Leanna Strohecker’s Stories, Lessons & Insights

Leanna Strohecker shared their story and experiences with us recently and you can find our conversation below.

Hi Leanna , thank you so much for taking time out of your busy day to share your story, experiences and insights with our readers. Let’s jump right in with an interesting one: What is something outside of work that is bringing you joy lately?
After living full-time on a 36-foot sailboat for four months, one thing that’s been bringing us joy is the simple luxury of a nice hot shower.

While we were on board, water was limited, so our showers consisted of a quick rinse off the back of the boat, often with cold water and only sometimes with soap. It was something we grew accustomed to, so we didn’t mind it, but now that we’re back on land we’ve really been enjoying the creature comforts we used to take for granted.

We have a new found sense of gratitude for a hot shower that lasts longer than a minute!

Can you briefly introduce yourself and share what makes you or your brand unique?
Hi, I’m Leanna Strohecker, and together with my partner, Will Travis, we make up Sailing Summit – a creative, adventure seeking couple sharing our first ever boat life experience! In the past year, we researched, planned, trained for, and successfully embarked on a sailing journey from South Carolina to The Bahamas and back aboard our Catalina 36’ sailboat, Summit.

We share our adventures on TikTok, Instagram, and now YouTube, documenting the ups and downs that come with a lifestyle on the water, and one that challenges you in all the best (and worst) ways. Our goal is to inspire people to get outside, chase adventures, and follow what brings them joy!

Our story began back in college at SCAD, where I studied production design and performing arts, and Will studied cinematography. We met on a student film set and bonded over our shared love of film, as well as adventure, the outdoors, and living life to the fullest. Our original plan was to move to LA or Atlanta after graduation and begin our hustle in the film industry, but it just so happened that we graduated in the height of the industry strikes.

Instead of letting the situation discourage us, we let it inspire us to embark on a totally different adventure. Will grew up sailing on Lake Dillon in Colorado and had always dreamed about pursuing a larger sailing adventure. I had always wanted to live an “alternative lifestyle” at some point, so with the industry at a standstill and the new found freedom of being done with school, I couldn’t help but think “now is the time.” After just one FaceTime call with each other, the idea of sailing to the Bahamas was born. We knew it was going to take a ton of work – in hindsight we weren’t fully aware of what we were in for – but nevertheless we were passionate about our new shared goal.

After graduation, we spent the next several months working multiple jobs, living with family to save as much money as we could, and sailing together on Lake Dillon. Once we bought our boat, Summit, a 2001 Catalina 36’, the real work began! Restoring, outfitting, learning, and prepping for our very first major sailing voyage. From rebedding chainplates to testing our dinghy to learning how every different system on the boat operated, it was a whirlwind every day. Throughout it all our shared goal of making it to The Bahamas kept us motivated, and our growing community on social media encouraged us along the way.

On March 1st, 2025, over a year after the boat life idea was born, we finally set sail from Beaufort, South Carolina. We were filled with excitement and nerves, unsure of the journey that awaited us, but eager to be out on the water making it happen. After a month sailing down the coast, we made our first open ocean crossing to Bimini, Bahamas. I will never forget seeing the brilliant blue color of the Bahama water for the first time and feeling an overwhelming sense of joy and pride knowing that our hard work had paid off. We had achieved our goal!

We spent the next three months island hopping through The Bahamas! We went from Bimini, to The Berry Islands, to Spanish Wells, and then all around The Abacos. We explored the most stunning beaches and underwater reefs. We met other boaters who became fast friends that we’d share sunsets and stories with. We honed our sailing skills and had some phenomenal sails, continuing to learn and solve problems every day. It truly was the greatest and most rewarding challenge of our lives.

We continued to share our story online, and our community started to grow, especially on TikTok where we posted daily vlogs. People connected with our personalities and realness, were amazed by the fact that two people so young could go try something so crazy, and loved our joyful willingness to learn and push on, even though some days seriously tested our limits.

Will’s background in cinematography and my background in performing arts naturally blended into our ability to capture and share our adventure with the world through social media. We are so grateful for the online community we were able to grow, who supported us throughout our journey. Plus, the network of other sailors and people pursuing similar lifestyles who we continue to be inspired by.

After three amazing months in The Bahamas, we’re back in Colorado regrouping, working seasonal jobs, and planning for the next leg of our journey: another season of sailing in The Bahamas this winter, with the goal of reaching The Exumas and beyond.

Sailing Summit is about more than just sailing. It’s a reminder to fill your life with passion and joy. It’s a reminder to push yourself when everything feels too difficult and overwhelming. Most importantly, it’s a reminder that you can find purpose and success in the pursuit of adventure.

We’re so grateful for the community we’ve built, and we’re excited to keep growing it. You can follow us @sailingsummit to stay connected. We have a lot more ocean to explore!

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What relationship most shaped how you see yourself?
Every part about living on a sailboat required teamwork and trust, so the relationship that Will and I share was essential to our success and overall growth as individuals.

When Will and I first began planning our boat life adventure, I told one of my best friends, “We’re either going to come out of this hating each other, or more bonded than ever.” Luckily for us, we both agree that we came out of the experience a much stronger team.

