I grew up in one of the best cities in the world, Chicago. For the sake of being unbiased, though, I’ve chosen to omit it from this list. I’ve also mixed it up between large metropolitan areas and less populated places. Here are 5 of my favorites:
Chiang Mai
Chiang Mai, Thailand
The 2nd largest city in Thailand by urban population, and a place that I don’t forget. One of the reasons Chiang Mai is on this list is for the food. Northern Thai food includes some of my favorite dishes. The presence of sticky rice, chili paste, and everything in between is delicious. Even better, the most flavorful Thai salads and smoothies I’ve ever eaten were in Chiang Mai. Quality is prioritized here.
Beyond tasting the gastronomy, there are plenty of things you can do here: visit the beautiful temples, tour ethical elephant sanctuaries (probably bathe and swim with them), explore huge night markets, enjoy the delicious locally grown coffee, experience the nightlife, hike the nearby national park, take cooking classes, learn Thai massage, and more. The energy is great here, which helps you look past some of the overcrowded places and still appreciate them. It’s clean, pleasant, and subtropical, but also kind of in the mountains which gives it a unique feel.
One of the popular things to do from Chiang Mai is to take a day trip to Chiang Rai (home of the white temple), and Pai home of an amazing night street food market and beautiful hills you can ride through on a scooter. They are picturesque places nearby that add to the appeal of Chiang Mai.
The landscape of the particular region of Thailand is gorgeous, mountainous, and lush. Overall, Chiang Mai is a place that isn’t really missing anything. It checks all the boxes. I feel as though the locals, especially the younger generations, are friendly are less Jaded from tourism than people in Bangkok and southern Thailand. It’s also super easy to make friends here. Some of the coolest travelers I’ve ever met, I met here.
Definitely worth a visit!
Side note – Check out the museum, Art In Paradise
New Orleans
Louisiana, USA
My favorite city in the US, besides Chicago of course. This is The Big Easy. It’s a vibrant metropolitan area in the swampy south. I spent 6 months in New Orleans and really had the chance to experience it on a deeper level, volunteering at a ‘haunted’ guest house in the lower garden district, a beautiful green part of the city with huge plantation style houses and old creepy trees. At the guest house I saw a ghost, heard stories of black magic, and was cursed by some witches (all true). Voodoo is very real.
With all that set aside, NOLA has a beautiful culture, mostly known for Mardi Gras, a notorious live music scene (blues and jazz), and unforgettable creole cuisine. The people here too. They remind me of southern New Yorkers in a way – nice big American city with southern hospitality. I recommend learning the history of this unique place by taking a walking tour or some type of ghost tour. It’s fascinating. I loved walking around and seeing the street performers and tarot card readers, going to candy shops, drinking coffee and people watching.
The one thing you MUST do here is eat as much as possible. Creole food, a New Orleans specialty, is a refined, city-based cuisine that blends European, African, Spanish, and Caribbean influences, with a strong French foundation. Ask locals where to go and do your research.
Be sure to visit one the cemeteries, containing above ground tombs. It’s trippy to walk around a cemetery and hear stories of the history. I would consider getting a guide if you want. Also don’t miss touring the French Quarter, and Frenchman street, listening to live bands, going to a New Orleans Saints football game, checking out a farmer’s market for delicious oranges and lemons (citrus fruits are amazing there). If you’re into history, I suggest booking a plantation tour to learn about the former slave trade in Louisiana.
Fun fact, anyone can start their own parade. You just have to do it legally with the city and register.
Ride the street cars and enjoy some alcohol too!
Food recommendations – chef’s special omelette from Camelia Grill, charbroiled oysters from Drago’s seafood, coconut cream donut from District Donuts
Medellin
Antioquia, Colombia
i’ve spent about 9 months in Colombia during 2 separate trips. What a beautiful country. The reason why Medellin is my favorite city in Colombia is the combination of size, history, lifestyle, landscape, weather, public transport, and people. This large metropolitan area has tons to offer.
Let’s start with the people. Colombians from Antioquia in general are very polite and accommodating, which I found to be an attractive element to Medellin. Also, I was thoroughly impressed with the metro. I love to explore random neighborhoods and it was very easy to get around. I never waited more than 5 minutes for a train.
In addition to all of that, the city is esthetically stunning. It’s so green and lush. From the hills to the viewpoints and parks and gardens, it’s just beautiful. The fruits and vegetables you buy are also very fresh and affordable, grown in the nearby fincas. One of my favorite things to do was ride the cable car and overlook the beautiful hills and barrios.
