Welcome to Triple Crown Adventures, where we ignite your passion for exploration and connection. Our community is for those who crave movement, meaning, and the magic that comes with discovering new places. We design our trips not just to see the sights, but to immerse you in rich cultures, foster genuine connections, and embrace thrilling challenges. Join us for experiences that create unforgettable memories, ones that resonate deeply and don’t need a filter shine.
Empowering Exploration
Our Vision
At Triple Crown Adventures, we are committed to empowering riders, adventurers, and explorers to connect with the beauty of O‘ahu and beyond through cycling, outdoor exploration, and inspired community gatherings. Our vision is to blend adventure, community, and personal transformation, welcoming individuals of all abilities to explore with confidence and camaraderie.
Upcoming Adventures
Triple Crown Weekend Hawaii 2026Thu, Sep 24Honolulu
Triple Crown Weekend Costa Rica 2027Date and time is TBDSan José
Triple Crown Experience PortugalFebuary 2027 Date and time is TBDFaro District, Portugal
Plan Your Trip
Why Choose Us?
We are Passionate about Adventure
Tailored Experiences
Triple Crown Adventures isn’t just your average travel tour company; it’s like stepping into a world where boutique charm meets the camaraderie of group adventure. Think of it as your personalized, a la carte journey through stunning landscapes whether that’s the beaches of Hawaii or the rolling hills of Portugal crafted just for you.
We’re all about offering those unique, build-your-own experiences that let you mix and match activities like a fine menu. Every traveler can find their own perfect blend of cycling, hiking, cultural immersion, and pure relaxation. So, it’s more than a tour it’s your adventure, tailored exactly the way you want it.
Personalized Support
We go above and beyond to provide personalized support, from equipping you with route details and safety information to offering training tips and packing guides. Join our guided adventures with confidence, knowing that our team is committed to ensuring a fun, supported experience.
Unforgettable Memories
At Triple Crown Adventures, we are committed to creating unforgettable memories for every participant. From the moment you sign up for an adventure to the post-event celebrations, we are dedicated to crafting stories that you'll cherish for years to come.
