Long weekend in Puerto Rico!

Long weekend in Puerto Rico!

Yarimar Figueroa
This itinerary will give you a glimpse of what you can do in Puerto Rico on a short 3-4 night trip. Learn about the best time to travel, activities, and more! Fall in love with the culture and experiece the real "Isla del Encanto". We will cover north to east highlights. Composed by a real full-time concierge on the island!
Updated ago
Save
Share

Best time to travel:

Puerto Rico is warm all year round. However, there is a hurricane season to consider. The best time to travel is between November - May. My personal favorite months of the year are March and April. That said, you can travel during low season if you are looking for prices to drop on flights and hotels (particularly September-October).  However, keep an open mind that it is a tropical island located in an area of the Caribbean that is very propense to tropical storms and hurricanes between June-October. If there is not an announced storm during your stay those months, passing rain is not uncommon. During this, or any part of the year, it is best not to rely solely on the general weather pronostics to go on with your plans. There are many different parts of the island and while it may be raining in San Juan, Rio Grande might not be raining. Go with the flow!

Getting Around:

Choosing where to stay:

Old San Juan: The capital city is a beautiful 5-century arquitecture town. It's buildings are colorful and the structure is small and easy enough to walk through. Staying here could work for a night or two. There is no beach as the town is surrounded by a fortress and a bay.

Notable hotels to stay in Old San Juan:

Hotel El Convento
@yarimarfigueroa
Befitting its origins as a Carmelite convent more than 370 years ago, it'a a splendid Puerto Rico luxury hotel with loving restoration of Spanish Colonial architecture and design. Walk in the footsteps of world leaders and international celebrities at this world-class Old San Juan luxury hotel.
Add to
Details
Hotel Palacio Provincial
@yarimarfigueroa
The beautiful adults-only boutique hotel has a more modern take while still keeping the charm of staying in the old town. Even if you don't stay here, its rooftop Atelier is certainly worth the visit.
Add to
Details
The Gallery Inn
@yarimarfigueroa
Their ruins-turned-pool transports you to another era. A visit to their jazz lounge "The Cannon Club" is certainly a plus.
Add to
Details

Condado: Close to Old San Juan, this area has great resorts and airbnb's. Great for biking, kayaking and paddle boarding in the lagoon. The beach of Condado is not particulary a favorite amongst locals since it can be a dangerous one with strong rip currents. Best to only lounge under the sun and walk on the beach, but swim in your hotel pool.

Notable hotels in Condado:

O:live Boutique Hotel
@yarimarfigueroa
Beautiful accomodations, rooftop bar & pool will give you stunning views to the Condado Lagoon. For special occasions, check out their Olive Experiences on the webpage and plan ahead!.
Add to
Details
La Concha Renaissance San Juan Resort
@yarimarfigueroa
Variety of pools, direct access to the beach, family friendly & bikes to borrow.
Add to
Details
San Juan Marriott Resort & Stellaris Casino
@yarimarfigueroa
Add to
Details

Isla verde: Best area if you want to be by the beach. Conveniently located near the airport and reasonable rides into Old San Juan or to the east coast.

Notable hotels:

The Royal Sonesta San Juan
@yarimarfigueroa
Add to
Details
Courtyard by Marriott Isla Verde Beach Resort
@yarimarfigueroa
8/2024: Currently being renovated. This is a Marriott with a great location and a oceanfront restaurant.
Add to
Details
Aire de O:live
@yarimarfigueroa
Newly opened, beautiful bohemian bourtique hotel right in front of the beach! The only hotel in Isla Verde with a Rooftop restaurant.
Add to
Details

Day 1: Old San Juan & Santurce

Old San Juan is the capital of Puerto Rico, enriched with over 500 years of history. The city is best done on foot, since the streets are very narrow and made of cobblestones. Old Town can be done in 3-4 hours respectively. Be very mindful of the uphill/downhill streets, it is best to start in the north of the city and make your way down. When visiting Museums or National Park Landmarks such as Castillo San Felipe del Morro or San Cristobal, check the opening hours beforehand.  You can explore doing a walking tour or self-guided tour using the recommendations below. Note that, walking tour guides don't go inside the forts with you, but you can explore them before or after, purchasing the ticket at the entrance.

