Begin your adventure in the captivating port city of Trieste. Often referred to as 'Little Vienna by the Sea,' Trieste embodies a unique blend of imperial Habsburg architecture, Mediterranean flair, and Slavic influences.

What to do in Trieste

Upon your arrival and hotel check-in, take a stroll along the enchanting Canal Grande and explore the Austrian quarter. When it comes to dinner, choosing among the tempting options for your first day may be tough. If you want ideas for local specialities, our City Factsheet provides some suggestions.

On day 2, kickstart your morning with breakfast at one of Trieste's historic coffee houses, such as Caffè San Marco or Caffè Tommaseo. You will quickly understand why the city is also known as the 'City of Coffee.' Next, ascend to the beautiful San Giusto Cathedral atop Trieste's central hill and the historically rich Castello di San Giusto, offering breathtaking views. We found the Castello surprisingly interesting and well worth the ticket.

Whether ascending or descending, you'll conveniently pass by the ancient Arco di Riccardo, dating back to 33 BC—a nice photo spot. After a quick lunch, enjoy a relaxed coffee break at the majestic Piazza Unità d'Italia, the largest seafront square in Europe. Before sundown, make your way to the Pier/ Molo Audace, relishing the romantic vista it offers.

Recommendation where to eat

Wrap up your Trieste visit with a delightful dinner at the remarkable waterfront restaurant Pier. (Make a reservation(!) on the seafront terrace) We timed our visit perfectly to coincide with sundown, and the enchanting view of the numerous boats was quite memorable. (Especially the boat behind us, named ‘Out of Office’!) Afterwards, head up to the rooftop area known as 'The Roof'.

Parking Tip: Use the centrally located parking garage "Park San Giusto". We found it very convenient.

Start your breakfast early and head to the Castle Miramare for half a day. Marvel at its architectural beauty, learn about the fascinating downfall of Habsburg Archduke Maximilian and enjoy the extensive gardens. It's the perfect appetizer before a delightful dinner in Padua.

Photo-Tip: Before visiting the Castle inside, walk down the terrace for some truly magnificent pictures. This way you avoid the unfavourable midday sun.

Parking

If you arrive early, you should find enough parking spaces. In September on a week-day, we had no issue, but in peak season it might be more difficult. Right before the park entrance, there is a parking area for a fee. You pay at an automat before leaving.

Your next destination brings you to the charming, small city of Padua. Often overlooked, perhaps due to more famous Venice, Padua is a sweet gem. What we loved about Padua is its laid-back atmosphere. Wandering through its streets adorned with numerous arcade walkways felt like a journey back in time. Visit the Scrovegni Chapel to marvel at Giotto's frescoes and wander through the historic Prato della Valle square. Explore the prestigious 800-year old University of Padua and its anatomical theatre, where Galileo Galilei once taught. We found that Padua invites you to take a moment to just breathe and savour life at a leisurely pace.

Recommendations

Culinary Tip 1: Sit in the iconic Caffè Pedrocchi, a must-visit for coffee enthusiasts. Their regional specialty, the green Pedrocchi coffee, is truly memorable with its unique blend of coffee, mint and chocolate :)

Culinary Tip 2: Hand to heart, we experienced the best dinner of our entire three weeks in Padua. Head to Boho Padova Ristorante and treat yourself to a menu degustazione. The garden setting is perfect for a romantic dinner, and I promise you and your partner will relish every second of it. The experience was so delicious, that we longed to return on our way back. Unfortunately, the entire town was fully booked, leading us to an unexpected detour to... Venice!

For a quick lunch break, we can recommend Dalla Zitta, where you can get excellent sandwiches.

Ravenna is the city, that surprised us the most. We knew that it is famous for its mosaics, but we had no idea how beautiful and truly amazing the architecture with its rare Byzantine mosaics is. We suggest you spend 2 days here to fully appreciate the art. The city offers a combi-ticket for 5 sights and you can visit them within 3 days. There is quite a bit to see, but what impressed us the most, is the Mausoleum of Galla Placidia and the Basilica of Saint’ Apollinare Nuovo. Also take a quick peak into Dante's tomb and walk along the charming streets of the historic center. For dinner, choose one of the excellent trattorias in town (see our city guide for recommendations).

Day trip to the beach

If you are wondering whether to also spend time on the nearby beach: We think it depends on the season. We actually stayed in Punta Marina Terme to relax on the beach. Unfortunately, in September a lot of places already had reduced hours and we had trouble finding open restaurants. We also didn’t have luck with the weather. So in hindsight, it would have been better to stay in Ravenna directly.

Since San Marino is so close to Ravenna, visiting this state is a definitive must-do. The highlight of this tiny state is both its medieval flair, and its stunning views.

If you have the budget, splurge a bit and take a room with a balcony. Watching the sunset from your balcony in the arms of your loved one is well worth it :)

What to do in San Marino

Make reservations in La Terrazza Ristorante for a great lunch or dinner with an amazing view over the Piazza della Liberta and the surrounding landscape.

