The Ideal Puerto Rico Itinerary for a Single Day - Hexbag

The Ideal Puerto Rico Itinerary for a Single Day


Plan Your Trip to Puerto Rico

If you’re planning a Caribbean trip, Puerto Rico is a great option. As a US territory, going to Puerto Rico is considered merely a local vacation! This is particularly advantageous for Americans who prefer not to deal with complicated matters such as passports, currency exchanges, and international SIM cards.

An abundance of tourists visit San Juan, the capital of Puerto Rico, every year to embark on Caribbean cruises. Just as I think San Juan should need more time to really shine, I also think Puerto Rico would be perfect for an island-only vacation someday.


On my three trips to Puerto Rico—two with my husband Elliot—I’ve seen various regions. From Viejo San Juan to the El Yunque jungle and Rincon’s beaches, my seven-day Puerto Rico itinerary hits all the major points, according to my previous travels.

To help you arrange your own week in Puerto Rico, below is an itinerary. Feel free to use it!


Puerto Rico mountain panorama
In the highlands of Puerto Rico…
Going to the beach in Puerto Rico! This is the beach in Vieques!

When is the ideal time to visit Puerto Rico?

The weather in Puerto Rico is hot and humid all year round due to the tropical monsoon environment. Temperatures often range from the low to mid-80s Fahrenheit. December through March, the North American winter, is peak tourist season in San Juan because to the milder temperatures, less humidity, and lack of hurricane danger.

You can locate the most affordable hotel rooms in the Caribbean during hurricane season, which typically spans from June to November (a time when Puerto Rico is often impacted). However, bad weather, including rain and storms, is always a possibility.

If you’re looking for a more off-season experience, April, May, or June are other great months to visit Puerto Rico; nonetheless, my favorite was February.

Here is my recommended schedule for seeing the major island of Puerto Rico in only seven days! It comprises:

  • Old San Juan and the rest of San Juan
  • The Rainforest of El Yunque
  • Exploring the west coast, Rincon, and Ponce
  • Angling or ziplining in the mountains is an optional activity.

Since this schedule takes you all over the island and public transportation is nonexistent outside of the main towns, a rental vehicle is a must. Because this plan makes it simple to pick up and drop off a rental vehicle at the SJU airport, I normally use Discover Cars to do my search.

First Day: Viejo San Juan Street and Old San Juan

With a history spanning over 500 years, San Juan, Puerto Rico, is among the Caribbean’s oldest cities. Though the Indigenous Taino people had lived in the region for a long time prior to the 1521 formal foundation by Spanish colonists, who dubbed it “Ciudad de Puerto Rico,” meaning “rich port city,” the city had been there for much longer.

I suggest beginning your journey in Old San Juan, where you will find the beautiful old colonial buildings and the Spanish forts that date back hundreds of years—those are the sights that most people picture when they think of San Juan today.

Sunrise: The fortifications of San Juan

The San Juan National Historic Site, which includes Castillo San Cristóbal, is a great place to begin your day. There are two forts and the remnants of the city’s walls and gates at this historic location. Because it is conveniently located within walking distance of most hotels in Old Town, Castillo San Cristóbal on the northeast end of Old San Juan is a good place to start.

The Spanish constructed Castillo San Cristóbal and other forts to protect Puerto Rico. Beginning in the 1600s, construction on this castle continued during WWII, when American forces utilized the lookouts and sentry boxes to detect German U-boats in the ocean.

The “Devil’s Sentry Box,” also known as “La Garita del Diablo,” is off-limits.
During Old San Juan’s era as a walled city, this stronghold served to guard the land entry. Covering 27 acres, it is the biggest Spanish stronghold in the New World. It is also quite huge.

The historic property offers a lot for the low, low price of just $10 per person. Most of the stronghold is open for exploration, and you can even go inside some of the old jail cells.

Additionally, you have the opportunity to take in breathtaking views of San Juan from every angle.

A word of advice: if you want to enjoy Castillo San Cristóbal mainly to yourself, come there early, for the cruise ship tour busses will start rolling in 1-2 hours after opening.

In the morning, take a stroll along Viejo San Juan.

The next step is to wander aimlessly around Old San Juan’s vibrant streets. Picturesque backdrops abound, including historic city walls, pastel-painted buildings, and Puerto Rican flags flying from every direction.

Among the many activities to do in Old San Juan, apart from just taking in the picturesque buildings and plazas, are:

Cuatro Sombras is the place to go for Puerto Rican coffee.
Barrachina has the title of “the birthplace of the Piña Colada,” so get yourself a Piña Colada there.
Stop by Chocobar Cortes to sample some chocolate-infused meals.
Take some pictures on Calle de la Fortaleza while you’re at La Fortaleza, the home of the current governor.
View the ocean while sipping cocktails on La Vergüenza’s rooftop.
San Juan’s Old Town, a colorful street

Afternoon culinary adventure

In San Juan, a culinary tour is an absolute must! Traveling on a cuisine tour is one of my favorite things to do since it is a great way to learn about the history and culture of a place.

Flavors of San Juan is the best culinary tour business in San Juan, and their traditional Old San Juan culinary Tour would be perfect for this day. Get your taste buds ready for some Puerto Rican cuisine and drink on this 3-hour small-group trip. With a little walking, you can burn off some of those extra calories while enjoying a combination of history and delicious food.

Not to spoil the surprise, but this trip stops at least five independently owned businesses where you may sample chocolate, pastries, and Puerto Rican coffee. The portion of the trip when we prepared our own mofongo was the highlight for me.

Mash-up mofongo
Several times daily, you may choose to go on the Old San Juan Food Tour. If you want to avoid eating supper afterwards, I suggest coming for the late afternoon tour (there’s often one at 3 p.m.).

Afternoon: Sundowners and the setting sun

Those who choose the afternoon culinary tour will have the option to either continue along the ancient city walls past Paseo de la Princesa and La Fortaleza or walk all the way to Castillo San Felipe del Morro, San Juan’s second castle, to see the sun go down if you get there before sunset.

Las Princesas Paseo
Old San Juan’s Paseo del Morro at sunset, with Castillo San Felipe del Morro in the background.
As the sun sets above Castillo San Felipe del Morro
If you didn’t have a Piña Colada at Barrachina earlier, you may swing by there for one later on. Another option is La Factoria, which is a well-known gathering of seven pubs and dance clubs that also offers delicious beverages.

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