Italy
Italy evokes life’s simple pleasures with ease and style to spare. From picturesque vineyards to dazzling coasts, it’s impossible not to be filled with delight (and carbs) at every turn.
The basics.
What We Love Most
Exuberantly warm people, amazing food, breathtaking landscapes, fascinating history.
When to Visit
Year-round, depending on location (plan carefully for holidays and summer).
Favorite Places
Sicily, Puglia, Lake Como, Emilia-Romagna, Tuscany, Sardinia.
Private Trip Pricing
US $900-$1,200 per person per day and up, including accommodations, in-country transport, unique private tours, and more (see what our trips include).
“I still dream about my time traveling the sun-soaked northern Sicilian coast. From Cefalù’s picture-perfect beach, to streetside arancini in Taormina, Sicily is a food, wine, and beach lover’s dream come true.”
— Roni Sivan, Trip Designer (About Us)
Everyone’s perfect trip looks a little different.
We’ll design your itinerary around you (learn about our process), but to whet your appetite here’s a tiny taste of what you can expect to experience on a private Italy trip with us.
Sicily
Visit vineyards and pistachio groves on Mount Etna. Stroll through a bustling Palermo market and sample street food. Take a dip in Cefalù’s dreamy beach. Explore ancient Greek ruins and Roman temples. Wander the cobblestone backstreets of tiny Ortigia and cliffside Taormina.
Tuscany
Savor wine at generations-old family vineyards. Stroll the ancient streets of outrageously charming Montepulciano and Cortona. Immerse yourself in Florence’s art and history. Explore traditional markets and artisanal shops. Go truffle hunting in the countryside.
Puglia
Eat the best cheese of your life. Wander white-washed Ostuni and enjoy a spritz in the historical center. Take in the gorgeous coastline and incredible seafood in Polignano a Mare. Visit the UNESCO villages of Matera and Alberobello. Sample olive oil in an ancient olive grove.
Food, wine… and food!
Food is a highlight of any trip to Italy, and throughout the country we’ll introduce you to some of the most irresistible artisanal products and dishes. From tortellini in Bologna and balsamic vinegar in Modena, to pizza in Naples and olive oil in Puglia, you’ll get customized suggestions based on your taste and interests, whether you want to get behind the scenes with a local chef, visit family-run wineries, or simply enjoy an incredible meal at a cozy trattoria you won’t find in any guidebooks.
Local insights.
Whether you normally explore on your own — or realize how much a fun, in-the-know guide enhances the experience — your private trip will be designed to highlight hidden gems (and skip touristy spots).
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.
There are times when it makes sense to stay at a luxury hotel in the city (like the spectacular Aman Venice), but sometimes a stunning private villa in the middle of nowhere is just what you need.
Italy has no shortage of awe-inspiring properties, such as Grand Hotel Tremezzo in Lake Como (pictured above), and Hotel Santa Caterina on the Amalfi Coast.
For a true farm-to-table experience, stay at an agriturismo farmhouse in the countryside. Our favorites include the beautiful estate of Monaci delle Terre Nere in Sicily, and historic Masseria La Chiusa Delle More in Puglia.
We don’t believe one size fits all, and will help you pick the perfect hotels to match your style and priorities.
“In summer, towns all over Italy celebrate sagre — festivals, which more often than not revolve around food — and we happened to be staying in a small Abruzzese town when an artichoke festival was taking place. We tried our fair share of dishes but the most memorable part was sharing wine with locals and dancing late into the night.”
— Ashley LaBoda
Notes from the field.
Our team spends a lot of time exploring Italy, and we love sharing travel tips.
(Plan your trip with us, and many more details are coming your way.)
+ Click for more travel tips.
- Especially if it's your first visit to Italy, try and resist the lure of the best-known places. Its most famous cities and towns are rightly renowned, but so much of Italy's magic lies in farther-flung areas of the country. For most first-time visitors, a good approach is to consider including one or two "famous" spots in your itinerary, complemented by some more off-the-beaten-path regions.
- Where to get off the beaten path? If we spilled all our ideas, we might help spoil the magic of lesser-visited places! When planning together we'll take into account not only your interests and travel style, but also consider geography and which regions fit best with your other priorities.
- Especially if you've never visited, a bit of time in Roma is essential, and while the city has many touristic aspects, it's nevertheless full of magic and authentic life as well. The same goes for other iconic destinations such as Firenze (Florence), which — when away from the crowds — can truly feel like an otherworldly step back in time (turn the right corner and you can actually get away from the masses of fellow tourists).
- Sicily is known for its street food, and Palermo's Capo Market does not disappoint. Spend a morning weaving your way through the market, where fishmongers shout out the morning’s catch and fruit vendors offer samples (like fresh cherries!). Take a few more steps then savor a fresh-squeezed pomegranate juice and a plate of fritto misto di mare — chickpea-dusted seafood fried lightly to perfection!
- Try to find one of Florence's 16th century buchette del vino — "wine windows" — that have made a comeback during Covid for socially distanced curbside wine. And if labels aren't your thing, take empty bottles to one of Venice's vinaie to fill up on some good, no-fuss wine by the liter.
- So much of Italy's magic lies in the countryside, where tiny medieval towns, extraordinary wineries, and stunning scenery abound. It's possible to get off the beaten track even within Tuscany, and even easier in countless other regions. For intrepid travelers who enjoy a bit of adventure, there's nothing like the feeling of driving through stunning landscapes, visiting charming villages with incredible local wine and cuisine. Naturally, private drivers are also available for those who prefer to let someone else handle the driving!
- If you want to stand out immediately as a foreigner in Italy, order a cappuccino (or any other dairy-based coffee) in the afternoon or evening. Italians consider cappuccini to be a strictly morning drinks, with espresso being the coffee of choice the rest of the day.
- Why not enjoy an Aperol Spritz in its birthplace, the Veneto region? There’s nothing like a late afternoon aperitivo in Italy, and ducking into a Venetian bàcaro (traditional tavern) is a great place to order a spritz alongside delicious cicchetti snacks.
Take the next step.
Get in touch to start planning or brainstorm your next adventure.