As an anchor on Eastern and Southern Caribbean itineraries -- not to mention a turnaround port for many ships -- San Juan is a place where just about all cruisers, at some point or another, are going to wind up. Puerto Rico is a U.S. territory, and San Juan is its urban hub. The city, by and large, is divided into new and old. The new includes a business district and outlying neighborhoods, concentrated with hotel chains like Isla Verde. The old is, of course, the historic city within ancient walls. Both offer many Americanisms. (Senor Frog's has a prime outpost, and you'll never want for a McDonald's Big Mac.)
Get beyond that, though, because of all America's Caribbean islands, Puerto Rico offers the most exotic aura. The melange of indigenous Taino culture, combined with European and African influences in San Juan (and all of Puerto Rico, for that matter), is one major factor. Add to that its own unique influences in areas ranging from cuisine and music to history and art. And there's more: folks who have traveled to Cuba say that Old San Juan reminds them more of Cuba, at times, than Cuba itself! It's also very Spanish (think Seville) and even a bit Italian (reminiscent of Naples). Finally, the city evokes just a wee taste of South America (like Buenos Aires).
For those who visit San Juan as a day-stop on a Caribbean itinerary or embark or disembark there, the island's biggest appeal is the old city. Most cruise ships dock right in the heart of Old San Juan, which dates back to the 16th century. The old, walled city has been exquisitely preserved, and its sprawling forts, cobblestone streets, antique shops and art galleries make it an ideal first stop. Its mainstream attractions include the imposing El Morro fort, which dates back to 1539; the Cathedral of San Juan, where the island's first governor, Ponce de Leon, is buried; La Fortaleza, the oldest governor's mansion on U.S. soil; several colonial plazas; and the triumvirate of Calle del Cristo, Calle San Jose and Calle Fortaleza for shopping. Calle del Cristo, in particular, is chock-full of art galleries, artisan studios and distinctive boutiques.
But, if you're a "been there, done that" visitor to Old San Juan, there's much more to explore.
And there's one more thing to keep in mind: many cruises stay in port until late at night. That makes it possible to sample some of the city's vibrant restaurants and nightlife (as long as you keep an eye on the clock).