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: Antarctica

Favorite Insider Trip: Yachting in Croatia

Dream Destination: Norway

Fun Fact: I’m the oldest of 5 and a musician!
Chief of Staff

Jules Schroeder

Jules Schroeder

Photo Location: The Great Wall, Beijing, China

Favorite Insider Trip: McEnroe Tennis Safari in Tanzania

Dream Destination: Buffalo

Fun Fact: Have tracked 12 gorilla families in Uganda over six years and was one of the few Americans to visit the IK, one of Africa’s last tribes only found in the Karamoja region.
Managing Director of Destinations

Paul Cohen

Paul Cohen

Paul Cohen brings nearly thirty years of experience in the global travel and tourism industries working with tourism marketing organizations, destinations, and travel suppliers. Paul has helped to drive tourism arrivals, spend and investment to dozens of destinations, including those in the U.S, China, the British Virgin Islands, Iceland, Botswana, Seychelles, Uganda, South Africa, Nicaragua, Italy, Greece, Nigeria, Jamaica, Egypt, Israel, Ethiopia, Mongolia, Bhutan and Vietnam. He has also provided strategic consulting for Fortune 500 corporations and ancillary partners in the travel space, including Visa International, Sony Pictures, Discovery Networks, Universal Studios and the Travel Channel. Paul is also a managing partner of our favorite eco-resort in Central America!

Photo Location: Solar Eclipse Trip

Favorite Insider Trip: Virgin Galactic Solar Eclipse Western Australia

Dream Destination: India

Fun Fact: Commercial Pilot by trade
Director Strategic Partners

Steve Pirie-Nally

Steve Pirie-Nally

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
Chief Design Officer

Sarah Pirie-Nally

Sarah Pirie-Nally

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!)
Director Special Programs

Hannah FitzMaurice

Hannah FitzMaurice

From a young age, Hannah was a lover of travel logistics and details – by the age of seven she insisted she research and coordinate all family vacations going forward. Her love for the “minutia” of travel has only deepened over the years, and after taking a gap year between high school and college to travel the world, she decided she wanted to experience every cultural and geographical landscape possible. An anthropology major who has worked in marketing and project management for other companies, Hannah takes her passion for design, details, and especially epic travel experiences into her role as the Manager for Insider’s special projects. As a health fanatic and foodie, Hannah is keen on making sure all trips have the best culinary and wellness options possible.
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!)
Director of Travel Programs

Nakimera Moore

Nakimera Moore

When your first travel memory is of a tropical bird of prey swooping down for the fish tensely gripped in your four year old fingers, it’s only natural to want to continue chasing such phenomenal experiences. Upon completion of her MA from University of London, Nakimera determined to explore two new countries every year. After spending half a decade in luxury travel, she has since smashed that goal with expeditions to over 30 countries, setting up residences in four. Her new goals are to broaden the pool of people who have access to uncommon travel experiences, and encourage newcomers to venture outside of their comfort zones. As a Program Manager, she specializes in designing unique programs that stimulate the five senses, ensuring an indelible experience.
Photo Location: White Pass Ski Resort, Cascade Range, WA, US

Favorite Insider Trip: Mike Posner Iceland

Dream Destination: Pondicherry, India

Fun Fact: First Argentinian you will meet that doesn't drink mate
Customer Experience Director

Josefina Blanquet

Josefina Blanquet

Photo Location: Boulder, CO

Favorite Insider Trip: Mike Posner Iceland

Dream Destination: Japan

Fun Fact: I'm also a dancer / acrobat
Marketing Lead/ Program Manager

Raya Schroeder

Raya Schroeder

Photo Location: Petra, Jordan

Favorite Insider Trip: Tanzania 2023 with WOW It’s Now

Dream Destination: Tonga (to dive with humpback whales)

Fun Fact: I have my advanced scuba license! My favorite diving destinations (so far) are the Komodo Islands in Indonesia, and the Blue Hole in Belize

Alexandra Saper

Alexandra Saper

After leaving her corporate law career in Washington DC in 2018, Alexandra booked a one-way ticket to Bali where she established herself as travel expert and content creator through her award-winning travel blog, The Wayfaress. Through creative photography and story-telling, she’s promoted off-the-beaten-path destinations, women’s empowerment, and sustainable travel to her global audience. She’s visited over 65 countries, including stints solo trekking through the Himalayas, free-diving with sharks in Indonesia, multi-week adventuring along the Transsiberian Railway, and tracking the Great Migration in East Africa. When she isn’t traveling, Alexandra still resides in Bali, Indonesia, and uses her expertise in sustainable, adventure, and luxury travel to plan once-in-a-lifetime travel experiences for conscious travelers.

Photo Location: Croatia

Favorite Insider Trip: Unconventional Life Croatia, (operated in partnership with IE)

Dream Destination: Galapagos

Fun Fact: I'm a very talented hip-hop artist! (Check out my tunes on all major platforms by searching for the artist name Zen Tempest.)
Customer Support Lead

Gabriel Rima

Gabriel Rima

Photo Location: Medellin, Colombia

Favorite Insider Trip: Palm Tree Music Festival Ft. Kygo

Dream Destination: Patagonia, Argentina

Fun Fact: I have a lucky object for each trip/group I organize. (I discovered 80 while cleaning out my old office!)
Junior Program Manager & Customer Service Support Specialist

Sini Abrego

Sini Abrego

Sini’s middle name is Wanderlust! With 14 years of experience in the travel industry, She’s here to turn your vacation dreams, corporate retreats, incentive trip, or the wedding of your dreams into reality. From breathtaking destinations to unforgettable adventures, she can create memories that will last a lifetime. Pack your bags and let’s explore the world together! 

Photo Location: Capri, Italy

Favorite Insider Trip: Climate Discovery Tour Antarctica

Dream Destination: Antarctica

Fun Fact: I do triathlons, hike and trail run
Executive Assistant to the CEO & Web/ Design/Research Support

Eva Martinez

Eva Martinez

Eva is an adventurous soul with a passion for exploration, travel, and pushing her limits through sports. As an avid traveler, she believes that life is meant to be embraced with an open heart and a willingness to embrace challenges. 

Photo Location: Lake Kawaguchiko, Japan

Favorite Insider Trip: WIN Egypt

Dream Destination: Spain

Fun Fact: I volunteered as a teaching assistant in Cambodia
Executive Assistant to the Chief of Staff & Tech and Design Support

Christine Aragon

Christine Aragon

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!
Customer Support Assistant

Daryll Robles

Daryll Robles

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!
Design & Research Assistant

Kei Nakajima

Kei Nakajima

Kei is a blend of Filipino and Japanese heritage. Born in the Philippines, she loves exploring her home country, and from time to time, she goes on vacations to Japan, searching for the best onsens and uncovering the hidden gems of its provinces. She has over 5 years of expertise in the airline sales industry, but the Covid-19 pandemic prompted a realization – life is too short to hold back. Kei boldly shifted her career into the world of marketing and creative endeavors to explore her untapped potential. Solo traveling is her passion, offering her a fresh perspective on the world’s beauty and diversity. In her free time, she hits the road, taking the wheel of her pickup truck to discover new places. Recently, she finds serenity in yoga and pilates. But it doesn’t end there! When the geeky child mode kicks in, she’s all about anime, manga, and PC gaming adventures!

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.