Stumped about the best places to travel? You’re not alone. In the past, it was somewhat easier — especially if your job asked you to go to business events, client meetings, etc. An opportunity to extend that stay. “Bleisure,” as they say, is still quite relevant. But the reasons why we travel for business or personal have been shifting.
What hasn’t changed, at least from my perspective, is that “experiences” truly drive some of our motivations. When we think of best places to travel, these often come to mind:
- Culture
- Outdoor activities
- Food and drink
- Sports, wellness
- Visiting family or old friends
Other factors that can influence both include cost, relaxation and wellbeing, cultural opportunities, timing, leveraging loyalty programs and planning ahead, according to Booking.com for business.
But a more fundamental question remains: Where should you travel? Business travelers have another layer of complexity: Where should I extend my work trip and see the sights?
With this in mind, let’s assess some best places that seem to hit many lists along with three reasons to go to each based on the experiences they offer. Many I’ve made it to, some I still need to go (in alphabetical order):
The capitol of Catalonia situated on the Mediterranean is among Spain’s best places to travel with its artists, architecture and cultural options. Pablo Picasso is one of the most important artists of the 20th century and his family moved to Barcelona when he was 14. Barcelona’s Picasso Museum is one of my favorites. Another artist who influenced modernist architecture (which flourished in the late 19th and early 20th centuries) is Antoni Gaudi. Some of his must-see unconventional spots include Sagrada Familla, Casa Mila and and Park Guell. And the gastronomy in Barcelona is foodie paradise.
Boston, MA
Boston is steeped in history, offers cultural experiences and its culinary experiences. Founded in 1630 by the English Puritans, Boston is synonymous with the American Revolution, but has also established itself as a political, financial and academic hub. Those interested in culture, Boston has a vibrant arts, museums and sports scene. Food lovers can take advantage of its fresh seafood and regional specialties, including its particular focus on clam chowder and lobster rolls (visit the Boston Fish Pier). I visited Boston earlier in my career for work and have only had a chance to return once since then. Definitely on my bucket list to return.
Charleston, SC
Charleston is known for its historic charm, food scene and beautiful architecture, frequently showing up on best travel lists. Charleston is known for its culinary options, including its famous low-country cuisine and French southern options. Discover Charleston’s Colonial, Georgian and Victorian eras through a walking tour and experience the charm of ironwork along its dwellings and copper lantern-lined streets.

© 2015 Rob Hard
Architecture, culture and the food scene. These are some of the top reasons to travel to Chicago — which is also my hometown. Chicago is the birthplace of the skyscraper and the evolution of Chicago reflects a range of building styles. Chicago offers a unique blend of cultural options, from museums to theater to live music (including a vibrant jazz and blues scene). Chicago also have a rich mix of dining options that reflect all ethnicities — go beyond the downtown area and explore authenticity and creative food and drinks in one of Chicago’s 77 neighborhoods.
Denver has experienced tremendous growth in business, travelers and residents. It’s focus on outdoor activities, city and suburban sprawl, Located near the Rocky Mountains, Denver offers easy access to Rocky Mountain National Park (with its 355 miles of hiking trails and lakes). It also allows you to extend your stay or to visit Vail, Copper Mountain and other nearby mountain towns for a mix of adventure and indulgence. It has been a while since I’ve visited Denver — seems worthwhile to return soon.
Dublin offers a rich history and entertainment in one of the most walkable and easily navigated cities I’ve been. Dublin’s story started about 1,000 years old as a small, walled medieval town, and the cobblestone streets still exist. Top activities include a tour of Dublin Castle, National Gallery of Ireland, Kilmainham Gaol (the famous prison that housed many political and military leaders), the Guiness Storehouse, Jameson’s Distillery, St. Stephen’s Green Park, Grafton Street and, of course, nightlife in Temple Bar. The size of Dublin makes it one of the best places to travel and enjoy activities throughout the day. Remember to take in an Irish dance and music show.
Las Vegas is more than the U.S. capital of entertainment, it seems to be the world’s capital for it. One of my favorite cities to escape reality, Las Vegas is a resort city in the middle of the Mojave desert. It appeals culinary delights to every palette, headliner shows, performances, convention space, wedding chapels, swimming pools, spas, shopping, gambling, nightlife — and none of it stops. The Strip and Old Las Vegas both offer unique experiences that you can’t get anywhere else. It’s no wonder it frequently is flagged as a best place to visit.