Plaza Colón
@yarimarfigueroa
Uber or Taxi drop off location to start!
Add to
Details
Castillo San Cristóbal
@yarimarfigueroa
Click to find audioguide link!
Add to
Details
Castillo San Felipe del Morro
@yarimarfigueroa
Click to find audioguide link!
Add to
Details
Casa Blanca
@yarimarfigueroa
Originally built in 1521 as the main residence for Puerto Rico's first governor, Juan Ponce de León, this landmark is Old San Juan's oldest residence. Nowadays, the residence serves as a museum housing 16th and 17th-century artifacts.
Add to
Details
Cuartel de Ballajá
@yarimarfigueroa
The Museo de las Américas is located inside the historic Cuartel de Ballajá, which in Spanish colonial times was used as the military's barracks.
Add to
Details
Catedral Basilica Menor de San Juan Bautista
@yarimarfigueroa
Add to
Details
La Fortaleza
@yarimarfigueroa
Add to
Details
Capilla del Santo Cristo de la Salud
@yarimarfigueroa
Add to
Details
Parque de las Palomas
@yarimarfigueroa
Add to
Details
Calle de la Fortaleza
@yarimarfigueroa
Great for shops!
Add to
Details
Paseo de la Princesa
@yarimarfigueroa
Add to
Details
Puerta de San Juan
@yarimarfigueroa
Add to
Details

Extras:

Plaza de Armas
@yarimarfigueroa
Add to
Details
Sign ¡Boricua!
@yarimarfigueroa
Add to
Details

Restaurants / Bars:

Deaverdura
@yarimarfigueroa
No RSVP needed
Add to
Details
El Jibarito
@yarimarfigueroa
No RSVP needed
Add to
Details
Cafe Berlin
@yarimarfigueroa
No RSVP needed, Vegan/Vegatarian friendly
Add to
Details
La Factoría
@yarimarfigueroa
Rated one of the world's top 50 best bars!
Add to
Details
La Taberna Lúpulo
@yarimarfigueroa
Add to
Details
Scryer Rum Barrelhouse & Rooftop
@yarimarfigueroa
This place also offers a rum tour!
Add to
Details

Santurce offers a window into a colorful, free-spirited neighborhood that invites you to immerse yourself in the artistic heartbeat of the island. Located south of Condado, Santurce is enjoying a “renaissance”, including an influx of new restaurants, shops, galleries, museums, and more. Make sure to pause and admire the abundance of bright murals and street art as you stroll through this barrio. I would recommend getting into this late afternoon to nighttime to appreciate the murals, or depending on your schedule and interests you may just want to dine and take advantage of the vibrant nightlife. You don't need a tour for Santurce, but if you are an art enthusiast you and have extra time, you can consider one!

La Placita de Santurce
@yarimarfigueroa
Add to
Details
Esquina El Watusi
@yarimarfigueroa
Add to
Details
La Casita Blanca
@yarimarfigueroa
Add to
Details
Museo de Arte de Puerto Rico
@yarimarfigueroa
Add to
Details
Add to
Details
Museo de Arte Contemporáneo de Puerto Rico
@yarimarfigueroa
Add to
Details
La Terraza de Bonanza
@yarimarfigueroa
Add to
Details

Day 2: Piñones & Loiza

Piñones is a picturesque ocean drive from Carolina to Loíza where you can enjoy local dining experiences and practice what Puerto Ricans call chinchorreo. Sample delicious specialties while you hop from food stand to food stand and go back and forth to the beach. What makes Loíza distinct from any other part of Puerto Rico is the rich African heritage that permeates its identity. A fun way to explore these areas is doing a Can-Am tour, suggestion below, or self guided. Don't miss out on taking a Bomba class!

Mi Casita Seafood
@yarimarfigueroa
Excellent seafood dishes!
Add to
Details
Kiosko El Boricua
@yarimarfigueroa
THE BEST ALCAPURRIAS YOU WILL EVER FIND!
Add to
Details
Terraplen La Posita de Piñones
@yarimarfigueroa
Add to
Details
Vacia Talega
@yarimarfigueroa
Add to
Details
Taller de Bomba N"Zambi
@yarimarfigueroa
Coordinate with Sheila Osorio to participate in her native Bomba dance class, on the beach! An experience you will not soon forget.
Add to
Details
Estudio de Arte Samuel Lind
@yarimarfigueroa
Local world-renouned artist's house and studio. Mr. Lind is a great host and very passionate about the Bomba, which inspired most of his art.
Add to
Details

Extra stop on the way back to San Juan:

