The pristine white beaches of Tarifa are just as majestic as the 800-year-old castle that stands proudly in this southern Spanish town. Windsurfing or kitesurfing is an absolute must, and the sea sparkles with the promise of bustling marine life—perfect for enthusiastic scuba divers. At night, Tarifa itself sparkles with bars, nightclubs and tapas bars galore.

Unlike many of its coastal neighbors, cultural tradition remains strong in Estepona. With more than 12 miles (20 kilometers) of palm-fringed coastline and a historic old town famously decorated with bright blooms, this harbor town is undoubtedly one of the prettiest on Spain’s Costa del Sol.

The past runs deep in Cadiz, where cobbled medieval streets spill out into whitewashed Spanish plazas and Roman ruins. As one of Europe’s oldest cities, it has the feel of an urban island, marked almost entirely by beaches and ultramarine harbors dotted with fishing boats.

The Costa del Sol juxtaposes gorgeous Mediterranean old towns and inland national parks with developed beach resorts. Famed for being the birthplace of Picasso, Malaga serves as a gateway to family-favorite stops such as Benidorm and Fuengirola.

Southwest of Seville, Jerez is a well-heeled place. It’s the home of the Royal Andalusian School of Equestrian Art and its famous dancing horses; if you’re on a budget or can’t be there for a formal performance, it’s worth dropping in to catch a morning training session. The other major reason to visit Jerez is to sample its most famous product—sherry. You can do this at a number of bodegas associated with the world’s best-known brands, including Bodegas Tio Pepe, The House of Sandeman, Jerez, and Pedro Domecq. They’ll soon have you knowing your amontillado from your oloroso. There’s also an Alcázar, dating back to the time of the Almohads, which features a small mosque, now the chapel of Santa María Real.

In the chic, sun-drenched Costa del Sol town of Marbella, hints of its former Moorish occupation mingle with modern-day resort amenities. Bask on the sands of famous La Fontanilla beach or ricochet among the area's family-oriented water, wildlife and theme parks. Experience the Andalusian charm of the historic quarter, filled with whitewashed buildings, remnants of a ninth-century Arab fortress and fragrant orange trees. End a relaxing day with a dish of the cold almond soup ajoblanco and some of the region's excellent dessert wine.

While many visitors come for the beaches, arts celebrations and fiestas, San Sebastian-Donostia is serious about its food and drink. The Old Quarter’s narrow, winding streets are full of bars and restaurants, and in the modern city, sidewalk cafes are all around. The city specializes in seafood. Just make sure you know not to expect dinner at 6 or 7 p.m.—that’s much too early in Spain. Instead, tide yourself over with tapas, and enjoy eating and drinking late into the night.

Galas, regattas, the Film Festival and an outrageously attractive and affluent set characterize Cannes. Vast yachts obscure the view and the town lives up to its motto, "Life is a festival." People-watching is the activity that brings most visitors to Cannes, and hotel-lined La Croisette provides a fine promenade. First popularized by Coco Chanel, Cannes beaches are a huge draw. Get expensive seaside food and drinks service on hotel sand or opt for the free public beaches, Plages du Midi and de la Boca.

For visitors, the best thing about Galway is that you can walk everywhere. As soon as you arrive, enjoy a walk through the city streets. There, you'll find lively pubs, independent shops and winding cobblestone streets packed with students, artists, writers and craftspeople. You may even hear Gaelic spoken. For a day trip, take a ferry to the island of Inis Mor. You'll return refreshed by the ocean air and Inis Mor's breathtaking scenery. Oh, and be sure to wear sunscreen on the island, no matter how chilly it is. (Just trust us, okay?)

The capital of Grand Bahama Island, founded in 1955 as a center of tourism, has undergone recent redevelopment and again offers nearly every amenity an island visitor could hope for: pristine beaches, golf, water sports, diving, gambling, duty-free shopping, boating, nightclubs and fishing. Want more? Try the Pirates of the Bahamas theme park, Freeport's International Bazaar, Port Lucaya marketplace, Garden of the Groves botanical garden, the Rand Nature Center or Lucayan National Park.

Kissimmee offers an ideal blend of theme-park thrills, outdoor adventure and unspoiled natural beauty. Find world-famous attractions just minutes away at Walt Disney World, Universal Orlando and SeaWorld Orlando. Continue the adventure with a zipline ride through the treetops, or soar above it all on a hot air balloon ride. Seeking more solitude? Retreat to the headwaters of the Everglades to discover an ecosystem alive with birds, alligators and exotic flora.