ITALY
At approximately 11:26am on your first morning, sitting at a table on the terrazza of Caffè Florian in Venice, you'll fall in love with Italy forever. Or maybe it will be over a lunchtime bowl of pasta in Bologna, or perhaps it will happen hearing the fishmongers argue over arancini at the Palermo market. And you haven't even smelled an Amalfi lemon yet. The problem with Italy is that most people visit the same 10% and go home thinking they know it. Of course, stroll the winding streets of Trastevere, stop for some cacio e pepe, but don't miss the truffle hunters of Langhe or the baroque excess of Lecce. If you show up curious, we'll make sure Italy rewards you.
A Taste of What's Possible
Snorkel with a marine biologist in Sardinia's La Maddalena archipelago
Farm-to-table cooking lesson on a lemon grove on the Amalfi Coast
Intimate wine-tasting at a family-run vineyard in Tuscany
Where You'll Stay
We spend a lot of time obsessing over the perfect accommodations. Our favorites tend to be smaller, boutique properties with a unique sense of style and fantastic service.
Here are just a few of our favorites...
Three of Our Favorite Spots
Emilia-Romagna
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If you eat seriously, this is the pilgrimage. Bologna is the undisputed capital of Italian food culture, Modena has balsamic vinegar aged longer than some family businesses, and the region doesn't perform for tourists particularly well, which is precisely why it we love it.
PUGLIA
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The heel of Italy's boot spent decades being overlooked while everyone else got in line for Tuscany. The food and people carry the easy confidence of a place that never needed the attention. Ancient whitewashed villages, brilliant cyan waters, burrata made that day, and casually luxurious masseria stays.
LAKE COMO
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The most beautiful lake in Europe is not a controversial claim when you're standing on a terrace above Bellagio watching the dusk light fade to stars. Como asks for a slower pace, is unabashedly romantic, occasionally crowded, and entirely worth it when you know where to stay and when to go.
“There were many highlights of the trip overall, but the most important thing we want to express are our gigantic compliments to our extraordinary guide in Rome! Giuilia was truly outstanding. She was particularly great with our kids and made all the historical stuff so much fun. Just as one example, when we went to Ostia Antica, she made up a narrative so the kids would feel like they were traveling from Rome in their chariots as merchants, stopping for a bite to eat, going to the laundry and the baths to spiff up, taking our business associates out to the amphitheater, having dinner in their fancy villa, etc.
Her enthusiasm and energy made Roman history come alive for all of us each day, but especially the kiddos. There is incredible wealth of knowledge, of course, but she truly went above and beyond in a multitude of ways. For our anniversary picnic she put together the most unbelievable lunch spread (including getting her dad to go to his local market where they apparently sell yummier fruits than they have in the city) and she also brought toys and games for our kids to play with at the park. In summary, she is a true gem and you should make sure to request her for all your Boutique Explorer guests especially if they have kids.
Even though the cities we visited were pretty busy, we were able to beat the crowds because we had guided tours and advance reservations. Everything was very smooth and well organized. It was helpful to have in-country support for when we had questions or needed to make changes on the fly. Our hotel in Florence was really, really luxurious (more than was necessary for us, honestly) but it was cool to stay in a place owned by the Ferragamo family and their concierge was A+ at getting us last minute dinner reservations!”
Lauren and Terapat // Seattle, Washington
Sample Itinerary
From the Piedmont to Sicily: Highlights from North to South
Day 1: Welcome to Italy! On arrival in Milan, you’ll be met and transferred to your hotel in the heart of the city. Time permitting, step out and explore the vibrant neighborhoods of central Milan—each offering its own unique charm.
Day 2: A full day to explore Milan’s iconic highlights, starting at the majestic Duomo di Milano, with sweeping city views from its rooftop. Wander through Italy's oldest active shopping plaza, Galleria Vittorio Emanuele II, and take a stroll along the Brera district’s charming streets and art galleries.
Day 3: Enjoy another full day in cosmopolitan Milan with your private guide, exploring Sforza Castle and the vibrant Navigli district to stroll its canals, browse vintage shops, and admire local street art.
Day 4: Enjoy a private transfer from Milan to The Langhe, where you will immerse in the rich culinary traditions of the Piedmont region, celebrated for its world-class wines, prized truffles, and breathtaking hilly landscapes. Join a local truffle hunter and his dog for a foraging adventure, followed by lunch at a local trattoria to savor traditional local recipes.
Day 5: Delve further into the rich flavors of Piedmont today, focusing on its famous hazelnuts. Learn about the growing, harvesting, and processing of hazelnuts at a local farm, followed by a delicious lunch featuring hazelnut-based dishes and a locally produced bottle of wine.
Day 6: Spend today hopping between the countless charming villages scattered around this beautiful region, including Serralunga d’Alba, Barolo, and Murazzano. Along the way, enjoy world-class farm-to-table dining at some of the region’s hidden gem restaurants.
Day 7: Today you will travel onward to the historic city of Turin, where you’ll uncover the many layers of what may be Italy’s most unsung city. Take in its lovely piazzas, baroque gems, and famous chocolatiers in the old town, perhaps stopping to indulge in a decadent bicerin.
Day 8: Today you will bid farewell to the mainland and fly south to Palermo on the stunning island of Sicily. Step into the heart of Palermo’s old town as you explore its atmospheric alleys, from the historic Cala district to the lively streets of La Vucciria, where the city’s famous food market comes alive at night.
Day 9: Discover Palermo’s rich artisanal heritage as you explore the workshops of the city’s most skilled craftsmen. Wander through the backstreets of the old town, meeting artisans who proudly carry on the traditions of their ancestors, preserving techniques passed down through generations.
Day 10: Travel back in time with a day trip to the ancient settlement of Segesta and the hilltop town of Erice. Stop at a renowned pastry shop to sample exquisite Sicilian sweets on your way back to Palermo.
Day 11: Head east along the northern coast of Sicily to your next destination, Taormina, stopping along the way to visit magnificent Cefalù. Stroll through the seaside town's medieval streets or hike up La Rocca di Cefalù, a cliff offering stunning panoramic views over the town and sea below. Continue your journey along the scenic coastline to the enchanting town of Taormina.
Day 12: Venture to Sicily's mighty volcano, Mount Etna, and take in its unique landscape of lush forests and quaint villages on a scenic hike. As you head down the mountain through ancient pine forests, stop off at a local family farm to sample artisanal wine, pastries, olive oil and honey.
Day 13: A full day to spend relaxing by the sea in Taormina. In the evening, experience the region’s iconic sights at sunset in a vintage Italian car with an expert driver, taking in stunning scenery while the quaint hilltop villages around Taormina are bathed in golden hour light.
Day 14: Head out on a full day trip along Sicily’s east coast bound for ancient Syracuse and the island of Ortigia in the heart of the town. Continue onward to Noto, an antique city where you can admire Baroque palaces of incredible architectural value, before heading back to Taormina for a final relaxing night.
Day 15: Transfer to the Catania airport for your onward journey home.