Parque Histórico Cueva María de la Cruz
@yarimarfigueroa
Add to
Details

Day 3: El Yunque National Rainforest & Luquillo 

El Yunque is the only tropical rainforest in the U.S. National Forest System but it is also a sacred place in Puerto Rican culture. Today, this national treasure is an excellent destination if you want to immerse yourself in nature. From bathing in natural pools beneath waterfalls to taking in the gorgeous scenery from its many hiking trails, you can take a tour of the Rainforest with transport or check it out self-guided with your rented vehicle. Which places you visit will be reliant on the park's status and your own personal stamina. Make sure to check the El Yunque U.S. Forest website for the latest info about weather, park closures, and safety protocols. Allow 3-4 hours to explore the basics, or up to 6 hours if you plan on doing stronger trails. No reservations are required, however, there will be a limit of 200 cars at a time so if it's busy you may need to wait. Would recommend arriving early morning.

El Yunque National Forest
@yarimarfigueroa
Add to
Details

After the Rainforest, a stop at the Luquillo Beach & Kiosks is a must! Specially of you are looking to have a good meal.

Kioskos de Luquillo
@yarimarfigueroa
Add to
Details
Terruño
@yarimarfigueroa
This is kiosko #20
Add to
Details

Extras: You can consider doing a ATV, Horseback ride or Zipline at one of the below locations. Remember to book in advance!

Carabalí Rainforest Park
@yarimarfigueroa
Add to
Details
Junglequi Zipline Park
@yarimarfigueroa
Add to
Details

Day 4: Island hop & Biobay

After your caribbean island trip, depending on your drive or stamina to experience another unique adventure, you can head to a tour of the Laguna Grande Bioluminescent Bay in the same town of Fajardo. This is one of three in Puerto Rico, and one of five of its kind in the world. In order to experience it, there's a few factors to consider: previous kayaking experience & moon phase. The bay's luminiscence is not guaranteed, being that it is a natural phenomenon. The chances to see it's glow are higher on a new moon, and lowest on a full moon. The bay is protected, therefore a guided tour is required. There are many kayaking companies that offer it, and only one boat experience. Below are some recommendations. TIP: You can switch this day up with Day #2 or other, if it fits best in your schedule. Book tickets or tours in advance! There are many restaurants in Fajardo to grab a meal between activities.

La Cueva del Mar
@yarimarfigueroa
Add to
Details
Rincon Del Faro
@yarimarfigueroa
Add to
Details
Las Tortugas Adventures, Inc.
@yarimarfigueroa
Add to
Details
Bio Island BioBay in boat
@yarimarfigueroa
Add to
Details
Pure Adventure Bio Bay Location
@yarimarfigueroa
Add to
Details

Additional thoughts & Tips:

You can stay in one area of San Juan throughout the entire weekend. However, it is not uncommon to switch areas for half the trip in order to be closer to the east. If this is an option for you, below are some additional hotel recommendations out east. 

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
@yarimarfigueroa
Add to
Details
Fairfield by Marriott Luquillo Beach
@yarimarfigueroa
Add to
Details
Casa Coral Luquillo
@yarimarfigueroa
Add to
Details
Fajardo Inn
@yarimarfigueroa
Add to
Details

Bag essentials: in a tropical island it is most convenient to carry sunscreen, bug spray, a rainjacket or umbrella. Don't forget to always have your water bottle handy and some cash - even though there will likely be card systems in most places, Puerto Rico suffers power outages every now and then. 

Enjoy!

Feel free to mix up the date orders of your itinerary to how best suits you. Enjoy la "Isla del Encanto", go "Despacito", and have a good time!

~"Puerto Rico esta bien Cabrón!."

-Bad Bunny

* * *
ABOUT THE AUTHOR
Yarimar Figueroa
A warm welcome to all fellow travelers! My name is Yari and I am a proud Puertorrican female who loves to travel. I am a full time concierge at several different hotels in my island. My goal here is to help others discover my island's enchantments like the locals. I have traveled to more than 20 countries, but to me there is no place like home. While I may share a few other itineraries, my island is my expertise and I am eager to share my knowledge with you all.
Send A Tip
Support Yarimar Figueroa’s work.
Select your tip amount
$5
$10
$20
$50
Or type in other amount
Explore related destinations
Powered by Thatch
The home for unique & authentic travel
Powered by Thatch: Where great trips are made.
© Yarimar Figueroa 2024 Help Privacy Terms Copyright Become a Seller Seller Academy About Careers Blog Explore Places