Ideas for a 3-Day Mini-Vacation in San Juan, Puerto Rico

BY MARK CHESNUT

As Puerto Rico's largest city and capital, San Juan offers lots of diversions for travelers — from wide beaches to historic architecture, from Puerto Rican music and art to live dance performances, from sophisticated shopping and nightlife to world-class cuisine. But what if you''ve only got a few days? 

I've been visiting San Juan for years (decades, actually). My first visit was way back in the 20th century, and, since my husband is from Puerto Rico, I've had even more excuses to visit the Isla del Encanto ("Island of Echantment"). But since his family is from the western part of the island, we often find ourselves spending just two or three days in San Juan. 

San Juan, Puerto Rico, is a vibrant destination that is worthy of a much longer visit, of course. I've always loved its unique blend of old-world charm, vibrant culture and modern amenities. The city's historic heart, Old San Juan, is a maze of cobblestone streets lined with colorful colonial buildings, where centuries-old forts like El Morro and San Cristóbal stand as sentinels of the past. Walking through this area feels like stepping back in time, with every corner offering a new discovery, from quaint cafes to bustling plazas.

Beyond its historical allure, San Juan is one of the few destinations in the Caribbean where you can easily combine sophisticated culture with natural beauty. The popular Condado, Ocean Park and Isla Verde areas are perfect for sun worshipers, with beaches offer a variety of water sports, from paddleboarding to jet skiing. After a day soaking up the sun, you can end the day with a sumptuous dinner and perhaps enjoy the extensive nightlife that San Juan is famous for, with numerous bars, clubs, and casinos providing endless entertainment options.

San Juan's culinary scene is another major draw for visitors. The city is a food lover's paradise, offering a delectable array of Puerto Rican dishes like mofongo, tostones, and fresh seafood (mofongo and tostones — both of which are made with plantains — are two of my personal favorites). The burgeoning farm-to-table movement has also made its mark here, with many restaurants focusing on locally sourced ingredients. 

Whether dining at a high-end restaurant or enjoying street food from a local vendor, the flavors of San Juan are sure to leave a lasting impression. It's no wonder that travelers like me keep coming back year after year.

On our most recent visit (highlights of which are featured in my Instagram reel), we spent three nights that included a bit of sun, a bit of sand, some great cocktails and one of the best dinners I've ever had on the island. 

Here are the highlights, in case you need inspiration for your own quick vacation getaway in San Juan: 

• We stayed in Condado, our favorite neighborhood, since it's easily walkable and everything is a quick stroll away — shops, restaurants, nightlife and (of course), the beach. 

• Fab cocktails at Sheraton Puerto Rico Resort & Casino, which has a great lobby bar with an excellent menu. 

• An absolutely stunning, multi-course dinner at 1919, the Michelin-starred restaurant at the Condado Vanderbilt Hotel. This was, hands-down, one of the best meals I've ever had on the island — at one of the best restaurants in San Juan, Puerto Rico. 

• A bit of time on Condado Beach, the sun-soaked stretch of sand that lines Condado's cost. 

Granted, three days isn't enough to do everything I'd like to in San Juan. This was strictly a repeat visitor's hurried (yet relaxed) stopover. But it was wonderful. Next time we need more time in San Juan, in addition to enjoying other parts of the island! (We spent a lot of time in western Puerto Rico on this visit — check out my previous reel and photos for western Puerto Rico travel tips.)