The Journey
Captain Program
You Bring the Crew,
We’ll Navigate the Journey
Download our simple step-by-step guide to becoming a Journey Captain — gather your favorite people, let us handle every detail, and set sail on an unforgettable adventure together.
We traveled to Tuscany in 2024 with Jason’s Journeys to celebrate our 60th birthday, and it was truly unforgettable! We organized a group of 16 friends and family, and from start to finish everything was seamless. The trip was so well-organized and personalized that we didn’t have to think about a thing—just hop on the bus and enjoy.
It was the perfect mix of relaxation and adventure, with an emphasis on incredible food experiences, community, and the chance to take in Tuscany’s stunning architecture and historic sites. Every detail was thoughtfully handled, which allowed us to simply be present and soak in the memories with our loved ones.
Jason’s Journeys exceeded our expectations in every way, and we are already looking forward to planning our next adventure with them—this time with friends and family all over again!
It was truly the trip of a lifetime!!
- Kristen & John, Ten Days in Tuscany 2024
YOUR ROLE, SIMPLIFIED
Understand exactly what it means to be a Journey Captain — gather your crew, dream big, and let us do the rest.
EFFORTLESS PLANNING
How Jason’s Journeys handles every detail — from flights and villas to behind-the-scenes experiences — so you never feel overwhelmed.
CUSTOMIZED ITINERARIES
How we tailor each journey to your group’s style, passions, and pace (whether that’s cooking classes, private wine tastings, or hiking coastal trails).
MEMORIES THAT LAST A LIFETIME
Why small-group, curated travel creates deeper connections and unforgettable shared experiences.
...and more
“Jason’s Journeys is recommended on WeTravel with a 4.6⭐ rating from happy travelers.”
Hi, I'm Jason - founder of Jason’s Journeys. I help discerning travelers like you create intimate, small-group journeys through Italy that go far beyond the ordinary.
The Journey Captain’s Program was designed to take away the overwhelm of planning and show you how simple and rewarding it is to bring your favorite people on a once-in-a-lifetime trip — without having to play travel agent.
Without it, group travel can feel complicated, stressful, and chaotic.
With it, you’ll have the clarity, confidence, and structure you need to rally your crew and let us turn your travel dreams into reality.
So, let’s make it unforgettable.
WHAT ACTUAL CLIENTS HAVE TO SAY ABOUT JASON’S JOURNEYS…
"Jason's Journeys is the most wonderful way to see Italy! A small group experience, led by Jason and Kelly, with every day more incredible than the last! We can't wait to go again and wouldn't go any other way! I nostri cuori sono pieni! (Our hearts are full!)♥️"
Lisa & Tom
Autumn in Amalfi 2024
"I didn’t think it would be possible to top my trip with Jason to the Amalfi Coast two years ago but the Ten Days in Tuscany trip surpassed all my expectations. Each day was well planned with unique experiences and the meals were beyond belief. This is not your standard tour! Jason and Kelly- I will travel with you anytime!!"
Leslie
Autumn in Amalfi 2023 & Ten Days in Tuscany 2024
"Once again, Jason's Journeys did not disappoint! This was our second trip with Jason and Kelly and the itinerary, the food and the camaraderie were fantastic! Venice to Lake Como and every stop in between was a truly an amazing and memorable experience!"
Gina & John
Venice to Lake Como 2024 & Autumn in Amalfi 2023
Working less, stressing less, and experiencing more with your favorite people is just one click away…
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