Yacht Crewmember Turned Charter Entrepreneur

La Caja Miami offers a unique charter experience in Miami

The skills you acquire throughout life often prove valuable in unexpected ways. For former Bosun Matthew Wood, a childhood spent helping his father, who built narrowboats and did construction, laid the foundation for his own entrepreneurial journey. Teaming up with his business partner, Scott Lewandowski, he built his dream venture — La Caja Miami, a private charter boat — by hand over the course of a year while still working as crew. Triton spoke with Wood about his yachting career and the inspiration behind La Caja Miami.

 

How and when did you get into yachting? 

I began my career in yachting more than 11 years ago, but my journey in hospitality started even earlier. At 18, I set out to live and work abroad for the first time, an experience that ignited my passion for travel and service. Upon returning to the U.K., I refined my skills at two of the country’s most prestigious hotels, The Corinthia and Hotel Tresanton. It was there that my appreciation for high-end hospitality truly took shape. A friend introduced me to the world of yachting, describing it as an industry where I could combine my love for luxury service with travel, all while making a living. I saved up for the necessary courses, booked a one-way flight to Antibes, and never looked back. The rest is history.

Was it challenging moving ashore? 

It was different, not necessarily challenging, but a refreshing change. Having my own place and a full-sized bed worked wonders for the mental health. As much as I love cooking, having a chef prepare meals was a luxury I truly appreciated. Don’t take it for granted, crew. I always knew yachting wasn’t my forever path. As I got older, the constant movement lost its appeal. Spending time around successful guests opened my eyes to the life I wanted to create for myself. I got to work.  

What is your company and what service do you offer?

La Caja Miami is a uniquely designed luxury vessel, built from the ground up with comfort, style, and versatility in mind. Inspired by the refined aesthetics typically found in high-end land-based venues, we’ve incorporated premium materials and meticulous detailing to create an elevated experience on the water. Available for private charter, La Caja Miami serves as a dynamic space that can transform to accommodate a wide range of experiences — from laid-back afternoons on the bay to vibrant celebrations, corporate events, or intimate dinners. To enhance each journey, we’ve curated exclusive partnerships that offer add-on experiences tailored to your event. From private chefs specializing in multi-course dinners to live music performances, wellness activations, and premium cocktail experiences — each collaboration is designed to make every voyage unforgettable. We’ve partnered with some of Miami’s top culinary talent, including Miami Sushi Bar, for a bespoke omakase experience at sea. Whether for a lively celebration or an intimate escape, La Caja Miami curates personalized luxury experiences, blending entertainment and hospitality against Miami’s stunning waters.

 

How did you create your company? 

Ever since my now business partner and I met in 2016, we’ve shared a dream of building a space that allows the community to come together. In early 2020, I decided to take a break from yachting and came to Miami to crash with my mate Scott. Then the pandemic hit, and like many others, I found myself at a standstill, passing the time with puzzles, charcuterie boards, and plenty of thinking. With time on my hands, I pursued something I’d always dreamed of: converting a van into a camper. Over a month and a half, I stripped the van down and, with Scott’s help, built a beautiful custom camper that became my home on the road. That project sparked a passion for design and construction, revealing our keen eye for design and craftsmanship. After four months traveling the U.S., I returned to Miami, and the ideas started flowing. One day, Scott said, “Why don’t we take your experience in yachting and our eye for design and build a boat?” Without hesitation, I accepted the challenge, and La Caja was born: a floating space designed to bring people together through unforgettable voyages.  

What has been your biggest challenge in creating the company? 

Building a vessel from the ground up for the first time has been a challenge in itself, but the biggest test has been juggling the many hats a start-up founder wears. From bookings and social media to marketing, accounting, and legal, it’s been non-stop. But I love it. Every day is a learning experience, and with that education comes greater efficiency. If it were easy, everyone would do it. The key is having the confidence and determination to keep pushing forward and celebrating every win, no matter how big or small.  

How did your yachting connections and experience help with building the business? 

My career in yachting is one of the foundations on which I can say this business is a success. Yachting taught me everything from guest experience to maintenance. I saw that one of the biggest expenditures, if not the biggest, is maintenance, and when we designed La Caja, I wanted to keep all systems as simple as possible and use materials that stand the test of time. Running a business, especially one involving a boat, could mean one breakdown costs you your margin. I’m happy to report that with the system we have in place, it is not only easy to maintain but also cost-efficient.  

 

What are some of the success stories you’ve seen from your company?

Some of the most exciting success stories we’ve seen from our business include the viral social media post that helped us gain over 2.3 million views, adding 40 to 50k followers and growing our email list by more than 10k. That moment really propelled us forward. We’ve also formed incredible partnerships with big brands and artists, allowing us to elevate our experiences on the water to new heights. But beyond the numbers, the real success is the genuine love and support we’ve received from the community; it’s been amazing to see how people resonate with our vision. 

What do you miss about yachting? 

I miss the traveling and the chef, haha. But with continued hard work, I know that’s in my future.  

What is your advice for crew looking to build a business? 

My advice for yacht crew looking to build a business is simple: Do it! Yachting is a unique opportunity; you’re in a bubble with minimal expenses and plenty of disposable income. Use this time wisely. Start saving your money (those watches and bags can wait) and focus on educating yourself during your downtime. Understand every aspect of the business you’re looking to build so that when the time is right, you can invest confidently and get started. When I began, I was still working full-time on a yacht. It took late nights and weekends, but I made it work, and you can too. Just put in the effort, and don’t let the fear of the unknown hold you back. I always ask myself: What would my life look like if I hadn’t taken the leap? Honestly, I’d regret not pushing forward. You’re already in a career that defies the norm, so why not keep pushing and see what else is out there? 

What’s next for your company? 

We’re incredibly excited about the future! While I can’t share all the details just yet, we’re in the process of expanding, and this time we’re venturing into the commercial space. We’re also exploring potential franchise models and looking at the opportunity to bring future vessels to other states and even internationally. It’s an exciting time for the company, and we can’t wait to see everything come to life.

Crew, mention TRITON in the booking comments, and get an extra hour on board, completely free! 

Topics: