Curator’s statement
If you’ve never been to Italy, I am sure you have fantasized about visiting at some point. There is no denying the extraordinary allure of Italy’s enchantment. While the heart of Italian culture may lie in its culinary mastery (who else could live off of pizza and pasta for the rest of their lives? 🙋♀️), the passionate accents uttering one of the world’s most seductive and romantic languages are sure to sweep you off your feet. As you wander the streets, you’ll come to fathom the tangible proof of Italy's timeless contributions to human history through the engineering feats of Ancient Romans. Explore diverse landscapes, from beaches and lakes to mountains and cliffs, from busy cities to rustic vineyards while cherishing the playful tutting of scooters weaving through the narrow streets. Raise a glass and proclaim, “Saluti!” to fine Italian wine, a symbol of the country's dedication to craftsmanship and the joy of living la dolce vita. Even three weeks in Italy is hardly enough time to truly relish in the beauty, history and culture that makes Italy special (but that little taste will be certain to satisfy you for years to come - until your next visit back, that is).
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Things to do in Italy
Italy boasts such a diverse offering of activities, it’s nearly impossible to narrow it down to my absolute top 10 musts. Though, as a starting point, I recommend adding the following to your Italian bucket list:
Shop ‘Til You Drop in Milan
Milan is a mecca for haute couture, luxury brands and cutting-edge designs, drawing fashionistas from all over the world to renowned fashion districts such as Via della Moscova and the Quadrilatero della Moda. Home to some of the world’s most notable high-end designers, including Prada, Armani, Versace, Moschino and Dolce & Gabbana, Milan’s pulse on global style trends and exquisite craftsmanship are just a few of the many features that add to Italy’s glamor.
Take A Boat Ride Through Lake Como
Only a few hours by train or car from Milan, Lake Como is a must during your three weeks in Italy. Nestled against the backdrop of the Swiss Alps, Lake Como captivates visitors with its picturesque landscapes, crystal-clear waters and lush surroundings. Perhaps you’ve heard of Lake Como from the many celebrities that have vacation homes there (including George Clooney, Madonna and Richard Branson), but you don’t have to have a celebrity budget to enjoy the idyllic lakeside towns that span the lake’s 56 square miles. To really experience Lake Como’s serenity and allure, I recommend touring by boat. Not only will you get to soak in the sunshine, but you’ll also be able to explore much more of the lake’s expanse than you can by land.
Get Serenaded by Gondola in Venice
Venice’s distinctive charm arises from the intricate network of picturesque canals that replace traditional streets, the absence of cars and the mesmerizing architecture of centuries-old buildings lining the waterways. One of the most iconic and romantic means to traverse the city is by Gondola. Adorned with their infamous straw hats and striped shirts, gondoliers will guide you through the city’s enchanting waterways while you’re serenaded by traditional Italian melodies of soulful timbre and bellowing accordion.
Take a Cheesy Tourist Photo in Front of the Leaning Tower of Pisa
Perhaps one of Italy’s most archetypal emblems is the world-famous Leaning Tower of Pisa. Its distinctive tilt captivates visitors with this one-of-a-kind engineering fault that has endured for centuries, highlighting the beauty in imperfection. Even if you’re not one for being in front of the camera, in today’s world of “wanna-be influencers,” it’s just as fascinating to watch all of the other tourists pose, pretending to hold the tower in their hands or push it over.
Marvel at the iconic David sculpture in Florence
Located in the Accademia Gallery in Florence, Michelangelo’s 17-foot-tall marble masterpiece commands immediate attention. Stand before David in profound awe of the flawless craftsmanship, with each meticulously chiseled muscle conveying a sense of realism that is beyond the supernatural. If you're traveling during the summer, be sure to reserve your tickets well in advance, as tickets will certainly sell out even weeks ahead of time.
Tour the Colosseum in Rome
Colossal doesn’t begin to describe the magnificence of this ancient structure or the remarkable ancient Roman engineering that has endured through thousands of years. Once serving as the world’s largest amphitheater for gladiatorial contests, it now attracts millions of visitors who come to appreciate its historical significance and envision the dramatic events that unfolded within its ancient walls
Take in Michelangelo’s “The Creation of Adam” Masterpiece in Vatican City
The Vatican boasts an extraordinary collection of artworks from some of history’s most notable artists, including Michelangelo, Raphael, Da Vinci, Botticelli, Dali and Van Gogh. The guided Vatican tour ends at the Sistine Chapel, where the ceiling is decorated with Michelangelo’s world-famous masterpiece: “The Creation of Adam”. Visitors may be evoked with a spiritual awakening as they gaze upon this encapsulation of the divine moment when God imparts the spark of life to Adam through a celestial touch, their outstretched fingers conveying the transcendent connection between Creator and humanity.
Become an Italian Master Chef on the Amalfi Coast
Aside from admiring the striking contrast of the sky-high cliffs and never-ending ocean expanse, the Amalfi coast also offers a generous selection of fun activities. At this point in your three weeks in Italy itinerary, you’ve likely dined several times on some of the best Italian food you’ve ever had. Why have these culinary treasures as just a memory, when you can learn first-hand from Italian chefs how to recreate some of Italy’s finest recipes at home? These are two fabulous cooking classes on the Amalfi Coast that I can’t recommend highly enough: in Amalfi and Positano.
