San Juan

Noted local designer Lisa Cappalli sells her feminine, sensuous designs in this elegant boutique, which specializes in ready-to-wear and custom fashions including a small collection of whimsical, lacy wedding gowns.

Here designer Matilsha Marxuach, who is keen on sustainable fashion, sells her hip line of fair-trade messenger and handbags, as well as bathing suits, vintage clothing, and items made by other local designers.

Puerto Rican couture designer Harry Robles specializes in elegant evening and bridal gowns.

The quality clothing at Monsieur is very sleek and stylish—everything for the well-dressed man.

The window displays are almost as daring as the clothes at this shop, which caters to trendy young ladies looking for party dresses, jumpers, accessories, and shoes.

Otto Bauzá stocks international lines of casual and formal wear for younger men.

Sylma Cabrera sells chic resort wear made of natural fabrics by local artists and under her own label, Pure Soul. You'll also find stunning handmade jewelry with semiprecious stones like quartz and lapis lazuli.

Named for Puerto Rican playwright Alejandro Tapia y Rivera, the island's oldest theater hosts traveling and locally produced theatrical and musical productions. Matinees for families are also held, especially around the holidays.

With ticket counters available in many of the malls on the island, Ticket Center is a convenient way to score seats to most large-scale events.

This outfit makes it fast and easy to purchase tickets online for major concerts, sporting events, and other shows.

Family-run since the 1930s, this store is known for its large selection of pearls and precious stones, as well as for its jewelry design.

With four different theaters, the largest of which holds up to 1,900 people, this is the largest venue of its kind in the Caribbean. There's something going on nearly every night, from pop or jazz concerts to plays, operas, and ballets. It's also the home of the Puerto Rico Symphony Orchestra.

The Cigar House has an eclectic selection of local and imported cigars from Nicaragua, Honduras, and the Dominican Republic. At the lounge and bar, you can enjoy your purchase with a glass of your favorite spirit.

Club Jibarito has a fantastic collection of high-end watches by Audemars Piguet, Chopard, H.Stern, Harry Winston, Panerai, and other designers.

Stylish, upscale handbags for men and women can be purchased at Coach for a discounted price.

Seating up to 18,000 people, this relatively new arena, affectionately known as "El Choliseo," is the top venue for international musical events on the island. Past perfomers have included Ozzy Osbourne, Paul McCartney, Shakira, Beyoncé, and, of course, hometown favorites Ricky Martin and Bad Bunny.

Named after the baseball hall-of-famer, this arena has become an important island venue for concerts and fairs in addition to its status as a sports facility. Rap, reggae, salsa, jazz, and pop musicians play to crowds of up to 8,000 people.

This Old San Juan establishment has been in the Barquet family for four generations, and items from their Coquí el Original line—depicting the local tree frog—have become popular souvenirs. Choose from 14K-gold or sterling-silver coquí pendants, rings, bracelets, and more. If you’re looking for unique and high-end jewels, ask to browse the private back room.

Here the inventory, most of it Indonesian, ranges from bedspreads and furnishings to beaded jewelry and hand fans.

This legendary dive bar won't win any prizes for decor, but it has an irresistibly artsy and welcoming vibe. Add your own message to the graffiti-covered walls—they have a "B.Y.O.S." policy (Bring Your Own Sharpie)—or hang your business card alongside the hundreds that cover the light fixtures. The jukebox has the best selection of oldies in town, and locals crowd the back room for billiards.

At El Galpón, knowledgeable owners Betsy and Gustavo will fit you with a Panama hat ($65–$900), and you'll learn that the genuine article is actually made in Ecuador. They also carry a large selection of Puerto Rican santos, hand-carved wooden saints.

Particularly big acts often use this outdoor stadium (adjacent to the Coliseo Roberto Clemente), which hosts baseball games as well as large concerts. There's seating capacity for at least 18,000, more when the infield is used to accommodate fans.

For nearly three decades, Robert and Sharon Bartos have been selling antiques and objets d'art from all over the world, much of it from Europe.

This multifaceted foundation hosts a variety of events, including Latin music and dance performances and classes. Check the schedule online or call ahead.

This influential gallery displays art by the late Angel Botello, who was hailed as the Caribbean Gauguin as far back as 1943. (His works also hang in the Museo de Arte de Puerto Rico.) His paintings often feature the bright colors of the tropics and usually depict island scenes. Also on display here are works by other prominent local artists, Puerto Rican santos, and sculptures by Botello.

Among those who have displayed their works at Galería Petrus are Dafne Elvira, whose surreal oils and acrylics tease and seduce (witness a woman emerging from a banana peel); Marta Pérez, another surrealist, whose bewitching paintings examine such themes as how life on a coffee plantation might have been; and Elizam Escobar, a former political prisoner whose oils depict typically dark subjects. Exhibitions change frequently and focus on local artists like Bobby Cruz and Carlos Dávila.

This shop carries Haitian masks, statues, paintings, and wooden works of art. The second floor houses a large selection of paintings from the Caribbean.

