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Chris Colin experiences a Caribbean paradise from both sides of a resort’s walls.

In the country’s wine region, you can pick grapes, sing songs, and keep ancient harvest traditions alive. It’s so much fun, you can taste it.

In a square mile of West Texas, Chris Colin finds family and traces his roots back to a wilder America.

Whether you wander by boat, bike, or tuk tuk (or, highly recommended, a combo of all three), Bangkok spills over with places both new and very old to explore. Along the way, modern-day wonders rub shoulders with traditional Thai culture. Hop from the floating market to a day cruise on the Chao Phraya River to a cocktail at one of the city’s innovative bars. Make meals of tastes from street food vendors and mix in some table service at some of the city’s most renowned restaurants. Overwhelmed by all the options? Stop for a Thai massage. Need souvenirs? The weekend market awaits.

Toast your vacation at one of Maui’s many bars, which range from dives to rooftop lounges to thatched huts serving Champagne. Soak up the sun at Hula Grill or Leilani’s on Kāʻanapali Beach, then retire to spots like the island’s oldest bar, the Pioneer Inn, or Monkeypod Kitchen, which serves cocktails by the legendary Peter Merriman, a leader of Hawaii Regional Cuisine. End the night with dancing into the wee hours at local favorite South Shore Tiki Lounge.

With options ranging from fine French cuisine served in white-cloth dining rooms to local joints dishing out classic muffulettas or po’boys, and pouring perfect Sazeracs, New Orleans offers your mouth the makings of a great vacation.

The Spirit of Istanbul

Finding a charming alpine town snug at the base of Whistler and Blackcomb mountains may make skiers, hikers, and lovers of beauty feel like they’re having a fever dream, but the dream is real. Whether you come in winter for the world-class downhill skiing and snowboarding, or in summer for mountain biking, hiking, gallery-hopping, and long evenings spent on restaurant decks, you’ve found Whistler Village, one of the jewels of British Columbia.

This archipelago of more than 700 islands, most ringed with pink sand beaches and crystal-clear shallow water, offers diversions above and below the water: diving into shipwrecks, touring rum distilleries, exploring the architectural relics of British colonial rule, dancing at a fish fry, and shopping the boutiques of Harbour Island, among them. Find luxury—and simplicity—in your Bahamas vacation.

Lake Mary is as bike-friendly as a city can be. Throughout the day—especially on the weekends—locals and bikers from neighboring cities can be found out and about getting exercise or enjoying a leisurely and scenic ride. Alongside the bikers on the path are rollerbladers and walkers. The Lake Mary stretch of the Cross Seminole Trail is about four miles, and runs parallel to the residential Rinehart Road. Tip: A good place to park your bike and take a break is behind Panera or Peach Valley Cafe on International Parkway and Lake Mary Boulevard. This is also the prettiest portion of the trail, with pastoral scenery away from traffic.

A writer seeks out the disappearing workshops that have been the source of elegance in Naples for generations.

Tom Blake Trail is a beginning-to-intermediate trail for hikers and mountain bikers. Located on the lower side of Snowmass’s Burnt Mountain, bikers zip through groves of Aspen trees on a single trail with the sunlight flickering through the leaves. Pick up the trail in either two spots: near Owl Creek or follow the Snowmass Gondola up Assay Hill, and just after the mid-station on the left is an opening in the trees. This is the first mountain bike ride I ever took and it was an unforgettable experience—it’s just hard enough to challenge you but easy enough to gain your confidence as a rider.

The islands off the coast of Panamá—white-sand beaches, hammocks rocking between palm trees, clear emerald waves lapping the shore—are the stuff of vacation fantasies but, in truth, are dangerously close to your reality. Head offshore and take off your shoes. You’ve discovered the undiscovered.

You can take your rented bike and pedal down to a waiting Zipcar and get out of town. From the mountains to the coast—and everything in between—you’ll enjoy an easy break from the urban outlook, usually with an hour of driving, or less.

Fish fanatics beware: vacation in Turks and Caicos and there’s a good chance you’ll start dreaming about living on the islands forever. Conch and grouper are often the stars of the menus so you’ll have plenty of chances to try them served all kinds of ways. But, really, chance up your order a bit here and there. After all, there’s a lot to be said for a lobster dinner at a fine dining restaurant overlooking the water or for hanging out at the touristy but fun Thursday-night fish fry off of Grace Bay Beach.