Five Ways to Find New Adventures

We’ve all been there—excited to explore a new city but craving experiences that go beyond the typical tourist attractions. You’re a traveler, not just a tourist, right? At the very least, you’re hoping that your adventures feel authentic and some of them are off the beaten path.

If you’re looking for unique things to do in a new city or want to avoid the most popular (and often crowded) landmarks, these are a few of my favorite travel tips. They’ll help you discover hidden gems, local hotspots, and unforgettable experiences that won’t be found on every top-10 list.

1. Read a Book

No, I’m not talking about reading another travel guide. But I am talking about reading a book set in a city you’d want to (or are preparing to) visit.

One of my favorite examples of this is John Berendt’s book, City of Falling Angels, set in Venice, Italy. Most folks would recognize the author for his better known story Midnight in the Garden of Good and Evil (spoiler: Midnight is a better read, but there are literally organized tours of its key sites in Savannah, Ga.). For me; however, City of Falling Angels served as a great tour guide for Venice. Keep in mind, the book was published in 2005 (and I was last in Venice in ‘08), so proceed accordingly if you’re using it for adventures today.

Regardless of when the book was published, it serves as a good example that the story helped me find places I might not have otherwise gone, especially the story’s focal point: Gran Teatro La Fenice. The Teatro, or Opera House, is a short distance from St. Mark’s Square, but tucked away where many travelers might not end up (side note: the Ponte Maria Callas a block away was reportedly a location shot for Moonraker, the 1979 James Bond film).

Also in Venice, and in City of Falling Angels, is the Peggy Guggenheim Collection. This museum is a quirky, sometimes off-color collection from its’ namesake and a few others. It’s not far from other museums, but is smaller and perhaps not as well known.

For a glimpse into a seedier underbelly of a city, check out Chuck Palahnuik’s Fugitives and Refugees: A Walk in Portland, Oregon. Fugitives was published in 2003, when the Publisher’s Weekly framed it this way: “Written as much for first-time visitors as for those who already share Palahniuk’s passion for the city….Palahniuk’s fondness for his not-so-sleepy hamlet comes through in each gritty detail…” Things have changed a bit in 20 years, but much of it is still relevant, not to mention being fascinating offbeat history. It’s also part of the 7-book, 7 city Crown Journeys series from a variety of authors, so you need not limit your exploration to Portland.

Sarah Vowell is arguably one of my favorite authors. I love her dry, pithy humor, and I love learning off-beat and lesser-known parts of history from her books. While I’ve done less exploration to date based on her stories, kayaking across Kealakekua Bay to Captain James Cook Monument was especially interesting after reading about Cook in Vowell’s book, Unfamiliar Fishes. And I’d love to explore New England to follow her adventures in Assassination Vacation (minus the Bed and Breakfast – read the book and you’ll understand).

2. Go for a Brewski

It doesn’t really need to be a beer. Go for wine. Or tea. Or coffee. Or restaurants. You name it. But using the best of whatever your flavor is can help to map spots to check out that aren’t in an immediate vicinity you might otherwise explore.

Beer comes readily to mind for me given the proliferation of breweries and brewpubs across the U.S. My hometown of Ft. Collins, Colorado, and my adopted hometown of Portland, Oregon couldn’t be better examples, but we’ve put the same tactic to good use in Austin, Bogota, Minneapolis, Orlando, Tel Aviv and Vancouver, just to name a few.

As for Fort Collins, if you’re a beer aficionado, it would be a shame to miss taproom-only brews in New Belgium and O’Dell Brewing in Ft. Collins (or Denver). Both are just outside Old Town (where you’ll find other great breweries!) and as you make your way across the Cache La Poudre River, you can stroll along the riverfront path and across the pedestrian bridges. And even if you’re not a beer fan, both breweries feature live music regularly as well as great local eats courtesy of on-site food trucks. Or you could just pull up a stool at Mayor of Old Town after grabbing a bite across the street at Avogadro’s Number, a longtime hangout for CSU students and others.

If you’re in Portland, there are just as many beer options (if not more), but don’t miss out on the distilleries, either. Ft. Collins has those too, but Portand has its Distillery Row Passport—a sweet collection of many of the Rose City’s finest booze producers. Do NOT try to do them all in a weekend, but do use them as an excuse to wander into a variety of neighborhoods where you’ll also find great shops, eats, and other experiences.

