Travel-first life design

You already know there is more.

Small-group adventures for people who already feel the pull. Hosted by Jeff Holst and Jillian Sidoti. Egypt, the Dominican Republic, and wherever we are going next.

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The promise

You can write the book. You can climb the mountain. You can take the trip.

Most people we meet already know they want more. They are not skeptics. They are not lazy. They are not waiting for permission. They are just missing a hand on the shoulder pointing somewhere specific.

We are Jeff and Jillian. We have written books and climbed mountains and bought the buildings and sold the law firm and moved the family and taken the trips. We did all of it in various orders, with various amounts of fear, and we are still surprised when we meet someone who believes they cannot.

Last Life Ever is the answer we kept trying to give those people. Come with us on a trip. Not because the trip itself fixes anything. The trip just turns out to be the door.

Last Life Ever
Jeff Holst & Jillian Sidoti
Read the full letter →
Where we are going

Open right now.

Small groups, hand-built itineraries, no breakout sessions in a hotel ballroom. Pick one. Reserve a spot. We will send you everything you need.

Artist's rendering
Featured · Egypt

Egypt under an eclipse.

July 29 – Aug 8, 2027 · 11 days

Cairo, Luxor, Abu Simbel, and a four-night Nile cruise. The trip is timed so you are standing in Luxor when a total solar eclipse crosses directly overhead. Ancient temples as the backdrop for one of the rarest celestial events of the decade.

$9,750 per traveler Details →
Featured · Dominican Republic

Adventure Club Samaná.

October 18–25, 2026 · 7 nights

A week at Araya Resort on the Samaná Peninsula. A private catamaran into Los Haitises National Park, a hands-on Dominican cooking class, and as much or as little adventure as you want around it.

$3,050 per traveler Details →
Coming soon

The next place.

[Reveal soon]

We are scouting the next trip right now. Join the Tuesday note and you will hear about it before it goes public.

Announced soon Notify me →
Who is behind this

Jeff Holst & Jillian Sidoti

Jeff Holst was diagnosed with leukemia at twenty seven. He hiked Machu Picchu at thirty and has never stopped. He owns three hundred and fifty apartment units, is writing a book that no one asked for and everyone is going to read, and is the reason no one in his orbit gets to have a bad day.

Jillian Sidoti spent twenty years as a securities attorney helping entrepreneurs raise four billion dollars. She sold her law firm in 2024 and moved her family to Rincón, Puerto Rico, because the math finally worked. Now she runs the system that lets people fund a travel-first life.

Read the full story →
From past attendees

What it actually feels like.

"

Living life to the fullest in sound mind and body and heart, making a difference and knowing my mess is my message. My story is one of resilience.

Diana Gipe · Last Life Ever community member
Glimpses

A few moments from past trips.

No staging. No curriculum. Just what happens when the right people show up in the right place.

Two ways to begin

However you want to start.

The trip is the door. The conversation is the start. Either one works.

Pick the trip.

Reserve a spot on the next Adventure. We send you the prep packet and the rest is just packing.

See the Trips

Book a call.

A short conversation with Jeff or Jillian. No agenda. Tell us where you are stuck and we will tell you what we would do.

Schedule a Call