3 Week Italy Itinerary to Venice, Late Como, the Riviera, Rome, and Amalfi

We’ve left nothing to chance—you’re staying at celebrated hotels, with priority access to monuments, museums, and culinary extravaganzas. Plus tips for aperitivos-with-a-view. When can you go? Theoretically, now—borders are already open. But details are still being worked out and a safer bet might be to plan for July. Chances are, you’ll never see Italy like this again—without the crowds.

DAYS 1–3: BATHE IN BEAUTY—IN VENICE.

Where Venice and its islands. Why It’s the object of our collective desires and will likely never be this tourist-free again. How A private water taxi will take you from the Venice airport to (the choice is yours) the grand Gritti Palace; the resort-like Belmond Cipriani, on Giudecca; or the boutiquey Londra Palace. And then you’re off on a private introduction (or return) to the highlights: St. Mark’s Basilica, the Doge’s Palace, the Rialto market, the Peggy Guggenheim Collection, the islands of Burano and Murano. Get lost, also, among the little streets, bridges, and silent, palace-ringed squares. There will be gondolas and Riva yachts to board, memorable meals, and a perfect finale: a night at the opera at the famous La Fenice theater.

DAYS 4–6: LIVE DOLCE FAR NIENTE—ON LAKE COMO.

Where Lake Como. Why It’s been a deluxe resort since Roman times—and they knew how to pick ’em. How You’ll arrive via private car from Venice (with a brief stop at Verona or the Allegrini winery). Grand hotels include Villa d’Este (the one and only), Tremezzo (great new beach club), and Victoria (good for families). Over the next two days, with a guide and boat when you want them (or by bike, canoe, or helicopter), explore the surrounding towns: Griante, Cernobbio, Como, Brunate, Bellagio, Blevio, and Isola Comacina. And their restaurants. Too much excitement? There’s always Villa d’Este’s dreamy floating pool and spectacular gardens to consider, and the Tremezzo’s vast new T Spa.

DAYS 7–8: CROON “LOVE IN PORTOFINO”—ON THE ITALIAN RIVIERA.

Where Portofino. Why Crescent of sand, colorful houses, bobbing yachts, and the Splendido hotel overlooking it all—what’s not to love? (The redone Splendido Mare, down by the sea, opened on May 1.) How Arrive from Como by car, with a stop at La Raia winery, and after checking in, just succumb to the glamour. Sip aperitifs, eat delicious dinners, and (on the second day), tour the other villages of the Italian Riviera from a private yacht.

DAYS 9–12: HAVE DRINKS WITH THE DAVID—IN FLORENCE.

Where Florence and the Chianti countryside. Why It’s the cradle of the Renaissance and the ultimate place to experience Stendhal Syndrome: swooning from a surfeit of beauty. How Arrive after a stop in Lucca, check in (the Four Seasons? Portrait Firenze? Villa Cora? Villa La Massa? Your call), and stroll: the baptistry, the Giotto bell tower, and the Duomo itself (reserved tickets will get you in and up to see Brunelleschi’s dome). On the following days you’ll have an expert guide to the Uffizi and special after-hours entrée to the Galleria dell’Accademia, for private aperitifs in the presence (gasp!) of Michelangelo’s David. More: visits with the city’s master craftsmen, dining with its chefs, and a daytrip to Chianti.

DAYS 13–15: FLIP THE SWITCH IN THE SISTINE CHAPEL—IN ROME.

Where Rome. Why The Eternal City requires (and rewards) homage. How Arrive by car after stops at two Tuscan treasures, San Gimignano and Siena, and check into one of our five recommended hotels (the de Russie, De La Ville, the First Art Hotel, and Grand Hotel Villa Agrippina), followed by dinner in Piazza Navona. Over the next two days you’ll tour the city’s highlights in a special-access way: the Forum and Colosseum, the Vatican museums (including opening up the Sistine Chapel before anyone else enters). Haven’t yet seen the private Palazzo Colonna, one of Rome’s oldest and largest residences, and its art-filled Galleria Colonna? Now you will.

DAYS 16–19: SMELL THE LEMONS—ON AMALFI AND CAPRI.

Where The Amalfi Coast and Capri. Why Because they’re even more of a revelation now, without the crowds. How You’re booked on the fast train from Rome to Naples, where a driver will pick you up for a visit to either Pompeii or the Atlantis-esque flooded city at Campi Flegrei (snorkel among ancient underwater villas) before continuing on to your hotel in Positano (Le Sirenuse, Villa Tre­Ville, or Il San Pietro). Over the next three days: Go on an exploratory Amalfi drive (the views! the lemons! the flowers!), making sure to visit Ravello, the Amalfi cathedral, and the Villa Cimbrone gardens. Sail a private yacht to and around Capri. Laze on Positano’s Marina Grande beach. Or hike the aptly named Path of the Gods—both to work off all the divine meals you’re having and as a coda to your trip. You’ll depart for home the next day from Naples.

HOW TO BOOK IT:
This itinerary was developed with travel advisor Andrea Grisdale of I.C. Bellagio, a specialist in Italy with 30 years of experience in the country, excellent insider access, and an interest in both its classic and unexpected pleasures. You can book this trip as is, or work with Grisdale to customize it to your interests, time, and budget. The cost begins at $1,000 per couple per day, including accommodations, private transfers, tours, and logistics. Contact Grisdale at [email protected] .

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