15 Underrated Destinations in North America & Caribbean

By: Bruce Yaccato

Let’s face it, some famous places are so famous, it’s impossible to enjoy them anymore. They have become time consuming forced marches through hordes of tourists that kill the charm or grace of even the greatest destinations. As a result, we’ve compiled a list of the most underrated destinations where travelers don’t have to worry about getting caught up in the hustle and bustle of tourist traffic and can take a moment to enjoy the scene. We’ve even likely named a few you’ve never heard of! Although, you better act quick because there are warnings to heed as some of these places are beginning to grow. The New York Times recently noted that the lovely, uncluttered island country of St. Vincent built a $250 million dollar airport with non-stop flights to cities on both sides of the Atlantic. And the largely untouched Yellowstone National Park is even breaking ground and building hotels! On the reverse end of all this construction, a positive trend is emerging, especially among young travelers, it involves an interest in sustainable tourism, away from the destructive environmental footprints of tourist culprits like huge cruise ships. So here is the list of places that deserve more lovin’, respect and interest than they’re getting.

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15. Tulsa, Oklahoma

Beautifully set on the banks of the Arkansas River in the foothills of the Ozarks, Tulsa was the Oil Capital of the World after they hit the first gusher in 1901. The subject of many country songs, the old oil capital has now diversified into technology sectors. It has two highly regarded art museums, plus professional opera and ballet companies. Whether by luck or design, Tulsa’s impressive enclave of Art Deco buildings remained intact and oil money went to renovations and additions. They’re building a whole new waterfront with more museums to come including the Route 66 Experience in honor of the city’s legendary status of the birthplace of one of the world’s most famous highways.

Ffooter / Shutterstock.com
Ffooter / Shutterstock.com

14. Saint Kitts Island, Caribbean

­With its neighbor and sidekick Nevis known as the decadent playground of the idle rich, St. Kitts is looking to go up market from its usual cruise ship fare, as well at the price of some of its informality and unspoiled assets. Entrepreneurs with big plans for huge marinas, big name hotel chains and golf course builders are all passing through the new private jet terminal. A development called Kittitian Hill calls itself an innovative exercise in sustainable living with menus ‘foraged’ from land and sea. They claim Irie Fields is the world’s first edible golf course. ‘Instead of the usual shrubs and trees, you’ll find organic crops and trees bursting with fresh fruit. Smart water management and an abundance of crops will all serve to reduce the course’s environmental impact’. Built on a former marijuana farm, Irie is also an island word for being at peace. Obviously named by someone who has never golfed. But intriguing nonetheless.

St. Kitts

13. Taos Ski Valley, New Mexico

Taos hasn’t rated in the big time ski resort list, but it’s staking its claim. Its underdevelopment has been one of its many charms, but now previously inaccessible expert runs are being opened up, the most notable being Kachina Peak with an elevation of 12,500 feet. Snowmaking capacity has been enhanced. The base village is in the process of upgrades, though cranky traditionalists might call them downgrades. The town itself has maybe 7,000 permanent residents. It is a completely charming place with an artists’ colony and a strong native presence. The simple southwestern food is propelled to great heights by local green chili sauce and access to fresh Pacific seafood not far away. In between skiing seasons, it is a wonderful place for strenuous hiking and sightseeing. The great British author D.H. Lawrence spent some time here in the 1920’s, a testament to the presence of sights and sensibilities that stir the soul. The Times advises ‘visit while it’s still manageable’. Julia Roberts bought a spread here. Consider yourself warned.

Photo by: Kevin Muncie via Flickr
Photo by: Kevin Muncie via Flickr

12. Quebec City, Quebec

They have a brand spanking new arena and a down payment on a National Hockey League franchise to renew their bitter rivalry with Montreal which goes far beyond the ice. So visitors will just have to make do with the UNESCO World Heritage Site’s impeccably preserved 17th century Old Town, gourmet French and Quebecois cooking, alongside some fabulous skiing at Mont Ste Anne and kite-flying on the Plains of Abraham. The Marche de Vieux Port is a foodie flash mob every weekend. Visit Notre Dame de la Victoire, a church built to celebrate an audacious victory over the British in 1642. Have a drink at the bar in the old Chateau Frontenac and enjoy the sumptuous views of the lower St. Lawrence and the Ile d’Orleans. The Winter Carnival is the best and biggest on the continent and the summer music festival is worth a detour as well. The list goes on and on with more enchantment at every turn.

