Well & Wander Travel
Makenna Crawford
Hi! I was born and raised in California and graduated college with a Civil Engineering degree. Upon graduation, I moved to New York and began working in Operations at various financial services firms.
Although my career and my degree didn't have any correlation, it's safe to say I loved the attention to detail and organization that was required in both fields. Plus, on the side, I have always been the self proclaimed planner of any trip and the go to when friends need a restaurant recommendation or gift idea.
Experiencing the world has been the best gift I could have ever given myself. Nothing has solidified that more than when I took a year to travel full time with my partner. Now I want to help others achieve that exact same feeling.
My Travel Story
As a kid, I loved going to the auto club with my mom to pick up a map for our summer family vacation. I got to watch firsthand as my mom planned every detail meticulously, and no matter the hiccups along the way, each vacation was always a success. Fast forward to 2024: after years of collecting itineraries from my own trips, I felt confident that the planning would come easy to me when my partner and I quit our New York corporate jobs to travel the world for a year. After all, I’m a planner at heart—reading blogs, scouting the best restaurants, and curating experiences to make every trip unforgettable are all things that I love. However, the first task was a daunting one - where did we want to go?
Social media overflowed with bucket-list destinations, friends and family had endless recommendations, and we were optimistic we could see it all. But lesson number one felt more like a reality check: the world becomes much larger once you try and see it all. We didn’t want to bounce from place to place every three days, but staying a month in each spot would mean missing so much. Finding balance was harder than expected, and suddenly, a year didn’t feel like enough time.
Determined to make a plan, we covered a wall in our Manhattan apartment with a life-sized calendar and color-coded sticky notes listing every country/city/experience we could dream of. We tried to slot in every destination we could, and while exhilarating, it also became overwhelming. Getting that initial roadmap was tough, and after 12+ hour workdays, planning felt like, and very much was, more work. The post-its sat untouched for months until we finally decided on our first destination and booked a flight to Europe. That commitment made everything real: two months to move out, pack our lives into backpacks, and start the adventure!
Lesson number two came quickly: high-demand travel seasons and activities mean higher prices and limited availability. Our “loose” budget didn’t hold up against the realities of summer in Europe. Sure, we could have stayed in hostels or taken more inconvenient travel routes to save a few bucks, but at 30, we weren’t ready to strip away our standard of living entirely. We left with a detailed two-month itinerary and a vague idea for the next six—but when the plane landed, we fell in love with the experience of travel and unintentionally stopped planning. Before we knew it, our carefully crafted runway disappeared. Flights were booked, but we had no formal budget and no next steps.
Lesson number three was the hardest: balancing the joy of living in the moment with the need for logistical planning. I’d prided myself on my productivity and organization in corporate America, but suddenly, our lives were very much in freeform. We fell into a stressful cycle—losing ourselves in the current destination, panicking when we realized nothing was planned for our next destination, finding the most reliable WiFi we could to frantically organize the next few weeks, and repeating it all over again. It was unsustainable, took a toll on our relationship, and made us miss out on fully enjoying the incredible places we visited.
Looking back on those first six months, it’s funny how we faced the same challenges every other full-time traveling couple blogs about—despite thinking we were immune. Two ambitious people, one a plan lover and the other a free spirit, should have had the perfect balance. But reality humbled us. We were fortunate to be able to take some breaks along the way to stay with family, reset, and reflect. Yes, we spent unnecessary money fixing problems that better planning could have prevented. Yes, we wasted time and money rebooking travel and organizing last-minute plans. But was it worth it? A resounding yes.
This experience inspired me to create Well & Wander —a travel advisory service that helps long-term travelers avoid the very mistakes we made. Travel can be transformational, but the stress of planning, managing logistics, and balancing spontaneity can undermine the magic. Traveling the world has been the most rewarding, eye-opening, and exhilarating experience of my life. Now, I want to help others experience the same—without the midnight planning sessions, the stress, or the compromises. The world is vast, we can help make the journey to discover it smoother and more intentional.
