The countryside of Italy, part of our Italy road trip itinerary

So, it is actually happening. The time is coming for us to hit the road.

As Julie wrote about a few weeks ago, we are embarking on a European road trip, where we will be spending a bulk of our time in the Balkan region. However, our adventure actually begins in Italy, where we will stay two weeks cruising through the country on our very own Italy road trip.

So, we’re off. September 3rd. It’s official.

The crazy bit for us about ‘having a date’ is that we are leaving London with no place to move to. Our stuff will be relocated back to the US (where we will spend the holidays), but that will be temporary. We will continue to live abroad, we just don’t know where.

So starting in September, we will be living a gypsy life. No home, no apartment. And we begin in Italy.

The beautiful wine region of Barolo in Piedmont Italy. The start of our Italy road trip.

Days 1-4 Piedmont

My first ever trip abroad back in 2005 included three amazing days with my brother in the Piedmont region around the village of La Morra. We drank way too much Barolo (the king of Italian red wine, in my opinion) and ate fistfuls of truffles at the White Truffle Festival. I have been talking about going back ever since. Thankfully, this oversight will be rectified, as we begin our Italy road trip in the villages in the Langhe hills, the heart of wine country near Alba. We will be too early for the White Truffle Festival, but we will no doubt eat and drink like kings!

The picturesque hillside villages of Cinque Terre will be the second stop on our Italy Road Trip

Days 5-8 Cinque Terre

We had a conversation recently with an Italian friend who simply does not understand why Americans love Cinque Terre so much. And yes, I agree that Cinque Terre is crawling with American tourists, which takes a little bit of the shine off a destination. But I’m still a complete sucker for this place, and I love it despite the ever increasing crowds.

I imagine our days will include a little dip in the ocean, a glass of wine and a mid-afternoon nap, before gorging on the famous Ligurian pesto. It is Julie’s first time in Cinque Terre, and I can’t wait to see her set sight on those villages for the first time.

A lineup of Ferrari's, from the Italy town of Modena, a stop on our Italy road trip

Day 9-10 Modena

Modena, situated near Bologna in Emilia-Romana, is the home of the finest balsamic vinegar and Ferrari, one of the finest motoring companies in the world. Like most of the stops on our Italy road trip, we will eat well. I am also trying to convince Julie to spend a day with me at the Museo Enzo Ferrari and do a 10-minute thrill ride in a brand new Ferrari on the streets around the museum.

She doesn’t seem as thrilled by the idea as I do.

Even if that doesn’t work out, we will explore the historic core of Modena, including the Duomo, and head out to the countryside for some balsamic vinegar tastings. We will probably eat our weight in Parma ham and Parmesan, two of the most well-known products from this region.

the countryside outside San Marino, part of our Italy road trip

Day 10-11 San Marino

I’m going to be honest. I know almost nothing about San Marino. We will be in the area anyway as we begin our trek along the eastern coast, so we figured why not knock off another country from the list? With a population of 31,000, it won’t take too long to see most of the country.

Luckily, if we run out of things to see, we can duck back into Italy to the seaside city of Ravenna, home to legendary mosaics. If we feel like a little beach time, we could also head to the nearby coastal town of Rimini, known for its long stretches of golden sand.

Nothing like the beautiful clear waters of the Mediterranean, part of our Italy road trip

Day 12-15 Bari

The final destination of our Italy road trip is the city of Bari. My great-grandfather was born and raised just outside the city, in a village called Santeramo. I decided that a trip back to my Italian heritage is worth the trek to the southern part of Italy. Sure, Bari is supposed to have some good nightlife, thanks to the large student population in the city, but for me, this part of the road trip is about my past.

Aperol Spritz on our Italy road trip

At this point, our Italy road trip comes to an end, and our Balkans adventure begins. From Bari, we board an overnight car ferry, bound for Durrës, Albania, the next step in our journey.

And what a journey it will be!


  • July 13, 2016

    Italy is SO HIGH on my list right now, so I just zoned out dreaming about this itinerary! It sounds amazing and I can’t wait to read all about it. Good luck with your gypsy adventures!!
    Kacy recently posted…New DC Bars for Summer SippingMy Profile

    • July 14, 2016

      Thanks Kacy – I feel like Drew has been dreaming of a trip like this for years (maybe ever since his last one in 2005!). I’ll be sure to pack my stretchy pants for all the pasta and wine consumption!

  • July 14, 2016

    This itinerary really excites me! I really like visiting Italy (I’ve visited the country three times), but I haven’t been to any of the places your going to, so I can’t wait to read about it! This trip will be an amazing start to your lengthy Europe trip! 🙂
    Dominique recently posted…Rotterdam – Stairway to HeavenMy Profile

    • July 18, 2016

      it is going to be quite the journey. Italy will certainly be a fun way to begin the trip and I’m looking forward to seeing some familiar places and exploring some new areas as well!

  • July 16, 2016

    Great article! Beautiful website. Love a good Italian road trip.
    Skye recently posted…Meet Peta Shulman of GoodnessMe BoxMy Profile

  • July 16, 2016

    I love it. I would love to tag along and join you lol. Seriously that’s an amazing itinerary and what an exciting future.

    • July 18, 2016

      just keep an eye on the blog…lots of fun content coming down the pipeline!

  • July 16, 2016

    Guys -didn’t realise you’re also leaving permanently London. This sounds amazing. I’ve inter railed in Italy but to see it by car like you’re doing is gonna be so much fun. I’m so tickled to visit San Marino though.
    Stefan recently posted…Gay Tokyo: travel guide to Tokyo’s best gay bars, clubs and hotelsMy Profile

    • July 18, 2016

      yeah, we had to make the final decision recently. It is off to more fun things though, so we aren’t too sad…yet.

  • July 16, 2016

    This sounds like an awesome road trip! I still haven’t been to Italy and this seems like the perfect way to do a trip there!
    Claire recently posted…8 Cool Cafes in Penang That Have CharacterMy Profile

    • July 18, 2016

      It is going to be a fun 2 weeks! Not gaining about 50 pounds will be the biggest challenge!

  • July 17, 2016

    I just learned about Bari and have been aching to go there ever since. This itinerary looks FANTASTIC! I may have to follow in your footsteps…
    Lillie recently posted…Block Island, Rhode Island: Wild Beauty and RelaxationMy Profile

    • July 18, 2016

      I don’t know much about Bari except my family heritage, so excited to see what it has to offer!

  • July 17, 2016

    Sounds like a fantastic itinerary!! Too bad you’ll miss the White Truffle Festival this time because it sounds amazing! I would love to see Cinque Terre, as well–it looks so beautiful there. When we were in Italy, we did a food tour around the Modena area and saw how balsamic vinegar tastings, Parma ham and Parmesan were made, and we visited the Ferrari museum, too. It was so much fun! Hope you have a great trip!
    Jenna recently posted…A Photo Essay: Wisconsin Road Trip with AmericInn Hotels #InnToWinMy Profile

    • July 18, 2016

      Thanks! If you ever want to check out the White Truffle Festival (which is amazing as it sounds) it runs every weekend during October and the start of November in the city of Alba.

  • July 18, 2016

    The photos in this post are amazing, makes me want to pack up and leave! It was really lovely to read about your personal feelings and thoughts that crafted this itinerary 🙂

    • July 18, 2016

      We can’t wait to embark on the journey!

  • July 18, 2016

    A nice itinerary and looks like a must visit place. I just loved the photo of the swimmer. Will wait for your account after the vacation!

    • July 18, 2016


  • July 18, 2016

    Way to make me jealous. Nonetheless, good luck on your nomadic adventure and I’m sure it’ll be every bit of memorable no matter where you find yourself in

  • July 20, 2016

    Sounds like a great adventure coming up! Have fun, planning is always a big part of the enoyment already, at least for me!

  • July 22, 2016

    Sounds like a fabulous itinerary. Oh missing the White Truffle Festival isn’t good. I liked the pic of swimmer. Epic!

  • August 31, 2016

    Hi my name is Mehak and I am planning a 10 days trip to Italy with friends this November.
    Kindly help Me with an ideal itinerary that includes road and train journeys to cover maximum city and countryside attractions Italy can offer.