Since the city centre is small, one overnight stay is sufficient. The main attractions in San Marino are its three 13th-century towers Guaita, Cesta, and Montale. Check the opening times and plan sufficient time to walk around the fortifications and visit the museum. We also liked the neo-gothic palace, which is the seat of government. In addition, we found the shops quite curious. We couldn’t figure out why, but you will find a lot of different weapons in the shops. You can get anything from knifes, airguns to bows and crossbows.

Parking & Packing Tip

Parking was easy due to the great infrastructure (see city guide). However, next time we would pack an overnight bag with our valuables and only carry that up to the hotel. Our hotel was in the middle of the historic city centre and although the elevators helped, dragging the heavy suitcase up those steep, cobbled streets left us exhausted and in need of a shower.

Arezzo, the City of Gold, is a touristic underdog. If you are looking for gifts, this might be the right place for you. Arezzo is the cradle of goldsmithing and today it is the Italian centre for goldsmiths. But this authentic city offers more also in terms of architecture and history. Start your day at the Piazza Grande, surrounded by historic buildings and the Vasari Loggia. Climb up the clock tower for the best vista in town. Take a leisurely stroll through the quaint streets, exploring local artisan shops and cafes. Also visit the Basilica of San Francesco to view the renowned frescoes Legend of the True Cross. Conclude your visit with a delightful Tuscan meal in one of Arezzo's traditional trattorias, savoring the regional flavors that make this city a hidden gem in the heart of Tuscany.

Siena is easily our favourite city in Italy. Compared to Florence, it's so authentic, even quiet, but still vibrant. It's also home to the most stunning Cathedral we have ever seen. What's more, Siena is in the heart of Tuscany and thus the perfect region to rest from your first week of intense travel.

Accommodation

We actually didn't stay directly in Siena, but about half an hour away in a wonderful agrotourismo. We can highly recommend this. Choose one of the many agrotourismos in the middle of nowhere. Surrounded by olive groves, with a pool and a garden where you can enjoy a bottle of wine in the evening, is heaven on earth.

What best to do in Tuscany region

From here on, you can explore Tuscany at leisure. We have created a separate City Guide for Siena with all the details and day trip recommendations. Below we just give you an insight into our personal impressions and favourites.

First of all, after all the travels, we took a day or two to just relax in our awesome agrotourismo. Go to the supermarket, fill up on cheese, prociutto, ham and wine and you have the perfect evening.

Since we love Siena, we visited it twice. We walked to the iconic Piazza del Campo and visited the magnificent Siena Cathedral and the entire attached Museum Complex. We can easily spend 3-4 hours in there. And of course, we enjoyed the excellent Tuscan cuisine in town.

Since we fell in love with Italian wine, we also had to travel to the wine centres Montalcino and Montepulciano. Personally, we prefer Montepulciano. Take the scenic drive through the famous Val d’Orcia for postcard-perfect views! We also wanted to spend a day on the beach, so we drove to the Marina di Grosseto. We found it much more beautiful than the beach near Ravenna.

On our way to Bologna, we spend half a day in San Gimignano since it's more or less on the way.

Unfortunately it's time to slowly head back home! Bologna is a vibrant, lively student city. It actually is home to Italy's oldest university and you will feel the student vibe across town.

What to do in Bologna

Visit the Piazza Maggiore with the powerful Neptune fountain as well as Bologna's very own leaning Two Towers. We can also recommend to step into the enchanting Basilica di San Petronio, Europe's 6th-largest church and the Basilica di Santo Stefano. To find a place for lunch, go to the Quadrilatero market district. It is filled with market stalls, cafes and gourmet delis.

Planning Tip: We can highly recommend planning ahead and reserving a table for dinner before arriving. Although end of September isn't high season, we were wandering from place to place till we finally found a restaurant.

Itinerary option

If you are short on days, you can reduce your stay in Bologna to 1 night. That's exactly what we did. Of course, you won't be able to see all the attractions, but we found it enough time to at least get an impression of Bologna.

Return Stop Options

On your return way, you have the choice between Florence and Bologna. We went to Bologna, since we have been in Florence a couple of times already. Additionally, the driving distances between Siena - Bologna - Venice are convenient with 2 - 2.5 hours. However, if you haven't been in Florence yet, consider replacing Bologna in your itinerary. All in all, we find Florence way more interesting.

From Bologna it's only an hour drive to Ferrara. Including lunch, we spent half a day here, before heading to Venice. This small Renaissance town was once the centre of the powerful d'Este family, which rivalled the Medici's in power and prestige. Thus, it is no surprise, that Ferrara has its very own impressive Castello right in town - including a moat! If you are lucky, maybe the renovation of the 12th-century Cathedral will be done by the time you visit. We were sorry, that we couldn't enter this impressive building. Afterwards, head to a trattoria for some authentic pasta. We found a cute, hidden place that served simple, yet delicious ravioli with sage. A classic dish in Ferrara is also Cappellacci di zucca Ferraresi (the pumpkin hats of Ferrara).

We suggest, that you leave after lunch to arrive in Venice in the afternoon, have enough time for check-in and find yourself dinner. However, if you prefer to spend more time in Ferrara than we have listed a few more top attractions of Ferrara below.

Parking

It's best to park your car in the Parking Lot "Centro Storico". It's only a 10min walk from here to the historic centre, the parking area is monitored and we found it quite cheap.