I’ve mapped a number of breweries in several cities I’ve visited (but note that inclusion doesn’t mean endorsement, just that I’d pinned them on the map). Feel free to use my maps as a starting point if it’s helpful.

3. Expose Yourself to Art

Y’all, this one is tongue in cheek. Do NOT take this as permission to indulge your streaker fantasies. Good grief.

Museums are great too but that’s not what we’re here to talk about today. What we are here to talk about is public art.

I recently inserted myself in a discussion about public art in Chicago versus New York. Spoiler: they’re both pretty great (though the other parties of the discussion may not have agreed on this). But I think both folks in the previously-mentioned discussion would agree that public art in one city is different than another—and exploring it will take you to a variety of neighborhoods of each city you may not have had on your map otherwise.

In Chicago, Millenium Park is the obvious destination, but don’t stop at The Bean. The rest of the park is full of art. Check out the Crown Fountain, Boeing Galleries, and all the other exhibits. Alexander Calder’s “Flamingo” is another beautiful one, especially with the backdrop of Mies van der Rohe’s buildings. In fact, Chicago’s architecture is sometimes its best art.

In New York, one of my favorite explorations was to map out publicly-viewable art by Keith Haring. It wasn’t as, well … public as the art I sought out in Chicago, but it was a great way to have a pre-made map to explore wildly different neighborhoods in the city.

In Portland, I’ve traversed the city checking out Lee Kelly’s sculptures. They’re scatted throughout the city (and beyond) so a map of his art will take you all over Portland.

And street art is just as remarkable. In Barranquilla, Cartagena, and especially Medellin, Colombia, the cities’ vibrant street art helped me find some neighborhoods I would have never explored otherwise (in Barranquilla, some locals kindly re-directed us when we got near some areas that were a little less desirable). But street art is everywhere too: St. Petersburg, Florida; Minneapolis, Minnesota; San Diego, California. Open up Google Maps or Instagram (#streetart) and chart your course.

4. Take a Hike

A hike doesn’t always have to be of the muddy boots variety. City parks, railroads repurposed as trails, hidden stairways, and waterfront paths are equally great opportunities to explore a new place.

In New York City, the High Line may not exactly be off the beaten path, but the views are great. And venture a block or two away … or even down to street level, and you can often quickly escape the crowds (as much as one can in New York) at places like Mayhem Beer and Sandwiches or Milk and Hops.

In Chicago, the Bloomingdale Trail at the 606 is a relatively new cross-town trail, also on a former rail line. It’ll take you away from the typical tourist areas, whether you’re on foot, bike, or otherwise.

Urban Parks provide great hiking (whether the muddy boot variety or otherwise) all across the West Coast as well. San Diego’s Balboa Park has tons of trails. Portland is awash in them, whether along the waterfront, around Mount Tabor, or in Forest Park to Pittock Mansion or elsewhere. San Francisco’s Golden Gate Park is equally lush with trails.

Finally, your adventure guide need not be a novel nor a traditional tour guide. A couple of my other favorites focus on hiking the concrete jungle. Stairway Walks in San Francisco and Portland Stair Walks are both great books that helped me explore new parts of cities I’d lived in. Even better, climbing the stairs in each city often netted some of the best (and sometimes least common) views.

5. Hit the Socials

This one may or may not seem obvious, but my intent here isn’t simply to crowd-source recommendations from social media. Instead, check out location-specific feeds on Instagram or search for location-specific tips on friends’ and others’ pages.

In my hometown of Portland, the @TravelPortland Instagram is a wealth of off-the-beaten-path treasures, as well as highlights of more commonly-known spots. In Tel Aviv, the @SecretTelAviv account proved to be a great resource to find tucked-away restaurants and local favorites (the city’s @TelAviv page is also good).

But even if there’s not an official page where you’re going (or if it’s not obvious or helpful), search by location or search #hashtags (where the text is the city name) for your destination. Sometimes you may just end up with the internet’s most popular influencers and nothing terribly helpful, but other times and with some more creative search terms, you could find a real diamond in the rough.

So, wherever you’re going next, there’s no excuse not to have a great time exploring!