Budget-Friendly Caribbean Getaways
Escape winter with a sun-drenched trip even farther south—and just because it's high season doesn't mean you have to break the bank.
Start with welcoming locals. Mix in the lush, mountainous terrain fringed with white-sand beaches. Add liberal amounts of rum. Combine with a lilting reggae sound track. And you've found the formula for Jamaica's enduring appeal—nowhere more evident than in Negril.
Getting There: Fly to Sangster International Airport in Montego Bay (MBJ), and take a shared bus about an hour to Negril. (Prices range from $25 to $30 one-way.)
Entry Requirement: Valid Passport
Negril: Check In
While you can't beat the all-inclusive options in terms of convenience, going à la carte at boutique hotel Rockhouse (rockhousehotel.com; rooms from $180) has its perks, including a cluster of thatch-roof cottages, torchlit alfresco dining, and a dramatic cliff's-edge perch above the shimmering water.
Getting Around: If you're staying along the beachfront strip, you can walk almost anywhere you want to go. For trips into town or farther afield, book transport through your hotel. It's around $20 round-trip from the strip to the West End.
Negril: Local Flavor
Start the day with Jamaica's national dish, ackee and saltfish ($12)—a savory fruit sautéed with salted cod, onions, and peppers—at the beachfront IdleAwhile (idleawhile.com). Do not leave the island without tasting Jamaica's iconic beef patty from Hammond's Bakery (876/957-4734). On the strip, straddle a bench at Cosmo's Seafood Restaurant & Bar (876/957-4784), and enjoy a plate of conch with a side of the fried cassava bread called "bammy."
Insider Intel: West End's The Hungry Lion (876/957-4486) pleases veggie palates with meatless main courses, seafood platters, banana fritters, and freshly squeezed juices.
Negril: On the Itinerary
It's all about the sunset here, so don't miss the daily celebration—and a preshow of cliff divers—at legendary Rick's Cafe (rickscafejamaica.com). Island Routes' South Coast River, Rum, and Falls Adventure (islandroutes.com) includes a tour of the Appleton Estate rum distillery, swimming in YS Falls, and a boat cruise along the alligator-infested Black River. It's pricey at $168, but the round-trip taxi fare to Appleton Estate alone would set you back $140.
Negril: Best Beach
Sand-seekers flock to the strip, where bars, resorts, and strolling vendors preside. But for a break (albeit sans sand), head to the West End, where ladders in the rock face lead down to the clearest, bluest sea, perfect for snorkeling or simply floating the day away.
Easily accessible but offering a foreign feel, the capital of our closest Caribbean neighbor has all you need for a quick beach break: glitzy casino resorts, fancy restaurants, duty-free "shopportunities," and the probability of finding a Goombay Smash—the potent national cocktail—wherever you go.
Getting There: Regular direct flights from many Southern cities, including Atlanta, Miami, and Charlotte, to Lynden Pindling International Airport (NAS)
Entry Requirement: Valid passport
Nassau: Check In
Rates at the Comfort Suites on Paradise Island (comfortsuitespi.com; rooms from $279) include access to mega-resort Atlantis' beach, 11 pools, and water park. Your kids (and your wallet) will thank you.
Getting Around: Cabs are easy to find, but Nassau's buses (known as jitneys) are safe, reliable, and inexpensive. The public ferry runs hourly from downtown over to Paradise Island and costs $4 each way.
Nassau: Local Flavor
Conch salad and a bottle of the local brew, Kalik, is a classic pairing that will run you around $10 at Arawak Cay (known to locals as The Fish Fry). Satisfy your sweet tooth at Bahamian Cookin' (bahamiancookin.com), where you can try a guava duff ($4), a steamed jelly roll with guava sauce. Or sample the entire spectrum of local cuisine on Tru Bahamian Food Tours’ three-hour safari to six Nassau eateries, during which you’ll enjoy conch, plantains and rice-and-peas, as well as a healthy serving of local history. $69; trubahamianfoodtours.com
Insider Intel: Tour the 175,000-bottle wine cellar at Graycliff Hotel (graycliff.com) free with the three-course $30 lunch special.
Nassau: On the Itinerary
Join the interactive tour at Graycliff Chocolatier (graycliff.com; $50) to see how the organic chocolates are made, score samples, and then make your own bar of chocolate. Also downtown, the Pirates of Nassau museum (pirates-of-nassau.com; $12) is a fun exhibition detailing the city's history as a colonial-era center of piracy.
Nassau: Best Beach
White-sand beaches abound in Nassau, such as secluded Orange Hill beach or Cabbage Beach (shown here) with its wide, palm-lined strand. Spread your towel on the sands of Orange Hill beach on any weekday and you'll likely have the long strand of sugary sand all to yourself.
San Juan, Puerto Rico
Although it's only a 3½-hour flight from Atlanta, Puerto Rico's diverse culture makes it feel much farther away. Luxury high-rise hotels line San Juan's sandy coast. The dynamic dining scene reflects the city's multicultural roots. And strains of salsa carried on Caribbean breezes convey the island's joyful personality.
Getting There: Regular direct flights from many Southern cities, including Atlanta, Houston, and Charlotte, to San Juan Luis Muñoz Marín International Airport (SJU).
San Juan: Check In
In Old San Juan, the 32-room CasaBlanca Hotel (hotelcasablancapr.com; rooms from $189) features eclectic, souk-inspired style.
Getting Around: Metered cabs are plentiful in the resort areas, but most of the drivers will quote a flat fee ($19 from the airport to Old San Juan), which often works to your advantage. If you're staying in the historic district, just hoof it, but bring comfy shoes to navigate the famous cobblestones.
Insider Intel: There's no sign outside Jose Enrique's eponymous restaurant (joseenriquepr.com), but you'll know it by the crowd on the porch. Order the signature Naturola cocktail and consider your $9 well spent.
Recreation: On the Itinerary
El Morro (nps.gov/saju), San Juan's famous waterfront fort, is an absolute must-see. In Condado, the farmers' market Mercado Urbano at Plaza Ventana al Mar features local fried snacks and crafts. In Cataño, Casa Bacardi's free tour includes a rum cocktail sampling (casabacardi.org).
Best Beach: The balnearios (public beaches) at Isla Verde, El Escambrón, and Ocean Park draw sun-seekers in droves, but for a chilled-out, family-friendly vibe and the calmest waters, head to Playita del Condado, next to the Condado Plaza Hilton.