Italy is one of those destinations that seems to be on everyone’s travel bucket list; between the food, the art, the architecture, the food, the wine, the landscapes, and have I mentioned the food, Italy has an incredible amount of history, beauty and world-renowned cuisine to offer visiting guests.
And, whether it’s your first or fifteenth time traveling to Italy, there is always something new to discover. Many people who visit Italy for the first time try to fit everything in on a typical tour of the “big three” cities (Rome, Florence, and Venice), but many travelers who do this feel there was not enough time to see and do it all, and they are 100% right. So let’s not try to cram all that Italy has to offer into one jam-packed journey, let’s not be “typical,” and let’s plan a trip to Italy that fully immerses you in the Italian culture and lets you appreciate and enjoy your journey every step of the way.
Here we go!
Arrive in Naples, but instead of staying in the big city, make your way to the nearby seaside town of Sorrento, your home base for the next few days. There you can spend your first afternoon in Italy the way locals do, meandering down Corso Italia, the town’s main shopping thoroughfare, until you reach Piazza Tasso, where you’ll find sweeping views of the valley below.
From there, you can continue on to visit the historic streets of Sorrento’s old town, and visit the Marina Grande, where you may choose to dine al fresco by the water, or head back to one of the many restaurants in the main piazza.
Begin your day on the water by hopping on a ferry to the famously beautiful island of Capri. Here you can pop in and out of designer boutiques one minute, and stroll among ancient ruins the next, all the while taking in the views of the boat-dotted sea and the ocean-worn cliffs. While on Capri, you might sample the island’s signature aperitif, Limoncello, or even take a boat ride out to swim in the strikingly blue waters. Once you return to the mainland, head back to Sorrento for dinner at a restaurant recommended by locals.
If you thought Capri was beautiful, wait for the enchantment of Positano, one of the most photographed places in the world, and for good reason! With brightly colored houses nestled into the hillside above, and sparkling waters splashing onto pebbled beaches below, you will feel like you’ve walked right into a postcard!
Explore this magical fishing village full of myth and legend, and be sure to take a boat ride to experience the beauty of the Amalfi Coast from on the sea. On your way back to Sorrento, stop at a working bucolic farm, where you can learn to make your own pizza for dinner, and even enjoy a presentation of the Tarantella, the traditional Italian dance, while you dine.
Step into history, literally, with a tour of Pompeii, the city frozen in time by the eruption of nearby Mt. Vesuvius. Here you can walk right into houses preserved by the volcanic ash, and still see the pictures and murals on walls that ancient people used to look upon every day. From here, head to Naples where you can board a train to Florence, and settle in there for the second half of your journey.
It’s hard to imagine the amount of breathtaking and historic art one city can hold, but you won’t even have to try, because you’ll be immersed in the artistic world of Florence from the moment you arrive.
Start with a walking tour of the city (as Florence is known to be one of the world’s most walkable cities), where you can take in the glory of the Duomo, the unparalleled Gothic Cathedral, with views for miles from the bell tower, and make sure to stop and see Michaelangelo’s famous David at the Galleria dell’Accademia.
After lunch (and of course gelato), tour the Uffizi gallery with works by some of the world’s most famous artists, including Michaelangelo, da Vinci, and Botticelli. Then, dine at one of the myriad of renowned restaurants throughout the city.
Visit the nearby town of Siena, a quintessentially romantic medieval town, with a famed horse race that still takes place twice each summer. Explore the fan-shaped piazza, and the intricately designed and decorated Duomo, or cathedral, in the center of town; be sure not to miss the 14th-century tower with views of the surrounding town and countryside.
On your way back to Florence, stop at an authentic Tuscan farm, where you can taste homemade wine and olive oil, and enjoy a meal of fresh pasta and home grown produce. Once back in Florence, take the evening to explore the city by night, as it dazzles with lights and laughter.
Discover two new towns today, first the Renaissance city of Lucca, famous for the walls encircling the city center, the cobblestone streets, and the classic architecture. Bike along the walls for the best city views, and then stroll through the quaint streets of this peaceful city.
After a local lunch, head over to Pisa to see the world-famous leaning tower, and also to meander through the museums and galleries full of medieval art. After exploring for the day, head back to Florence for one last dazzling night of exquisite cuisine and merriment.
After one more fabulous meal in the morning, make your way to the airport in Florence, where your Italian journey will commence…for now, and bid Italy, “Arrivederci,” or, “Until we meet again,” as Italians say.
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