TUSCANY: Cycle. Drink. Eat. Re [...]
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Owner: Gone with the Wynns

TUSCANY: Cycle. Drink. Eat. Repeat.


Location: YEP BIKE - On the road in Chianti
Latitude: 43.65000000
Longitude: 11.18000000
Published: 14 May 2023

This was one of those days that filled me up until I was drunk on life and all the art, wine, food and people that make it worth living.

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Convincing my family to go to Tuscany is a dream I honestly never thought would happen.  Because between all the ups and downs of life, it's easy to let dreams slip away.

But between doctors appointments, work and the ongoing commitments of life, things magically fell into place!  My aunt Rebecca, uncle Mike and cousins (Matt & Keri) all managed to commit to the family trip of a lifetime.  We already admitted the trip didn't turn out the way we hoped...but, we still had some magical days.  The kind of days that fill you up until you're drunk on life and all the art, wine, food and people that make it worth living.

This was one of them.  So grab a glass and join us for a tour of Tuscany on two wheels.

On The Road In Chianti
A huge thanks to our friends Michele and Nanna who not only recommended and helped us set up the bike tour at YEP but also volunteered to meet us at each location with my Aunt and Uncle.  Our time in Tuscany wouldn't have been the same without you. 🙏

Now let's talk about YEP.  It's a husband and wife run bike shop.  Alessio (the husband) was our guide and having him with us made us feel like locals everywhere we went.  If you want to do the same trip, something more adventurous or perhaps more low key, the team at YEP can make any trip on two wheels happen.  They do tours or you can rent the bikes, grab some suggested routes and make your own adventure.  But we highly recommend the guided tour!


WE’RE JASON AND NIKKI WYNN. A couple of modern-day documentarians, perpetual travelers, and seekers of tall tales.

We’ve been chasing our curiosity around the world on wheels and keels since 2011. Why? Because curiosity is the key to unlocking life. It pushes us outside our comfort zone, softens our assumptions, and helps us embrace the great unknown. The more we let our curiosity lead the way, the more we discover about ourselves and the world around us.

Our home is also our transportation and we spend weeks away from civilization and sometimes land. Self-reliance and living a sustainable lifestyle are a must. It's all about managing our resources and we’re always looking for new and better ways to do so.

We've lived off the grid for over 10 years now in everything from a Van to RV to a Sailboat. And over time we have learned a lot about renewable energy, creating safe drinking water, and managing our waste.

Our journey is ever-evolving but the mission remains the same: #CultivateCuriosity

Timestamps if you like to Jump Around:

00:00 The Tuscany Adventure Plan
01:18 Renting Electric Bikes in Chianti YEP
03:02 More Adventure Than We Expected
04:14 A Famous Road to Wine & Dine
05:35 Insanely Beautiful Tuscan Winery & Village
09:03 The Problem Traveling with YouTubers
10:21 Abbey Badia A Passignano
13:00 Picnic in the Olive Grove at La Loggia
16:09 The Most Beautiful Tuscan Villa
18:15 The BEST Adventure for Exploring Chianti


#BoatLife #Catamaran #TravelVlog #DigitalNomad #LifeStyle #Sailboats

© Gone With the Wynns 2023