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Founded in 1521, San Juan is the United States’ oldest city. At turns charming and gritty, the metropolis is the political and cultural capital of Puerto Rico. Historical Old San Juan and the sugary, resort-laden Condado and Isla Verde beachfronts woo visitors—moving away from the sand, urban sprawl and factories dominate.
Diverse and historic, San Juan charms with oceanfront resorts, happening nightlife, and cultural flair – not to mention rum.
$69/nt+: Luxury Puerto Rico beach hotels Major Providers
$75/nt+: Puerto Rico resorts near top beaches Travelocity
$299+: Virgin Islands cruise on Carnival Liberty VacationsToGo.com
$399+: 7-nt exotic sail w/Dominica, Bonaire & Aruba CruisesOnly
$329+: 7-nt December cruise to the Virgin Islands CruisesOnly
$499+: Oceanview Caribbean sail w/Turks & Caicos VacationsToGo.com
Most travelers come for the sand and the casinos and Isla Verde properties cater to both with oceanfront locations and onsite gaming facilities. Those seeking a more intimate beach retreat do better down the road in Ocean Park, where the hotels are smaller and quieter. Old San Juan, though charming, is far from the beach. Prices range from $99 on the low end to $399 on the high end.
At Wind Chimes Inn
WiFi-ready rooms with high-ceilings, tropical motifs and terracotta floors are so charming that you’ll overlook the fact...
Numero Uno Guesthouse
This intimate waterfront property was originally built as a private home in the 1940s. Fourteen comfortable, internet-equipped...
Courtyard Isla Verde Beach Resort
Well situated on Isla Verde, the Courtyard Marriott’s 238 brightly decorated rooms sport free WiFi and ocean or city...
San Juan Water and Beach Club Hotel
Quite possibly the most stylish property in San Juan, this 78-room, Art Deco hotel is kitted with theatrical lighting,...
Hotel El Convento
Nestled in Old San Juan’s center, this former convent and charming getaway has bay views, a rooftop pool, and rooms with...
Ritz Carlton Spa + Casino - San Juan
The 416-room Ritz offers trademark touches like friendly service, Frette linens, and Bulgari bath products. Its oceanfront...
At Wind Chimes Inn
WiFi-ready rooms with high-ceilings, tropical motifs and terracotta floors are so charming that you’ll overlook the fact...
Numero Uno Guesthouse
This intimate waterfront property was originally built as a private home in the 1940s. Fourteen comfortable, internet-equipped...
Courtyard Isla Verde Beach Resort
Well situated on Isla Verde, the Courtyard Marriott’s 238 brightly decorated rooms sport free WiFi and ocean or city...
San Juan Water and Beach Club Hotel
Quite possibly the most stylish property in San Juan, this 78-room, Art Deco hotel is kitted with theatrical lighting,...
Hotel El Convento
Nestled in Old San Juan’s center, this former convent and charming getaway has bay views, a rooftop pool, and rooms with...
Ritz Carlton Spa + Casino - San Juan
The 416-room Ritz offers trademark touches like friendly service, Frette linens, and Bulgari bath products. Its oceanfront...
San Juan Water and Beach Club Hotel
Quite possibly the most stylish property in San Juan, this 78-room, Art Deco hotel is kitted with theatrical lighting,...
Puerto Rico’s many quality international restaurants—everything from Japanese to French—occasionally overshadow the native cuisine—a blend of Taíno, Spanish, and African flavors. Make time to explore both, but don’t expect any discounts. The prices here (entrées average around $18) are on par with those in New York and Los Angeles.
Aguaviva
Chef Roberto Treviño serves up island-fresh seafood, oysters and creative ceviche dishes to a fashion-conscious crowd...
Ajili Mójili
Arched entryways and brick walls recall colonial Puerto Rico in this pseudo-historical building. Try top-quality, traditional...
Trois Cent Onze
It’s easy to overlook this quietly elegant restaurant on bombastic Fortaleza street, but those who stop are rewarded...
Café Berlin
As the name suggests, Café Berlin, with its dark wood interiors, marble tables, and international, vegetarian-friendly...
La Bombonera
Stop by this no-frills Puerto Rican diner at any time of day for traditional island dishes like pork sautéed with...
Pinky's
This local favorite serves up deliciously creative sandwiches and smoothies to nearby sunbathers and surfers (they even...
Aguaviva
Chef Roberto Treviño serves up island-fresh seafood, oysters and creative ceviche dishes to a fashion-conscious crowd...
Ajili Mójili
Arched entryways and brick walls recall colonial Puerto Rico in this pseudo-historical building. Try top-quality, traditional...
Trois Cent Onze
It’s easy to overlook this quietly elegant restaurant on bombastic Fortaleza street, but those who stop are rewarded...
Café Berlin
As the name suggests, Café Berlin, with its dark wood interiors, marble tables, and international, vegetarian-friendly...
La Bombonera
Stop by this no-frills Puerto Rican diner at any time of day for traditional island dishes like pork sautéed with...
Pinky's
This local favorite serves up deliciously creative sandwiches and smoothies to nearby sunbathers and surfers (they even...