rooftop tubs 3

This is a guest post by Michael Bottomley and Emma Sky.

Puerto Rico is the good host to multitudes of visitors each month: day tourists from ships, spring breakers and weekenders seeking island nightlife, and the standard picture-taking resort-staying family vacationers. But I found that Puerto Rico reserves a special appreciation for the visitor who hunts for the local business—not just the locally appreciated, but the locally owned.

It was my self-assigned mission to find these local places in what is ostensibly the area of Puerto Rico that caters most heavily to visitors: San Juan Viejo (Old San Juan). It’s a tiny, colorful island on the north side of Puerto Rico proper. It houses everything from the legislature and Navy radio centers to forts and the Casablanca hotel.

colorful buildings


The Casablanca, like Humphrey Bogart in the film of the same name, is an unassuming, downtown experience with chic for days. The lobby looks like something Andy Warhol might have created under the patronage of Louis the XIV. TVs and projectors are looping Casablanca for you sans sound. The full color wheel greets you through the carefully selected furniture, oil paintings, and tile. But it’s the deft use of lighting that prevents the colors from visual assault: move toward the desk and watch the reds fade as yellows and purples rise to the fore. When you visit, stay in the lobby to find the hidden room–it’s literally under your nose.

bar casablanca movie Restaurant

If you don’t stay in this locally-owned hotel, you miss the opportunity to enjoy the exquisite rooms (air conditioned getaways with boutique, Casablanca-only bedding, many with street-facing balconies), the rooftop bathtubs (room for two or more, with a view of the entire island and even Puerto Rico’s mainland), and a discount on the kitchen’s amazing breakfast creations.

However, if you already have accommodations elsewhere, you can still pop in for a drink, a meal, and a quick question for the concierge–easily some of the most helpful and pleasant I have ever encountered.

breakfast2 rooftop tubs 2

Walking west of the hotel takes you through a gauntlet of gift and cigar shops. But if you stop on Calle de Cruz, you’ll get to drop into Cafe Poetico. It’s difficult to tell whether this is a coffee and dessert shop first or a gallery. But it doesn’t matter. The owners, a local poet and artist, who are also appreciators of fine baked goods and local coffee, opened the cafe to host the island’s local–and visiting–musical, artistic, and poetic talents.

Get a brownie and a coffee and stroll through the unique poetry books and works of art. If your stay in Puerto Rico happens on a Tuesday, go out of your way to attend the open mic on Tuesday night. It’s a mix of Spanish, English, and even French music and writing. (I’m not a huge fan of poetry, but there’s something about an evening serenade in Spanish that melts even the most hard-hearted entertainment critic.)

And of course, there are the obligatory, but merited, visits to the fort: Castille San Felipe del Morro. Skip the tour and bring water and sunscreen. It’s best if you begin with the fort on the North-West side of the island. Find an iguana basking on the unassailable walls that kept out the English, French, and Dutch and take in the vast, dream-blue sea.

iguana fort

Even if you detour through the shining white graveyard at the fort’s base, there is still a world of food and beverage choice on your trek between the castilles. If you’re the adventuring type, take advantage of the island’s relaxed attitude toward drinking pina coladas on the street. Hotel El Convento makes the best–order them to go, spend a few minutes in awe of this Carmelite convent-turned luxury hotel and restaurant, and make your way to the other fort. Drop in anywhere for a light bite. The empanadas on the south east corner of Calle del San Francisco are far tastier than they have any right to be at $1.

Transportation on Old San Juan is best done on foot. But if you’re itching to move faster, make your way to the south of the island for bicycle rentals. This is a great way to visit the beaches on the north side of the island and to cross over to the greater San Juan area where you can lay on the beaches and swim in the crystal-clear water just over the bridge.

There is no best way to close out a day in Old San Juan. If the famed island nightlife of dancing and drinks is your heart’s desire, you can simply walk through the twilight until you hear a song you like–most likely coming from one of the island’s more understated taverns. If waves and moonlight are more your taste, on the north side of the capital is a semi-secret beach known only to late-night fishermen and people leaving their daytime shifts; it’s perfect for stargazing–just be sure to steer clear of the sea urchins–rocky water is their home.
If you keep even a casual eye out for the locally-owned and the locally-frequented, your experience in Old San Juan will be an uncommon mix of adventure, relaxation, and supreme quality.

– Emma Sky and Michael Bottomely

Photographs by Emma Sky and Michael Bottomley for Socially Superlative

CasaBlanca Hotel
316 Calle Fortaleza
San Juan, 00901, Puerto Rico