Every single task required some level of communication and coordination. For instance, to raise or lower the anchor, I’d be at the bow operating our windlass and anchor, while Will was at the helm maneuvering the boat according to my hand signal, as well as his own best judgement. Lifting the dinghy up and down required pulling specific lines in unison, and obviously, actually sailing the boat required teamwork. A relationship can’t help but strengthen when success relies on that level of effective teamwork and communication. Of course we weren’t perfect at first, but it was in the practice of it that we grew and got better.

Living on a boat also forced us to confront our own weaknesses. For Will, it was indecision, and for me, it was my impatience. I tend to be a “figure it out as I go” sort of person, while Will is more methodical and likes to do lots of research before making a move.

We often joke that if it weren’t for me, Will would still be sitting at the docks reading the books, and if it weren’t for Will, I’d be adrift in the middle of the Atlantic. We found that, together, we balance each other out. I help Will make faster decisions on the fly, and he helps keep me from being too rash.

By leaning on each other when in the face of challenges, we both realized our strengths and worked to develop our weaknesses. We believe we started the journey as one version of ourselves, but came back as more capable individuals and an unstoppable team.

Was there ever a time you almost gave up?
There were so many moments when we almost gave up.

Living on a boat is hard and constant work. Not only were we adjusting to a smaller space and fewer comforts, but we also had to become incredibly self-reliant. We had to be sailors and navigators, as well as our own plumbers, electricians, diesel mechanics, cleaners, and general repairmen. All while trying to manage our social media platforms.

The first month of on board living and traveling was the hardest. We hadn’t made it to The Bahamas yet, and our days of traveling down the coast were long and tiring. Everything about managing a boat of that size still felt very new to us, so naturally there was a lot of stress and anxiety that we dealt with every day.

One of my most difficult days was unfortunately also on Will’s birthday. We’d had several days of bad weather, which meant we hadn’t stepped off the boat in nearly a week. In the beginning, we didn’t like to leave the boat in high winds since we were still learning to trust our anchor. We were in a super rocky anchorage, our holding tank was full (so we were using a bucket, gross, I know), and I couldn’t get our propane oven to work. We had planned to bake cookies for Will’s birthday and then go explore on land, but instead, I felt completely helpless, trapped, and sad.

I had a total breakdown that day. Everything was feeling harder than I expected it to, I was totally out of my comfort zone, and I remember thinking, “is this really what I want to be doing?”

Most boaters who live full time on board will tell you that boat life is filled with the highest of highs, but also the lowest of lows. That day was definitely my lowest low.

But we stuck it out and didn’t give up. We somehow managed to turn the day around and I even made Will some chocolate chip cookies on the stove top. They weren’t perfect, but we tried to embrace them anyway.

With time, the boat got less stressful and my tolerance for discomfort grew. I began to recognize the toughness and resilience I had inside of myself. I just needed to give myself the time and patience to adjust.

Sure, so let’s go deeper into your values and how you think. What’s a belief you used to hold tightly but now think was naive or wrong?
All throughout my years at school, I was an intense perfectionist. I had this crushing belief that success only came from straight A’s, and when I graduated, success would come from my career.

It wasn’t until my senior year of college, around the time the boat life idea was beginning to form, that I started asking myself, “What does success actually mean to me?”

I can’t tell you how liberating it was when I was finally honest with myself. For me, success didn’t have to come from a big career that would take all my time and energy. My success meant having the courage to follow my joy and filling my life with adventures and experiences that would expand my horizons.

It wasn’t an easy realization to make. I remember being terrified to tell my parents and friends that I wasn’t going to move to a big city and follow a traditional career path right away. I felt like I was letting down the expectations everyone had for me; however, as more people were excited about my adventurous pursuit, I realized the only one placing expectations on myself was me!

Redefining success is still something I am working on. Society has it engrained in my brain that purpose and success comes from a career, and sometimes when I see my peers moving to new cities and starting big jobs, I feel like I’m behind.

But the truth is, there’s no one correct timeline.

Now that I’m back to living on land with a “regular” job, I’ve realized how much purpose doing boat life actually gave me! Accomplishing such a huge journey at a young age is a huge success, and one that Will and I are deeply proud of. Just because our path looks different doesn’t mean it’s any less of a success!

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What is the story you hope people tell about you when you’re gone?
I hope that people will tell the stories of our sailing adventure. That they can confidently say, “Will and Leanna really lived life and had the determination to go out and do something different.”

I hope people will tell stories of our perseverance and great teamwork, and how we started our journey as lake sailors, but came back as seasoned ocean sailors with over 3,000 nautical miles of offshore sailing under our belt.

Through sharing our experiences on social media, we have had followers comment that our journey has inspired them to find the adventure in their own lives, and that is something I am so grateful and proud of.

I hope to continue to inspire people to follow their joy and chase the crazy dreams they have inside themselves.

When you’re out on the ocean, surrounded by nothing else but water and the sound of your boat gliding through the waves, you feel limitless. The open horizon reminds you that the world is filled with possibilities if you have the courage to pursue them. That’s the story Will and I hope to continue to live and inspire others to live as well – one that is limitless and filled with the pursuit of joy and adventure.

Contact Info:

• Instagram: sailingsummit
• Youtube: sailingsummit
• Other: TikTok: Sailingsummit

Image Credits
Leanna Strohecker and Will Travis