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A visit to Tahiti is about more than just chilling on the beach or swimming in a tropical lagoon, although both are possible. It can also be a culturally rich experience, offering visitors an opportunity to learn about Polynesian culture from ancient times to modern day. So whether you want to experience the power of dance or get a tattoo in the place the art form evolved from, Tahiti offers all kinds of cultural immersion.

Three days in San Sebastián leaves just enough time for the city’s essentials. Visit the hallowed bars of the town’s old part, eating, drinking, and repeating until you find your favorite pintxo, those small bites for which San Sebastián is known. Drink in the city’s views from the surrounding mountains, beaches, and islands. Whether hiking or splurging at the seaside spa, a visit to San Sebastián is a lesson in luxurious living.

Montego Bay and the west coast of Jamaica attract first-timers to the island, and it’s easy to see why: white-sand beaches, the most glorious sunsets in Jamaica, plush resorts, a wide variety of restaurants, and a lively music scene. But there’s also plenty to see and do in the west coast interior away from Montego Bay: rivers, cenotes, and waterfalls such as the stunning Mayfield Falls.

Spending two weeks in eastern Jamaica? Start in Port Antonio, head to Boston Bay and Long Bay, and end in the majestic Blue Mountains. Eastern Jamaica offers wide-ranging natural beauty in which to play: Two weeks is plenty of time to swim in secluded coves and walk deserted beaches, hike to jade pools and waterfalls, surf the waves of Boston Bay, explore ruins and forts, raft across the Rio Grande, bike at 7,000 feet, and, of course, sample both original Jamaica jerk and reggae.

The best hotels in Mexico fit well in a country that dazzles visitors with world-class art, museums, and food, but also relaxes even the most harried traveler with its beautiful beaches. Choose from boutique properties in the city, eco-friendly accommodations on the coast, or luxurious spots that offer the ultimate spa experience.

One of my favorite places in the whole world—Vieques! I’m actually a little apprehensive to share, because I’d love to keep it the semi-secret it is. If you time it well, you can have this beach all to yourself.

Nazare, a colorful fishing village, is about 1 hour north of Fatima in Portugal. It is famous for its fishing boats and traditional clothing of its men and women. The boats are gaily painted with upturned prows as they have been since the days of the Phoenicians. The men wear plaid shirts and long stocking caps in which they keep their cigarettes. The women wear the many colored skirts, shirts, vest, and 7 petticoats. The ladies sit outside their homes and entice you to rent their rooms, or they sit under umbrellas on the beach and chat as their salted fish stretched on wooden racks, dry in the sun. Some fishermen sit on the beach and mend their nets, others are out on the sea fishing. Before 1986, the fishing boats were hauled up on the beach by oxen. Today there is a large marina around the corner so you won’t get to see this ancient ritual. But Nazare is still old Portugal. It is charming . The beach and water are very clean and the waves can be a challenge. Surfers love this area with its huge waves. In January, 2013, a Hawaiian surfer rode a 100' wave off the coast of Nazare and broke a record. There are many shops and cafes in the town. Pick up a straw hat or a souvenir doll with her seven petticoats. Enjoy lunch at one of the great seafood restaurants. The choices are consistently fresh and well-prepared. Nazare is a must see for anyone traveling in Portugal. You can take a tour or drive if you have a car. However you get there, you will have a great time.

The 2,000-acre preserve that surrounds this sprawling resort offers enough diversions to keep visitors occupied for weeks. Activity lovers can book a tee time at the Pete Dye-designed golf course, play a game on the hydro-cooled clay tennis courts, or tour the Spanish Water Bay by kayak or stand-up paddleboard. Miles of hiking and biking trails lead to expansive island views and hidden caves, and guides are available to point out local flora and help feed the island iguanas. The resort spa even offers weeklong holistic health and wellness retreats.

If you’re seeking a more low-key vacation, relax on the property’s 1,500-foot stretch of white-sand beach or enjoy a massage overlooking the sea. Restaurant options include open-air fine dining at Shore, Mediterranean dishes and themed buffets at Medi, and the poolside bar and grill Splash, all of which you can visit for daily meals with an all-inclusive package. The downside of the resort’s size is that its location can feel isolated, and guests need a vehicle to dine off-site or explore more of the island.

