16-Nights Central America Escape: Guatemala to Costa Rica - Classic from $1,259

Founded on the shore of Lake Nicaragua in 1524 by Francisco Fernandez de Cordoba, Granada, Nicaragua, is the nation's oldest city, one of the oldest cities in the New World and foremost attraction for tourists from around the world.

Granada is the cleaner, better renovated and grander of Nicaragua's two colonial towns (the other being Leon). It's also superbly situated at the base of Mombacho Volcano and along the northern shore of huge Lake Nicaragua. It's also located within one hour of several noteworthy excursions to volcanoes, crater lakes, artisan villages, nature reserves and the nearby cities of Managua and Masaya. Thus, Granada makes a great base for visiting many of Nicaragua's main attractions.

Granada has two main streets, divided in their centers with greenery: Calle la Calzada leads from the main plaza and cathedral down to the lake's edge. For several blocks near the plaza it is lined by upscale restaurants, cafes, bars and shops. This is one of two major nightlife areas in town. Calle Real Xalteva heads west from La Merced Church uphill to Fortaleza de Polvora, passing upscale shops, two significant churches and a lovely park full of stone columns and greenery.

Located in northwestern Nicaragua, about 90 minutes northwest of the capital city, Managua, and just 12 mi/20 km from Pacific coast beaches, Leon, Nicaragua, was first established in 1524, though it was destroyed in an earthquake in 1610 and rebuilt in a different spot. To the north and east of Leon are several prominent volcanoes.

Leon served as the capital of Nicaragua throughout most of the Spanish colonial period until 1857 and was the center of politics, education, culture and religion. As a result, the Spanish built many grand government buildings, Catholic churches and city blocks full of smaller colonial buildings. Thousands of original colonial buildings fill the city—many have been restored and others are still undergoing restoration.

Universidad Nacional Autonomo de Nicaragua (UNAN), Nicaragua's first and most important university, is located on a huge leafy campus just south of the city center. Today, the city has a large university population and is considered the intellectual capital of Nicaragua. Long Nicaragua's liberal hub, Leon was one of the strongholds of the anti-Somoza forces during the revolution. The Sandinistas still remain a powerful force in the city.

For a glimpse of Leon's revolutionary spirit, visit the monument to the "Martyrs of the Revolution" across from the cathedral, where a fascinating mural portrays the history of Nicaragua, from pre-Columbian times through the present. Other colorful murals can be seen throughout the city, along with pro-Sandinista graffiti.

One of the city's greatest attractions is its spirited street life: Mariachi bands and marimba players often stroll the streets. Children often go door to door with 10-ft-/3-m-tall puppets, reciting humorous poetry and beating on drums and trash-can covers. One fun way to observe the activity is to take a ride on the inexpensive open bus that cruises the city on warm nights.

Situated some 25 mi/40 km southwest of San Salvador, the Pacific coast resort of La Libertad, El Salvador, offers some of the world's best surfing. Consequently, it is packed with city dwellers on weekends. A short distance west is Zunzal, where international surfing competitions are held.

But the big waves are not for novices, and beware of strong undertows when swimming—the beaches are not protected from the huge Pacific swells.

There's a pier on the black-sand beach, and good seafood is available in local restaurants.

Note: Exercise caution when visiting La Libertad and the surrounding area: There has been a high incidence of assaults and robberies. Avoid walking around town after dark. Surfers have also experienced problems with crime on the beach.

Founded in 1543, Santiago de Guatemala (now known as La Antigua Guatemala, or simply Antigua) was the capital of Spain's Central American confederacy and the fourth most important city in the Americas (after Mexico City, Lima and Zacatecas) in the 1500s.

Antigua was devastated by an earthquake in 1773, which, combined with damage from earlier earthquakes, persuaded the government to relocate the capital to the site of present-day Guatemala City. That seeming misfortune turned out to be a blessing in disguise.

Isolation and longtime neglect served Antigua well. More than two centuries of underdevelopment left the town with a treasure trove of dilapidated but historical structures, many of which have been rehabilitated into chic restaurants, shops and hotels.

Antigua can be seen on a day's excursion from Guatemala City, which is 28 mi/45 km to the east, but it deserves more time. Some visitors prefer to use this colonial gem as their base for touring the country (instead of the capital). It has a large English-speaking community, a wide range of accommodations, upscale and medium-priced restaurants, espresso bars, delicious baked goods, literally dozens of language schools, plenty of galleries, and for nightlife, jazz clubs and discos.

Antigua is also one of the best places to go in Guatemala if you want to learn to speak Spanish. About 75 schools in town offer intensive classes. But be sure to check ahead of time to know exactly what you'll get, as not all of these schools are on the up-and-up. Some courses include lodging with Guatemalan families.

Visitors also can study various arts and crafts (backstrap weaving, drawing, painting, ceramics, photography and so forth) at the Art Workshops in La Antigua Guatemala. It's not a fully Guatemalan experience, however, as a group of U.S. for-profit artists operates those workshops, not the Guatemalans themselves.