Jinny Oh asked on Trippy’s Q and A platform:

What are some underrated cities you’ve visited?

There are a handful of places I’ve been that I did not think I would enjoy like Seoul, Korea or Chicago, Illinois. However, when I visited these places, I found myself visiting more than once because they were simply amazing and totally underrated.
What are some places you’ve been that you thought weren’t going to be that great, but ended up being totally amazing?

Whether we deem a city as overrated or underrated depends on our travel expectations and travel style. Prior experiences and lifestyles also shape the way we perceive places and countries.

I found that out on my recent Europe trip covering 7 cities.

Prior to visiting, I heard numerous positive anecdotes about Vienna. My sister had visited twice already. By the time I left home for Vienna, in my mind’s eye, the city was a place with top class classical concerts, friendly people and rich Sachertorte (chocolate cake). Reality told a different story and experience in Vienna could be summed up by one negative experience: being hurled the F-word by a man dressed up in a Mozart costume.

Here’s the backstory: I had just arrived in Vienna and dropped off my bags at the hotel. The plan was to visit the State Opera House and possibly buy concert tickets for the night. The official ticket office didn’t sell any tickets for that day, but there were numerous unofficial vendors with folders selling tickets just outside. After being hassled to buy “tickets” from the man in the Mozart costume, I refused. He wasn’t amused, and the verbal barrage ensued.

My Vienna experience went downhill from there – even the Sachertorte didn’t taste right. I had placed Vienna on the top of my travel bucket list and thought I would enjoy it immensely. The truth is I left Vienna and marked it as an overrated city. However, I thoroughly enjoyed cities that I added to my itinerary at the last minute of our tour, which I had no prior knowledge of, or expectations for, like the underrated Bratislava and Vaduz.

To answer Jinny’s questions here are 11 of the most underrated cities in the world according to well-traveled Trippy members and from my travel experiences:

1. Fredericksburg and the Texas Hill Country

I agree with Trippy user Lindsey Silva about Fredericksburg and the Texas Hill Country where you don’t have to travel far to taste a German or Mexican food, drink beer and visit the wineries. She wrote:

… if anyone comes to Texas, they absolutely should not miss the Texas hill country. Southwest of Austin, northwest of San Antonio lies rolling hills, limestone and granite outcroppings, emerald-green and totally clear streams lined by towering cypress trees, and German/TexMex-inspired foods (think jalapeno bratwurst) and original German architecture. There are TONS of vineyards, wineries, distilleries and breweries, plus some killer biking routes (even though I’m not into biking) and tons of scenic drives, and the small towns have a lot of Texas character and friendliness.

And of course, I’d be remiss not to include Fredericksburg (Texas), as any guidebook of the Texas hill country would say that you need to visit it. Enchanted Rock is worth seeing (IF you get there early enough before the crowds set in), all of the surrounding vineyards and wineries are great, and Main Street is adorable and full of character. But my two recommendations for visiting Fredericksburg are to go to Hondo’s On Main for a VERY alcoholic jalapeno margarita, and Hilltop Café for a non-touristy, very excellent (albeit somewhat pricey) meal.

The good news is Fredericksburg is only 80 miles from Austin. You can combine your visit to Austin, Fredericksburg and the Texas Hill Country.

2. Roanoke and the Virginia Blue Ridge

Named the All-American City, America’s Most Livable Communities, and a top Digital City, Roanoke is also the gateway to the Virginia Blue Ridge and the Allegheny Mountains. Roanoke is known as the “Capital of the Blue Ridge” and has a railroad history that dates to 1852.

Roanoke has a small town feel but big city amenities and attractions. It caters to adventure travelers, history buffs, food enthusiasts and train enthusiasts. The Virginia Museum of Transportation in downtown Roanoke is in an over 100-year-old freight station and has an extensive collection of steam, diesel, electric locomotives, and other rail cars. See Norfolk & Western Class J 611 and Class A 1218, two of the most advanced steam locomotives ever built.

3. Belgrade

Joshua Moody-Arndt from South Africa wrote:

I enjoyed Belgrade. It’s great to explore because many things are hidden, leading to lots of opportunities to stumble upon not-so-obvious cafes and street art on random street corners. There’s also hearty, but cheap food and many hospitable people.