Quebec City

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11. The Catskills, New York

As recently as 2012, travel media were writing the Catskill’s obituary. For half of the 20th century, the Catskills were called The Jewish Alps. The Borscht Belt referred to the food, the clientele and a whole genre of comedy. Superstars like Woody Allen, Joan Rivers and Mel Brooks honed their skills at the legendary Grossinger’s Hotel, entertaining the Jewish clientele who flocked to the resort when many others denied them entry. Now the resurrection is underway with chic boutique hotels, snappy restaurants with uber-style—it has decider Vogue Magazine’s blessing of the Phoenicia Diner and Woodstock Way’s luxurious cabins.

The CatSkills, NY

10. San José del Cabo, Mexico

San José is the more mature, refined sibling of Cabo (Cape) San Lucas. The beaches and ocean is the same, just the people on them are perhaps a bit older and a good deal less hung over. It is joining the ever-growing trend to having more environmentally responsible tourism with Flora Farms, a resort with an organic garden in the foothills of the Sierra de la Laguna Mountains. Try the Farm Julep made with fresh watermelon juice. There is also a level of sophistication to engage the mind as well as the liver. Smart boutique hotels, good restaurants and art galleries showcasing Mexico’s best. This place offers a satisfying all-round vacation with a different far more satisfying version of the all inclusive.

San Jose del Cabo, Mexico

9. San Antonio, Texas

There is so much to see and do in America’s seventh-largest city, San Antonio. With over 20 million people visiting every year the tourist economy is booming. People flock to this city not only to remember Battle of the Alamo­, though they do that too, this famed battle site completely overshadows the city’s other UNESCO World Heritage Site, the San Antonio Missions National Historical Park with the ruins of four Spanish mission churches dating from the early to mid-nineteenth century. The River Walk is a must and recently grew 500% in length to a full 15 miles. It is celebrated in the country’s musical heart. The legendary blues player Robert Johnson recorded here. It is the “Guitar Town”, home of the great singer-songwriter Steve Earle and Lyle Lovett who sings of his love for his ‘San Antonio Girl”.

f11photo / Shutterstock.com
f11photo / Shutterstock.com

8. New Orleans, Louisiana

The year of 2015 is a somber milestone for New Orleans. A decade has passed since the devastation of Katrina. There will be memorials in honor of the victims, but also much pride to show how far the city and its people have bounced back. There are extra helpings of gumbo and jazz at the beautiful brand new venue of the People’s Health New Orleans Jazz Market which was built in dedication to the city’s greatest achievement: the creation of jazz. The South Market has got the resto/condo/boutique treatment, but the city’s unmistakable personality endures. In this time of reflection, go a little more native, beyond the cuisine clichés, a little couche-couche for breakfast, or try some comfort food like rice and beans and the aperitif called the official Cocktail of New Orleans, the Sazerac, named for the cognac that is its base.

Photo by: Bill Staney via Flickr

7. Squamish, British Columbia

The city calls itself “where the oceans meet the mountains”. There is no outdoor adventure activity that can’t be found here – mountain biking, kayaking, white water rafting, wind and kite surfing. It is an acclaimed destination for rock-climbing on the 2000 foot Stawamus Chief mountain which towers 600m (almost 2000 ft) above Squamish, as the 2nd tallest hunk of freestanding granite in the world, after the Rock of Gibraltar. But the most recent addition to attract some of the millions who flock to nearby Whistler is the Sea to Sky Gondola that takes visitors up 3000 feet in 10 minutes to a separate network of high alpine trails to hike and snowshoe. The Gondolas website promises “breathtaking views of the mountains and ocean below”. That is a gross understatement. Each year Squamish plays host to one of North America’s largest convocations of bald eagles who hang out in Squamish during the winter.

