Unparalleled in its splendor, Italy is simply magical. From the centuries-old vineyards of Tuscany to the enchanting waterways of Venice and the cobblestoned streets of Florence, the country’s charms are no secret. As Giuseppe Verdi once said, “You may have the universe if I may have Italy.”
Itineraries We Love
We believe that itineraries need to be personalized, and can work for anyone from honeymooners and adventurers to families and multi-gen groups as long as they are tailored to your interests. Here are some of our favorites; many more can be created by our expert team.
Iconic Italy: Florence, Tuscany, Rome
The classic first-timer trip to Italy includes three crowd pleasers: an ancient metropolis, a Renaissance capital and a lush countryside chock full of hilltop villages and vineyards. The best itineraries include behind-the-scenes and after-hours access, touring with specialty guides and reservations at staff-scouted restaurants.
The classic first-timer trip to Italy includes three crowd pleasers: an ancient metropolis, a Renaissance capital and a lush countryside chock full of hilltop villages and vineyards. The best itineraries include behind-the-scenes and after-hours access, touring with specialty guides and reservations at staff-scouted restaurants.
When to Go
While Rome is lovely year-round, it is quiet in the winter and some shops and restaurants in Florence and Tuscany will shutter in the coldest months. June and July see huge crowds so we recommend visiting in the spring or fall, when temperatures are milder and there are fewer fellow travelers in line for gelato.
Ideal Length of Stay
7-10 days
Itinerary Highlights
After-hours tour of the Vatican and Sistine Chapel, gladiator school with kids, gelato-making class, private tour of the Uffizi Gallery, personalized cooking class in Florence, Tuscan bike tour, winery visits
Days 1-4: Rome
Rome is a place where ancient history and contemporary life breezily coexist, where you can sip cocktails at a trendy bar while gazing upon a temple colonnade from the year 145 AD. The cultured traveler can spend a lifetime making discoveries—big and small—in la città eterna.
Days 4-6: Florence
Florence is best toured with a private guide who is well-versed in the city’s art history, architecture and hidden nooks; a chef who can take you to the food markets and host a cooking class; a cycling guide who can take you on a bike tour through the city and up to Fiesole; and an insider who knows the best remote nooks.
Days 6-10: Tuscany
Centered around Florence and encompassing such mystical towns as Siena, Montepulciano and Arezzo, Tuscany is known for its gorgeous countryside, vineyards and old-world charm. Staying in an Indagare-preferred castle resort is the best way to experience the historic, dreamy region.
Best of Amalfi Coast & Capri
A honeymooner’s dream, The Amalfi Coast and Capri are two of the world’s most romantic destinations. But they can also make for a fabulous family vacation. This is a place where land, sea and sky strike a note of otherworldly perfection and despite its jet-set status, is also an ethereal, soulful island with especially stunning, fragrant landscapes.
A honeymooner’s dream, The Amalfi Coast and Capri are two of the world’s most romantic destinations. But they can also make for a fabulous family vacation. This is a place where land, sea and sky strike a note of otherworldly perfection and despite its jet-set status, is also an ethereal, soulful island with especially stunning, fragrant landscapes.
When to Go
The Amalfi Coast and Capri have a short season, lasting from late spring through fall. July and August, however, are extremely busy and hotel rooms typically book up a year in advance.
Ideal Length of Stay
7 days
Itinerary Highlights
Late, in-room breakfasts with ocean views, hikes along the Amalfi coast, boat trips, shopping for custom-made sandals on Capri, long lunches at beach clubs, sunset (and then candlelit) dinners on terraces
Days 1-2: Positano
Known as the pearl of the Amalfi Coast, Positano is dotted with pastel houses that cling to steep ledges. Spend a day at sea to take in the stunning natural landscape or take a hike along the coast. Foodies should sign up for a cooking class at a local restaurant, a hands-on way to experience the regional cuisine.
Days 3-5: Capri
Surrounded by the Bay of Naples and Tyrrhenian Sea, the island of Capri lies some 17 miles off the Amalfi Coast. Days in Capri are best-spent pool-, or lido-, side, with the occasional shopping afternoon or spa treatment thrown in. Hire a boat for an excursion along the coast, mooring at secluded coves for swimming in the pristine water and stopping at one of the island’s more glamorous beach clubs for lunch.
