The Back Story

If you’re not sure what in the world I’m talking about, let me fill you in! Back in late July, Kara and I spent 10 days in the Italian countryside in a small town called Ripatransone.

We completely fell in love with everything about this region of Italy. The food, the wine, the people, the views, the beaches, the medieval hill towns, and the lack of tourists all combined to make the region of Le Marche one of our favorite places we’ve ever been!

If you haven’t already, you can check out a few of the episodes on our channel to see why we love Ripa so much!

While in Ripa we stayed with two of our friends who gave us access to their Vespa! When we weren’t eating delicious food or enjoying a glass of local wine, we spent our time cruising around the countryside on the Vespa exploring other hill towns, beaches, and wineries.

After driving the Vespa for the first time, we looked for excuses to take it for a spin the rest of the week. Everything about a Vespa makes it the perfect mode of transportation for exploring this region.

All of your senses are heightened when you’re driving a Vespa. You’re truly experiencing the area you driving through. You hear things, see things, and smell things that you wouldn’t notice if you were traveling by car.

Before we even left Le Marche, we were already making plans for when we could return! We started tossing around the idea of doing a Vespa road trip. We knew that we barely scratched the surface, and there’s so much more of the countryside that we want to see!

Then we started thinking, “We love this region of Italy so much that we want our friends and family to come back with us.” At this point, the planning just kinda snowballed.

“If we had a big group, we could rent an incredible villa to stay in each night,”

“Maybe we could get a private chef to cook delicious homemade Italian meals for us in the comfort of our private villa,”

“What if we brought a local guide along with us who could help us better appreciate what we’re seeing and help us connect with other locals?”

Fast Forward a Few Months

We are hosting three trips next summer, we have over 20 people signed up, and we are back in Italy finalizing the itinerary! Our original plans have changed a little bit, but I’m even more excited about our new itinerary! Seriously, this trip is turning out to be more incredible than we ever could have imagined!

The Villa

We had originally thought we’d stay in a few different villas, but then we decided no one wants to spend their entire vacation packing and unpacking their bag. Plus, we found the perfect villa in the perfect location, and if we were to move anywhere else during the trip it would just be a letdown!

The highlights of the villa include… A beautiful pool with an incredible view!

A huge common area where we can eat and hang out!

7 beautiful bedrooms!

A kitchen with a marble island (perfect for learning how to make pasta from scratch)

And it’s in the perfect location!

The Itinerary

The trip will be 7 days and 6 nights. Our goal is to leave most afternoons open so you can either spend your time relaxing at the villa, or take your scooter off on your own adventure.

You’re never going to be tied down to doing anything on this trip. Think of this itinerary more as more of a list of suggestions.

The villa where we’ll be staying won’t be near any huge cities, so there won’t be any “nightlife.” Our nights will consist of chill evenings at our villa.

The itinerary will be updated with more details in the coming weeks.

Day 1 – Arrival Day

Vespa orientation. Settle into the villa. Wine tasting. Italian dinner by a private chef.

Day 2 – Medieval Hill Towns

Explore medieval hill towns. Lunch at our favorite local restaurant. Our favorite gelato in Italy. Learn to make pasta from scratch.

Day 3 – Beach Day

Drive your Vespa to the beach. Take a dip in the Adriatic Sea. Seafood lunch. Back to the beach (or the villa). Outdoor dinner in a beautiful medieval hill town.

Day 4 – Local Delicacies

Tour and tasting at a local cheese factory. Tasting (and possibly a tour) at a local prosciutto factory! Dinner at an incredibly beautiful local winery.

Day 5: – TBD

A winery tour will probably be involved. We have a lot of ideas, we just haven’t made a final decision.

Day 6: – Pizza Party

Free day to do more of what you’ve enjoyed the most during the trip. The world’s best pizza party. Learn to make pizza from scratch in a wood-burning oven.

Day 7 – The Worst Day of the Trip

After you’ve shed a few tears while parting with your Vespa, we’ll transport you back to the train station/airport, say goodbye, and shed a few more tears together.

Who SHOULD NOT come on this trip

This trip is going to be incredible, but it won’t be for everyone. We want to be really transparent up front, so that no one signs up for the trip expecting it to be something it’s not.

This is a group trip after all, and we know from personal experience that the dynamics of the group play a huge role in the enjoyment of the trip! So in this section I’m going to try to eliminate anyone who I don’t think will have an awesome time and add to the enjoyment of the group!

If you fall into one of the categories below, please don’t take offense. It just means this trip isn’t right for you.

If you’re only content staying in 5 star hotels, you may be disappointed by this trip.

For this trip we’ve decided to stay in Italian Villas because it will give us the opportunity to bring in our own private chef and stay in some incredibly beautiful locations. Plus, we believe the group dynamic will be much better than if we stayed in hotels.

However, there are some drawbacks. Since these aren’t western hotel chains, they may not offer all of the comforts of home. For example, air-conditioning isn’t common in Italy. So our villas may or may not have air-conditioning. Hopefully the beds will be comfortable at these villas, but again, no guarantees. There won’t be room service or concierge at your beck and call.

I think these minor drawbacks are totally worth having our own private villa for the group, but I want to make sure that everyone who signs up for the trip agrees.

If minor discomforts put you in a sour mood

We’re going to be on a Vespa tour. I foresee us being on the Vespas for 3 – 4 hours per day. There’s a good chance your butt might get a little sore. If you’re going to let a sore bum ruin your trip, you shouldn’t sign up!

