5 Day Puerto Rico Exploration

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Advisor - Kimberly Sessions
Curated By

Kimberly Sessions

  • Puerto Rico

  • Active Travel

  • Adventure Travel

  • Outdoors

  • Entertainment

  • Hiking

Curator’s statement

Puerto Rico is the perfect destination for a couple or family who wants a vacation where you can see it all. It is a small Island that is cheap to fly to and easy to navigate. You can spend time on the beach, explore the rainforest, celebrate culture in the main city and even kayak in the #1 bioluminescent bay in the world. It is a beautiful island, with kind people, great music, delicious food and even better drinks. Perfect for couples, families or a weekend with friends, you can have it all on your trip to Puerto Rico.

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Day 1: Arrive in San Juan

woman poses on lookout over ocean

Head out on an early flight from your hometown and arrive in the San Juan Airport. Pick up a rental car and head into Old San Juan. I highly recommend staying specifically somewhere in Old San Juan, so you are walking distance from all the attractions. Park your car in the lot, drop your bags and grab a coffee and quesito at Cafe Cuatro Sombras. Quesitos are traditional Puerto Rican Pastries, usually with cream cheese and guava inside. Delicious!

Walk to Castillo San Fellipe el Morro. If you buy one ticket, you can also use it at Castillo de San Cristobal within 24 hours. Explore all levels of the fort and learn about the history. If you have a national park passport you can get it stamped here.

Walk to La Fortaleza, either through the town or on the Paseo de Morro and get a guided tour of the governor's house. Call 4-7 days before your trip to schedule your tour. Grab a fresh fruit popsicle nearby as Señor Paleta. This is one of my favorite things I ate on the whole trip!

Dinner: Head back to your hotel to change and head out for a night on the town. Get reservations at Marmalade, an upscale restaurant with a tasting menu, speciality cocktails and a wine pairing list awarded by wine spectator for 11 years. Then get ready to dance as you head to La Factoria to drink and dance the night away with locals and tourists alike.

Day 2: Fort to rainforest adventure

5 Day Puerto Rico Exploration - Day 2: Fort to rainforest adventure

Have breakfast at your hotel, a nearby coffee shop, or at Chocobar Cortes, a Puerto Rican restaurant that focuses on chocolate!

Head to Castillo de San Cristobal to learn more about this historic fort and the history of Puerto Rico. Bring your national park passport and a hat, because it can get hot and the fort is mostly outside. Remember to go within 24 hours of buying your ticket.

You can take time here to explore any parts of town that you have not seen in the past two days. There are so many beautiful streets with brightly colored houses that it is fun to just explore! Grab another popsicle if you want!

Then check out of your hotel, hop in your car and head out to El Yunque Rainforest. On the way there are many food stands on the road and by the beaches that you can stop at and try traditional foods. (Ex. Alcapurrias, Bacalaitos, Sorullitos)

Check into your rainforest stay. Have dinner there or nearby. I stayed at Yuquiyu rainforest and ate dinner at their restaurant, which was the best meal I had during my entire trip. It was a 4 course meal made with local ingredients and authentic family recipes and a cocktail. The chef came out and spoke with our table and the table was outside overlooking the trees. It was truly stunning.

Day 3: Rainforest adventure with montaña explora

Waterfall

Today was made for adventure! I spent the day with a company called Moñtana Explora, which gave me the best adventure experience I had ever had. Owned by Master Ricky, three incredibly experienced guides took my partner and I on a private tour of an adventure course through the rainforest. This included rock sliding, cliff jumping, climbing via ferratas hiking, swimming, traversing through water and so much more. I felt so safe the entire time and had a blast. They took pictures of videos of the entire experience. This was my favorite thing I did in all of Puerto Rico. The company will also tailor-make the adventure to however much time you want to spend and what you are comfortable doing. I can not recommend them enough! Make sure to pack snacks.

You will probably be exhausted at the end of the day, so grab something to bring back to your hotel or eat a quick meal.

Email montanaexplora@yahoo.com to learn more or message me and I can book directly for you.

Day 4: Surfing lesson and Luquillo Beach relaxation

Beach Day

Have breakfast in your hotel and get ready to head to the beach! Drive over to Luquillo beach and take a morning surfing lesson. I went with Surfing Puerto Rico and had such a fun time. I had never surfed before and I got up on my second try. Everyone in the group got up multiple times and most of us were beginners. I had a blast and had more then enough time in the water on my board. They provided snacks and water and a great guide. Super fun new experience! It is also a female-owned company, which I love to support.

Then drive just a few minutes over to the main area of Luquillo beach and spend the day relaxing and going in the water. I highly recommend eating at one of the food kiosks for lunch. Spend your day soaking in the sun!

Day 5: El Yunque and Vieques adventure

dusk on an island

Wake up early and head over to the El Yunque Rainforest visitor center. They have a great interactive exhibit and short film explaining the history of the rainforest and all the animals and plants that live there. Then drive over to the Ceiba Ferry Terminal. Make sure to BUY TICKETS IN ADVANCE ONLINE! They sell out quickly. You should arrive 45 minutes-1 hour early for your ferry. Take the ferry over to Vieques. Work with the hotel to have a pre arranged taxi pick you up at the terminal. It can get crazy out there. Check in to your hotel, go in the pool and relax if you have time.

Dinner: El Blok Hotel. Delicious food, super cool space and a beautiful view. The best part is it is directly across from where the shuttle picks you up for your tour.

Take a Bioluminescent Bay Kayaking Tour. I went with Blackbeard sports, which I had a great experience with. Puerto Rico has the brightest bioluminescent bay in the world. Vieques was named the brightest in the world in 2006. It was one of the most magical things I have ever done. It is difficult to describe how unique and special this place is.

On the way back from Vieques on the way to San Juan or while you are in El Yunque you have to stop and eat breakfast at Ekelekua. I stumbled upon it by accident and it was the best meal I had the entire time in Puerto Rico. I highly recommend the guava French Toast and the pulled pork Arepas. The local coffee of the day is also outstanding. 

P.S. On my last day while I was in San Juan there was a Piña Colada festival happening. My partner and I got to experience many different restaurants, meet locals and try all types of Piña Coladas. I always recommend checking to see what festivals or events are happening while you are on your trip. You never know what you may stumble upon.

Advisor - Kimberly Sessions

Travel Advisor

Kimberly Sessions

Get in touch with Kimberly

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Looking for more travel inspo? Check out Fora Travel Advisor Noah West's guide, Planning a Weekend Trip to San Juan, Puerto Rico.

This guide is part of our ongoing series on travel to Puerto Rico.