Days 5-7: Ravello
Ravello’s removed location and two stunning luxury hotels make it a perfect conclusion to a trip. Villa Cimbrone is considered by many to be the most beautiful garden in Italy. Even if you don’t time your visit to coincide with the summer Ravello Festival, be sure to check the schedule of the Ravello Concert Society for chamber music performances held throughout the year.
Courtesy 10 Corso ComoBest of Milan & Lake District
Milan has recently transformed into one of Italy’s chicest, most modern cities, and one brimming with attitude and sophistication. And as an international flight hub, it serves as an excellent jumping-off point for trips to Italy’s stunning lakes region.
Milan has recently transformed into one of Italy’s chicest, most modern cities, and one brimming with attitude and sophistication. And as an international flight hub, it serves as an excellent jumping-off point for trips to Italy’s stunning lakes region.
When to Go
While Milan is a year-round city, the best times to visit the Italian Lakes region is from spring through fall.
Ideal Length of Stay
5-7 days
Itinerary Highlights
Seeing Leonardo Da Vinci’s Last Supper and Milan’s Duomo, shopping in outrageously cool concept stores and major couture flagship stores, boat trips on Lake Como and Lake Garda
Days 1-3: Milan
Most of Milan’s major attractions–the Castello Sforzesco, Pinacoteca di Brera Art Museum, Teatro Alla Scala Opera House and Santa Maria della Grazie (Last Supper) Church–can be seen in a couple of days, but there are also a handful of overlooked but spectacular sights, including churches, contemporary art museums, off-the-beaten-path neighborhoods and tucked-away restaurants.
Days 3-6: Lake District
Described by poet William Wordsworth as a “treasure whom the earth keeps to herself,” Lake Como is the center of a region that’s both natural and civilized, decadent and low-key, enormous and intimate. From the grand hotels to the sinful cuisine, life here—and in nearby Lake Garda—is all about indulgence.
Best of Venice & the Dolomites
Combining a few days each in Venice and the Dolomites makes for a fabulous trip that includes glamorous city time as well as outdoor adventure surrounded by stunningly beautiful mountains.
Combining a few days each in Venice and the Dolomites makes for a fabulous trip that includes glamorous city time as well as outdoor adventure surrounded by stunningly beautiful mountains.
When to Go
The ski season in the Dolomites runs from late December through early April and Venice gets chilly in the winter, but its magic remains and some argue that the cooler weather increases the romance factor. Spring and fall are peak times to visit the city and for hiking in the mountains.
Ideal Length of Stay
7 days
Itinerary Highlights
History/culture walking tours, Venice lagoon exploration, market and food tours, private hiking and skiing guided day trips, cozy meals in mountainside refuges
Days 1-3: Venice
Make the most of Indagare’s excellent insider access in Venice with private-guided tours of the Doge’s Palace, Venetian mask makers’ workshops, the city’s secret gardens and the corners and views that inspired Tintoretto, Canaletto and numerous of artists from the Renaissance through today.
Days 3-7: Dolomites
Located in the northeastern part of Italy, just two-and-a-half hours north of Venice, the gorgeous limestone mountains of the Dolomites punctuate the Italian countryside. The region’s crown jewel is the town of Cortina d’Ampezzo, a small commune deep in an alpine valley and encircled by views of the Dolomites.
Craft Your Own
Indagare believes that personalization is a key element for transformative travel, and that every journey is unique. Thus, the perfect itinerary for you depends entirely on your likes and dislikes. To have the most meaningful experience in Italy, consult with the specialists at Indagare, who will craft a tailor-made itinerary just for you, including special access, private classes and guided touring.
Indagare believes that personalization is a key element for transformative travel, and that every journey is unique. Thus, the perfect itinerary for you depends entirely on your likes and dislikes. To have the most meaningful experience in Italy, consult with the specialists at Indagare, who will craft a tailor-made itinerary just for you, including special access, private classes and guided touring.
Plan With Us
Here are the top three reasons why you should plan your next trip with us.
Matchmaking
You dream out loud. We listen to your travel preferences and needs. And together, we craft the perfect trip.
Trusted Network
For more than twenty years, we have built relationships with a network of premier partners and guides, assuring that you will travel as part of the Indagare family.
Peace of Mind
From planning to execution, we have you covered every step of the way. We offer support on the ground and in our office, so you have a partner at all times.
