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My Dream Trip to Northern Italy

By Cindy Boatman March 24, 2024 Travel

Recently, I learned my DNA ancestry composition is only 3.4% Italian, and I thought “how could that be?” I assumed my love for Italy meant I have lots of Italian blood coursing through my veins. Turns out, I’m Italian mostly at heart!

Prior to September 2023, I’d visited Italy twice, once in my 40s and once at age 50. I was traveling solo then and opted to book with tour groups of around 20 people. The 1st visit was a food and wine tour through Tuscany and Umbria, the 2nd, a walking tour along the Amalfi Coast.

Finally, I Got to Plan My Dream Trip!

The prior trips to Italy via organized tour groups were amazing. Yet I had a deep desire to plan and live out my version of an Italian dream trip. That opportunity came later rather than sooner, but I finally insisted to my partner I intended to schedule a trip to Northern Italy for September 2023.

While planning the trip to Italy, an opportunity to travel to Japan for May 2023 materialized. My article “Wanderlust in Japan and Elsewhere” describes that trip. I was more than eager to travel to Japan, but I was not about to let that trip replace my long-awaited return to Italy!

Travel by Rail

Travel by rail in Japan (our first experience doing so) gave us the confidence boost we needed to take on Northern Italy by rail. Train travel is affordable and fun, eliminating the hassle of renting a car and the stress of driving in a foreign country. We could sit back, relax, and enjoy the scenery as we moved from one destination to the next.

How to Travel by Train in Italy” is an informative article if you are planning rail travel in Italy. There are several smartphone apps available to buy tickets and manage your trip. I relied on the user friendly Omio Travel App, and it worked great for me (small 3rd party fee). Rome to Rio is another app I found helpful in planning our travels.

My personal comfort cushion was to arrive 45 minutes before departure from large train stations such as Milan Centrale, and I especially recommend it if it’s your first time train traveling. For smaller stations, 30 minutes worked nicely for us. The trains we booked were mostly prompt, varying a few minutes here and there.

Beautiful Northern Italy

The article Northern Italy Region and Where to Visit provides information on the various regions of upper Italy. This area is truly a treasure, based on its culture and stunning landscapes. We had the pleasure of traveling to various destinations within each region.

I tailored our trip based on our personal preferences as to pace, destinations, hotels, and tours. Our style of travel will not suit everyone, but it works for us in this season of our lives. We prefer to take full advantage of new travel destinations, so we pack in a lot!

Our 19-day sojourn through Northern Italy was short/fast-paced as to city-time. We balanced it out with longer, more relaxing (yet active) stays in the countryside. I hope the following details of our itinerary and my reflections will be insightful and timesaving for anyone who wishes to plan and book such a trip themselves.

Romantic Venice


1 night. 9:25 AM arrival at Venice Marco Polo Airport via overnight flight. 5:18 PM departure next day via Frecciarossa high-speed train from Venice Santa Lucia Station to Verona Porta Nuova station.


St. Regis Venice (splurge/used points).


Alone in St. Mark’s & Doge’s Palace Tour‘ after hours (6 pm to 10 pm); evening in St. Marks Piazza; outdoor lunch on the Grand Canal (at the hotel); accidental visit to Murano.

Helpful Link

Venice Travel Tips


I planned a brief visit to Venice, thinking I would not want to stay long. In retrospect, I would have enjoyed another ½ day and night in the unique atmosphere of the ‘Floating City’. In route from the airport to our hotel, we accidentally exited our Alilaguna Water Bus on the Island of Murano (a destination I didn’t think I could fit into our brief stay). Murano is famous for its long tradition of glassmaking, and we enjoyed our unintentional visit!

By booking night tours, we could perfectly accommodate our tight schedule, while also avoiding large daytime crowds. The break between our tours allowed us to relax and enjoy one of many outdoor cafes in St. Mark’s Square.

Sipping cocktails and eating nibbles, while enjoying orchestra music, people watching, and a stunning view of St. Mark’s Basilica. Our favorite splurge in Venice was a water taxi transfer from our hotel to the train station upon departure. It was a wonderful way to experience the Grand Canal.

Charming Verona


1 night. Departed Venice Santa Lucia station at 5:18 PM via Frecciarossa high-speed train and arrived at Verona Porta Nuova station at 6:30 PM.


Hotel Giulietta e Romeo


Piazza Bra (Arena); Piazza Erbe (Juliet’s house, Torre Dei Lamberti); Ponte Pietra Bridge.

Helpful Link

Verona Itinerary-Best things to do in Verona in 1, 2 or 3 days


Verona, a less touristed but charming city, is renowned for being the backdrop of Shakespeare’s Romeo and Juliet. The city embraces the story yet has many other attractions. We enjoyed self-touring and loved experiencing our one evening in the electric atmosphere generated by a summer opera performance at the historical Verona Arena.

Because of our brief visit, we opted to tour the city on foot rather than attend the Verona Opera, but I can’t imagine a more magical opera venue. It would have been ideal to tour Verona for another half day.

