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Unveiling Lost in Sicily: A Vespa adventure

If you’ve been a follower of Lost Travel you’ll know we fancy ourselves a bit of an expert in the arena of bicycle and kayak based adventures of the Type II variety here in the continental US. We’re running the eighth edition of the Drifty, a bicycle and canoe/kayak based adventure in the driftless region of Wisconsin. We’ve ran the sea kayak-based “Cascadia” out in the pacific northwest. We’ve hosted a couple editions of a pack-rafting/hiking adventure in the Ozark/Ouachita regions of Arkansas. We’ve also experimented with sea kayaks and bicycles in the Everglades of southern Florida. And of course the North Carolina-to-Tennessee ”AshtoNash” cycling trip. But we’ve fielded a lot of requests from people looking to us for a solid Type I trip they could do.

Rewind to the 1st annual Lost offsite company meeting in Montana this Fall. We all sharpened our pencils and pitched ideas for the next pioneer trip. After the dust had settled and we ran a few things by our lawyer we came to the agreement that our next adventure should involve an active volcano, plenty of cannoli, the Mediterranean Sea, and a world-renowned classic Italian icon of transportation: the Vespa. I bet you didn’t see that coming did you?

We quickly put our intern to work researching the largest island in the Mediterranean Sea (as we would later learn). She came back letting us know it’s the birthplace of the Mafia as well as third century polymath Archimedes who claims to have created a heat ray to melt enemy ships over 1800 years ago. Oh also Cyclops. We were also informed that Sicily is home to the world’s most active volcano, Mt. Etna, which has grown over 100 feet taller in 2021 due to its eruptions. It’s also lusted-after as a cultural, architectural, linguistic, and culinary melting pot.

Finally we were given a handwritten list with two columns and told one half contains some of the Mediterranean’s most epic white sand beaches and the other are delicious Sicilian desserts. We’re still not sure which is which but we’re keen to find out.



Frutta Martorana

Brioche con Gelato

Fedde del Cancelliere

Granita alla mandorla


Fontano Bianche

San Vito lo Capo


Lido Mazzarò

Spiaggia dei Conigli

We’ve also made some friends with locals in Sicily who didn’t hang up on us when we told them what kind of unscripted experience we want to have. So, after all that – after the beaches, and blue seas, and volcanoes, and gelato, and ancient cities, and pizza, and tiny Italian scooters we said yes.

To be clear: this is not a guided tour but we are trying to curate a collection of interesting experiences that you probably wouldn’t have if you just showed up in Sicily on your own. There is no set route, just a few checkpoints. If you didn’t know already, that’s the part we really like.

For our Sicilian pioneer trip we are asking participants to show up in the capital city of Palmero with just a smile and an appetite for adventure (and all the pasta and wine they can put inside themselves). In Palermo you’ll be provided food, drink, and accommodations for Sunday night (ideally at a castle, or a vineyard, a cave, or an old church or something like that). It is there you’ll first lay eyes on your Italian steel.

After a couple days of exploring Sicily on two tiny wheels you’ve undoubtedly formed an unconditional relationship with your Italian steel horse and also an appreciation for gelato. It is at this point Lost will host a mid-trip meetup on Wednesday where we expect you to tell everyone about your adventures, enjoy some local food and wine, and a place to rest your weary eyes for the night. 

By the next morning your pasta bingo card is filling up and you’ve acquired a nice selection of Sicilian wine bottles in the luggage strapped to your Vespa. Keep working your way West (that’s toward the ocean) to the finish line party where you’ll enjoy an adventurer’s welcome with food and drink and accommodations for the finish line party.

We are targeting mid/late September for the trip as this gives us a slightly off-peak visit that still has great weather. If the stars align you could be there during the world famous Pistachio Festival. And to make it easy on the time-off bank the trip is structured so you could squeeze it in using only one week of vacation time.

While we still have some details to flush out (we aren’t going to tell you everything by the way) we have something like this sketched out:

  • Entry includes food, drink, accommodations for three of six nights. This would be kickoff party (Sunday), mid-week meetup (Wednesday), and finish line party (Wednesday).

  • Includes Vespa rental along with helmet and insurance for the trip.

  • Expect several “Lost” style surprises and challenges along the way

We debuted the 2022 Pioneer trip at the 2021 Lost meetup in Chicago on November 13th and little did we know we would sell the trip out that night. We currently have our contacts in Italy scavenging the place for more Vespas. In the event they are able to cobble together a few more with spare parts we would be incredibly excited to have you join our waitlist. We will reach out to you (first come first served) with availability for the trip.

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