David Ciccarelli, Chief Executive Officer
Management and Business Administration
Toronto, Canada

Expertise
Strategy, Product Development, Customer Experience
Education
Harvard Business School
  • 39 Countries visited
  • Lake Muskoka Favorite
  • Titanium Highest hotel status

If you want to go fast, go alone. If you want to go far, go together.

Highlights

  • Member of the Muskoka Lakes Association.
  • Walked 400kms and finished the Camino de Santiago three times.
  • Lived in London, San Francisco, New York and Sydney.

Expertise

My story began in Thunder Bay, a place where the forest met the lake and looked onto the Sleeping Giant. Here, my love for the outdoors was kindled. Growing up in northern Canada allowed for plenty of time outside, swimming, rafting, mountain biking and even cliff jumping. In the winter, my friends and I skated, went skiing, and heated up by campfires or a sauna. From a young age, I learned some of life’s most essential lessons such as being prepared, situational awareness and navigation and orienteering skills. My childhood was marked by summers spent at various camps, where I achieved the Eagle Award. I also honed my leadership skills at the Ontario Pioneer Camps in Huntsville. These experiences weren’t just about fun and games; they were where I discovered my potential to lead and inspire others. The leadership training I received at the Ontario Pioneer Camps was transformative. Here, I learned the true essence of being a leader: to serve, guide, and inspire.

As a camp counselor, I had the privilege of shaping young minds. Those years were about more than just teaching camping skills; they were an opportunity to pass on the values ​​of teamwork, respect for nature, and the joy of discovery. My passion for the outdoors continued to grow. I traveled the world, drawn to the beauty of lakes, oceans, valleys, and mountains. With each journey, my love for adventure deepened. Earning my boating license led me to many summers spent navigating Lake Muskoka. Navigating Lake Muskoka was not just about steering through the waters but mastering my fears and embracing the unknown. Father-Daughter Bonding: Hiking the Camino de Santiago One of my most cherished adventures was hiking the Camino de Santiago with my daughter.

This 400 km trek was a physical journey and a religious pilgrimage that brought us closer than ever. Walking 20-30 kilometers daily with nothing but a backpack, shoes, and hiking poles was a challenge that tested our limits. But the memories we made are etched in my heart forever. Becoming an outdoorsman wasn’t just a hobby but a calling to found Lake. I realize how nature has molded me. Reflecting on my adventures, I am filled with a sense of accomplishment and a thirst for more. These experiences have been about reaching destinations and the journey itself. As I look to the future, I am excited for the new adventures that await. The path ahead is uncharted, but one thing is sure: the journey is far from over.

Education

I attended Harvard Business School and completed the Owner President Management Program from 2019 to 2022. This program, delivered in three units over 24 months across three calendar years, was a transformative learning experience. It prepared me, as a CEO, to elevate both my company and my leadership expertise to new heights. Back in 2017, I completed the QuantumShift Program at Ivey Business School at Western University. QuantumShift was a unique challenge, bringing together forty of Canada’s most promising entrepreneurs. It pushed me to enhance my leadership style, inspire my business partners, and seize maximum growth opportunities. This program was designed for CEOs like me, whose businesses have moved beyond the startup phase and are poised to scale up significantly.

Recent posts

Best Lakes for Canoeing: An Adventurer’s Guide

Discover North America’s Most Stunning Lakes for Canoeing Picture yourself gliding across mirror-like waters, surrounded by breathtaking vistas and pristine nature. Canoeing offers an unparalleled way to connect with the outdoors, providing serenity, adventure, and a chance to explore some of North America’s most stunning lakes. Whether you’re a seasoned paddler or a curious beginner,…

Experience the Thrill of the Milwaukee Air Show 2025

Your Guide to the Milwaukee Air Show 2025: What to Know The Milwaukee Air Show 2025 is set to take flight over McKinley Park on July 19 and 20, bringing a weekend of thrilling aerial performances to Wisconsin’s shores. Featuring iconic teams like the Blue Angels and Thunderbirds, this event promises heart-pounding action, family-friendly activities,…

Lake Superior Circle Tour: A Boating Adventure Around The Greatest of the Great Lakes

Explore North America’s Greatest Boating Adventure The Lake Superior Circle Tour, part of the iconic Great Loop, offers an unparalleled adventure around the world’s largest freshwater lake. This journey blends stunning natural beauty, rich history, and unforgettable activities. Whether you’re setting sail for the whole Loop or focusing on this majestic stretch, Lake Superior promises…

Listing Your Vacation Rental on Lake

Getting Started on a Niche Online Travel Agency While the large OTAs are great for broad exposure, niche OTAs like Lake.com can provide a more targeted audience. Studies have shown that niche platforms can increase booking quality by 20% since guests are more likely to find exactly what they’re looking for, resulting in fewer cancellations…

Accessorizing Vacation Rentals to Transform the Space into a Welcoming Haven

Tips to Make Your Vacation Home Functional, Cozy, and Uniquely Yours Stepping into a rental can often feel like entering a blank canvas. The walls may be neutral, the furniture practical, and the overall atmosphere impersonal. But with the right accessories, you can turn even the most generic space into a reflection of your style—without…

Why Renting a Boat with a Captain is the Ultimate Angling Experience

Expert Guidance, Hassle-Free Adventures, and Unmatched Access to Prime Fishing Spots Have you ever wondered what it’s like renting fishing boats with a captain? Imagine gliding across pristine waters, the anticipation of a trophy catch building with each passing moment. Renting a fishing boat with a captain transforms this vision into reality, offering a stress-free…

Exploring the Road in Style in a Class A RV Rental

Luxury, Space, and Adventure Combine in These Ultimate Motorhomes Dreaming of a spacious home on the road? Class A RV rentals are like luxury liners of the highway! With deluxe features, they’re built for comfort and style. Think of these rigs as rolling estates that bring a touch of home wherever you roam. Key Attributes…

Inflatable Kayaks Are The Perfect Paddle for Adventure Seekers

Portable, Affordable, and Surprisingly Durable—Explore Why These Kayaks Are Making Waves Inflatable kayaks have revolutionized the paddling world, offering unmatched convenience for outdoor enthusiasts. My personal experience began on Lake Muskoka, where my brother-in-law unveiled his foldable kayak from a compact bag—it was a game changer. These lightweight marvels are portable, easy to store, and…

The Cost of Renting a Fishing Boat

Navigating the World of Fishing Boat Rentals Curious about the true cost of renting a fishing boat? Let’s break down the expenses and what to expect before you hit the water. Weighing the Costs of a Boat Rental Renting a fishing boat can be like choosing the perfect lure—there are many options, and the costs…

Choosing the Right Property for a Short-Term Rental

How to Select the Right Market for Short-Term Rentals Short-term rentals can be a rewarding venture, but choosing the right market is key to your success. By focusing on factors like familiarity, property evaluation, and strategic negotiation, you can make a well-informed decision that maximizes your investment. Let’s explore how to effectively select the best…