Throughout most of my travels, I have typically gone with friends and family. I tend to stay away from travel companies, mostly because I feel like I can put together a trip better myself. I suppose that’s partially why I’m now in the travel business with the launch of the Fearless Journeys community, which includes a travel component.
While I tend to opt for the smaller do-it-yourself trips with a family member or friend, or small group of family and/or friends, there have been very memorable experiences I have taken with groups that I did not plan. In fact, because a lot of planning goes into most of my travel experiences, sometimes it’s nice to just go along for the ride - especially when you trust those who are in charge.
On several occasions, I’ve taken group trips planned, organized, and led by my friend Joe Lindsley. In 2014, he put together a trip for about 30 or so of us to travel with the band Scythian on a one-week trip to Ireland. I went with my mom and it’s an experience we had together that no one can take away from us! We also met plenty of others along the trip and we all had a shared interest: live music - including from the band we were with that week, Scythian!
Joe also organized other trips I’ve gone on, including 5 days in Mexico City, where about 13 of us in total explored the city together in November 2019. A few of us knew each other prior to the trip, but many of us did not. Nearly two years after this trip, we still have a very active group text on WhatsApp where we keep up with each other and always pass along birthday wishes and other encouragement - as well as plotting our next adventures together. Two of the friends I made on that trip recently came to visit me in Guatemala, where we hiked two volcanoes together.
In 2015, I took an amazing week-long group sailing trip around the Greek islands as part of a nonprofit organization I support, SailFuture. I took along three friends, and met about a dozen new ones, some who remain close to this day. The next year, I did another week-long sailing trip with SailFuture -- this time around the U.S. and British Virgin Islands. We brought a few more of our friends along and made a few new ones there as well. In both of these experiences, we were out on the open seas, getting a new perspective on life while sharing thoughts and ideas with our friends, who challenged us to think broader.
Then I can think of perhaps the best trip I’ve ever taken - to Israel. This one was organized by the Israel Collective for about 30 of us. They had done this same trip about 18 times before the one we attended in August 2018. Two of my colleagues at the organization I worked for were also invited to join - it was nice to experience it with them. I also made plenty of other friends on that trip too, including with the trip’s leaders, Josh Ahrens and Raj Nair. One of the people I met on that trip was my friend Kyle Huwa, who I later visited in May 2019 while he was living in Guatemala (and yes, he introduced me to the art of volcano hiking). I also made some connections in Guatemala on that trip and now I’ve been the one back living in this Central American country for most of 2021.
Many bonds are made when we travel with others. And, when organized group trips are done right, many new friendships can be made as well. We learn more about others when we discover new places together with them. And, in turn, we learn more about ourselves. It’s hard for me to think of the person I am today without being formed by those great experiences in Israel, Ireland, Mexico City, and so many other places. But it’s equally difficult to think about what life would be like without the people I met along the way.