old san juan things to do on a cruise
Flying at kite at El Morro is a lifelong memory.
Caribbean

Visiting Old San Juan on a Cruise? Here’s How to Make Your Day Memorable, From a Legendary Piña Colada to the Perfect Souvenir

By: Alexander Britell - April 23, 2025 - 5:14 pm

There’s something about the way the frozen Coco López dances with the Ron del Barrilito. When you try a Piña Colada at Old San Juan’s legendary El Barrachina, you get it. It’s the best piña colada in the world, and if you go by the history of this street, it’s the true birthplace of the cocktail (though the Caribe Hilton makes a competing claim). 

This is the sort of of memory you can make if you do your visit to Old San Juan right. Sure, you can do a shore excursion with the cruise line, or you can get off the ship and explore.

This is the way to take a regular port call and turn it into something unforgettable, and our knowledge of the city and its charms means you can find some unique, colorful things to do when you’re visiting the five-hundred-year-old city on a cruise. I’m also sensitive that time goes quickly when you’re on a cruise, so I’ve picked my five favorite things to do with just a few hours in OSJ. Think of it as the perfect day in Old San Juan.

the courtyard at barrachina in old san juan
Are you cruising to Old San Juan? This is a must.

The Original Caribbean Cocktail 

So what do we like to do? Well, for starters, it’s Barrachina, where they make their frozen drink with our favorite rum in Puerto Rico, Ron del Barrilito, and the vibe is classic, golden-age Puerto Rico. The food is actually quite good, too, particularly the mofongo (Puerto Rico’s famous mashed-plantain dish). 

Old San Juan’s Greatest Souvenir  

Just up the street on Calle Fortaleza, you can head to our favorite shop in the town: Olé, the best Panama Hat shop this side of the canal and where you can actually order a bespoke hat:

You can choose the shape and size, the headband and they’ll make it for you in just a few minutes. It’s a very cool experience and a worthy souvenir that isn’t touristy. 

el patio de sam
El Patio de Sam in Old San Juan. CJ Photo.

Going Gonzo at El Patio de Sam

Loved The Rum Diary? Well, Hunter S. Thompson did actually live in San Juan, and this was his favorite haunt: El Patio de Sam, a greasy, fun bar with spectacular burgers that’s just off the lovely Plaza de San José (and down the block from the world-renowned La Factoria bar). Think of it as a more casual PJ Clarke’s, Puerto Rican style. (We wrote about the full experience here). 

Flying a Kite at El Castillo San Felipe del Morro 

flying a kite in old san juan
Kite sellers are abundant. You learn quickly.

Traveling with your kids? There’s simply nothing more magical than buying a kite and flying it on the sprawling grass field of the El Morro castle. The kites are abundant and easy to buy, and it will literally be a core memory for everyone involved. Thank us later. 

Rooftop Delights at the Palacio Provincial 

One of my favorite things to do on a cruise is to retire to a hotel bar — first, you’re enjoying the destination in a different way, far from the crowds. Second, they’re often some of the coolest places in any city, where you know the place will be friendly and welcoming, with attentive service and inspired drinks. If you’re in Old San Juan, there’s nowhere better than the rooftop at the Palacio Provincial hotel, the newest hotel in the city (though it’s actually set in a centuries-old former diplomatic building). It’s called Atelier, and it’s a full-fledged cocktail workshop with stunning views of the colorful streets of Old San Juan. 

Popular Posts trinidad beach maracas

This Trinidad Beach Has Golden Sand, Green Hills, and the Country’s Most Famous Sandwich

Golden sand. Beach shacks and cold beer. Perfect street food.  Maracas Beach isn’t just the best beach on the island of Trinidad. It’s the best place on the whole island. The sand is perfect, a coastline edged by Trinidad’s verdant green […]


One of the Best Beaches in The Bahamas Comes With a World-Famous Blue Hole

the beach at dean's blue hole in the bahamas

It doesn’t look real at first. You step out from the pines and palms onto a curve of soft, white sand, and there it is—this perfect, impossible circle in the sea. A portal. The blue gets darker the longer you […]


American Airlines Is Adding a New Nonstop Flight to Curacao, a Caribbean Island That Is Buzzing Right Now

caribbean island curacao american airlines

The colors of Willemstad. The waves of Cas Abao. The rosé at Saint Tropez. The live music at the Avila. Curacao is a rich mosaic of culture, food, art and vibes. And the Caribbean island is as buzzy as it’s […]


Related Posts food truck saint martin

The Caribbean’s Coolest New Food Truck Just Opened in Saint Martin

It’s got all of the essential ingredients: a young, energetic team of chefs; a plum perch in one of the region’s foodie capitals; and a bold, innovative menu.  This is the coolest new food truck in the Caribbean, and it’s […]


Puerto Rico Air Traffic Keeps Up Strong Numbers, Driven by International Growth 

puerto rico international growth

The biggest story for Puerto Rico’s air passenger traffic isn’t its fast pace. For years now, the island has been seeing a surge in passenger traffic at its main hub in San Juan: Luis Muñoz Marin International Airport.  That’s not […]


Antigua and Barbuda’s Culinary Month Is Back — With Harbor Dinners, Chef Demos and a Local Food Journey 

antigua and barbuda culinary month

You can smell it before you see it — a curl of spice in the air, the sizzle of fresh seafood on the grill, the sound of laughter echoing down a cobblestone lane. Culinary Month has begun in Antigua and […]