Highlights of Italy: A Luxury Vacation in Venice, Florence & Rome

This nine-night vacation to Rome, Florence and Venice will see you sample the delights of this culturally rich and passionate country in true Black Tomato style. Rest your head in some of Italy’s most romantic urban hideaways, indulge your senses at some of our favorite local food haunts, and get exclusive behind the scenes access to some of the most highly acclaimed museums and galleries in the world. Now that’s amore.

Take to the water in Venice

Touch down in Venice, and you’ll be whisked across the water by private water taxi with views of the iconic, water-based city laid out in front of you. For the first three nights, you’ll stay at Ca Maria Adele, an opulent hotel overlooking the canals in the Dorsoduro neighborhood home to Venice’s contemporary art scene.  From the hotel, you’re a short walk from the best of the city’s galleries and historic landmarks. For a unique way to experience the waterways of Venice grab a paddle and set out to explore the waterways by canoe with a knowledgeable guide in tow.

Make this itinerary yours

Like what you see? Contact us today to find out more about our exclusive itineraries. But remember: each and every Black Tomato trip is tailored exactly to who you are and what you want to do so tell us about yourself and we’ll create something that’s entirely you.

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Paddling around the city you’ll get a unique perspective on Venice’s islands, buildings, homes, churches, and monasteries. After all that paddling you’ll have worked up quite an appetite, luckily Venice is home to a host of Bacari bars, typical Venetian eateries where locals stop by for a refreshing ombra e chicetto (drinks and Italian style tapas dishes). For the rest of your time in Venice amble the cobbled streets admiring the majestic cathedrals and beautiful squares. Or for those looking to delve into the heritage of the city we can arrange a private tour with a historian or if you’re more of a die-hard foodie take to the streets with a local chef sampling the delicacies this region is known for.

Explore Florence with an expert guide

From Venice hit the rails and head south to your next stop, the museum on the streets: Florence. Here you’ll stay at the beautiful contemporary Hotel Continentale for three nights, situated in the center of the city, next to the Ponte Vecchio, overlooking the River Arno. Start your stay in Florence gliding down the River Arno, glass of champagne in hand, before heading out to one of our favorite restaurants. The birthplace of the Renaissance movement, take your pick of the countless museums and religious sites from the Uffizi to the Basilica di Santa Maria Novella to explore with an expert guide.

A cultural vacation in Rome

In so many ways, Rome is everything the rest of the world wants to be. Beauty piled high, layer upon layer of history and centuries of tradition, substance and power. From your base at the stylish Inn at Spanish Steps, you’ll have three nights to explore Italy’s capital. Spend your time on this Rome vacation strolling down the Via del Corso, or visit the vibrant Campo del Fiori where you can sit, coffee in hand, and watch the stylish Romans go about their day. Or head east of the city to the bohemian Travestere district, where you can browse the many markets or experience the areas colorful nightlife that sets in after dark.

99.9% of the world’s ceilings are boring. Fact. Even if all the planet’s walls were topped and joined with a colorful lick of paint, very few would hold a candle to the Sistine Chapel. We can arrange an after-hours tour of the Vatican Museum and a once in a lifetime chance to skip the crowds and experience Michelangelo’s peerless masterpiece unencumbered by the tour groups. Take your time to contemplate one of the art world’s true wonders and appreciate it in a way few will ever get the chance to.

In a city whose classical remains inspired the Renaissance; if art’s your thing then this vacation to Rome is the trip for you. Our expert guides will take you around the Galleria Borghese, the Palazzo Doria Pamphilj, or both. Here’s your chance to rack up the cultural kudos and feast your eyes on exquisite works by Raphael, Caravaggio, Titian and many more. For insight into the shady labyrinth of Italian politics, we’ll guide you through the corridors of power at the Palazzo del Quirinale.