Rough Draft: 4 Day Itinerary for Puerto Rico

Rough Draft: 4 Day Itinerary for Puerto Rico

April 2021

Rough Draft Itinerary: Puerto Rico

Due to the COVID quarantine, I am creating rough draft, “off the shelf” travel itineraries for when travel resumes normal operations so we do not waste any time getting out and exploring!

Travel plans for 2021 seem more optimistic but still wildly unpredictable. Domestic travel still seems to be the only option for the near future but I am itching for an international spot as soon as it becomes available – oh how I miss Europe! In any matter, 2021 travel needs to be flexible. Despite my hesitance to commit to anything more than a few weeks away, the vaccination rate seems to be driving up domestic travel demand.

In keeping with my covid-friendly travel trends thus far – all outdoor activities, low covid case count, mask mandate, ease of travel – Puerto Rice came to mind. “Hey Kev, what do you think about Puerto Rico?” Umm, Yes!” Well then, that was easy! Puerto Rico has the advantage of outdoor activities and dining being the primary means of tourism as well as good weather all year round. The flight from the northeast area is an easy 4 hour non-stop flight – winner! Which is why I cultivated a long weekend, four day itinerary – this should make for an easy getaway.

Puerto Rico counts as domestic travel from the USA – domestic travel with an international feel! As of this post, the requirements to travel include arrival with proof of a negative COVID-19 molecular-based test within 72 hours and travel declaration form.

Visiting Puerto Rico is not the same all year round. Winter time is the best weather but also the most busiest season for tourists. The summer is very hot and humid, leading to the island’s rainy season and hurricane season continues into the fall, sometimes as late as November. into the fall is hurricane season. Springtime is actually the most ideal and is considered shoulder season – win win!

In terms of where to stay in Puerto Rico, the two most popular areas are Old San Juan and Condado. Condado has some awesome looking Airbnbs, is centrally located, home to some awesome beaches, shops, and restaurants, but I read it is most comparable to Miami which is generally not our style. I think we would stay in Old San Juan but the choice is yours!

What is there to do?

We are not “lounge on a beach” type of vacationers and I was surprised to learn how much there is to do on the island besides enjoy the sand. Because the island is small, it is easy to hit all of these things in just a few days.

Old San Juan

  • With buildings dating back to the 16th century, Old San Juan is the historic center and heart of Puerto Rico. The iconic colorful buildings are restored in their Spanish colonial style and make for some lovely photos. Along with just wandering around Old San Juan, there are two fortresses to explore. Definitely take a walking tour if you are able to appreciate all the history.
  • And do not forget all the food! There are tons of spots to grab a wide variety of food for any mood.
  • One thing to note is this area does receive cruise ships which could be a pro or a con depending on what type of traveler you are. Personally, I would be pleased to travel here before the cruise ships are blessed to resume operation.

El Yunque National Forest

  • One of the highlights of a Puerto Rico adventure is exploring El Yunque National Forest – the only tropical rain forest in the United States. The rain forest is filed with lush vegetation, twenty four miles of trails, and tons of waterfalls and towers.
  • There are two options for accessing this forest – renting a car and exploring on your own (self guided) or booking a guided tour which included transportation. The forest is under an hour drive from San Juan. The guided option is not required but for some adds a level of convenience and there are tons of companies that offer this. Ride shares are not reliable for getting to this part of Puerto Rico so do not plan on that as a viable option.
  • There is no park fee to access the trails but currently you must make reservations to enter the park (two dollar fee). There is also a visitor center which charges a very small fee for entrance ( four dollars). Due to the popularity of this destination in a traveler’s Puerto Rico itinerary, it is recommended to arrive early due to crowds and limited parking. Like most things these days, always check the park website to make sure roads and trails are open before making the trip.

Bioluminescent Bays

  • There are only five bioluminescent bays in the world, and Puerto Rico has three of them! Basically, dinoflgaellates (microorganisms) in the water glow bright blue when disturbed. You have to book a tour in order to experience these bays but there is some flexibility in how you see the bay. Personally, I would opt for a kayak over a motorized boat. You want to book the latest tour possible and while this is largely out of your control, try and book a night with no or little moonlight.
  • Mosquito Bay – found on the island of Vieques and requires an overnight on the island to complete this excursion but it is the best and brightest of the three bays.
  • Laguna Grande – is located on the mainland Puerto Rico by the town of Fajardo, which is only an hour away from San Juan, and is the second brightest bay.
  • La Parguera – is the most out of the way location for a short trip but it is the only bay you can swim in, which may be why this is the least brightest of the three bays in Puerto Rico.

Island Hopping

  • Neighboring islands make for a fun day trip or even extended trip. Vieques and Culebra are just a ferry or plane ride away and offer more island life. Shorter itineraries like the one I am building here, choose one island to visit, but if you have a longer trip towards a week, it is easy to fit both islands into your trip.
  • Here is another change to decide on a self guided experience or book an excursion with a tour company. Some of the guided tours require you to get to the island on your own while others include transportation. Don’t consider that a deal killer – the ferry out of Fajardo looks very easy and cheap to navigate.
  • Culebra: The smaller of the two islands means you can get away with a day trip to explore the ideal waters for snorkeling and diving and visit one of the best beaches in the world, Flamenco Beach.
  • Vieques: A larger island that most recommend an overnight stay to explore the more developed island and to experience the most famous bioluminescent bay.

And do not forget all the beach and water activities, including boat charters, snorkeling, surfing, kayaking.

Where to eat?

I think the food is one of the main reasons Kevin perked up at the idea of a Puerto Rico trip. There are tons of great places to find a good meal! Since I am assuming we are staying in Old San Juan, the food focus was heavy here but there are tons of great spots outside of Old San Juan as well.

Old San JuanMore Old San JuanOutside Old San Juan
Don Ruiz – coffee
T-tuan Old San Juan – tapas 
La Factoria – bar
Verde Mesa
Senor Paleta – ice cream
Cafe El Punto
Deshistoria: Birra & Empanadas
Chocobar Cortés
El Jibarito
La Vergüenza Viejo San Juan – bar
Café Cuatro Sombras – coffee
Cafe Mimosa
The Parrot Club
Waffle-era Tea Room
La cocinita food truck
Mario Pagan
Ascere Cubano
Lote 23
1919 restaurant

Based on the above information, here is how I would structure 4 days in Puerto Rico, excluding the travel time to get there. Days are interchangeable and are grouped by location on the island so mix and match depending on weather and what you are up for that day.

Day 0AfternoonArrive / Check in
EveningExplore neighborhood where staying
Day 1MorningExplore Old San Juan
– Castillo San Felipe del Morro
– Plaza del Quinto Centenario
– La Fortaleza
– Catedral Basilica Menor de San Juan Bautista
– Puerto Rican Flag Door Historical Location
– La Perla
AfternoonPlaya El Escambrón
EveningExplore Downtown
Day 2MorningEl Yunque National Forest
Guided Tour or Self Guided Tour (car rental)
AfternoonFood: Terruño
Beach time – Luquillo Beach, Seven Seas Beach
EveningFood: Rest. El Pescador
Farjardo Bio Bay Kayak Tour
Day 3MorningDay trip to island – Culebra
AfternoonDay trip to island – Culebra
EveningExplore Downtown
Day 4Morning Explore Conado
AfternoonExplore Conado

If you have been to Puerto Rico before, let me know what I missed and what your favorites are!

Don’t forget to check out all DESKRIB itineraries here!

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