Italian Holidays - Vacanze Italiane, LLC
"Take the Road Less Traveled. Explore Italy's Hidden Gems" Our Italy tours are guided by a bilingual and experienced tour guide, Michael Cross, who showcases particular regions throughout Italy.
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Our Upcoming "Best of Italy" Tours for 2025
ROME & TUSCANY 2025
Discover the Essence of Italy
Trip Dates: May 20 - 29, 2025 (SOLD OUT)
ROME & TUSCANY 2025
Discover the Essence of Italy
Trip Dates: May 20 - 29, 2025 (SOLD OUT)
Join us May 20 - 29, 2025 for a once in a lifetime tour of Rome and Tuscany! On your 10-day tour, experience stunning architecture, rich history, vibrant culture, and world-class cuisine as we make our way through two of the most beautiful and historic regions of Italy. Spend 4 nights in Rome as we explore the winding cobblestone streets and top highlights of the Eternal City. You'll take a private tour of the St Peter's Basilica and the Vatican, walk down the streets of the Ancient Roman Forum, dine in the medieval Trastevere neighborhood, see the Pantheon, Colosseum, Trevi Fountain, sip wine on a rooftop garden bar, and get to truly live like a Roman. Enjoy a day trip outside the city to the famous Villa d'Este with its 51 fountains and nymphaeums, 398 spouts, 364 water jets, 64 waterfalls, and 220 basins, fed by 875 metres of canals, channels and cascades, and all working entirely by the force of gravity, without pumps. Spend 5 nights in the heart of Tuscany, Massa Marittima, exploring hilltop villages, dramatic landscapes, and historic vineyards all while being treated to first-class foods and top-notch wines. We will visit the famous town of Siena with its magnificent cathedral. Enjoy a day trip to Florence with a private guided tour of the Accademia Gallery, which houses the famous Statue of David as well as the Uffizi Gallery which houses the great masterpieces of the Italian Renaissance.
DATES & PRICES
Tour Dates:
May 20 - 29, 2025
Pricing:
Double: $2,800 per person
Single: $2,950 per person
Non-refundable Deposit: $300 per person
To reserve your place, email [email protected]. The tour coordinator will then contact you to complete your reservation and tour deposit.
RESERVE NOW
Questions about the tour? Schedule a call with the tour coordinator by email sending an email to: [email protected]
May 20 - 29, 2025
Pricing:
Double: $2,800 per person
Single: $2,950 per person
Non-refundable Deposit: $300 per person
To reserve your place, email [email protected]. The tour coordinator will then contact you to complete your reservation and tour deposit.
RESERVE NOW
Questions about the tour? Schedule a call with the tour coordinator by email sending an email to: [email protected]
TRANSPORTATION
We have a professional chauffeur who will take care of all your transportation needs to and from the airport as well as to our various destinations on our trip.
HOTELS
All of your premium hotels are included on tour. Our 4-star accommodations are perfectly situated in each destination, and private transfers to and from the airport are included in your tour experience. Breakfast is always included each day of your journey.
FLIGHTS
Tour members will fly into and out of Roma Fiumicino "Leonardo da Vinci" Airport (FCO). If you are departing from the U.S., you will need to depart on May 19, 2025 in order to arrive in Rome on May 20. Tour will begin early afternoon of May 20, concluding in the morning of May 29, 2025. To allow for maximum flexibility, your flight arrangements are not included. Your tour guide, Michael Cross, can assist with booking airfare as requested, shopping out the best rates and flight schedules.
ITINERARY
(The meals included with the tour will be mentioned in the itinerary below: B = Breakfast ; D = Dinner ; L = Lunch ; NI = Meal Not Included)
Day 1 | Eccelso Hotel & Suites, Rome
Arrival & Welcome Dinner
Arrive at Roma Fiumicino "Leonardo Da Vinci" Airport (FCO), where your tour guide, Michael Cross, will welcome you. Our professional chauffeur will transfer you to the Eccelso Hotel & Suites situated two blocks from the Vatican. Our journey begins in the afternoon by exploring the Prati neighborhood with our first stop at Castroni (NI) to enjoy their famous coffee and pastries. After walking the historic Passetto di Borgo from the Piazza San Pietro to the Castel Sant'Angelo, you'll visit the stunning Piazza del Popolo. Enjoy a welcome dinner alongside your fellow travelers at the Terrazza Les Etoile, a luxurious rooftop restaurant and garden with one of the most panoramic views of Rome, setting the stage for an incredible Italian experience. D
Day 2 | Eccelso Hotel & Suites, Rome
Trastevere: Rome's Most Enchanting District