Enjoy a Wine Tasting in the Tuscan Hills
Any wine aficionado is likely well aware that Chianti originates from the Chianti region of Tuscany, though this is only one of the several Italian wine varietals produced in Tuscany’s wine country. Immerse yourself in Italy’s wine-making heritage as you soak in the breathtaking views of the sun-drenched vineyards weaving through the Tuscan hillsides.
Eat Pizza in Naples
Sometime between the 16th and 18th centuries, one of mankind’s greatest inventions was born: pizza. As the birthplace of this modern masterpiece, Naples undoubtedly is home to some of the best pizza in the world. For specific restaurant recommendations, check out the food and drink section below.
Honorable Mentions:
There are truly too many amazing adventures in Italy to list them all, but here’s a list of some additional “musts” for your itinerary:
Venice
Check out St. Mark’s Square
Take a guided tour of St. Mark’s Basilica & Doge’s Palace
Florence
Peruse the vast collection of sculptures, paintings, and artworks at Uffizi's Galleria
Climb to the top of the Duomo Cathedral
Rome
Discover the Pantheon
Explore the city by bike
Make a wish and throw a coin into the Trevi Fountain
Amalfi Coast
Hike the Path of the Gods
Browse the ceramic, linen, and tailor-made sandals boutiques in Positano
Take in the natural beauty of the Blue Grotto in Capri
Pompeii
Explore Mt. Vesuvius' impact on the legendary Pompeii ruins, a UNESCO heritage site.
For a more comprehensive itinerary, please don’t hesitate to reach out to me via the “Contact Traci” button. It would be my pleasure to craft your ideal Italian getaway.
Places to eat & drink in Italy
Italy’s food is so divine that I’m not even going to waste my time (or yours) by highlighting anything other than restaurants in this section. I’m drooling just putting this together - I might even have to crash your trip!
Venice
Top of the Carlton Sky Lounge: Hands down one of the best rooftop dining experiences in Venice, where you can feast on exquisite Italian fare while taking in the stunning panoramic views. Recommended dish: Garganelli with veal ragout, herbs and pecorino cheese
Florence
Trattoria Sostanza: Make a reservation as far in advance as possible, as this cozy Italian hideaway is certain to be booked solid any night of the week. Recommended dish: Tortellini with butter sauce. Thank me later!
All’Antica Vinaio: This beloved sandwich shop is so popular, they’ve opened four storefronts all within the same block, and even that isn’t enough for the massive lines that form at all hours of the day. Take my word for it, the artisanal cured meats and gooey Italian cheese coalescing between the warm, crunchy, fresh-baked bread is well worth the wait (dare I say, heavenly?). And the line moves quicker than it looks. Recommended dish: The Italian, 20-month-old Parma ham, buffalo mozzarella, tomato and basil
Gustapizza: Like any notorious eatery throughout Italy, you’ll likely encounter a line here, especially during the busier summer months. However, outside normal meal hours, the wait is considerably more manageable. Gustapizza draws its crowd through wood-fired pizzas, topped with fresh, local ingredients and a crispy crust that envelops a pillowy cloud of dough. Recommended dish: I had the Porcini, but you really can’t go wrong with any of their pizzas!
Rome
Osteria da Fortunata: Another Italian hot-spot that doesn’t take reservations, but the reward at the end of the long wait is so gratifying, you won’t believe your tastebuds! While you wait, watch through the window as pasta artisans hand-craft fresh pasta right in front of your eyes. Recommended dish: Strozzapreti Carbonara. The crisp outside juxtaposed with the tender inside of each guanciale crumble served as the perfect complement to the fresh-made pasta coated in a cacio-e-pepe-like sauce and sprinkling of courgette flowers, one of Italy’s most treasured delicacies. Caution: you may be craving this impeccable cacophony of flavor for years to come, with nothing coming even close to satisfactory in comparison
Mariuccia: If you’re on a quest for the best pizza & suppli (fried appetizers and snacks) in Italy, search no further than Mariuccia. Their savory, donut-like pizza dough warms you to your core, and the pizza will leave you speechless. They accept reservations, so make sure you get on that! Recommended dish: Diablo Pizza with olive oil, pomodoro la torrente, fior di latte, basil, spicy salami and 'nduja.
Roscioli Salumeria con Cucina: Even making a reservation several weeks in advance, I couldn’t secure a table any earlier than 10:00 pm, so you’ll definitely need to plan ahead! The cucina is attached to the renowned Roman Salumeria (an Italian deli with fine meats and cheeses) and sources premium, local ingredients in their gastronomic take on traditional Italian fare. Recommended dish: Burrata con perle di tartufo. Quite literal to the translation: burrata with caviar-sized winter black truffle pearls. Is your mouth watering yet?
Naples
The birthplace of pizza touts several world-class pizza joints, though only one can take the title of “Best Pizza in the World”: Gino e Toto Sorbillo. Just don’t make the same mistake I did and confuse it with the other two Sorbillo restaurants right next door (all three of them will have lines out the door). Triple check you’re at the right place before waiting in line, even if Google maps says you have reached your destination. Not that I’m still bitter or anything…
Amalfi Coast
La Tagliata: The views alone from atop the Positano coastline are enough reason to visit La Tagliata, so it’s all the more impressive that the prix fixe family-style dinner bursts with traditional Italian flavors, complemented by exquisite house wines.
La Moressa: Overlooking the Tyrrhenian Sea in the cliff-sides of Praiano, the commanding view on La Moressa’s outdoor terrace provides an enchanting backdrop to savor your meal in, day or night
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Traci Shapiro
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This guide is part of our ongoing series on travel to Italy.