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London is a cultural, culinary and world class city with plenty to do. It’s a business city, so there are plenty of convention and meeting space options. Key attractions include the London Eye, Tower Bridge, Buckingham Palace, Churchill War Rooms, Westminster Cathedral, boat tours on the river Thames, shopping, theater, sports, gambling, dining and more. One of my most favorite cities, I enjoy walking its many parks, including Green Park and Hyde Park. No doubt, London belongs on the best places to travel lists.
Madrid is a beautiful city. The capitol of Spain, it’s stylish, cultural, green and modern. It’s rich in art — with the Prado Museum, Reina Sofia (home of Picasso’s Guernica) and the Carmen Thyssen-Bornemisza museum (a stunning collection). The old town is an extensive maze of shops and restaurants and political buildings that you must experience. There are plenty of reasons why business events are hosted here, and its hospitality industry is quite cutting edge. I also highly recommend Madrid as one of the best places to travel, and suggest you spend a night or two in the nearby town of Toledo, Spain.
Miami, FL
Miami offers beaches, nightlife and a melting pot of people. But with all this, there are business reasons to visit here, too, including the fact that the weather is incredible between November and March each year (when many meetings and conventions are held). Other reasons to visit Miami include its culinary scene and arts and culture. It stands without comment that Miami offers a vibrant nightlife and stunning art deco historic district. I haven’t had an opportunity to visit (yet), but it’s on my radar for the best places to travel.
Nashville, TN
Nashville has been booming with business and those relocating there. It has been a couple decades since I last went there, but always really it fondly. It has an amazing and best country music scene (more like an entertainment capitol), architecture and foodies love it. The Gaylord Opryland Resort & Convention Center is outside the downtown area, but it’s classic. I need to travel there again.
Nassau, Bahamas
The Bahamas is composed of 16 islands and offers clear blue waters to those who go there by cruise ship or direct flights. It has been a while, but I can say that Paradise Island (home to the Atlantis, which offers gambling) and downtown Nassau are memorable. The water offers many activities, including swimming, diving, sailing and deep sea fishing, among others. To be sure, there are plenty of other hotels and resorts that you can definitely consider for your business trip or getaway.
There’s much more to Orlando than Walt Disney Resort and Universal Studios. Sure, both offer an incredible range of theme park options for anyone visiting. But Orlando is also more than the family trips that sometimes comes to mind. Orlando has been growing its reputation for art and food tourism. New entertainment and shows are getting established there all the time contribute to its reputation for being on the best places to travel lists. I recall attending a major internal training for a former employer of mine there, and the mega hotels are able to handle a large number of people (more than 475 hotels serve the greater Orlando area!). I’ve been back since and need to return again.
San Antonio, TX
San Antonio offers history, the San Antonio River Walk and Tex-Mex cuisine as top reasons to travel here. The Alimo played a key role in the Texas Revolution, and a small group of Texans became the symbol of Texas resistance in 1836. Now it’s a museum and World Heritage site and part of the San Antonio Missions. The San Antonio River Walk stretches 15-miles long and offers restaurants, shopping, parks and more along the way. You’ll find some of the best flavors and fusion of cultural flavors in Texas. San Antonio is one of those many popular cities where a foodie can dive into this cuisine. San Antonio has been called an urban oasis. I haven’t been there yet, but it’s not surprising that it makes the best places to travel lists.
Washington, DC

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Washington, DC is the political hub for the USA and the world. It’s historic, and offers culture and entertainment. Known for its cherry blossoms in the spring, the nation’s capitol offers several cultural experiences for anyone to consider, such as The National Mall, Washington Monument, White House, Smithsonian National Museum of Natural History (which is actually composed of several individual museums) and green spaces, among others. I’ve been there once for a meeting in the travel industry (hearing on flyer’s rights bill) and another time for work. I can vouch that Washington, DC belongs on the best places to travel lists.
Do you have thoughts on these or other places you’ve visited and recommend as being among the best places to travel? Let me know about them. And check back — I will update this list from time to time.
Photo: Almundena, an official guide in Toledo, Spain, gave a thorough overview of the city’s historic past. (c) 2011 Jackie Scheckler Finch.