t your forte, Rincon is also a hub for other watersports including sailing, kayaking and diving. The best part is that when you need a break from the water, you can spend some time exploring the Camuy Cave Park (which is home to the third largest cave complex in the world!), the tropical trails around the beach via horseback, or the Lighthouse Park.


If you’re looking for white sand and crystal clear water, drive 45 minutes down the coast and you’ll find yourself at Cabo Rojo. Jump into Playa Buye for a turquoise water swim. Per Jessica’s recommendations, stop at Annies for a Sangria. A glass (or two) of the fruity island drink and a side of fresh conch makes for one tasty afternoon treat.

But if white sand beaches just aren’t your thing, no need to worry. Cabo Rojo is also has pops of pink for those who like a little more color in their world. And don’t forget a quick look out over the salt marshes - with a bit of a different landscaping than the rest of island, it’s an interesting escape from the pristine Caribbean beaches. For an all-inclusive, panoramic view, just head over to the Faro Los Morillos lighthouse, complete with classic Spanish architecture and beautiful scenic outlooks.

Playa Buye at Sunset - image by Jessica van Dop DeJesus of Dining Traveler 


When traveling back to San Juan from Rincon, drive the southern route and head up the center if you have the time. The nature route is worth losing sight of the ocean for a bit, and with a sprawling sunflower field along the way, this route offers a great rest-stop to stretch those legs and snap a few Instagram photos. This path is great for those who seek a more well rounded perspective of the different areas of the island.

Don’t be fooled over its label as a U.S. territory - with Puerto Rico’s rich Spanish heritage and Caribbean environment, it’s a completely foreign experience compared to the continental U.S. The island is an absolute must on the bucket list as you start to plan all of your 2017 adventures.

What side of Puerto Rico would you like to explore?