I Asked for Travel Advice From Five Generations of Women and Here’s What They Said

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Regardless of how many times I’ve planned trips, it’s fun and interesting to ask advice from fellow travelers. By doing this, I’ve learned about small towns in Panama, mezcal spots in Los Angeles and tiny beaches in Mexico that I probably would never have ventured to had I not asked for recommendations.

Lake Atitlan, Guatemala, is a great spot to relax and enjoy the view. (Photo courtesy of Lucy Brown – loca4motion/Shutterstock)

The beautiful thing about discussing travel is that it builds such strong bonds among those who are sharing their experiences. So I thought it would be fun to ask five women from five different generations two questions we have all asked at one time or another. Here’s what they had to say:

20s: Interview With Caroline, Just Returned from Two Weeks in Iceland, Amazing Plant Whisperer

What advice would you give someone who is planning to travel for the first time?

My advice for anyone traveling for the first time is proper planning and preparation. Planning is ingrained into my DNA, so I already have the compulsion to make checklists and scour over every detail, but I have found it comes in handy, especially when traveling. The more prepared I am for a trip, the smoother things tend to go and I am not left wondering where to next or why am I so damn hungry and where do we get quality food?

Now this doesn’t mean that you must stick to every detail on an itinerary. Traveling is meant to be fun so if the itinerary is a bit too much for one day, cut back on that day’s activities and relax. Have a glass of rosé and kick back by the pool for the rest of the evening. When traveling abroad recently, the most useful thing I found was downloading offline Google maps for the areas I was going to be traveling in. This way I didn’t have to use data or Wi-Fi and could still navigate to any destination. It took the stress out of driving in a foreign location and made it easier to enjoy the gorgeous landscape.

There is no one way to travel. If you’re like me, then you fill every moment with an activity or an attraction, but some people like to relax. My advice is to fill your time with things that sound enjoyable to you and make the most of your visit at your travel destination. For me, that means seeing everything in case it’s the only time I will ever travel to that place.

What is the biggest lesson you’ve learned about traveling so far?

The biggest lesson I’ve learned about traveling is to talk to the locals! Who knows what is better to do in a town than the people that live there? I definitely will check out all the tourist must-sees and that’s what I fill my itinerary up with, but once at your destination, I find it pays to make friends with some locals in a bar and ask them what to do, where to eat and what to see around town. Not only may you make some new friends, but you get the inside scoop on something that may not be talked about in the usual travel guides.

30’s: Interview with Laura, LA Native, Lived and Traveled Through Mexico for Four Years, Loves Animals

What advice would you give someone who is planning to travel for the first time?

Don’t over-plan. Keep enough wiggle room in your agenda so that you can change plans based on what you learn/hear about once you get there. Be realistic with your agenda based on where you’re traveling and who you’re with. Even though it might seem counterintuitive when you’re on the go, be sure to allow for rest. Remember that no one has fun when they are exhausted or sick!

What is the biggest lesson you’ve learned about traveling so far?

Try not to have too many expectations as oftentimes the least expected is what is most interesting. For example: When in Colombia, taking the wrong bus and getting lost in “la Frontera” for almost an entire day seemed like a tough break at the time. But those are the moments and experiences that I remember about Colombia and laugh about, not the perfectly planned days that I almost cannot recall.

A Mexican guy I talked to once about travel said that he learns the most about a new town he visits by going three places: the market, cemetery and church. Try to do activities that might not seem like tourist destinations. You will probably learn more about the culture/people.

40’s: Interview with Sue, World Traveler, Badass Mother of Two, Still Finds Time to Camp on the Weekends

What advice would you give someone who is planning to travel for the first time?

Plan well, but not too well. Allow yourself time and freedom to accept unexpected invitations, surprise adventures, and unanticipated detours. Pack minimally. Less is best (on your mind and back!). You can buy almost anything you need anywhere you are going… and it’s fun to immerse yourself into the fashions of a different culture. Save up. Chances are, you may not get a chance to come back, so you want to have the budget you need to take advantage of opportunities/adventures/delicious food and drinks as they present themselves.

What is the biggest lesson you’ve learned about traveling so far?

Travel is such a privilege. You’ll learn more than you ever expected and reflect back on it the rest of your life (almost daily for me!). I’ve always tried to soak it all in and immerse myself into the cultures that surround us. I’ve also learned that travel is infinite….There are all different types of traveling that you’ll do, at different stages of your life. From backpacking around the world, staying in hostels and wandering beaches, to shorter, safety-minded trips with babies and toddlers, to off-the-grid adventures, and everything in-between. It’s really all incredible and all amazing.  Sometimes the hardest part is putting it on the calendar, committing to it and knowing that regular life will still be here when we get back.

50’s: Interview with Nancy, Part-time Nomad and Full-time Dreamer About Travel (When Not Traveling)

What advice would you give someone who is planning to travel for the first time?

It can be easy to become overwhelmed when planning a trip, so try not to be intimidated by all of the information out there. Start out within your comfort level and take it from there. If you’re a planner, own it! If you’re more of a see-where-the-wind-takes-me, own that. Remember that “travel” is just another word for “vacation,” which means you’re unwinding, taking your time and relaxing. Don’t overthink it and make sure to pack enough undies.

What is the biggest lesson you’ve learned about traveling so far?

There are no mistakes. Every time I’ve missed a flight, a bus, a train, or ended up in a weird hotel, it was a temporary miss that later made for a great story. In the line of your life, there will be both bumps and easy sailing. It all adds up to a wonderful narrative, a great adventure. You never know where it will lead. That’s the beauty of travel.

60’s: Interview with Carmela, Adventure Junkie Who Also Appreciates Hyatt Luxury Hotels, Always Down to Dance (Anywhere!)

What advice would you give someone who is planning to travel for the first time?

Do your homework, but don’t stay within the lines. Be open to a change in plans, or a reroute in your travels. You’re going to miss trains or not have a visa (Sydney, who knew?), your luggage will get lost and your rental car may break down. It’s all part of the journey and ultimately, you’ll survive and it will make for a great story. Take a deep breath, relax and embrace the adventure of it all.

What is the biggest lesson you’ve learned about traveling so far?

Forty-some years ago, I stood in a train station somewhere in Italy by myself, trying to decipher signage and a schedule in a language I couldn’t understand. I remember thinking, “This first time will be the hardest, then it will be easier, and then it will be no big deal.”  In 45 years of traveling on my own and with friends and/or family, what I’ve learned is that time is short and life is sweet and the time to do it – is now.  Yes, it helps to be prepared and to do your research (how did we ever find our way without Siri?), but it’s also a whole lot of fun figuring out how to go with the flow.  Some of the most amazing experiences I’ve had were because I put my faith in the Universe and let it take me down the path less traveled. Sometimes you have to step out of your box and detour from your initial direction to figure out where and who you want to be, literally and figuratively.

What advice would you give? What’s the best advice you’ve ever received? I’d love to hear your thoughts in the comments section below!

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