Discover Rome's most famous neighborhood, Trastevere, a charming labyrinth of medieval cobbled lanes flanked by atmospheric bars, cafes, and restaurants. We begin in the main piazza, the central square, home to one of the oldest churches in Rome and a primary hangout in the evening to watch street performers and entertainers. You'll explore the grand Basilica di Santa Maria in Trastevere. The church, as you see it, now mostly dates back to the 12th century, with its tall campanile (bell tower) and embellished facade with golden mosaics. The church sits on its original fourth-century foundation and its interior is stunning. Enjoy a typical Roman lunch at the Prosciutteria Cantina Dei Papi (NI) before stopping for a sweet treat at Biscottificio Innoccenti (NI), the best shop for Roman biscotti. The afternoon brings you two options: 1) Enjoy some free time by strolling through the cobbled streets, dipping into vintage shops and little boutiques. One of the hippest neighborhoods in the city, Monti is filled with independent clothing brands and interior decor shops. 2) Take a walking tour with your tour guide, Michael Cross, across the Tiber River to the Colosseum and Roman Forum where you'll walk in the footsteps of the Caesars. The evening brings you back to Trastevere where you’ll savor the authentic flavors of Roman cuisine with a typical Roman dinner at Impiccetta Ristorante in the heart of Trastevere. B, D
Day 3 | Eccelso Hotel & Suites, Rome
Treasures of Rome: The Pantheon, Trevi Fountain, & Piazza Navona
Our third day begins with a private tour of the stunning Italian National Gallery of Art at Palazzo Barberini with famed art curator, Yuri Primarosa. You'll see timeless works of art by Caravaggio, Piero di Cosimo, Fra Angelico, and many other Italian and international artists. After our tour we'll stop for lunch (NI) on our way to the majestic Trevi Fountain (Fontana di Trevi), the most famous of the Roman fountains: a jewel of water and stone. The fountain is fed water by the only ancient aqueduct (from 19 BC) continuously to this day. Before leaving, don't forget to throw a coin into the fountain, you will definitely return to Rome, as the custom says. If, on the other hand, you are looking for a bit of romance, perhaps even an Italian love, you will have to toss a second and a third coin to make sure that the wedding bells will ring soon. The afternoon first takes us to Venchi Cioccolato e Gelato, (NI) Rome's famous chocolate shop and gelateria, and to the nearby Pantheon, built during the reign of Caesar Augustus (27 BC – AD 14) and rebuilt by Emperor Hadrian in 126 AD. The Pantheon's dome is still the world's largest unreinforced concrete dome. After a stop in the iconic Piazza Navona, you'll enjoy dinner at an authentic Roman pizzeria. B, D
Day 4 | Eccelso Hotel & Suites, Rome
The Vatican & St Peter's Basilica
After breakfast, we embark on a tour of St Peter's Basilica in the Vatican. Construction of the present basilica began on 18 April 1506 and was completed on 18 November 1626. Designed principally by Donato Bramante, Michelangelo, and Carlo Maderno, with piazza and fittings by Gian Lorenzo Bernini, St. Peter's is one of the most renowned works of Italian Renaissance architecture. Inside you will see Michelangelo's Pietà and Bernini's Baldacchino. We then climb the Cupola of St. Peter's Basilica, the tallest dome in the world, where you'll see one of the most stunning views of Rome. Enjoy some much-deserved free time for the rest of this glorious day by going to one of the many shopping districts, watching the street artists in Piazza Navona, climbing the Spanish Steps to the Convent of Trinità dei Monti, soaking up the artistic vibes of Via Margutta, wandering the paths of Villa Borghese, or just relaxing at your hotel. Dinner will be on your own this evening. B
Day 5 | Tenuta il Cicalino, Massa Marittima, Tuscany
Villa D'Este & Arrival in Tuscany
Today we venture to the region of Tuscany, the beating heart of Italy. On our way, we take a scenic detour to visit a UNESCO World Heritage Site, the majestic 16th century Villa D'Este in Tivoli with its lush gardens, 51 fountains and nymphaeums, 398 spouts, 364 water jets, 64 waterfalls, and 220 basins, fed by 875 metres of canals, channels and cascades, and all working entirely by the force of gravity, without pumps. We arrive at our charming agriturismo, Tenuta il Cicalino, a rustic villa surrounded by vineyards and olive groves managed for generations by the Vecchioni family. After settling in, enjoy a delightful Tuscan apericena prepared for us by Chef Riccardo Zanni at the villa's restaurant. B, L, D
Day 6 | Tenuta il Cicalino, Massa Marittima, Tuscany
Tuscan Wine Tour in the Heart of Maremma
Today is a relaxing day at our villa in Massa Marittima. After a bounteous breakfast, take a swim in one of the five outdoor or indoor pools, discover the property by taking a stroll on the many pathways on the campus, enjoy one of the Finnish saunas, the mineral spa, or one of the three Jacuzzis. Our tour of the property winery begins just after noon where we'll sample the many vintages that the Vecchioni family tend. The present vineyard covers an area of about 15.000 sq.mt and the principal wine variety is the Cabernet Franc which uses the cordon trained and spur-pruned system. Il Cicalino's olive oil is among the finest in the country and is produced right alongside their renowned wine. Olives and wine grapes share similar environmental requirements – the region's climate, along with an abundance of prime soil conditions, create an environment for olive trees and grapevines to thrive. Enjoy an olive oil tasting, providing you with the opportunity to savor and learn about different varieties and blends. In the heart of the olive groves and facing the ancient town of Massa Marittima, is the villa's restaurant, where you'll have the opportunity to dine in a typically Tuscan environment relishing traditional dishes. B, D
