Ever booked something and immediately wondered what you were thinking?

That was me, about six weeks before I got on a plane to Croatia. Eight days. Five islands. Thirty to sixty kilometers a day on a mountain bike, with a boat waiting at the end of every ride. I plan trips for a living, and I still had a moment of “who exactly do you think you are.”

I went anyway. It turned out to be one of the trips that reshaped what I want to offer my clients this year.

The Setup

The trip was the Island Hopping in Croatia: E-Bike & Boat Tour in South Dalmatia with 57hours, an eight-day route through South Dalmatia where your hotel is a yacht that moves while you sleep. You ride an island during the day, come back to the boat, and wake up somewhere new.

The e-bike is the part people get wrong when I describe it. It is not a scooter. You are still pedaling, still climbing four hundred to seven hundred meters most days, still arriving at lunch genuinely hungry. What the motor does is flatten the gap between the strongest rider in the group and the least experienced one, which in our case was me. Nobody waited at the top of a hill for forty minutes. Everyone rode together.

That one design choice is why this trip works for families and for friend groups where the fitness levels are not remotely matched. I have clients who have quietly opted out of active trips for years because they did not want to be the person holding everyone up. This solves it.

The Islands

Brač came first, and it starts with a fact I have not stopped repeating. The limestone quarried here was used in the White House in Washington and the Reichstag in Berlin. You ride past the quarries on the way from Milna, and the whole island glows white in the afternoon.

Hvar is the lavender one. The climb out of Hvar Town is steady and long and it takes you up through small villages and fields that smell like the inside of a linen drawer, then drops you into Stari Grad on the far side. The descent is the kind you talk about at dinner. Stari Grad Plain, at the bottom, is an ancient Greek agricultural field system still laid out the way it was set up in the fourth century BC, and it is a UNESCO World Heritage site.

Vis was previously closed in the last 30 years or so. Not quiet, not undiscovered, actually closed. It was a Yugoslav military zone off limits to foreign visitors until 1995. That history is why the island still feels like it belongs to the people who live there. We rode the coastline and stopped for wine tasting and sat down with the owner of the winery and a local guide who grew up on the islands.

Korčula was the longest day, across the island to a walled town of narrow fishbone alleyways that claims Marco Polo as its own. The alleys are angled deliberately, to catch the breeze and block the wind, which is the kind of medieval urban planning detail I now bring up at dinner parties uninvited.

Omiš is not an island, which is the first thing worth saying about it. It sits on the mainland where the Cetina River cuts a canyon down to the sea, and we finished there on the water instead of on a bike. Rafting is the good kind of adrenaline, fast enough through the rapids to keep you honest and calm enough in between to look up at several hundred meters of rock going straight above you. After a week of climbing hills in the Dalmatian sun, getting on fresh water was exactly the right way to end it.

57 Hours Adventures is What Made this Trip Worth It All

A group trip isn’t always the best way to travel But 57 Hours curated the perfect group and crew.

Our guides Marko and Filip were hands on, encouraging, and patient with every pace in the group, and I say that as the beginner they were being patient with.

They also cooked. And somewhere between the riding and the meals, they kept handing us the context that turns a beautiful place into a place you understand. Whose village that was. Whose vineyard. Why the stone looks like that. Why the island was empty for fifty years.

That is the thing I keep coming back to when clients ask me whether a guided trip is worth it. You are not paying someone to point at things. You are paying for the layer underneath, the part that is not on any sign and not in any guidebook, delivered by someone who grew up in it.

Why Adventure is On My Radar, And Should Be on Yours, Too

I thought I was booking a beautiful week on a boat. What I got was information about myself.

There is something that happens when you are far enough from home, from the Zooms, from the daily routine, that you actually find out what you can handle. I made it up the hills. I made it down the descents. I was proud of myself in a way I have not been in a long time, and I was surprised by how much I needed that.

Croatia was not the only one adventure trip this year.

I have been building out adventure itineraries in Costa Rica too, and the two answer very different versions of the same question. Croatia is the one where the effort is physical and the reward is a coastline. Costa Rica is the one where three generations can travel together and everyone gets their own version of adventurous. Some trips are beautiful. A few change the idea on what you think you are capable of, and Croatia turned out to be the second kind.

Ready to plan something that pushes you a little further than usual? Reach out here and let’s start building it. I would love to tell you about Croatia, Costa Rica, and where I think you and your family should go next.