The Perfect One-Day Itinerary for Old San Juan, Puerto Rico

San Juan, the capital of Puerto Rico, is home to just under 350,000 inhabitants and sees countless tourists on a day-in, day-out basis. Puerto Rico is a favoured tropical destination from the United States’s East Coast due to its ease of access given the travel time and entry requirement (no passport needed for U.S. citizens).

The view from El Morro (photo credit: canuckrunningamuck)

The part of San Juan known as “Old San Juan” deserves a day all to itself for exploring. To get a thorough glimpse of this quarter, make sure you start your day early. With historic forts, romantic streets, and plenty of dining and drinking options, there’s lots to see in a day. Plan for lots of walking, pack plenty of water and SPF, and bring a camera!


Get up early to head for breakfast at Cafeteria Mallorca in Old San Juan. This unassuming eatery features baked goods, cooked breakfast options, smoothies, and your quintessential cup of Puerto Rican coffee to set you up well for the day. The ham, egg, and cheese mallorca (served as a breakfast sandwich) is the perfect mix of savoury and sweet- a must-try for your introduction to Puerto Rican cuisine!

El Paseo de la Princesa (photo credit: canuckrunningamuck)

Next, head for a stroll along El Paseo de la Princesa, a romantic thoroughfare beloved by locals. Lined by trees that provide some welcome shade, this promenade culminates at the Fuente Raíces (“Roots” fountain). The fountain was unveiled in 1992 to mark the 500th anniversary of European voyaging to the Americas and sits at the perfect vantage point for views of San Juan Bay.

Fuentes Raices (photo credit: canuckrunningamuck)

From El Paseo de la Princesa, continue on to El Paseo del Morro, a boardwalk that follows the perimeter of the city walls. Informative placards along the route provide historical context; make sure to stop and admire the red San Juan Gate, once an important entry point into San Juan. The walkway is treated to a cool breeze off the water, and in the morning hours, provides a sense of calm contemplation away from the bustle of the city. Keep an eye out for iguanas (an invasive species, unfortunately) sunbathing on the rocks by the water!

The San Juan Gate (photo credit: canuckrunningamuck)
(photo credit: canuckrunningamuck)

El Paseo del Morro will eventually lead you to the foot of San Juan’s most famous fort, El Castillo San Felipe del Morro (or “El Morro”, as it is often shortened to). Climb up the winding staircase along the cliff’s face to quite literally come out on top- of the fort, that is.

View from El Paseo del Morro (photo credit: canuckrunningamuck)
Along El Paseo del Morro (photo credit: canuckrunningamuck)

Part of the San Juan National Historic Site, El Morro is managed by the National Park Service and is a must for any visitor to San Juan. The fortress has been renovated, modified, and expanded over nearly 500 years as the city’s defensive needs changed; El Morro has withstood attacks from the Dutch and the English, and was used by the U.S. military during both World Wars.

View toward San Juan from El Morro (photo credit: canuckrunningamuck)

Take your time to see the fort. Recreated rooms bring the space to life as it would have looked centuries ago, and displays walk visitors through El Morro’s architecture, military features, and connection to the geography.

Inside El Morro (photo credit: canuckrunningamuck)
One of the hallmark sentry boxes at El Morro (photo credit: canuckrunningamuck)

It is easy to understand why the fort was built atop a headland overlooking the bay: panoramic views allowed guards to monitor incoming and outgoing traffic to the busy port. As the first stop for European merchant ships arriving to the Caribbean, San Juan was a key location for resupplying, trade, and defense.

The chapel in El Morro (photo credit: canuckrunningamuck)
The courtyard of El Morro (photo credit: canuckrunningamuck)


After your visit to El Morro, venture into Old San Juan for a bite to eat. Its charming, blue cobblestone-paved streets are lined with historic homes and shopfronts, and wandering the maze of alleyways and main thoroughfares is a delight in itself. Keep an eye out for some of San Juan’s most recognisable street art as well!

Old San Juan (photo credit: canuckrunningamuck)
Old San Juan (photo credit: canuckrunningamuck)

There is no shortage of dining options in Old San Juan, but if you’re looking for something light but filling, try any of the menu options at the Stuffed Avocado Shop, a casual dining establishment featuring healthy bowls that all incorporate avocados. Select combinations from their menu, or create your own bowl- and be sure to grab a cup of one of their freshly-squeezed juices (the passionfruit one is especially refreshing) as well.

Even though you’ve already stopped at one fort today, make time for Castillo San Cristóbal, San Juan’s second fort. San Cristóbal tends to be marginally less busy than the more-popular El Morro but is filled with just as much history. Be sure you don’t miss the graffiti of one of the fort’s 18th century prisoners, a curious feature that drives home the darker side of the colonial fortresses.

San Cristobal (photo credit: canuckrunningamuck)
The view from San Cristobal (photo credit: canuckrunningamuck)

As the sun starts to set on Old San Juan, take your time wandering through the romantic streets and enjoying the cool breezes, cleverly channeled by the city’s architects to funnel down the roads and deliver welcome relief from the heat. During the day, the streets thrum with the hundreds of cruise ship passengers who disembark for a brief excursion in the city. At sundown, however, as these visitors return to their vessels, a leisurely sense of relaxation settles into Old San Juan. Strolling hand in hand under the lamplight or catching a sunset near the bay are perfect ways to end your day in the old city.

(photo credit: canuckrunningamuck)

If you’re in need of some refreshment, the Alegría Patio Bar at Hotel El Convento is a welcome oasis of calm located in the historic El Convento, once a Carmelite convent nearly 400 years ago and now a luxury hotel. Sit back and take a moment to soak in the soothing atmosphere of the indoor/outdoor patio space while sipping on a coconut mojito.

Drinks inside El Convento (photo credit: canuckrunningamuck)
The courtyard of El Convento (photo credit: canuckrunningamuck)

After dinner in Old San Juan (Restaurant Raíces, Barrachina, and Marmalade are all popular options), save room for dessert in the form of a popsicle from Señor Paleta. This beloved shop offers popsicles made from fresh fruit in a dazzling variety of flavours, including (but not limited to!) papaya and pineapple, guanabana, coconut, guava, and passionfruit. Keep in mind: they melt fast in the tropical heat, but they’re so delicious and refreshing you should have no problem finishing yours! It’s a sweet way to cap off your time in Old San Juan.

Passionfruit popsicle from Senor Paleta (photo credit: canuckrunningamuck)

What are you must-sees in Old San Juan? Any hidden gems you’d recommend? I’d love to know- leave a comment or send me a message!

View along El Paseo del Morro (photo credit: canuckrunningamuck)

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