Day 7 | Tenuta il Cicalino, Massa Marittima, Tuscany
Poggetti Estate Winery & Massa Marittima
Just a few minutes away from our villa is the Poggetti Estate, the Moris family's historic property in the Tuscan Maremma. Situated at an elevated position just 10 minutes from the Bay of Follonica, the property boasts spectacular views of pristine agricultural plots and the islands of Elba and Montecristo beyond. Enjoy a private wine tasting and tour of Morisfarms Winery with Giulio Parentini, owner of the property. In this iconic property, the Parentini family produces olive oil and wines from the IGT Toscana and DOC Maremma Toscana appellations. After touring the medieval town of Massa Marittima, we enjoy a bounteous dinner at the Poggetti Estate with the Parentini family. B, D
Day 8 | Tenuta il Cicalino, Massa Marittima, Tuscany
Florence & Uffizi Gallery
Today we embark on a road trip to Florence (Firenze) where you'll see one of the world’s most recognizable statues with an express visit to the Accademia Gallery, home of Michelangelo’s Statue of David. You'll climb to the top of Brunelleschi’s famous dome which caps the Florence Cathedral. A private guided tour of the Uffizi Gallery awaits you in the afternoon. Famous worldwide for its outstanding collections of ancient sculptures and paintings (from the Middle Ages to the Modern period), the Uffizi has collections of paintings from the 14th-century and Renaissance period and include some absolute masterpieces: Giotto, Simone Martini, Piero della Francesca, Beato Angelico, Filippo Lippi, Botticelli, Mantegna, Correggio, Leonardo, Raffaello, Michelangelo and Caravaggio, in addition to many precious works by European painters. The Gallery boasts an invaluable collection of ancient statues and busts from the Medici family, which adorns the corridors and consists of ancient Roman copies of lost Greek sculptures. Enjoy a free evening in one of the most beautiful Italian cities, Florence. B
Day 9 | Tenuta il Cicalino, Massa Marittima, Tuscany
Siena, Medieval Jewel of Tuscany
Not far from our villa is the iconic town of Siena. Its entire historic center is a UNESCO World Heritage Site. We begin our tour at the Piazza del Campo, the large square that hosts the Palio horse race, stopping for a Sienese coffee or gelato (NI). You’ll then tour the Duomo di Siena (Siena Cathedral), the city's top attraction. Consecrated in 1179, the Gothic cathedral took hundreds of years to build: generations of families contributed to its construction through the 14th century, and the church features sculptures by artists like Michelangelo and Donatello. If you're not afraid of heights, you’ll see the Porta del Cielo (Gate of Heaven) which takes you in and around the cathedral's dome. Our final dinner on this fabulous journey will be at one of Siena’s top restaurants near the Piazza del Campo, an experience you'll be sure to never forget. B, D
Day 10 | Departure
Arrivederci (Farewell)
Enjoy a final breakfast at Tenuta il Cicalino as we depart for Rome airport. B
HOTELS
All of your premium hotels are included on tour. Hand selected 4-star accommodations are perfectly situated in each destination.
WHAT'S INCLUDED
A small group of just 8 -15 people
9 nights premium, 4-star accommodation
Full-time services of expert tour host Michael Cross
Private Transportation with driver and tour director
Airport transfers to and from hotel on arrival and departure
17 meals (9 breakfasts, 1 lunch, and 7 dinners)
9 nights premium, 4-star accommodation
Full-time services of expert tour host Michael Cross
Private Transportation with driver and tour director
Airport transfers to and from hotel on arrival and departure
17 meals (9 breakfasts, 1 lunch, and 7 dinners)
ITALIAN RIVIERA & CINQUE TERRE 2025
From Coastal Beauties to Inland Gems, Discover a Foodie Paradise
Trip Dates: September 5 - 14, 2025 (Only 4 Spots Left!)
From Coastal Beauties to Inland Gems, Discover a Foodie Paradise
Trip Dates: September 5 - 14, 2025 (Only 4 Spots Left!)
Join us Sept 5 - 14, 2025 for a once in a lifetime tour of the Italian Riviera and Cinque Terre! On your 10-day tour, experience the beauty of the Ligurian coast, stunning architecture, rich history, vibrant culture, and world-class cuisine as we make our way through one of the most beautiful regions of the Mediterranean. This foodie centric tour includes cooking classes, a boat cruise, and several winery tours. You'll see Genova (Genoa) with its noble palaces and medieval alleyways, while the beauty and elegance of Portofino will amaze you. Cinque Terre, with its colorful little towns, picturesque landscapes and breathtaking views of the Mediterranean Sea will be a highlight of our tour. This culinary centric experience will take you throughout Liguria, allowing you to discover the culture of the region through its food. By moving just a few kilometers, you will discover radically different ingredients and culinary traditions, all the while immersed in breathtaking landscapes. Connect with local people and travel off the beaten path to get in touch with Italy’s most authentic side. Your journey begins with 2 nights in Milan, the city of the famous Duomo cathedral and the Galleria Vittorio Emanuele II, with its rich history, fashion culture and museums. We then venture to our boutique accommodation for 8 days on the Italian Riviera near Cinque Terre.