Realizing how much of the world is there and how limited the time and resources are to experience it can be overwhelming. Sandy Cunningham, co-founder of Outside’s Adventure Travel Company Outside Go, says that in her 25+ years there has been no lack of inspiration, but hundreds of pre-built bucket lists (including Outside) and myriad social media accounts for the Experience Planning a dream vacation. The key to good travel is making a list that focuses on the types of experiences that meet, challenge, and transform you, rather than pretty destinations. My bucket list will change over time. But to get started, I spoke to Cunningham to make a list of five buckets or experiences I would like and filled it out.
1. The bucket with a twist
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Start with an experience that you have thought about a lot, no matter how familiar or exaggerated it seems. But instead of going to Hawaii for surfing or Nepal for hiking, tailor it to you and your budget by choosing an unusual place where the activity is offered. During the pandemic, Cunningham used this approach to safely navigate travel restrictions – and introduce their customers to places they would never have thought of if their destinations had been available. For those wanting an African safari, for example, she suggested Alaska instead for its fly-in wilderness lodges, which could be linked together for a racetrack, world-class guides, and an abundance of wildlife.
I always wanted to see wine country with my mother. Napa seems like an obvious choice, but we’ve both spent a lot of time in California. After doing some research, I found, to my surprise, that Moldova, a small Eastern European country north of the Balkans, has three historic wine regions and is home to the largest wine cellar in the world, the Milestii Mici with 120 miles of underground tunnels. We’ll settle from the capital, Chisinau, for easy access to over a dozen wineries, as well as thickly forested mountains, winding rivers, and the Tipova Cave Monastery, an ancient church built on a cliff.
2. The journey that scares you
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Traveling is about challenging yourself in a variety of ways. So why not go one step further and confront your fears directly? Step 1: Pick something that scares you or feels uncharacteristic. There is no need to make it a festival of suffering – if the entire journey fills you with fear, it will be a chore Instead of an experience that you want to invest your time and money in. Go with an experience that is as fearful as it is fascinating. Step 2: pair it with a place you really want to see or someone you love to travel with.
As a kid, I kept having nightmares about tsunamis and deep water. When I travel I usually stay in the mountains. For years my best friend, who loves the sea and is a certified open water diver, has been trying to convince me to go on a trip with her. She throws me up in Cairns, Australia, which she thinks is ideal for beginners: warm waters, stunning biodiversity and still living coral reefs. She says it’s like “swimming through a children’s book”. I would trust her with my life and everything we do together is fun. So Bucket List Item # 2: Get certified Down Under with my best friend by my side.
3. The repetition
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I was on a high school trip in Costa Rica and have since considered going back, but trips to new places always seem to be a priority. During my first trip, we spent a week in a remote turtle sanctuary on the east coast of the country, doing day hikes through the rainforest and rafting on the legendary Pacuare River.
Cunningham says that one of her favorite types of planned trips are those that “give people reasons to return to places they have already loved”. Pick one of your all time favorite trips – the one you always say you would return immediately – and go deeper. You can never see all of the locations at once, so there are still corners to explore. To make your next trip extra special, Cunningham recommends reaching out to a local expert such as a local guide or agent.
When I return to Costa Rica, I would like to take longer guided hikes in the rainforest to learn more about the unique flora and fauna. I would love to see the country’s west coast, known for its beaches and incredible volcanoes, which I completely missed right away. And I also want to spend more time in cities like San Jose to get a taste of the country’s culture and – my favorite part – the food.
4. The white whale
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Not all trips on the bucket list have to be far-reaching, one-off ventures. There are many ways to have great adventures nearby or on a budget. To make this type of excursion possible, Cunningham recommends cutting down on accommodation and gaining experience. But if the trip of your dreams requires some savings and you are struggling to spend all that money on a once in a lifetime adventure, then you should choose one that comes with long term reward.
During the quarantine, I started putting some of the money I normally spent on going out, traveling, and events into a separate savings account to get the most out of my time at home. It wasn’t until I figured out a way to combine two of my travel destinations – buy a van and go on a month-long cross-country road trip – that the account really started to grow. I realized that the hardest part is convincing myself that it is worth spending so much of my hard-earned money on a single trip. I overcame this barrier by planning a trip that felt like an investment in myself that was expensive but made a lot of money.
In my case, the van and free time are expensive, but a long-term, inexpensive way to see my loved ones scattered across the continent is invaluable. If #vanlife isn’t on your list, consider getting certified for an outdoor pursuit in a place you’ve always wanted to visit (you can often find cheaper courses overseas) or go somewhere where you can improve your skills for a short time, like a sports camp or a beginner friendly destination.
5. The off-map excursion
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Cunningham says the most memorable moments for her clients are often the unexpected. “There must be some surprises when you’re down,” she says. She often builds them into the trips she plans, like the time she added on an itinerary to hide a surprise sunrise hot air balloon flight in Namibia.
If you are planning the trip yourself, build Serendipity into your vacation by leaving some of it unplanned and going offline. Choose a place where you can speak the language, don’t consult the guidebooks and leave your phone at home. You will be surprised 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 greatest joy when I travel because they feel more deserved.
For this bucket list entry, I’d like to take a trip across the unexpected by going to Barcelona for a week – no cell phone allowed. I speak enough Spanish to get through and am familiar with the city because I’ve been there before. During my short-lived stay a few years ago, the best moments were the ones I hadn’t planned on, like when I was swept into a street party with fireworks and costumed dancers and when I went to a hidden place next to an incredible church.
Main photo: Juan Carlos Hernández Hernánde