Six Perfect Days in Puerto Rico: An itinerary for Vieques, Old San Juan & Condado Beach

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Vieques Beach Float - Kelsey Social
Bahia La Chiva, Vieques

I'm not sure how Puerto Rico was off my radar for so long. After I saw a few pictures of both the mountains and the beaches, I was set on going. I had hoped to celebrate my 28th birthday there, but plans fell through and the trip got pushed back to over July 4th weekend. Because I work full-time, I always try to travel during U.S. holidays in order to save my vacation days.

A few months after my visit, Puerto Rico was hit by Hurricane Maria causing destruction across the island. Now, cruise ports, airports, and hotels have reopened and tourism officials are encouraging travelers to visit. Staying at their hotels, eating at the restaurants, and buying from local businesses is a great way to support Puerto Rico... and I highly recommend it!

Below is my six-day itinerary (including two travel days) outlining how I spent my vacation in Puerto Rico. The islands are small but have a lot to explore from pristine beaches to tropical rainforests and the central mountains. Six days was a nice amount of time for a quick visit, but of course, I'd like to return to explore more.

Condado Beach Pina Colada - Kelsey Social
Condado Beach, San Jose, Puerto Rico
Day 1: Fly to San Juan, Puerto Rico

Left Washington, D.C. in the morning and arrived in San Juan at noon. From D.C. to paradise in a quick 4-hour flight? Yes, please! We checked into the beautiful beachfront La Concha Renaissance San Juan Resort and then went to grab some Mofongo (a Puerto Rican dish with mashed plantains) and daiquiris across the street at Orozco's. They have happy hour prices all day and the $3 rum punch will get you a quick little buzz if that's what you're after!

Condado beach outside the hotel is gorgeous - white sand with clear water. We drank Medalla beers in the sand until the sun went down and then hopped in one of the two infinity pools overlooking the beach.

El Yunque Coconut - ATV Tour - Puerto Rico
El Yunque, Puerto Rico
Day 2: El Yunque + El Condado, San Juan

Woke up early to catch a 7 AM shuttle to the rainforest. We arranged our trip with Carabali to pick us up at the hotel and bring us to El Yunque National Rainforest for a 2-hour ATV ride. On the tour, we stopped to swim in the Mameyes River and then took another stop to drink fresh coconut water.

For dinner back in San Juan, we found the best spot: Vagon. It's a Mexican food truck with a fun outdoor patio. It's a no frills place with fast service and good food. Get the nachos! I'll definitely be back next time I'm in San Juan. 

Vieques Air Link - Travel Blogger - Kelsey Social
Antonio Rivera Rodríguez Airport on Vieques Island
Day 3: Vieques

In the morning, we flew to Vieques Island from San Juan Isla Grande Airport with Vieques Air Link. Once in Vieques, we picked up our rental jeep from Island Car Rental and drove across the island to the town of Esperanza to check into Malecon House. They helped us load our car with beach gear and we hit the road to find good snorkeling at Blue Beach. We caught a great sunset at Punta Arenas (Green Beach) before heading back to town for dinner at one of the many beach bars along Calle Flamboyan.

[Pro tip: Order this giant inflatable flamingo that packs easily in your luggage. We had no trouble inflating it on the beach and I loved floating on it in the water!]

Sunset on Vieques - Punta Area - Kelsey Social
Punta Arenas, Vieques Island
Day 4: Vieques

After a filling breakfast at the hotel, we ordered picnic lunches from Bananas and set out for a full day of off-roading to find the best beaches. And we weren't disappointed. Playuela, Caracas, Pata Prieta, Bahia La Chiva, and La Escondida were my favorites. That evening, we ordered delicious fish tacos from Lizzy's Lunchbox, a small food truck on the beach.

Vieques Secret Beach - Kelsey Social
Bahia La Chiva, Vieques Island
Day 5: Vieques + Old San Juan

We had our last delicious breakfast at Malecon House, checked out, and returned the jeep. The rental company drove us to the ferry port to catch our boat to Fajardo. Once in Fajardo, we had prearranged a ride to our next hotel: Courtyard San Juan Miramar. I have a Marriott Credit Card and used my yearly free night certificate for our stay. We chose this hotel to be close to Old San Juan and the airport.

For the afternoon, we wandered around Old San Juan to see the colorful buildings, El Morro, El Castillo de San Cristobal, and La Fortaleza. I wanted more mofongo so we found El Jibarito for dinner.

 San Felipe del Morro Fortress, Old San Juan, Puerto Rico
San Felipe del Morro Fortress, Old San Juan, Puerto Rico
Day 6: Fly home

Before flying home from Luis Munoz Airport, we stopped in La Pradera for breakfast. The Mallorca sandwiches on sweet bread were delicious and the coffee was good - I ordered two cups of their café con leche.


I hope this itinerary helps with your planning or inspires you to book your trip. I plan to return to Puerto Rico in the next years and would love to hear any recommendations for my next visit!


The Perfect Puerto Rico Itinerary: El Yunque, Vieques, Condado & Old San Juan - Kelsey Social

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