Belgrade is the largest city in Serbia, located at the confluence of the Danube and Sava rivers. It was the capital of the former Yugoslavia. If you love coffee, you’ll love Belgrade because coffee has been the most important drink in the city since 1522.

Bratislava – Blue Church

4. Bratislava

Bratislava is the capital city of Slovakia, the other half of the former Czechoslovakia. Sandwiched between two vastly popular cities – Vienna and Budapest, Bratislava is only 50 miles from Vienna and 126 miles from Budapest.

Danish writer Han Christian Andersen remarked on Bratislava in 1841:

If you want a fairy-tale, then just look at your city, it is a fairytale itself.

Bratislava had everything I wanted to see in a European city – a historic town center, castles, friendly people, good cafés and pubs, authentic food and walkable streets. Most of all it isn’t crowded. Prague received over 28 million tourists in 2015, while the whole country of Slovakia (including Bratislava) had just over 5 million in 2016.

It’s a city waiting to be discovered. My sisters and I took a private tour with Peter Blazicek of Best Slovakia Tours.

5. Tbilisi

Trippy member Sam Lockhart from Auckland said:

Tbilisi. Easily one of the most underrated cities! It’s so historical (first Christian churches are in Georgia!) and beautiful. Not to mention inexpensive and the food is to die for. It’s a perfect blend of western and eastern cultures.

Tbilisi is the capital city of Georgia, a country that was part of the former Soviet Union. Tbilisi was one of the stops on the historic Silk Road leaving traces of Eastern influence amidst churches and ancient fortresses.

6. Toledo, Spain

Move over Madrid and Barcelona, because according to Trippy member Peter Dorfman there is Toledo. He said:

I don’t know whether Toledo is underrated, but before deciding to go there, I’d noticed that James Michener, in his book “Iberia,” was down on it — he described it as noisy and dirty and unpleasant. So much for Michener (generally a lousy, uninsightful writer in my opinion). Toledo is wonderful, with a truly medieval ambiance, magnificent views and what was, at least when I visited, a great Parador (Parador de Toledo).

Toledo is close to Madrid. Trippy user Deborah Boughner from Toronto said:

Toledo is very close to Madrid and trains go every 30 minutes. You can take a taxi or airport shuttle to Atoch train station then get the train from there. The journey only takes 30 minutes. No need to prebook tickets as they are just commuter trains. However if you have alot of luggage you may be more comfortable taking a taxi straight there from the airport. There is a great app you can use called Cabify. Disfruta!

Montevideo – Palacio Salvo

7. Montevideo

Montevideo, the capital city of Uruguay, is often overshadowed by Buenos Aires. I spent two months in Montevideo, and I would highly recommend the city to anyone looking for a peaceful city with beaches, a historic town center, high-quality beef, football (soccer) games and friendly locals.

Daily ferry services are available between Montevideo and Buenos Aires. It takes only three hours to travel between both cities.

8. Quito

Most travelers to Ecuador bypass Quito or stay in Quito only for a day before venturing to the Galapagos. You’re missing out if you don’t stay for at least two days in the capital city of Ecuador. I’d visited Quito twice (a duration of seven days) and have yet to see all the city has to offer including many of the main attractions.

Trippy user Lekshmi Nair highly recommended Quito. She wrote:

I have to mention Quito as it was a pleasant surprise on my stopover to Galapagos. I ended up going back to spend more time in and around Quito. Very picturesque, set in a valley at around 10000 ft elevation, and surrounded by snow-capped volcanoes.

Here are the recommended things to do while in Quito per Scott Mahaffy from Fort Collins if you have just two days:

I would recommend either a taxi ride up to Panecillo to for views of the Virgin Mary statue and great, sweeping views over Quito. Stop into the restaurant, just below the statue, for a cocktail. The food was OK, but the drink, and views were a nice experience. If the weather cooperates, take the Teleferico cable car. Unfortunately, there was a low cloud deck, so we were unable to do this on our trip. I would spend at least a half day in Old Quito and take in the San Francisco Church, and some of the shops in and around the square. There is a fantastic shop just to the right of Iglesia de San Francisco with lots of Ecuadorian hand made crafts. It’s kind of cave/maze like and is really enjoyable to walk through. We found a few items for purchase there that we really enjoy. If you want to take a day trip, Otavalo Market is a good choice. By far the best meal we had was at Zazu. I would also suggest a stroll through El Ejido Park, where there should be numerous local vendors out selling their wares. Have a great time there and enjoy the Galapagos. One of my favorite travel experiences. Hope that helps and safe travels!

