An ”Adventure Report” from our family trip to Italy

Welcome to this week’s edition of ‘The Adventure Capitalist’. Twice a month, you’ll get a jolt of inspiration to get out there and live a bigger more adventurous life.

Here’s what you can expect in this issue:

• An ”Adventure Report” from our family trip to Italy

• The most fascinating interview of 2023

• An assortment of links to get your blood flowing

Adventure Report:

In September we took a 3-week trip to Italy with our 14-month-old son.

Before the trip, we were nervous about how it was going to go. We’d never taken our son on a 20-hour travel day before. Were we just setting ourselves up for disappointment? Was this going to be more challenging than it was worth? Up until a week before the trip, we even considered canceling it.

I'm grateful we didn’t because it turned out to be an epic time. We returned home feeling optimistic about continuing our travels with our son.

Almost all of the highlights of the trip were things my son did for the first time. From eating gelato and going on his first big hike to meeting donkeys and bunnies, tasting his first croissant, riding in a horse-drawn carriage, and watching him enjoy breadsticks while we did some wine tasting, every moment was magical.

It was the most memorable three weeks of his young life, which in turn made it magical for us as well.

Itinerary:

• ATX → London → Florence

• One week in Umbria at Casa San Gabriel

• One week in Umbria at Agriturismo Borgo Laurice

• One week in the Dolomites at Hotel Maria Explorer

• Milan → London → ATX

Highlights/Things That Worked:

• Traveling at 14-months

• Hiking in the Dolomites.

• The Family Hotel Maria Explorer

• Minimizing transit

• The flights from ATX to Europe

14 months was the perfect age to take him on such a big trip. He was old enough to walk, already adjusted to a "one nap per day" schedule, and still young enough to sleep whenever needed. He was also at an age where he would just go along with whatever mom and dad wanted to do, without having strong preferences. If you're considering taking a longer trip with a young child, I recommend planning it around this stage of development.

Hiking was a perfect family activity. We spent the last week in the Dolomites doing a lot of hiking as a family. We loved it and he loved it. We purchased a backpack carrier from Osprey before we left and it was the MVP of the trip. We’d hike straight up the mountain and the whole time my son would be giggling and laughing. By the end of the trip, he would beg to go in the carrier. It was a great overlap between fun for mom and dad and fun for kids.

Family hotels are amazing. In northern Italy, Germany, and Austria, you can find lots of "Kinder hotels" specially made for families. These hotels are usually small, with around 20-30 guests, and they offer all the services you need for a super relaxing vacation with the whole family. We stayed at the Hotel Maria Explorer thanks to a recommendation from my friend Drew Sanocki and his wife. It was a great suggestion and a perfect intro to family hotels.

Our room had a main bedroom and a kid’s bedroom with a crib, bunk beds, and blackout curtains. The hotel took care of all our meals and the food was delicious. They even had an early kids dinner at 6:00, so my son could eat and go to sleep before my wife and I had our dinner together. The hotel was small enough that we put my son to bed and used a baby monitor at our dinner table so we could fully enjoy our time together.

On top of that, the hotel provided top-notch childcare services, which allowed us to drop off our son for 2 hours (or even longer) and relax at the spa. I'm really surprised this idea isn't more popular in the United States, because it's a fantastic way for families to travel.

Transit is the enemy. The most challenging moments of the trip were when we were in transit. However, booking hotels and cottages for one week at a time worked well for us. It allowed us to settle into a fun routine and take things a bit slower while still exploring a lot. Our main focus was finding small bed and breakfast accommodations with amenities like a pool, a spacious yard, and a playground. All the places we stayed are linked above.

Renting a car was key. Driving in Italy was easy and having the flexibility of the car made the trip a lot more fun. We realized quite quickly that cities were not as appealing with a little one. Having a car gave us the flexibility to explore the outskirts of the city and head on outdoor adventures.

Booking a red eye to Europe. We were understandably concerned about the long flight. Fortunately, our worst fears didn’t come true as my son slept for 7 hours of the 9-hour flight. Here’s what worked for us:

1. We booked a redeye eastbound. The flight took off at around 7 pm so he was naturally tired and ready to go to bed. Pajamas went on and he was out by 9 pm.

2. We bought a blow-up sleep tool that extended the seat and allowed him to sprawl out. This was really helpful and was worth the money. (note: each airline has different regulations on usage)

3. We created a sleep cave with blankets. This blocked a bunch of the light and allowed him to remain sleeping with people moving around in the cabin.

4. We planned for the worst and hoped for the best. At the end of the day, we were mentally prepared to have a hellish 9 hours in exchange for a great 3 weeks. It was a pleasant surprise when he slept through the flight, not an expectation.

Lowlights/Things That Didn’t Work:

• Trying to work on the trip.

• Late dinner times in Italy.

• One evening when our son was sick.

I got very little work done. That seems to be the reality of life and travel going forward. In the past, my wife and I were able to travel somewhere and keep making progress on my business by working part-time. With my son in tow, it just wasn’t as realistic. I came to terms with it pretty quickly and just wrote it off as a time for me to be present with my family.

Dinner time in Italy was a challenge. Most of the good restaurants in Italy open for dinner at 7:30 pm. That led to some tough decisions because no matter what we did, by 8:00 pm - 8:30 pm, my son was firmly in meltdown city. We either had to choose a) to cook at home, or b) to rush through dinner and drive home with a crying/exhausted baby. We ended up choosing to eat at home most nights and just accepting the new travel reality. Fortunately, we’d planned for this and had booked only guesthouses that included a full kitchen.

One night our son got terribly sick. Nothing makes you rethink your decision-making process faster than a sick child. One night our son woke up sick with a 104-degree fever in the middle of the night about an hour away from the closest hospital. It was a scary night and we felt bad for him. We were fairly prepared, but reminded us to take a couple of extra things next time.

The Weekly Savage:

Paul Rosalie's interview with Joe Rogan was the most fascinating interview I’ve listened to this year. Paul left New Jersey at a young age to pursue a career as an explorer and has spent over a decade living in the Amazon.

His stories from his time deep in the bush are incredible. He has tracked and wrestled anacondas, encountered (and survived) uncontacted tribes, and even woken up face-to-face with a jaguar. He truly embodies the spirit of a modern-day Indiana Jones.

I included a clip below, and if you’re interested, his full interview is linked at the bottom.

🎙️The full interview is here.

The Lifestyle:

🌎 Global Adventure:

There has never been a better time to go to Japan as an American. The Yen is incredibly weak right now compared to the dollar, so if you’ve been thinking about pulling the trigger on a Japan trip now is the time. 2024 is the Year of Japan!

If you’re interested in learning more about the Dolomites, here’s a great profile in the NYT about the hut-to-hut hikes. I think we’re 5-7 years away from this being one of the hottest travel areas in Europe. So, now is the time! (link)

💰Wealth, Business, and Life:

An excellent breakdown of how to raise money for your first real estate deal (link)

🚁 The Best of the Best:

This leather-bound “100 Hikes of a Lifetime” is the coolest coffee table book I’ve seen (link)

Want to make your house look 75% better? Here are 8 rules you can follow to instantly improve the vibe (link)