Enchanting Ortisei



4 nights. 12:20 PM departure Verona Porta Nuova station; 1:48 PM arrival at Bolzano/Bozen Station via Frecciarossa high-speed train. Short walk to catch Bus 350 (inexpensive/hot/crowded) to Ortisei.


Hotel Gardena Grodnerhof


Seceda Peaks; Alpe di Siusi; Lago di Braies; stunning views; multi fitness levels of hiking.

Seceda Peaks
Lago di Braies

Helpful Link

Dolomites (Rick Steves’)


Ortisei served as our home base for exploring the Dolomites, one of my favorite destinations on our itinerary. Heaven on earth is not an exaggeration when describing this beautiful area. The Dolomites were one of the places we visited where a rental car would be useful, but we managed without one. It was easy to get around the town on foot. It was a short walk to each of the two lifts that access the scenic Seceda Peaks and the Alpe di Siusi.

We spent the better part of two days exploring the foregoing, taking short hikes that included stops at cute little alpine huts to enjoy the scenery, a bite, and a beverage. Otherwise, we had the hotel arrange a car/driver for one full day to explore other parts of the region, including visits to the stunning Lago di Braies (a hike around this lake or boat rental not to be missed) and the city of Cortina. I would absolutely love to visit the Dolomites again!

Fabulous Milan


1 night. Departed Bolzano/Bozen Station at 1:12 PM via Frecciarossa high-speed train, arriving at Milan Centrale at 4:21 PM.


Hotel Milano Castello


The Best of Milan Tour; Da Vinci’s ‘The Last Supper; ‘ Duomo; the Galleria.

Helpful Link

Where to Stay in Milan; 8 Incredible Areas and Epic Hotels


We experienced Milan in a whirlwind! Similar to Venice and Verona, it was a city I wished to see on the way to the next countryside stop. I was mainly interested in the Milan Duomo and Da Vinci’s The Last Supper, the latter of which requires a timed reservation. The only available tour on the needed date was a full day of walking to see multiple sites in Milan, which included tickets to The Last Supper.

So, after a good night’s sleep, we ate an early breakfast, checked out of our hotel and had them store our luggage. We then set off on foot to meet our tour group and enjoyed a busy day sight-seeing in Milan. By the time we finished the tour, retrieved our luggage, and headed to the train station, we were happily exhausted!

Relaxing Lake Maggiore/Stresa


3 nights. Departed Milan Centrale station at 5:25 PM and arrived at Stresa station at 6:37 PM via Regionale Trenord train.


Grand Hotel Des Iles Borromees


Isola Bella; strolling lake promenade; shopping; restaurants; town center.

Helpful Link

Where to Stay on Lago Maggiore


My original plan was to visit the more popular Lake Como. Unfortunately, I didn’t book early enough to secure a reservation. Stresa, on Lake Maggiore, is a great alternative. If not better! We splurged on a historical hotel frequented by the likes of Ernest Hemingway and savored the most beautiful sunsets from our balcony overlooking the lake.

Mostly, we relaxed and self-toured, taking a boat ride out to see the stunning Isola Bella, whose gardens are not to be missed. Also, Stresa provided the perfect opportunity to do laundry, since we each traveled light with a carry-on and backpack. For an extended stay, a car rental would be handy to explore the area and take a day trip to Switzerland.

Moody Piedmont-Wine, Truffles and Turin


2 nights. Departed Stresa station at 12:36 PM via Regionale train and arrived at Rho Fiera metro station (Milan) at 2:00 PM. Transferred to Frecciarossa high-speed train and departed at 2:29 PM, arriving at Turin Porta Nuova station at 3:21 PM.


Turin Palace Hotel


Barolo wine tasting; farmhouse lunch with truffle dishes; truffle hunt; alluring scenery.

Helpful Link

The Piedmont Region of Italy: Complete Guide to Best Places


Turin served as our jump-off to visit wine, hazelnut, and truffle country in Northern Italy. With such a quick visit, we didn’t tour Turin itself, only visiting what was within walking distance of our hotel. That said, Turin is a lesser traveled, but worthy destination. A rental car would come in handy if visiting the Piedmont wine region. Since we didn’t have one, we opted for our hotel to secure a car/driver for the day.

We then set out for wine country to enjoy a lovely Barolo wine tasting and vineyard visit, followed by a delicious truffle centric lunch at a lovely little farmhouse. After lunch, we enjoyed taking part in a truffle hunt, our enthusiastic truffle dog securing one black truffle for us! We were back at our hotel by late afternoon and able to see a bit of Turin before our departure the next morning.

Magical Santa Margherita Ligure/Italian Riviera


3 nights. Departed Turin Porta Nuova station at 10:25 AM via Regionale Veloce train and arrived at Savona station at 12:41 PM. Then switched to Regionale train departing at 1:10 PM and arriving at Santa Margherita-Ligure-Portofino station at 3:01 PM. To visit Cinque Terre, we took a Regionale Veloce train from SML, then traveled between villages (5 minutes apart) via the Cinque Terre Express train system.


Grand Hotel Miramare


Waterfront; restaurants; day trip to Cinque Terre; ferry ride to visit Portofino.