Also, we can’t control the weather. We’re going to hope it doesn’t rain and do our best to avoid driving in it, but you may have to ride in the rain at some point during the trip. If you can’t handle that, this isn’t the trip for you.

If a change of plans will ruin your day

Based on the weather and other factors, we may have to change plans at the last second. If you don’t deal well with change, this definitely isn’t the trip for you.

One time Kara and I were on a cruise, and for whatever reason there wasn’t time to do a city walking tour that was on the itinerary. There was a group of 10 people who were livid because they didn’t get to do one thing that was on the itinerary. They made a big fuss about it, and it made everyone else on the boat feel really awkward.

Take a deep look inside yourself. Would you have been one of the people causing a ruckus and making the rest of the group uncomfortable? If so, that’s fine. I understand some people want to ensure they get exactly what they paid for, but please don’t sign up for this trip.

If you’re a picky eater that isn’t willing to try new things

This trip is going to take place in the countryside of Italy. There will be no McDonald’s available, and our private chef won’t be cooking you your own personal serving of chicken nuggets.

We’ll be eating a lot of delicious pasta, pizza, and other local dishes. So if that doesn’t sound good to you, maybe you shouldn’t sign up.

If you see the glass half empty

Optimists only on this trip please 🙂 This is a group, we don’t want one bad apple bringing everyone else down. Come ready to make the best of every situation, or don’t come at all.

If you expect everything to go perfectly

I’m trying to be really transparent about the fact that we’re making this up as we go along! WE ARE MAKING THIS UP AS WE GO ALONG.

We are going to do everything we can to make this the best trip of your entire life, but we’re not a professional tour company with a big staff. I’d say there will definitely be a hiccup (or two) along the way!

If you don’t handle hiccups well, maybe book your Italy tour with a company that has a long track record. (not us)

If you’re going to be uncomfortable riding a Vespa

You don’t need prior experience riding a Vespa to come on this trip! We can teach you, and it’s super easy once you get the hang of it!

It may be a little scary at first, but come with a good attitude and bit of bravery, and you’ll be good to go!

However, you must drive a Vespa (or ride with someone else) in order to take part in the trip! We won’t be able to arrange other forms of transportation at the last minute!

If you’re a history buff or a connoisseur of art…

I think you’ll be disappointed by this trip. We are arranging this trip in our own travel style, which means the main focus of this trip will be food and adventure with a bit of history culture mixed in.

If you’ve watched any of our videos, you’ll know we’re not that into museums and art, so there will be very little of those two things included in the trip.

We definitely plan to learn about each little town we visit, but we won’t spend hours looking at the statues, paintings, and museums.

If you’re into the nightlife scene

Our villas won’t be located near any big towns that have a nightlife scene. Most (if not every) night of the trip will be spent hanging out at our villa enjoying lots of carbs, local wine, and good conversation! If this doesn’t sound good to you, don’t come.

I think that about covers it! I hope this doesn’t come across as mean, but we don’t want your money if you’re not going to enjoy the trip!

If you were looking forward to this trip but fall into one of the categories above, it’s better that you are disappointed and mad at me now rather than after you’ve arrived in Italy!

Who SHOULD come on the trip

If this trip sounds awesome to you, and you don’t fall into any of the categories above… You should probably join us on the adventure of a lifetime, and we can’t wait to hang out with you!

Cost of the trip

The cost of the trip is going to be $2,800.

A $1,000 down payment will be required to reserve a spot when we release tickets next week. The remaining $1,800 will be due 2 months before the start of the trip.

What does the price include?

Accommodations. Every meal. Unlimited local wine (when we’re at the villas). Your Vespa for the week. Insurance on the Vespa. Helmets and other necessities.

I hate being nickel and dimed. So if there’s something small you think of that isn’t included on this list, it’s probably included. However, feel free to shoot me an email if you have specific questions.

FAQ

Are flights included in the price?

No. You will be responsible for getting yourself to the starting point which will be somewhere in the Le Marche region of Italy. Don’t worry, we won’t leave you hanging. We’ll do everything we can to make the trip as easy as possible for you!

Will the trip be cheaper if I share a Vespa with a friend/partner/family member?

Yes, if you share a Vespa each person will receive a $100 discount.

Do I need experience riding a Vespa?

No. We’ll happily teach you! We learned how to ride a scooter for the first time last year, and now it’s our favorite mode of transportation. It’s a little scary at first, but you’ll get the hang of it quickly!

Do I have to stay with the group when we ride?

Nope. If you want to find your own way to the next villa, go for it!

Will I have internet access?

Hopefully. The villa we booked should have internet access, but no promises.

I’m in! What’s Next?

Registration is now open, and spots are filling up fast! You can register for any of the remaining trips using the links below!

July 1-7 Individual Registration SOLD OUT
July 1-7 – Couples Registration SOLD OUT
July 8-14 – Individual Registration SOLD OUT
July 8-14 – Couples Registration SOLD OUT
July 15-21 – Individual Registration SOLD OUT
July 15-21 – Couples Registration SOLD OUT

In order to reserve your spot, we’ll be asking for a $1,000 down payment. We’re doing this to make sure only people who are 100% serious about coming get access to the limited spots.

If you have any questions, doubts, or just want to tell us how excited you are about the trip, shoot me an email at nate (at) karaandnate (dot) com