San Juan isn’t just Puerto Rico’s capital. It’s the largest capital in the Caribbean, a bustling metropolis that forms the historic, cultural, economic, and political heartbeat of the island. Exploring this city can be a daunting task, because it has so much to offer.

Fortunately, there are several tours of San Juan that introduce you to some of its best sights and attractions, combining sightseeing with shopping, dining, and even Segway experiences.

Walking Tours of Old San Juan

In my humble opinion, the best way to see Old San Juan, the historic crown jewel of Puerto Rico, is on foot. Nothing captures the old city quite like a walk among its narrow alleys and blue-tinged cobblestone streets (called adoquines). The old city makes for a slightly hilly trek and can be a bit taxing on a hot day, but it’s very much worth it.

If you want an outstanding walking tour that combines history, legends, and entertainment, consider contacting Debbie at Legends of Puerto Rico. Her Night Tales of San Juan Tour will take you in and out of some of Old San Juan’s iconic buildings at night, after the crowds have gone, while the lamplight bathes the walled city in a romantic and nostalgic glow. She also offers tours during the day, as well as a variety of excursions outside of San Juan.

Culinary Tours

Among my favorite tours is Leslie Padró’s Flavors of San Juan Tour. Leslie is a wonderful guide who will introduce you to Puerto Rican cuisine on this unique night out. The walking tour covers Old San Juan, with stops where Leslie provides interesting anecdotes and historical facts. Along the way, you will stop at three or four different restaurants to sample the diverse flavors San Juan is renowned for.

Moreover, Legends of Puerto Rico offers a culinary experience called the Spirits of Puerto Rico tour, which combines a historical tour with dinner and rum tasting—this tour is tailored for adults only.

Old San Juan Trolley

If walking the streets of Old San Juan seems too strenuous, you’ll be pleased to know that a free trolley operates throughout the old city all day until 7 p.m. This convenient transportation allows you to hop on and off at designated stops, covering every major site in Old San Juan. The trolley makes 26 stops and has three different routes, providing an easy and stress-free way to get around, although it may not be the quickest ride available.

However, it’s important to note that this isn’t a tour, and there are no guides available to provide information about the attractions that the trolley visits. It’s simply a helpful means of transportation.

Nature Tours

Interestingly, the Puerto Rico Conservation offers birdwatching tours in Old San Juan. They also host a “Discovering Nature in Old San Juan” tour, which introduces you to the natural environment that exists beyond the pastel facades and ancient installations of the city.

Segway Tours of San Juan

Segways are now a unique option for exploring Old San Juan. The tour will take you from the base of the city all the way to El Morro, with your guide providing historical facts along the way. Even if you’ve never operated a Segway before, your guide will show you how to ride it, and they are surprisingly easy to master.

You can choose between two Segway tour options: a full two-hour excursion covering 28 sites or a shorter 45-minute tour that includes 14 stops.

Shopping Tours of San Juan

Get Shopped offers a fantastic opportunity to tour San Juan while combining shopping delights with culinary experiences. They provide VIP shopper services and excursions to the Barceloneta or Canóvanas Outlet Malls. As you explore, your guide will recommend where to enjoy a delicious Puerto Rican meal or where to visit boutiques for the best shopping experience.

iPod Tours

Lastly, for those who prefer a do-it-yourself approach, check out downloadable podcasts that deliver a sightseeing tour of Old San Juan right onto your smartphone. Just press play and let your smartphone be your personal guide.