Stawamus Chief Mountain

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6. Campeche, México

Campeche has everything. It’s a UNESCO World heritage Site. Nearby Mayan ruins perhaps 3000 years old and jungle biosphere that is also declared a UNESCO World Heritage site. Well preserved Spanish colonial architectures from the 17th century on, some of which have been turned into charming hotels. Not to mention the great seafood! Yet it remains relatively well-know bypassed perhaps for Yucatan’s hyper-popular beaches. The ruins of Calakmul, including the imposing five pyramids lie under the forest canopy teeming with monkeys and toucans. The Times seductively promises visitors “can experience a solitude unthinkable at tourist-clogged Maya sites like Chichén Itzá”.

Campeche Mexico

5. Cleveland, Ohio

Wait let me get my glasses. I thought it said Cleveland. It’s actually true! It’s no longer the ‘Mistake by the Lake’. The city has reconnected to the waterfront with the renovation of the warehouse district, The Gordon Square Arts district has a gaggle of spiffed up theaters – the stage kind. Waterfront warehouses are being transformed and the glassy geometric new home to the Museum of Contemporary Art is the height of sophistication. One wouldn’t expect the iconic symbol of Rust Belt decline to have miles of hiking and biking trails, but it does. And don’t forget the Hall of Fame. Go Cavs.

Cleveland Flats

4. Miami, Florida

South Beach has become the ultimate in North American chic. Loads of celebs, designer hotels and elegant restaurants. It is now larger and if at all possible, becoming more chic. They have hired Norman Foster and Rem Koolhaas, two of the world’s greatest living architects, both winners of the Pritzker Prize, the Nobel Prize of architecture, so this will be something to see. Designer giant Tommy Hilfiger bought the historic Art Deco gem, the Raleigh Hotel which has been famous since it opened in 1940. Did you hear that? It was the sound of a lot of coin being dropped. When future archaeologists find the ruins, they will think it the Versailles of Florida Panhandle, the center of a society dedicated to above all, conspicuous over consumption.

Fotoluminate LLC / Shutterstock.com
Fotoluminate LLC / Shutterstock.com

3. Saint Vincent and the Grenadines, Caribbean

It is everything you could want in a Caribbean getaway. Superlatives like ‘idyllic’ and ‘unspoiled’ are often used. Divers love the coral reefs and Saint Margaret beach is one of the nicest on the planet. There’s not that much to actually do on the tiny country’s 32 islands, unless you’re one of the one per cent who have private islands and hidden mansions. There’s not that much riveting history, architecture of culture really, except for the one that preaches of blissful relaxation in an impossibly beautiful setting. However, they did shell out a quarter of a billion dollars for a new airport with nonstop flights to and from North America and Europe. Might be good to see it before everyone else does.

Saint Vincent and the Grenadines

2. Yellowstone National Park, Wyoming

Yellowstone National Park is the oldest National Park in the United States dating back to 1872. A 500 room lodge is being modernized. A few ‘sustainable’ lodges are opening making the home of Old Faithful a more welcome destination to spend more time in. It is staggering to know that most of the world’s geysers are here. Within the confines of the duty to protect and preserve this treasure, the Park Service is partnering with local nonprofits to responsibly open up the venerable park for both accommodation and exploration. There are new hiking and biking trails. You can take your own snowmobile tour for the first time in over a decade. And veteran visitors swear it is even more spectacular in winter.

Yellowstone National Park

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1. Philadelphia, Pennsylvania

No seriously. It’s a different way to build a city into a popular destination. Sure, there are famous things to see. The Liberty Bell, the Rocky statue on the Library steps.  But there’s not much of the ‘biggest this-’ or ‘oldest that-’. It’s more about creating a very engaging urban space. It’s a very livable, people-friendly functional urban space with European overtones. Which is saying a lot for a city whose previous contributions to American culture were cheese steaks and the most notorious sports fans in the country. There are free yoga classes on the Race Street Pier in the home of hockey’s Broad Street Bullies. Fairmount Park is the largest city park in the United States, bigger even than Central Park, and very runner/rollerblader/cycler friendly. It must be said pockets of shameful poverty remain. But cities in the world without a regrettable blemish are rare. A civilized city to savor.

Philadelphia Pennsylvania

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