From designing world-class itineraries to planning trip logistics to unrivaled customer experience, we make your trip unforgettable.

About Us

Welcome to Insider Expeditions, where extraordinary journeys come to life, and dreams become unforgettable realities. Step into a world of endless possibilities, where we go above and beyond to curate experiences that leave you in awe. Our passion lies in crafting one-of-a-kind adventures that are as unique as you are, guiding you through uncharted territories, and opening doors to breathtaking moments.

At Insider Expeditions, we are not your ordinary travel company. Our dedicated team of creative experience designers are true masters of their craft, obsessed with the tiniest details, weaving together bespoke trips that shatter the mold of traditional itineraries. Because we know that in a world celebrating individuality, your adventure should be as exceptional as you are.

Embrace the allure of sustainable travel with us, as we make a conscious commitment to responsible tourism. Experience a journey that not only enriches your soul but also uplifts the well-being of local communities. Together, we can explore the world while preserving its beauty for generations to come.

Calling all adventure enthusiasts, luxury seekers, tennis fanatics, and travel lovers – you are invited to a celebration of life’s most exquisite experiences. Picture yourself courtside, witnessing an unprecedented tennis match, sharing the thrill of the game with none other than the legendary McEnroe brothers. An exclusive rendezvous that transcends the ordinary, where your passion for sports collides with your love for adventure. These are the sorts of adventures we create!

For those with an unquenchable thirst for luxury, Insider Expeditions is your gateway to the extraordinary. Immerse yourself in the lap of sophistication, relishing top-notch amenities and exceptional service throughout your journey. Rub shoulders with fellow high-profile individuals, forming connections that last a lifetime.

To the devoted tennis fans, we hear your heartbeat for the sport. Our meticulous planning ensures an immersive tennis experience that leaves no detail overlooked. Meet your idols, the McEnroe brothers, in person and feel the magic of their passion reverberating through your soul.

And for the wanderers at heart, our tailored trips take you far beyond the tourist trails, unlocking the hidden treasures of the world. Dive headfirst into the heart of local cultures, experiencing life as a true insider, creating memories that linger forever.

With over 500 awe-inspiring experiences spanning all seven continents, Insider Expeditions stands as a beacon of trust and reliability in the luxury travel space. Our carefully designed itineraries, guided by experienced hosts, promise seamless logistics, leaving you free to revel in every moment.

Join us on this adventure of a lifetime – a journey that awakens curiosity, ignites hope, and fills your heart with joy. Together, we’ll redefine the way you travel, setting new standards for authentic, extraordinary exploration.   Discover more than just destinations; join the Insider Expeditions family, and let’s craft your story of a lifetime. Your adventure awaits.

The Insider Advantage

Commitment to Our Clients

Our commitment of providing world-class service to our clients is our highest priority. From tour conception and marketing strategies to tour implementation and program evaluation, we partner with our clients to make sure they are included at every stage and ensure that their expectations are exceeded.

Planning Once-In-A-Lifetime Itineraries

We pay attention to the little details that make any journey extraordinary. From early engagement materials to the itineraries themselves – every detail is refined and curated. Our itineraries are filled with exclusive opportunities not feasible through independent travel or with another operator.

Executing With Ease While You Enjoy

We provide opportunities to engage with industry experts, renowned artists, and local communities. Enjoy relevant discussions and interactive activities that enhance every program. Most of our itineraries also contain an impact component, honoring both our traveler’s interests and our commitment to the communities we visit and the planet we love.

Some Of Our Partners

Our Leadership Team

As the founder of Insider Expeditions, I’m proud to have led travel programs in more than 100 countries. After riding my bicycle across the country as a college senior with a motley crew of 30 riders raising money for Habitat for Humanity, I have dedicated my life to creating group travel experiences which combine the qualities I so enjoyed that summer: a fun, inspiring, curated itinerary, lots of memorable surprises, local community engagement, and a journey that leaves behind a positive impact. Shortly after that trip, I moved to South America with a local tour operator, leading cultural exchanges, service projects, and innovative travel itineraries throughout the region. Honored a few years later with a World Peace Fellowship by Rotary International, I then moved to Japan for my Masters and worked with Peace Boat, whose circumnavigational voyages focus on meaningful interactions and cultural exchanges with local communities, service efforts, and unique educational and enrichment opportunities for their passengers.

Since founding Insider Expeditions, I’ve had the opportunity to organize business delegations for Fortune 500 companies, donor experiences for international non-profits, trade missions on behalf of the US government, educational trips for top universities, creative brainstorming journeys for entrepreneurs, extraordinary family reunions, world-class destination weddings, epic birthday celebrations, wild dancing adventures, and remote wellness retreats.

Through Insider, it’s my mission to share our team’s love of this beautiful and magical world through travel and thoughtfully curated experiences, no matter your group, interest, or mission. It’s our own mission to have you look back and say, “wow, that was one of the best trips of my entire life”. On behalf of our fabulous, dedicated, and experienced team, we can’t wait to travel with you.

Carl Shephard

Founder & CEO

Photo Location: Melbourne, Australia

Favorite Insider Trip: Antarctica

Dream Destination: Nepal and also India (and the moon!)

Fun Fact: I have 5 kids and a series of successful side hustles, I’m a design thinking expert and have a diploma in neuropsychology
Photo Location: Solar Eclipse Trip

Favorite Insider Trip: Virgin Galactic Solar Eclipse Western Australia

Dream Destination: India

Fun Fact: Commercial Pilot by trade
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Photo Location: Antarctica

Favorite Insider Trip: Yachting in Croatia

Dream Destination: Norway

Fun Fact: I’m the oldest of 5 and a musician!
Photo Location: Aqua Resort in Nicaragua

Favorite Insider Trip: Antarctica with Wow It's Now/Daybreaker!

Dream Destination: New Zealand

Fun Fact: I am a certified instructor of Yoga Sculpt (yoga with weights!)
Photo Location: Jaipur, India

Favorite Insider Trip: McEnroe Brothers in Tanzania (coming 2023!)

Dream Destination: Zanzibar

Fun Fact: I was in Hakone, Japan when officials believed Mt. Fuji was sure to erupt (very scary!)
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Abbey Wilkin
Photo Location: Lake Kawaguchiko, Japan

Favorite Insider Trip: WIN Egypt

Dream Destination: Spain

Fun Fact: I volunteered as a teaching assistant in Cambodia
Photo Location: Shibuya Sky, Japan

Favorite Insider Trip: Sardinia with Dr. Hyman

Dream Destination: Hokkaido, Japan

Fun Fact: I'm a certified coffee master by a renowned coffee brand!
Photo Location: Asakusa, Japan

Favorite Insider Trip: Tanzania with Tennis Legends 2023

Dream Destination: Iceland

Fun Fact: I once took voice lesson classes so I could skip swimming lessons!
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olivia rogers
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Carleton Shephard
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Hannah - Headshot

Trusted Networks

We remain engaged with global networks that keep us informed of trends, new hidden gems, and destination updates that allow us to bring our clients the best experiences possible.

Insider Expeditions is a proud member of IATAN and the Educational Travel Consortium.