Medellin also has a captivating history of politics, crime, and culture in general, which can be learned through tours and the museums there. For visitors in general, there is a well functioning expat community too, supported by whatsapp groups and many social events. I personally spent a lot of time studying Spanish and I consider this city a great place to learn.
The city of eternal spring has plenty of activities: Tour comuna 13, hike one of the cerros, attend a language exchange, take salsa classes, watch movies outdoors on a projector, take spanish classes, go to a local soccer game, visit museums, walk around Plaza Botero, check out the free art galleries at El Palacio Nacional, rollerblade down steep hills, attend the myriad artistic events, spend an evening at a mirador (viewpoint), take a trip to Guatape, and visit a coffee farm. More importantly though, make an effort to hang out with locals! You can easily meet them at one of the several language exchanges that take place every week.
I also recommend connecting with some type of event website to find out what’s happening in the city. There’s a lot to do!
Unfortunately, there are a lot of “passport bros” that visit strictly for sex tourism and hopes of meeting beautiful Colombian women from Medellin, who are notoriously gorgeous. In turn, I feel like Colombians feeling towards ‘gringos’ has soured a bit. However, I wouldn’t let that deter you from knowing this amazing city.
Hoi An
Quang Nam, Vietnam
Hoi An is a former famous port that developed a lot between the 15th and 19th century, which is displayed in it’s architecture, ranging from Vietnamese, Portuguese, Dutch, Malay, or Indian. It’s a UNESCO heritage site decorated with colonial houses, beautiful lanterns that light up the little city when the sun goes down, well preserved bridges, and many shops, art galleries, and coffee houses. I found myself attracted to this place like a magnet. It’s so unique and chill.
This charming foodie port town still has an authentic feel, with an excellent backpacker scene. It’s fun to just stroll around, look at everything in the old town and appreciate the colonial kind of feel. This is also a great place to dine. I even had the best greek ever here at Mix Greek food restaurant. Consider booking a street food tour as well or going off the beaten path and eating what only locals eat.
For me, coming here inspired me to explore, which is what you should do. Rent a bike or scooter and ride through the rice fields, take a boat ride through Nipa palm forest, see cave temples, ancient ruins, cross the Japanese Bridge and check out the markets, etc. On any night, just walk around and marvel at the unique lanterns that light up the streets and the canals flowing through the city. And you should definitely buy one from one of the shops!
Not to be missed, one of the most unique things to do here is visit Hoi An Silk Village and learn more about the textile industry and weaving techniques. Hoi an is renowned for its tailors and fabric shops. Among male tourists, it’s common to purchase a quality suit for a great price.
I would consider Hoi An a magical place. I hope it stays the same forever.
Playa Del Carmen
Quintana Roo, Mexico
Choosing a 5th city for this list was a difficult decision. These were my options:
- Antigua, Guatemala
- Rio De Janeiro, Brazil
- Mexico City, Mexico
- Playa Del Carmen, Mexico
As you can see, I went with #4, a vacation destination with a population of around 350,000, and one of Latin America’s fastest growing cities. I particularly chose it for it’s walkability, location, transportation, beaches, cenotes, scuba diving, and hot weather.
Playa Del Carmen is totally a touristic beach town, and I have no problem with it at all. It’s centrally located between Cancun and Tulum, in the Riviera Maya, one of the most unique places in the world. The bus transport, specifically ADO, to and from other destinations along the coast is very well run, and extremely convenient. It’s super easy to visit cool places like Bacalar, Akumal, Isla Holbox, and every other place in the state of Quintana Roo.
Another reason I love PDC is it’s cheaper than Tulum and Cancun, more authentic, and less trashy. I particularly love the fact that the downtown area is so concentrated and lively, but just a 15 minute walk and you’re in a quiet residential street. It’s both family friendly and adult friendly, catering to visitors very well, including digital nomads and backpackers that want to chill in one place for a while. Everything I needed was in walking distance. Now to the good part.
The best thing you can do here is take a scuba diving course and dive in the crystal clear warm waters of Cozumel, which is full of life, or dive in one of the thousands of cenotes (underwater caves) that are just mind blowing sometimes. Don’t pass up the opportunity if you want do it! I personally dove with Good Vibes Diving and I’d highly recommend them. If you’re just here to dive, that’s good enough. But….
Some other things I suggest you going to Playacar beach, swimming/snorkeling in cenotes, visiting the Mayan Ruins of Chichen Itza, buying Mexican silver, Checking out Coco Bongo for a fun show, finding some jungle parties, or just chilling and enjoying life. Accomodation near the beach is affordable, and hostels are up to par. I even had an airbnb for a month and used to feed a Coati that lived in the tree next door.
PDC is really solid on many levels and I will be visiting again for sure.







