Trying to sample the pleasures of some cities over a weekend can be a bit like entering a pie-eating contest. Sounds like a madcap lark, but after a while you're likely to feel overstuffed, foolish and maybe a little sick. Sure, you could do Paris without the Louvre, but why? Even negotiating the fabled museum itself in that time frame would be a challenge. San Juan, the capital of Puerto Rico, poses no such problems. True, as with any major metropolis, you could pass a week in the city and still not probe all its corners. (As it turned out, I did: planning a weekend visit, I was forced to extend my stay a few days when Hurricane Sandy struck.) But the major highlights of San Juan can be easily accommodated in 36 hours, even accounting for the leisurely pace that seems appropriate to the tropics.
4 p.m.1. Buy a Hat
A walk through the central streets of Old San Juan reveals a city in ferocious competition to become the most souvenir-clogged metropolis on the planet. Perhaps because it's a popular stop on Caribbean cruise tours, the central city is so chockablock with stores selling tacky gewgaws that you could conceivably furnish an entire apartment with merchandise announcing its provenance in Puerto Rico. (There's even a shop that calls itself the Tourist Trap.) But since a hat is necessary on a steamy afternoon, visit the tiny, old-fashioned emporium called Olé (105 Fortaleza Street; 787-724-2445), which sells hand-fitted Panama hats that you can customize yourself. I chose one in a color somewhere between mauve and brown, and accessorized it with a nice striped ribbon ($60). The proprietor, Guillermo Cristian Jeffs, will describe the history of the Panama hat in effusive detail, and assure you that none of his hats -- in contrast to the piles to be found filling shelves elsewhere -- are made in China. Also for sale: an assortment of touristy trifles and a few used books: I picked up a slightly worn copy of E. M. Forster's "Howards End" for a few bucks.
7 p.m.2. Cool Oasis
Make your way to the famous Hotel El Convento (100 Cristo Street; elconvento.com), an Old San Juan institution. The name derives from the grand building's history: founded as a convent -- the first in Puerto Rico -- it housed Carmelite nuns for 250 years before entering a period of tumultuous decay, for a time becoming a flophouse and eventually (Dios mío!) a parking lot for garbage trucks. The structure was rebuilt beginning in 1959 on the foundations of the original, reopening some three years later as a hotel. The bar and restaurant overlooking the grand open-air courtyard is the perfect spot to grab dinner or a drink.
10 a.m.3. Pick-Me-Up
Breakfast is served all day at Caficultura (401 San Francisco Street; 787-723-7731), a bustling coffee house that sits on a corner of the Plaza Colón, near the eastern end of Old San Juan. Black glass chandeliers hang from the high ceilings, and marble floors magnify the convivial sound of locals and tourists lingering over a morning meal. Although sandwiches are on the menu, the range of breakfast options, with local twists like banana pancakes with rum ($12), is most appealing, along with local pastries. A table with a view of the passing scene is recommended, since as with many restaurants in San Juan, the byword here is not necessarily efficiency.
1 p.m.4. Explore the City
Old San Juan is justifiably cherished for its beautifully preserved buildings and its sleepy charm. Wander its streets with their distinctive blue-glazed cobblestones: check out the cathedral on Cristo Street, stop for a rest in the slightly seedy central Plaza de Armas on San Francisco Street, stroll along Fortaleza Street until you come to the western end, where the grand governor's mansion sits. While you walk, tally up all those souvenir shops, and note the occasional anomaly: What's Dooney & Bourke doing here? I found myself preferring to avoid the sometimes dreary spectacle at street level and cast my eyes upward to the ornate balconies, or let the myriad colors of the buildings collect into a sort of visual kaleidoscope.
5 p.m.5. History With a View
Just before dusk is a prime time to visit the Castillo San Felipe del Morro at the north end of Del Morro Street, where it intersects with Norzagaray Street, one of the two historic fortresses that more or less bookend the north side of Old San Juan. The majestic structure takes on a soft glow as the sun falls over the horizon (it's open daily until 6 p.m.) and offers views of the bay and the ocean that are best savored when pink and orange bands of light begin to settle over the water. Construction on the castle began in 1539, when Spain was in control of San Juan. It's from here that the Spanish forces fended off various maritime attacks, and you can peek through windows where cannons once stood.