I would add La Compania de Jesus, the gold-studded baroque church in Old Town Quito and the Presidential Palace (Palacio del Gobierno).


9. Medellin

Trippy user Amanda Kingsmith from Canada wrote:

Medellín in Colombia is definitely an underrated city. Actually, Colombia as a whole is underrated. This country rocks! Medellin is modern, and the El Poblado area is a great place for tourists and backpackers to stay. They have a plethora of hostels, coffee shops, and restaurants to choose from, as well as many bars. There are also multiple yoga studios there… awesome! In and around Medellin, there are lots of great hikes and areas to enjoy nature in. Medellin can offer something for everyone, and after spending a week there, I would most definitely go back for longer.

Medellin, once dubbed the world’s most dangerous city is now one of the most sought after retirement havens because of its year-round spring-like weather. Located in the valley of the central and western ranges of the Andes Mountains, Medellin has beautiful parks, cultural events, and good food at affordable prices.

10. Ipoh, Malaysia

Ipoh is situated between Kuala Lumpur (the capital city of Malaysia) and Penang (an island paradise). It has been under the radar for years, and it is time to discover this city for its history, food, coffee and street art.

Take a 30-minute walking tour to see the street art created by Lithuanian street artist Ernest Zacharevic in collaboration with the local Old Town White Coffee company. The street art can be seen along Market Street, Jalan Bijeh Timah, Jalan Tun Sambanthan and Jalan Padang.

Wellington – Cable car

11. Wellington

New Zealand’s capital city Wellington is at the southern end of North Island and a three-hour ferry ride from Picton, the northern-most town in South Island. Lonely Planet called it “The Coolest Capital City in the World” and rightfully so.

The city with a sparkling harbor, rolling hills, and lots of green spaces is also home to many museums and art galleries showcasing Kiwi and international artwork. Rob McQueen from Los Angeles wrote:

Personally, I just love Cuba St, Wellington’s famous inner city slice of bohemia, Cuba Street, is a place with culinary and creative soul. It’s where people meet, busk, shop, dine and the best place in town to soak up the capital of cool’s culture. The street has been a registered Historic Area under the Historic Places Act since 1995.” From the Wellington website.

It’s one seriously cool street with plenty to do, the food is especially fantastic. Check out El Matador – Cafe, Asador Grill & Bar for beautiful Argentine tapas, wines, and steaks!

Also, head over to Mexico Wellington at 41 Dixon Street, name drop me to Chris Dobson, the manager, he’ll look after you. He’s one of my closest friends in New Zealand and makes fantastic cocktails!
Have fun!

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Photos and article by Claudia Looi

Mentioned in this post
  1. Vienna
    City in Austria

    Vienna Austria
  2. Fredericksburg (Texas)
    City in Texas

    Gillespie Texas
  3. Austin
    City in Texas

    Austin Texas
  4. Roanoke
    City in Virginia

    Roanoke Virginia
  5. Belgrade
    City in Serbia

    Belgrade Serbia
  6. Serbia

  7. Budapest
    City in Hungary

    Budapest Hungary
  8. Bratislava
    City in Slovakia

    Bratislava Slovakia
  9. Tbilisi
    City in Georgia

    Tbilisi Georgia
  10. Toledo
    City in Spain

    Toledo Spain
  11. Madrid
    City in Spain

    Madrid Spain
  12. Montevideo Dept
    State in Uruguay

  13. Uruguay

  14. Buenos Aires
    City in Argentina

    Buenos Aires Argentina
  15. Quito
    City in Ecuador

    Quito Ecuador
  16. Medellín
    Medellin Colombia

    Medellin Colombia
  17. Colombia

  18. Ipoh
    City in Malaysia

    Ipoh Malaysia
  19. Kuala Lumpur
    City in Malaysia

    Kuala Lumpur Malaysia
  20. Penang
    City in Malaysia

    Penang Malaysia
  21. Wellington
    City in New Zealand

    Wellington New Zealand
  22. Picton
    City in New Zealand

    Picton New Zealand