Travel Planning

First Stop: Italy!

It’s hard to believe that we’ll be leaving New York City, the place that we’ve called home for over a decade, in less than 2 months! But with such exciting travel plans on the horizon, we really don’t have any regrets.

Our travels will officially begin on September 3rd and likely run through the first several months of 2020 (with a short break back in the US over Christmas). While we have a general idea of where we would like to go, our goal is to maintain a healthy degree of flexibility along the way, allowing us to explore the world at our own pace without ever feeling locked into a single destination or itinerary. In other words, we will not be planning the entire trip before we leave in September!

That being said, we do have to start the planning process somewhere. And after careful deliberation, we are so excited to share our plans to kick off this adventure in one of our favorite countries in the world, Italy! We’ve visited Italy together twice before and both times were absolute magic. With it’s heavy emphasis on food & wine, Italy truly is our spirit country (that’s a thing, right?).

Our planning is still in its very early stages at this point, but a general structure for the trip is slowly starting to come together.

Here’s what we’re thinking…



Anywhere and everywhere! We want to spend at least 2 months in Italy, so we should be able to cover a lot of ground during that timeframe. Our three priority regions at the moment are Tuscany, Piedmont, and the Southern region (mostly Sicily and Puglia).

Tuscany and Piedmont are priorities on the food and wine front (no surprise there), while the Southern region presents an opportunity to explore scenic Italian towns that are a bit more off the beaten path. Also, more food and wine!

“If you like Italy as far south as Rome, go further south. It gets better. If Italy is getting on your nerves by the time you get to Rome, think twice about going further. Italy intensifies as you plunge deeper.” – Rick Steves


Slow Travel vs Road Trippin’

One of the benefits of traveling for extended periods of time is the awesome ability to slow travel. That is, finding a long term rental in a single town and using it as a home base for at least a week. The slow travel method is a great way to truly live like a local and lower the stress levels associated with overly packed vacation itineraries. It’s also a much more affordable way to travel.

The natural downside of slow travel is that you don’t get to experience a meaningful breadth of locations during your trip. And while lower stress levels are generally a good thing, you obviously don’t want to be too settled in while traveling or you might miss out on unforgettable adventures waiting just around the corner in a neighboring town or country! The FOMO can be so real…

In Italy, we want to strike a healthy balance of slow(ish) travel and active exploration on the road. Our current plan is to fly into Rome the first week of September and stay somewhat locally in one AirBnb for about a week. We can use that time to slow down a bit, get our bearings, and map out a course for the following weeks – likely South toward the Amalfi Coast and ultimately to Sicily.


Car vs Train

The train system in Italy connects much of the country in a reliable manner and is fairly easy to navigate. This is particularly true in the Northern and Central parts of the country. On our last trip to Italy, we bounced around several towns in the Emilia-Romagna region exclusively via trains and loved it. We will likely rely on trains again for parts of our upcoming trip.

Christina living that Italian train life


In addition to taking trains, however, we’re also planning on renting cars as we work our way through Italy. There are many regions of the country that are less accessible by train, so the only way to get the full experience is to get behind the wheel and go! We’ve always appreciated the sense of freedom that we get from renting cars abroad and imagine we’ll feel the same way while in Italy.

One of the complicating factors of renting a car in Italy is insurance. Auto insurance in Italy is typically very expensive because a lot of people drive like lunatics and apparently theft can be fairly common in some cities. In fact, many credit cards exclude Italy from the relatively common CDW coverage benefit because the risk of car damage and theft is so prominent throughout the country. Fortunately, our Chase Sapphire Reserve card does not exclude Italy, so we should have insurance coverage for physical damage or theft as long as we don’t rent the car for longer than 31 consecutive days.

We did explore the option of leasing a car for the full duration of the stay, an option that is commonly recommended for people who plan to stay for 2 months or longer. You can review this option at Auto Europe. The leasing option typically allows you to have a nicer car (with GPS included) and better insurance coverage with a lower deductible. Ultimately, we decided against this option because we didn’t want to be responsible for a car during the entire trip. It was also a bit too pricey for us, though not unreasonable (~$1,700 for 2 months, including insurance).


Hotels vs AirBnB’s

Our previous trips to Italy both took place several years ago and we stayed exclusively in hotels and B&B’s. At the time, we felt that these “regular” housing options provided a higher degree of reliability and had less of a sketch factor than AirBnB’s. They were also more expensive, so we definitely paid for those benefits.

View from one of our better hotel finds in Cinque Terre

With AirBnb becoming more and more common over the years, we would guess that we’ll end up staying primarily in AirBnB’s during our upcoming trip. Our hope is that this will save us some cash, while giving us greater flexibility to stay in towns and neighborhoods where hotel options are more limited.

While our default approach with AirBnB’s has always been to select the ‘Entire Place’ option, one of our friends recently commented on how much they love the ‘Private Room’ option when traveling abroad because you typically end up sharing an apartment with a local who can give you tips on places to visit during your stay. This might be a bit too adventurous for us, but maybe we’ll give it a shot at some point!



Last, but certainly not least, what in the world are we going to do with Riggins!? For those who haven’t met Rigs, he is our 4-pound toy poodle who has been a part of our family since 2013. He’s basically a perfect Manhattan dog: small, quiet, and an abundance of attitude.



Fortunately, Italy (and most of Western Europe for that matter) is generally dog friendly so our plan is to take Riggins with us. There’s definitely some planning that needs to take place around successfully getting him to Italy (and eventually getting him back!) but those details are better shared in a dedicated post. For now, just know that we’re excited to take the little guy with us!

Be sure to check in with us as we continue planning our trip to Italy!

Have you spent an extended amount of time in Italy? Share a comment and tell us about it!

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