La Factoría, the former Hijos de Borinquen, is hands-down the best cocktail bar in San Juan. Here, artisanal drinks are crafted with the highest-quality ingredients. Many bitters are homemade, as is the ginger beer, which is used in the popular Lavender Mule. Whether it's sweet, spicy, bitter, or something completely out of the box, these drinks will blow your mind. Behind the bar, there is a secret wooden door that leads to Vino Wine Bar, which has a great speakeasy feel. Tasty tapas are available and can be enjoyed in the adjacent room. These bars stay open till sunup, and a DJ spins in the back room on weekends. Salsa is played on Sunday and Monday. There's no sign on the door, so just look for the terra-cotta building at the corner of San Sebastián and San José.

If you love beer, don't leave Puerto Rico without visiting Lúpulo. At the island's largest craft beer bar you'll find over 25 varieties on tap and more than 100 bottles of the finest European and American brews. This casual hipster bar is open late and a great option for night bites.

You might find a reproduction of your hotel at this shop, which specializes in tiny ceramic versions of San Juan doorways. The works are created by hand in the shop, which also carries fine art prints.

On the roof of the San Juan Water Beach Club Hotel, this sexy spot offers some of Isla Verde's best ocean views. On weekends there's a DJ, and locals pack in to relax at the bar or on the white leather beds. Don't miss the creative cocktails, delicious pizzas, and tasty tapas.

This is a good place to shop for high-quality folk art from around the island. You can also pick up local coffee and other food specialty items like hot sauce.

Aficionados of the famous Panama hat, made from delicately handwoven straw, should stop at Olé. The shop sells top-of-the-line toppers for as much as $1,000, as well as more affordable options that can be custom-fit. Take a few moments to browse the other goods for sale like decades-old santos (hand-carved wood figurines of saints) and used books.

Under the direction of conductor Maximiano Valdés, this 80-member orchestra performs a 52-week season that includes classical music, operas, ballets, and popular music. The orchestra mainly plays at the Centro de Bellas Artes Luis A. Ferré, but they also do outdoor concerts at museums and universities around the island, in addition to educational outreach in island schools. Pablo Casals helped create the group in 1956.

About 15 minutes east of San Juan, you'll find Plaza Carolina, with locals shops, as well as chain stores like Clarks, Forever 21, and T.J. Maxx. Get there via Route 26.

Plaza del Sol has Old Navy, Bed Bath & Beyond, Home Depot, and H&M, among other stores. It's about 30 minutes west of San Juan.

For a complete shopping experience, head to the massive Plaza Las Américas, which has more than 300 retailers, including Zara, Gap, Macy's, Sephora, and Kiehl's, as well as multiple restaurants and movie theaters.

Portofino has an especially good selection of watches.

For one-of-a-kind santos, art, ceramics, and festival masks, head to Puerto Rican Arts & Crafts. All the items are made by local artists.

Ralph Lauren's shop in front of the piers has some of the best deals around. Stop here toward the end of your trip, as there are plenty of items (e.g., peacoats and scarves) that you won't be wearing until you get home.

Reinhold Jewelers sells designs by Stephen Dweck, David Yurman, Tiffany & Co., and others.

The crowd is casual and the decor tropical and bubbly at this spacious gaming room. Right outside, there's a huge bar where Latin musicians perform on weekends, and an adjacent café.

Off Avenida John F. Kennedy, about 15 minutes south of San Juan, San Patricio Plaza has a T.J. Maxx and a Bed Bath & Beyond, a movie theater, and several restaurants. For the best dining in the area, head to Bottles or Avocado.

Kitchen items, cookbooks, jams, spices, and sauces from around the Caribbean are on offer.

Fittingly for a shop named after the Italian word for "sole," the boot-shape country is the origin of many of the mile-high heels that it sells. Look for designs by Christian Louboutin, YSL, Roberto Cavalli, and John Galliano.

The Casals Festival has been bringing some of the most important figures in classical music to San Juan ever since Pablo Casals, the famous cellist, conductor, and composer, started the festival in 1957. Casals went on to direct it until his death in 1973, and it has continued to serve as a vibrant stage for top-notch classical performers since then. Most of the shows are held at the Centro de Bellas Artes Luis A. Ferré, but performances are also at the University of Puerto Rico and other venues. The festival takes place from mid-February through mid-March. Tickets are available at the box office of the Centro de Bellas Artes Luis A. Ferré.

Set in the former headquarters of the Nationalist Party, this contemporary take on a 1920s speakeasy is a chic space that's conducive to sipping a creative cocktail. Tapas are served all day, making this an even more refreshing stop after walking the hills of Old San Juan. Although the Mezzanine is typically closed on Monday, from Tuesday to Friday (4–8) it hosts one of the best happy hours in town, with half-priced select tapas and cocktails. You can't beat that in San Juan! Weekend brunch is also very popular.

This complex in Canóvanas, about 25 minutes east of San Juan, has more than 50 factory outlet stores, including Adidas, Nautica, Guess, Tommy Hilfiger, and Calvin Klein. Those who aren't into shopping can head to the entertainment center, where offerings include kart racing, virtual reality experiences, bowling, and an arcade.