I live in San Francisco. After these past couple years, I feel an overwhelming need to get out, meet people, see things, and remind myself why I'm alive.

My office is work-from-home until (at least) late October. I'd like to spend that time riding around Italy - maybe through the Dolomiti, the Swiss/Italian Alps, down the Amalfi Coast, etc.

I've been investigating this for a few days, but the logistics are complicated. Here's what I've learned so far. I would love your advice!

Timing

I'd like to leave soon to maximize my time on-the-road. I'm thinking of arriving mid-next week.

Experience

I've had a Vespa GTS 300 and a California M1 license (unrestricted - same as a class A in Europe) for two years. In that time, I've ridden 30,000 KM, including a 3000 KM/12 night tour from SF to Crater Lake and back.

Acquiring a moto

I really like my Vespa: it's got a reasonable top speed (130kph), ABS and traction control, and some built-in storage. It's also what I'm comfortable riding: it's automatic and maneuverable. I have a strong preference to ride one in Italy.

Rental options

Most places that rent Vespas cater to amateurs on day trips. The going rate seems to be about €60 per night, without much discount for longer trips. This quickly adds up to thousands of EUR for something that probably has a small engine and might not be in-shape for a long trip.

Monthly rentals (Cooltra/OnMovo)

There are a couple of places that also rent by the month. Both have low monthly caps (~2000KM) and no clear way to buy more. (Even if I could, paying-per-KM adds up quickly.) OnMovo does carry the GTS, but is out of stock until late September. Cooltra only has the SYM Joymax. These are appx. €500 per month for 2000km.

Shipping options

I haven't requested any quotes yet, but shipping my Vespa is an option.

Big pluses for familiarity, novelty (how cool would it be to see my own Vespa in photos overseas?!), and not having to ask a friend to babysit it while I'm away. As the original owner, I also know that it's been maintained well, and would be happy to continue investing in maintenance abroad. I also know it has all the safety features.

The risks are pretty clear: if anything happens to it, it's my bike that gets damaged. There's also the logistical headaches (maybe being without it in the days before/after the trip, and figuring out how to get it crated and to the airport). I haven't requested any quotes yet, but this is only even an option considering how expensive rentals seem to be.

I'd also need to contact my insurer (State Farm) to see how my policy applies abroad.

Purchase options

Considering the more obvious choices seem ridiculously pricey, I'm also wondering if purchasing is the way to go. As many here know, buying a motorcycle as a foreigner seems particularly challenging.

Use a friend

I have friends in Como. Perhaps I could convince one of them to buy it for me, and they'd either get a great deal on a Vespa, or we'd sell it after and work out a deal.

I am nervous about hassling a friend, especially since I don't know what this entails, and what the risks would be.

• What are the costs beyond the purchase price (for instance, the bollo tax, registration, etc.)?
• Are there other fees to consider? The friend I floated this by was afraid there might be, for instance, year end effects on his property tax that would be hard to account for.
• How does smogging work? It seems vehicles <4 years old don't need to be smogged. If a vehicle is more than 4 years old, does the last owner's revisione count, or do I need to do a new one as the new owner?
• What about insurance? If I have a wreck or a theft on my friend's insurance, will that impact his future premiums?

Rent from a private seller

An alternative would be to find a private seller on FB or Subito, and convince them to rent me the moto they are selling. Could be an appealing offer for them: "I'll pay you €___ to borrow this for 2 months, and then you can sell it for close to what you're already selling it for."

It has similar open questions to buying with a friend, plus the additional risk of dealing with a stranger: one of us will be risking thousands of € in trust on the other. What happens if one of us screws up?

Local lease

There are shops that rent al mese, but they have 18 month contracts and require a codice fiscale. I think these are equivalent to a US lease, and unlikely to work for a foreigner. They also have KM limits.

French purchase-repurchase

It seems the French have a loophole that allows tourists to temporarily own a vehicle, but I couldn't find any information for Piaggio or Nice.

Buying it myself

My GTS is nearly identical to the current model, so I have no need for a new one, but given the lack of a great alternative, it's also worth considering.

Italy and the neighboring countries all seem to restrict vehicle ownership to residents, unless you export the vehicle outside the EU.

Fly-n-buy

I know people have bought cars directly from the European manufacturer, and ridden them locally. I haven't found any evidence that Piaggio has a similar program, but I need to call to confirm.

Get EE Plates

I have seen rumors online of EE plates, Italy's temporary tag for vehicles to-be-exported. If I can find more information, maybe I could purchase one locally, ride it, and then ship it back to California.

It would save me 1/2 the hassle of shipping my Vespa, traded for the hassle of selling one of them upon my return, and for making whatever modifications I need to pass customs (e.g. adding reflectors). I'd also have to worry about break-in and having the 1000km service done.

Between the shipping, depreciation, and DOT modifications, I doubt this is cost effective.

German export plates

There's more written online about the German export plates. I could ride back from there. Same downsides as EE plates, plus German prices seem higher.

Other concerns

San Francisco just reinstated its mask mandate due to anxiety about the Delta variant of coronavirus. My Italian friends suspect that Italy will keep minimal restrictions through the high tourist season of August, but lockdown could be reinstated in September.

On one hand, maybe having a motorcycle would make it easier to get from a more restricted place to a less restricted one. But if the whole country shuts down, I need an escape route. Having to get a motorcycle back to a particular rental shop, to a particular friend to sell, or to a particular exporter adds a layer of complexity (which may be unavoidable if I insist on taking this trip on 2 wheels).