Plan Your Dream Italy Roadtrip: Where To Go & Lessons Learned From Ours
Our 2 Week Italy Road Trip:
I’m so excited to share our Italy road trip itinerary with you and everything we learned about what we’d do different next time. Our trip was truly amazing but we might have tried to squeeze in too many places, too spread out for a 2 week trip.
The good news is we saw and learned a lot so I feel like I can give you some really good advice about what to do and what to not do.
Montepulciano, Tuscany Italy
Here’s what we originally planned:
Lake Como: 3 nights
Dolomites: 3 nights
Venice: 1 night
Montepulciano: 3 nights
Sardinia: 3 nights
Milan: 1 night
Here’s what actually happened (due to cancelled flights and other “redirections”):
Lake Como: 1 night
Verona: 1 night (full travel guide here)
Dolomites: 3 nights (full travel guide here)
Montepulciano: 4 nights (full travel guide here)
Sardinia: 3 nights (full travel guide here)
Milan: 1 night
If you don’t mind driving and really want to see a wide variety of Italy, this would be a great trip for you (I’d just skip Lake Como and add an extra night to Verona). If you want to have a more relaxing trip, I’d focus on just a few places closer to each other so you’re not traveling so far between places (this is what I personally would recommend if you’re like me and don’t want to feel like you’re rushing from one place to the next before really getting to enjoy it).
What I’d Do Different Knowing What I Know Now:
If you have 1-2 weeks, I’d pick a region (Tuscany, Northern region/Dolomites, Southern half/Amalfi Coast, Siciliy, Sardinia etc) to focus on. It’s temping to want to go everywhere and see everything but I’ve learned from too many trips trying to fit in too many places, that for me, it’s better to keeps trips logistically simple. Go to a few places that your intuition feels most called to and trust that you’re not “missing out” on the places you don’t go.
I’m SO glad it didn’t work out for us to stay the night in Venice. We went for a few hours because my husband really wanted to see it (I’d already been) and it was SO crowded. We had a great time but were very glad to leave after a few hours.
We flew into and out of Milan because it was a lot cheaper. But looking back, it probably would have been worth the extra money to fly into where we were starting and out of where we were ending the road trip.
I’d skip Lake Como. I don’t know if we were just in the wrong area but we thought it was super overrated. If I could go back, I’d try Lake Garda instead.
I’d also skip Bologna. We stopped by for a couple hours on our drive and didn’t love it.
Our FAVORITE place was Montepulciano. The hotel we stayed in was the whole vibe and everything about Tuscany is truly amazing. You could easily do a whole week in Tuscany. If you enjoy sunshine, pools, beautiful architecture and amazing food, I’d recommend centering your trip around Tuscany and if you want to add variety, I’d add somewhere along the coast or go to Sardinia for a few days.
4 nights is really our sweet spot for how long to stay in one place. For us, it’s the perfect amount of time to really see a lot and also have time to relax/settle in. For our next trip, we’d probably do a minimum of 3 nights in each place, ideally 4.
If you have any questions about where to go and planning your trip, feel free to leave a comment below :) I’m happy to answer as best I can.
How to plan a road trip in Italy:
This is how I typically plan our trips :)
Start by researching different places and make a list of all the places that spark joy or feel like they’re intuitively calling you to go. For example, maybe you feel called to Tuscany, Sicily, Amalfi Coast and the Dolomites. I’m also in Intuitive Life Coach if you didn’t know and this could actually be a really fun topic to do an inner voice session on if you want to let your intuition guide the planning of your trip.
Choose the one place you MOST want to go and then plan the rest of your trip around that place. What other places are within 2-4 hours that you’d want to see? What day trips are near there? Use google maps to plan the best routes. For example, maybe you feel most called to Tuscany so you could research towns near there you may want to see like Florence, Montepulciano, Pienza, etc.
Decide how many nights you want to stay in each place. 4 nights is our personal sweet spot for most places.
Choose the closest airports to fly into and out of.
Book your places to stay. I like to use booking.com and Airbnb. On booking.com, I look for places with at least 9/10 stars and 100 reviews. On Airbnb, I look for places with at least 4.9 stars and 100 reviews. If I feel really good about a place, I’ll book something with less than 100 reviews. I will also read A LOT of the reviews in detail; this will give you some really great insight. You also want to look at the locations and make sure it’s an area you want to stay.
Research and book activities (if you want to). Besides where we are going and where we are staying, we don’t plan too much before our trip. We like to flow and wander with what we feel in the moment, hence the blog name ;) The only time we’ll book stuff is if there’s a restaurant we feel like we HAVE to try or a something like a boat tour that we really want to do. Otherwise, we like to keep our plans open so we can flow with what feels aligning at the moment.
To find the best things to do while traveling, we use Yelp (4 stars and up and ideally at least 100 reviews) or Google Reviews (4.5 stars and up and ideally 100 reviews) for restaurants, Pinterest and Google for ideas of things to see (and of course you can use my travel guides and recommendations here) and ask locals for recommendations as well.
Surrender and go with the flow as best you can ;) Shit doesn’t always go to plan and it’s so much more enjoyable when you just let go and lean into where life is taking you in each moment!
Driving in Italy:
Renting a car and driving, for the most part, is pretty easy in Italy; just reserve it ahead of time on Kayak and you’re good to go.
Driving was pretty smooth everywhere we went but some parts of Italy are “scarier” to drive in. For example, we went to Positano a few years ago and the driving there is terrifying. I wouldn’t recommend driving there.
Driving in the Dolomites was also a little intense; the roads are super windy and sometimes you’re driving on a narrow road along the mountain cliffs. My husband is a very good/confident driver and we’ve driven in the mountains before so it was fine for us but just something to keep in mind when planning your trip.
In case you’re wondering, they drive on the right side of the road in Italy.
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