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, and combine sightseeing with shopping, dining, and even Segwaying (is that a word?).
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, call my friend Debbie at Legends of Puerto Rico. Her Night Tales of San Juan Rico. Debbie will take you in and out of some of Old San Juan's iconic buildings at night, after the crowds have gone and the lamplight bathes the walled city in a romantic and nostalgic light. She also offers tours during the day, as well as a variety of excursions outside of San Juan.
Right up there with Legends of Puerto Rico on my favorite tours list 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 takes you through Old San Juan, with stops along the way where Leslie will provide an interesting anecdote of historical fact. You will also stop at three or four different restaurants, where you'll get to sample some of the different flavors that San Juan is famous for.
The aforementioned Legends of Puerto Rico puts a different spin on a culinary tour with its Spirits of Puerto Rico tour, which combines a historical tour with dinner and rum tasting (obviously, this one's for adults only.
Old San Juan Trolley
If walking the streets of Old San Juan seems like too strenuous for you, I have good news. A free trolley putters around the old city all day until 7 p.m., letting you hop on and off at designated stops. The trolley offers convenient transportation that will take you to (or near) every major site in Old San Juan. The trolley makes 26 stops and has three different routes, so it's not the quickest ride in the world, but it's an easy and stress-free way to get around.
However, to be perfectly fair, I have to note that I'm cheating a bit here. This isn't a tour, and there are no guides to provide information about the places the trolley visits. It's just an easier way to get around.
Even I didn't know about this until a reader brought it to my attention, but the Puerto Rico Conservation actually runs birdwatching tours in Old San Juan! They also have a "Discovering Nature in Old San Juan" tour that introduces you to the environment beyond the pastel facades and ancient installations.
That's right ... segways have come to Old San Juan. The tour will take you from the base of the city all the way to El Morro, with your guide providing historic facts and info along the way. And if you've never been on a Segway, don't worry. Your guide will show you how to ride and operate one, and they are surprisingly easy to master.
You have two options for your Segway tour: the full two-hour excursion, which covers 28 sites, or an abbreviated 45-minute tour that includes 14 stops.
Get Shopped is all about touring San Juan while combining the delights of shopping and cuisine. They provide VIP shopper services as well as excursions to the Barceloneta or Canóvanas Outlet Malls. Along the way, you can let your guide show you where to eat a terrific Puerto Rican meal or bar-hop between boutiques.
Finally, for the do-it-yourself crowd, check out these downloadable podcasts that put a sightseeing tour of Old San Juan in the palm of your hand. Just press play and let your smartphone be your guide.