Hit Seven Mile Beach, a beautiful and—as the name would suggest—long stretch of shoreline to see why it’s one of the Cayman Islands’ most fabled features. Facing out to sea, you’d be forgiven for thinking you were beholding a life-size Rothko installation, with bands of the palest aqua, the richest cobalt and every gradation of blue-green in between. Also keep an eye out for the schools of fish that sprint along the water parallel to the shore.

Here’s your chance to ride on a hands-free Segway, where you can tour the boardwalk on a 30-ft promenade over three miles long. The Hollywood Beach Boardwalk is one of the best beachfront paths. You’ll see all kinds of restaurants, the gorgeous emerald waters of the Atlantic, and plenty of locals. You’ll pass historic hotels, volleyball courts, and shuffleboard players. You’ll hit top speed going north for a full mile. The wind hits your hair as you cruise the intracoastal waterway going south. It’s truly the best way to fly across the boardwalk.

This hotel is on our list of The 11 Best Hotels in Chicago.

Often rated the best hotel in Chicago since it first opened in 2001, the Peninsula Chicago keeps its reputation by offering the finest high-end Chinese cuisine in the city and easily one of the top hotel spas in the Midwest. The Magnificent Mile mainstay has 339 spacious guest rooms and suites, outfitted in an understated style with floral motifs by artist David Qian. Thoughtful details include soaking tubs with hands-free televisions, a table for two set beside a window with a view, and linens custom created by Pratesi.

No stay would be complete without a meal at the Shanghai Terrace, where chef de cuisine Elmo Han earns accolades for his modern interpretations of Shanghainese, Cantonese, and Sichuanese classics. During the warmer months, you can dine (or just have a mocktail) on the actual terrace, the whole of Chicago displayed before you. Also required: an afternoon at the 15,000-square-foot Peninsula Spa, with its floor-to-ceiling windows, facials using Biologique Recherche products, and an Olympic-size pool and sun deck.

Twenty-four hours before check-in, be sure to request “Peninsula Time,” which allows guests to access their rooms as early as 6 a.m. and stay as late as 10 p.m.—a lifesaver for international or early-bird travelers. And eco-conscious travelers take note: The Pen recently received Gold Status from EarthCheck, its second consecutive Gold Status award.

The capital of the state in which it takes its name, Oaxaca is a destination for both art and food. Casa de Las Bugambilias, a bed-and-breakfast inn in Oaxaca’s Centro neighborhood, features locally-made artwork and crafts throughout its rooms. Travelers with more modern tastes might prefer the nearby Azul de Oaxaca Hotel + Galeria, which is housed in an 18th-century building but decorated in modern furnishings. Foodies should stay at Hotel Casa Oaxaca and book a chef-led food tour.

Independent for 1100 years, Venice still looks and feels very distinct from much of Italy. It’s been overrun by tourists, especially cruise lines, but still has so much to offer that it’s well worth spending a few days here. The city is one massive atmospheric experience so stroll far and wide. One note about dining: Venice is overrun by tourist traps. You’ll know them by their plastic coated menus and hawkers. Look for the Slow Food snail icon in the window as a guide to quality.

It’s easy to fill a long weekend with Orlando fun. Spend one day at the Magic Kingdom and Epcot (with some Morimoto and tequila, to insert some adult-pleasing activities to the classic theme park day), of course. Engage in some other local magic, too, like the wildlife of Central Florida with a kayak exploration of the headwaters of the Everglades, or an afternoon viewing the work of Louis Comfort Tiffany at the Hosmer Museum in Winter Park. Try some of Orlando’s food truck fare and sip international vintages at a wine bar. And, if you have some time, get out and explore the charming neighborhoods, up-and-coming restaurants, and boutique shopping in this sprawling and modern metropolis.

Located near the National Constitution Center and Philadelphia’s historic district, Franklin Square is an urban oasis that offers fun family activities. One of the city’s five original town squares, it has evolved into a fairground with both daytime and evening attractions. Highlights include the nostalgic Liberty Carousel, a playground, fountain, and a charming Philly-themed miniature-golf course. Visitors can refuel at the popular SquareBurger restaurant. Special events include a winter holiday festival in December, when more than 50,000 lights illuminate the area. During the festival you can also do some holiday shopping, or kick back with a local brew (there’s also a hot-beverage menu just for kids). The park is open from March through December.