Dear Here,

I recently quit my job to become a freelancer and one of my goals for the new year is to spend more time traveling. I never studied abroad in college and I didn’t really get to travel much with my family growing up. I feel like it’s time to make this a priority in my life and I want to get out of my comfort zone. Of course, juggling my budget will be a challenge, but I’m also a little worried (read: overwhelmed) about the planning process. I feel like there’s so much I don’t know about how to travel well and there’s so much information out there. How do I parse through all the noise? Where should I start?

Sincerely,

The Travel Virgin

Dear Travel Virgin,

We love this question. While there are so many things about travel that are full of reward, it can certainly have its downsides, particularly when you’re just getting started. The pre-travel dread can make it tough to get out of the weeds and onto the plane (or train, boat, car—see Chloe’s advice below!)

The internet, while often a gift of convenience, is not a help in this department, especially this time of year. Top ten lists and 2019 travel destinations circulate the internet like wildfire, and while there are any number of places or trips that could be right for you, you’re not asking “What’s the best place to go?” You’re asking, “How do I make travel part of my lifestyle?”

You want something more personal than the most Instagrammable destination. Getting out of your comfort zone means connecting with some part of yourself that’s just waiting to be discovered—and this can happen for travelers on any budget. And for that, our editorial team has some very specific advice.

Ally Betker, Editorial Director:

Most of the time, I’m traveling for work, which means that I’m meeting and interviewing local people and exploring a city through their eyes. It’s a much deeper way to travel, and I feel lucky that my job acts as an excuse to send cold emails or DMs to people I admire. But the thing is, you don’t really need an excuse. More often than not, people are excited to tell you about themselves or the city where they live. Remember, flattery will get you everywhere. Find someone who works in a similar career as you, or has a cool job that you want to know more about. Reach out to them via email or Instagram DM, and ask them about their favorite places in their city. If you’re feeling extra outgoing, ask them to grab coffee or a drink with you while you’re in town. I promise it will be the highlight of your trip.

Chloe Scheffe, Senior Editorial Designer:

Consider the how as much as the where. Just after graduating from high school, my twin sister and I took a month-long train trip around the United States, using Amtrak passes that allowed us an unlimited number of stops within a certain date range. We started in Seattle and circled the entire country, stopping everywhere from Chicago to New York City to Kansas City. The train has become the realm of the Monday-to-Friday commuter, but there’s a whole world of longer-haul railroad travel that’s incredibly historied and romantic. It’s a shame it gets forgotten. From a train you literally see the land—I recommend an observation car, which is usually glass-roofed—and you’ll have plenty of time to plan your stops in each city. Next on my list of under-appreciated modes of transport: ferries. There’s a multi-day ferry from the Washington coast to Alaska, for example, that looks pretty unbelievable.

Emma Glassman-Hughes, Senior Associate Print Editor:

Talk to people you love and care about, whose life experiences you really admire. Ask them about the places that have been meaningful to them, or the places they’re dying to visit. If not people you know personally, tune into where your favorite artists and creators are traveling, or where they grew up and what they love about those places. All the listicles about the “next big destination” kind of go out the window when you have places in mind to which you’ve made a really personal connection. That connection will deepen the experience for you when you’re traveling, too. And never be afraid to talk to people on the ground! You’ll almost always meet some wise and wonderful person who can lead you down an unexpected (but hopefully fruitful!) path.

Annie Werner, Managing Editor, Digital:

For some reason I can only think of what not to do. Don’t expect to keep up any sort of routine while you travel. Don’t try to pack too much in to one trip. Don’t overpack your suitcase. Don’t follow the advice of only one guide or source. Philosophically? Don’t travel to fill a void. Decide what you truly value—being outdoors, relaxation, meeting new people, indulging your favorite hobby or interest (mine are usually food-related)—and organize your itinerary to optimize that. This is how you make travel an extension of yourself as opposed to traveling for the sake of traveling. In Tokyo, I skipped the Sensō-ji Temple—one of the city’s “must-sees”—because I prioritized sampling every kind of street food in the markets. But if you value spirituality or architecture, I’m sure it’s a great stop. Also: keep a journal. Or write things down in some way. Pictures are great, but they can be a crutch. Remember the smells. Remember what your taxi driver said to you. Remember how it felt to set out on a goal, into the unknown, and see it through.

Happy New Year, travelers! We hope you found this helpful. To submit your own questions to “Dear Here,” shoot an email to editorial@awaytravel.com with the subject line “DEAR HERE.”