I've been fortunate enough to do a fair share of traveling in my lifetime, especially since I studied abroad in various cities throughout Spain, Italy and Greece. I've found, although major cities are cool and hold a variety of interesting opportunities for tourists, I felt most connected to the smaller cities and towns. This list is comprised of cities I mostly knew nothing about before traveling, and now will never forget.

Here are a few of Europe's most underrated cities and why you should pay them a visit:

1. Segovia, Spain

Only an hour bus ride from Madrid, this hidden gem is perfect for a day trip, or a month trip! Segovia's claim to fame is the nearly 2,000-year-old, 93-foot tall aqueduct that imposingly cuts through one of the city's main squares; however, the Alcàzar de Segovia and Segovia Cathedral are also both stunning, history-rich features worth exploring.

The real beauty of Segovia is in the air. While it is a decent sized city and draws in tourists, the authentic, small-town vibes are what really bring it to life. The winding cobblestone streets and crumbling churches give you the impression you're all on your own, fully immersed in Spanish life -- even if only for a short while.

Pro tip: try their local dessert, Ponche Segoviano, for a sweet and unique marzipan-covered treat.

2. Bruges, Belgium

Bruges would have scored its place on this list based completely on the fact that there's a dog who is known for lounging out of his picturesque ivy-covered window overlooking the canal. However, amazingly, Bruges has even more going for it. Reminiscent of Amsterdam with its plentiful, quaint canals, this small medieval town could be from straight out of a storybook.

Pro-tip: eat the chocolate. Eat lots of chocolate.

3. Siena, Italy

Located in the heart of Tuscany, Siena embodies the classic and homey olive-grove-lined and carb-loaded Italian feeling. Its winding, narrow streets leave little room for cars once inside the medieval city walls, which inspires the hunch that there's always still more to be explored. Siena's Duomo is beautiful and comparable to the one in Florence without the crowds. It has an even more interesting and intricately designed interior.

Siena is also home to the Palio, a semi-annual festival in which the main event is a horse race around the Piazza del Campo between competing contradas, or neighborhoods. Siena embodies Tuscany and holds many treasures waiting to be discovered among its small shops and bars.

Pro-tip: take a trip to nearby San Gimignano for some cool medieval towers and some even cooler (World-Cup winning) gelato.

4. Saint-Malo, France

With a tide-altering landscape similar to Mont-Saint-Michel, Saint-Malo is magical in more ways than one. Beautiful island fortresses dot the rocky coastline and the Saint-Malo Cathedral boasts stained-glass windows more beautiful than even the ones in the Notre Dame Cathedral in Paris.

This small seaside village is perfect for spending a day at the beach collecting sea-glass, exploring a small town with a lot of character or strolling along the stone wall that separates the city from the sea.

Pro-tip: seriously, check out the stained glass in the Cathedral, especially the Rose Window. It's more impressive than it sounds.

5. Thessaloniki, Greece

It's not as iconic as Athens or as picturesque as Santorini, but Thessaloniki has a lot more to offer than meets the eye. Located farther north than most Grecian destinations, Thessaloniki sports a bustling downtown that melds together urban shops, a large, chaotic open-market, chic bars that line the water and crumbling, proud monuments so old they're practically sinking beneath the city, which results from the continuous trend of rebuilding atop earthquake-demolished structures.

Mount Olympus is also within sight of the city -- a relatively short bus-ride lands you at the base of the mountain range. For all lovers of the outdoors, hiking Mount Olympus is definitely meant to be on your bucket list.

Pro-tip: there are a few companies that offer free, half-hour cruises around the shoreline. All you have to do is buy a drink -- definitely a win-win. Do this.