Helpful Link

The 7 Best Italian Riviera Towns and How to Enjoy Them


Just when you think it can’t get any better, it does! The Italian Riviera is magical, meeting my expectations based on the amazing online photos I’d viewed. The town of Santa Margherita Ligure (SML) is one of its gems, serving as our seaside base camp and a jump-off to explore the area. I would easily agree to an extended stay in this dreamy resort region!

We had the grace of lovely weather during our visit, enhancing our stay and our ferry ride to see the popular celebrity destination of Portofino. The villages comprising Cinque Terre were a highlight despite the crowds (even in September) and despite the equally busy Cinque Terre Express trains. You can also hike between villages if preferred. My favorite experience was taking in a stunning sunset in the Village of Riomaggiore. I recommend visiting Cinque Terre early in the morning, or late afternoon/early evening when the crowds are smaller.

All Roads Lead to Rome!


2 nights. Departed Santa Margherita Ligure-Portofino station at 7:12 AM on a Regionale train, arriving at Rapallo station at 7:15 AM. Switched to Frecciarossa high-speed train departing at 7:57 AM, arriving at Rome Termini station at 11:32 AM. Upon departure from Rome, we opted to take a cab to Leonardo da Vinci Fiumicino Airport (about 40 minutes from our hotel).


Baglioni Hotel Regina


Skip the Line Vatican Tour with Sistine Chapel and St. Peters; Special Access Colosseum Arena Floor Tour/Roman Forum, Palatine Hill Tour; Pantheon; Trevi Fountain.

Helpful Link

Planning a Trip to Rome


My partner really wanted to explore the ‘Eternal City’ even though it is not in Northern Italy. Turns out, it was a perfect place to end our trip! We departed SML early in the morning, embarking on a relaxing 3 and a ½ hour scenic train ride along the coast and through the Tuscan countryside.

Upon arrival in Rome, we transferred to our hotel for early check-in, then took a cab to Café Vaticano, the meeting spot for our 2:30 PM Vatican/St. Peter’s Basilica tour. We had just enough time to eat lunch before the tour began. Honestly, the crowds touring the Vatican Museum and the Sistine Chapel were claustrophobic during this time. I’d highly recommend a private or small group tour in the evening for a more meaningful experience.

As for hotel accommodations, it was hard to choose where to stay in Rome, partially since I waited too long to book. If your primary goal is sightseeing ancient landmarks, I recommend booking early to secure a hotel near those attractions.

Our 2nd tour, taken the next morning, was the most enjoyable for us. After the tour, we spent the afternoon exploring on our own with visits to the Pantheon and the Trevi Fountain (other areas to visit early morning or evening to avoid the massive crowds). Our busy day culminated with dinner at a street café and then back to the hotel to pack for our early morning flight home.


No doubt, this trip was a big splurge for us. It was expensive but using banked travel points helped with airfare and hotel expenses. Good news, you can enjoy this itinerary on a tighter budget! September was a lovely time to visit Italy. May is another good choice, with both months being just off-season.

Best of all, we created such lovely memories! Such as immersing ourselves in the incredible culture and scenery of Northern Italy (and Rome) and visiting many historical sites. Tasty Aperol Spritz aperitifs were fabulous in the late afternoon, as was eating delicious gelato anytime! Until next time, arrivederci and Viva Italia!

Let’s Have a Conversation:

Have you traveled to Italy? What are your favorite Italian destinations and why? What tips and hacks do you recommend for traveling in Italy?

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Wonderful information. Hoping to plan a trip to Northern Italy in the next couple years,


Northern Italy is amazing but don’t cheat yourselves of the South and Sicily, they are no less beautiful. I’m glad you made it to Rome, one of my favorite cities. Btw, next time take the train to Fiumicino, it couldn’t be more convenient, inexpensive, and might be faster.


I love Northern Italy and am only about 3 or 4 hours away by train. I had 5 days in Milan last May which was lovely, then in September I spent 10 days in Como in an apartment 5 mins walk from the Old Town and 15 mins walk from Lago di Como itself. I’ve also been to Florence, Venice and Bologna. Bologna is a bit faded and has a lot of political graffiti, but nevertheless it’s interesting as it was built in medieval times as a city to rival Florence.

On the other side of the border I recommend Ticino in Switzerland, especially Lugano on Lake Lugano and Ascona on the magnificent Lake Maggiori – it’s full of funny little winding back streets and is very pleasant even in early autumn.


What a wonderful trip! I really want to
Visit the Dolomites and your experience sounds amazing. I just got back from two weeks in Florence with a friend. We both just retired and this was our celebration. I’ve been to Italy many times and never tire of it. It’s probably my fav country in the world. Thanks for sharing tips and apps for train travel !


Oh my goodness! Your article wants me to put this trip on my bucket list! Thank you!!

The Author

Cindy Boatman is excited to share her research and personal insights, hoping to help others live their best lives as they age. She is retired, pursing her dream to write, enjoying nature, travel, and her grandkids. She completed a 200-hour yoga teacher training certification program in 2020.

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