8 p.m.6. Home Cooking, High Style
After exploring the old town, set off for a new neighborhood that feels almost like another city entirely. Condado hugs the beach to the east of Old San Juan, and has the glittery feel of Miami Beach. Here's where high-end hotels, and the casinos inside most of them, attract night-life-seeking locals and tourists alike. Although a native of the Bay Area, the chef Roberto Treviño has established a small restaurant empire in San Juan. Opened in June of 2011, Casa Lola (1006 Ashford Avenue; casalolarestaurant.com) is his new, higher-end flagship, on the main strip in a stand-alone house painted a festive pink. The stylish main dining room has a view of the city across the lagoon. Try the mahi mahi with sweet plantains and local sausage ($28) or a sublime risotto with pork loin and chimichurri sauce ($21.75).
10 p.m.7. Nighttime Beach Beauties
For a late drink, and a stronger dose of the white-clothes-tanned-skin ambience of Miami, stroll down the Condado strip to Oceana (1853 Mcleary Avenue, oceanapuertorico.com), a hotel that houses a popular two-tiered restaurant and bar, for a drink on the patio that practically sits right on the beach. That's one of the virtues of this prime people-watching spot: when you tire of the human spectacle swirling around the bar, you can cast your eyes up at a star-filled night sky, let the pounding of the music subside and tune your ears to the gentle sound of the surf pounding at the shore seemingly right beneath your table. And for a night spot with the feeling of a fashionable club, the prices are surprisingly reasonable: a rum and tonic costs a mere $4.50.
11 a.m.8. Culture With Coffee
Sunday morning is a good time to add some cultural fiber to your visit. Since two of the city's major art museums are within walking distance of each other, a few hours can be spent looking at Puerto Rican art both old and new. The museums are outside the tourist circuits of Old San Juan and the strips along the beach, so walking between the two, you can also absorb the atmosphere of the city as locals experience it: a mixture of progress and decay that is a sobering reminder of the lagging economy that most tourists remain unaware of. Start at the Museo de Arte de Puerto Rico (299 Avenue de Diego; mapr.org; admission $6), where the history of local art is laid out in handsome galleries on two floors. The collection runs the gamut in terms of media and eras (José Campeche, the 18th-century painter considered the first notable Puerto Rican artist, has a room to himself), but pay particular attention to the rich history of the country's poster art. A 10-minute walk away, the Museo de Arte Contemporáneo de Puerto Rico (Avenue Ponce de Leon and Avenue Roberto H. Todd, museocontemporaneopr.org; opens at 1 p.m.; admission $5), in a graceful former school building, is home to exhibitions of works by local and locally born artists that are arrayed around a courtyard.
2 p.m.9. Lunch, Local Style
Another reasonable walk from the museums brings you back to the Condado strip, which has a far sleepier aspect during the day. For dependable classic local fare, the Café del Angel (1106 Avenue Ashford; 787-643-7594) is a stalwart, where you can eat your fill of the indispensable mofongo -- the fried plantain dish that is the mainstay of the local cuisine -- for a reasonable price ($14.95 with crab). The sandwiches are excellent, too, and the décor is, ahem, authentically unglamorous: the most notable fixture in the indoor dining room where we ate was the abuela (grandmother) slumbering away on a chair in the corner during the quiet lunch service.
3 p.m.10. Time Out, with Surf
Exit the urban vibe and slouch onto the sand in Isla Verde, where most of the big hotels are. Happily, you don't have to be staying at one of them to enjoy the surf. The beaches at Carolina are dotted with pale-skinned visitors working on their winter tans, but locals come here too to enjoy the light surf. It's the perfect way to wind down your visit and recharge your batteries.
6 p.m.11. Farewell With a View
End your stay with a drink at the bar and restaurant Mist (2 Tartak Street; waterbeachhotel.com) atop the San Juan Water Beach Club Hotel. There's a skyline pool and a D.J., and oversize white couches that invite mellow reveries of your trip as the sun dips.
In Old San Juan, the Villa Herencia Hotel (23 Las Monjas Street; villaherencia.com), once a haven for nuns, has eight rooms, each handsomely appointed. (A charming touch: bathtubs on the sun deck.) Standard queen from $150.
Water Beach Club Hotel (2 Tartak Street; waterbeachhotel.com), modeled on South Beach boutique style. In winter, rates start at $219.
This article originally appeared in The New York Times.