Celeste River, Costa Rica
But now that I’m vaccinated and starting to think about getting out again, decision paralysis has set in: there are just too many beautiful places to go and incredible things to do. (Photo: Juan Carlos Hernández Hernánde)

How to Build the Perfect Adventure Bucket List

Start by figuring out the kinds of experiences you want to have, not where you want to go

Celeste River, Costa Rica

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It can be overwhelming to realize how much of the world there is to see and how limited one’s time and resources are to experience it all. While there is no shortage of inspiration, from hundreds of pre-made bucket lists (including from Outside) and countless social media accounts, Sandy Cunningham, co-founder of Outside’s adventure travel company Outside Go, says that in her more than 25 years of experience planning dream vacations, the key to traveling well is creating a list that focuses on the types of experiences that will fulfill, challenge, and transform you, rather than of pretty destinations. My bucket list will change over time as I do. But to get started, I talked to Cunningham to create a list of five buckets, or experiences I want to have, and filled them in.

1. The Bucket With a Twist

Vineyard rows with grapes. Grapes harvesting season in the Repub

Start off with an experience you’ve thought about often, no matter how familiar or overdone it seems. But rather than going to Hawaii to surf or Nepal to trek, tailor it to you and your budget by picking an unusual location where the activity is offered. During the pandemic, Cunningham used this approach to safely navigate travel restrictions—and introduce her clients to places they would have never thought of if their go-to destinations had been available. For those who wanted, say, an African safari, she instead suggested Alaska for its fly-in wilderness lodges that could be linked together for a circuit, world-class guides, and abundance of wildlife.

I’ve always wanted to see wine country with my mom. Napa feels like an obvious choice, but we’ve both already spent a lot of time in California. After some research, I found—to my surprise—that Moldova, a small country in Eastern Europe, just north of the Balkans, has three historical wine regions and is home to the world’s largest wine cellar, the Milestii Mici, which has 120 miles of underground tunnels. We’ll base ourselves out of the capital of Chisinau for easy access to over a dozen wineries, plus densely forested mountains, winding rivers, and the Tipova Cave Monastery, an ancient church built into the side of a cliff. 

2. The Trip that Scares the Sh*t Out of You 

Scuba Diving at Coral Reef

Travel is about challenging yourself in all kinds of ways. So why not take it a step further and use it to confront your fears head-on? Step 1: Pick something that scares you or feels out of character. There’s no need to make it a sufferfest—if the entire trip fills you with dread, it’ll be a chore instead of an experience you want to put time and money into. Go with an experience that holds as much fear as it does fascination. Step 2: Pair it with a place that you really want to see or someone you love traveling with.

As a child, I used to have recurring nightmares about tsunamis and deep water. So when I travel, I usually stick to the mountains. For years, my best friend, who loves the ocean and is a certified open water scuba diver, has been trying to convince me to go on a trip with her. She’s pitching me on Cairns, Australia, which she says is great for beginners: warm water, stunning biodiversity, and still-living coral reefs. She says it’s like “swimming through a children’s book.” I’d trust her with my life, and everything we do together ends up being fun. So bucket list item #2: get scuba certified down under with my best friend at my side.

3. The Re-Run 

Catarata del Toro waterfall with surrounding mountains in Costa Rica

I went to Costa Rica on a high school trip and have been thinking about returning ever since, but travel to new places always seem to take priority. During my first trip, we spent a week on a secluded turtle preserve on the country’s east coast, went on day hikes through the rainforest, and rafted on the legendary Pacuare River. 

Cunningham says that one of her favorite types of trips to plan is those that “give people reasons to go back to places they’ve already loved.” Pick one of your all-time favorite trips—the one that you always say you’d go back to in a heartbeat—and go deeper. You can never see all of a place in one go, so there are bound to be corners left to explore. But to make your next trip really special, Cunningham suggests seeking help from a local expert like a guide or agent who lives in the region.

When I go back to Costa Rica, I’d like to go on longer guided hikes in the rainforest to learn more about its unique flora and fauna. I’d like to see the country’s western coast, known for its beaches and incredible volcanoes, which I completely missed on the first go. And I also want to spend more time in cities like San Jose, so I can get a taste of the country’s culture and—my favorite part—its food.  

4. The White Whale

Vanlife in the dolomites
(Tom Bardeck/iStock)

Not all bucket list travel has to be far-flung, once-in-a-lifetime endeavors. There are lots of ways to have big adventures that are closeby or on a budget. To pull these kinds of trips off, Cunningham recommends saving on accommodations and splurging on experiences. But if the trip of your dreams does require some saving, and you’re having trouble reconciling spending all that money on a one-off adventure, consider picking one that comes with a long term reward. 

During quarantine, I started putting some of the money I’d usually spend on going out, traveling, and events into a separate savings account as a way to make the most of my time stuck at home. It wasn’t until I figured out a way to combine two of my travel goals—buying a van and embarking a months-long cross-country road trip—that the account really started to grow. I realized that convincing myself that it’s worth spending so much of my hard-earned cash on a single trip is the hardest part. I got over that barrier by planning a trip that felt like an investment in myself, and one that, while expensive, would give me a lot of bang for my buck. 

In my case, the van and the time off will be costly, but having a long term and cost-effective way to see my loved ones who are scattered across the continent will be priceless. If #vanlife isn’t on your list, consider getting certified in an outdoor pursuit in a place you’ve always wanted to visit (you’ll often find more affordable courses abroad) or going somewhere that will help you advance your skill level in a short amount of time, like a sports camp or a beginner-friendly destination.

5. The Off-Map Excursion 

Almudena Cathedral of Madrid, Spain

Cunningham says that the most memorable moments for her clients are often those that are unexpected. “There’s got to be some surprises when you’re on the ground,” she says. She often builds them into the trips she plans, like the time that she added time on an itinerary to hide a surprise sunrise hot air balloon flight in Namibia.

If you’re planning the trip yourself, build serendipity into your vacation by leaving some of it unplanned and going offline. Pick a place where you speak the language, don’t consult the guides, and leave your phone at home. You’ll be surprised by how small interactions with locals will deepen your experience and lead you to unexpected discoveries. I’ve found that the things I discover myself often give me the most joy when it comes to travel, because they feel more earned.

For this bucket list item, I want to make a trip all about the unexpected by heading to Barcelona for a week—no cell phone allowed. I speak enough Spanish to get by, and am familiar enough with the city from being there once before. During my short lived stay a few years ago, the best moments were the ones I didn’t plan, like the time I got swept up into a street festival filled with fireworks and costumed dancers and when I wandered into a hidden plaza adjacent to an incredible church.

Lead Photo: Juan Carlos Hernández Hernánde