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Florence - Chianti Wine Region and Amalfi (Self Drive)
9 Customer Feedbacks
10 to 15+ Nigthsfrom $1,731*
This sample price: priced within the past 7 days for arrival on 10/8/2025, departure from Charlotte CLT (NC), US. Choose your own departure city, cabin type and dates.
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9 Customer FeedbacksWonderful trip through Italy. Each hotel met our expectations and were accurately describ ...
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This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
Sample Italy with this unique, customizable vacation package!. Visit Florence (home to Renaissance Art and architecture), then pick up your car and spend a few days in one of the charming towns of the Chianti Wine Region (famous for its wines). Ride along south to Amalfi Town, on the scenic Amalfi Coast (known for its stunning coastline, cliffs, and beaches and colorful villages with steep and narrow streets). Drive to Naples for one last stay, before returning home.
What Makes Tripmasters Vacation Packages Different? Unique, fully custom approach to vacation planning Choose your preferred flight cabin class Select up to 14 nights in each city during your stay Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more) Add transfers, activities and experiences, and more services to enhance your vacation Live phone and chat support
Naples (41)Florence (230)Amalfi Town (14)Chianti Wine Region (11)Amalfi Coast (25)
Trip Summary
3 nights in Florence
The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.
Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.
3 nights in Chianti Wine Region
Chianti, located in the heart of Tuscany between Florence, Siena and Arezzo, is a charming hill-covered region offering a picturesque landscape of small stone villages, sprawling vineyards and olive groves. With tall green cypress trees and woods bordered with yellow broom, its palette of colors combine to create a painting beautiful enough to rival those of the famous art museums nearby.
Discover and explore the amazing Siena, Castelnuovo Berardenga, Gaiole in Chianti, Radda in Chianti, Castellina in Chianti, Poggibonsi, Monteriggioni and so much more.
3 nights in Amalfi Town
Amalfi Town is a jewel of a seaside resort that has an ideal climate, breathtaking views and unique natural beauty, plus the most vibrant, typical Italian atmosphere. Its cluster of white buildings amble up the hillside from the water rather than clinging vertically to it like the other towns in the area, making it a bit easier to walk around. The city starts at the water's edge with a pretty promenade along the Mediterranean and a marina full of colorful boats. The focal point of the historic center is the Piazza del Duomo, in front of the striking cathedral. The piazza offers sidewalk cafes and elegant shops.
Visit and explore the Piazza del Duomo and the cathedral, the Emerald Grotto at Cape Conca as well as the Convento di San Francesco and so much more.
1 nights in Naples
Naples reputation as the most vibrant city in Italy can be a double-edged sword, explaining why some tourists love it and others hate it outright. As far as Italian cliches go, Naples seems to encapsulate them all, from the home of pizza and gelato to mandolin playing musicians. Nonetheless, the charm of Naples resides in its narrow streets, ancient churches, street markets, cafes, bars and restaurants, all contributing to the cacophony of sounds and images embodying the spirit of the Italian South.
Visit and discover the Ancient Ruins of Pompeii, Climb Mount Vesuvius, sail to the Island of Capri, explore the Nativity Markets, visit the National Archaeological Museum, the Secret Underground World and the San Gennaro Catacombs, visit the Ruins of Herculaneum, enjoy the Piazzas of the city, and so much more.
For centuries <b>Italy</b> has drawn foreign visitors - mostly for its architectural, artistic, and scenic splendors. Italy can truly be all things to all people. From the passion and excitement of noisy urban crowds to the quiet, rural idyll where the traditional life can be experienced, Italy's great cities are replete with rich attractions and culture alongside some of the most pristine beaches and spectacular mountains in the world.
The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected.
You can change details after selecting your travel date.
*Sample prices on display include ALL taxes & fuel surcharges... read more
close [x] * Sample prices displayed include international and domestic airline tickets as per itinerary and ALL airline-related taxes and fuel surcharges and are per person, based on double occupancy, and are dynamic in nature. Prices do not include insurance or delivery charges which are optional and customizable by the traveler. The airfare portion of the itinerary price is based on economy class, midweek departure. Prices do not include fees for carry on or checked baggage which can add additional fees per ticket on a roundtrip flight based on carrier charges. It also does not include any entrance fees or visa fees that may be charged at international airports. Some cities may charge local taxes that can only be collected by hotel at destination.
Prices were accurate at the time we posted them. Sample prices were for a specific travel date and specific departure airport, as indicated. Your prices will vary according to departure cities and travel dates. We do not control prices (airlines and hotel reservation systems do). Prices may change dynamically and at times significantly numerous times during any given day.
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Florence - Chianti Wine Region and Amalfi (Self Drive)
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Florence
The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.
Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.
Chianti, located in the heart of Tuscany between Florence, Siena and Arezzo, is a charming hill-covered region offering a picturesque landscape of small stone villages, sprawling vineyards and olive groves. With tall green cypress trees and woods bordered with yellow broom, its palette of colors combine to create a painting beautiful enough to rival those of the famous art museums nearby.
Discover and explore the amazing Siena, Castelnuovo Berardenga, Gaiole in Chianti, Radda in Chianti, Castellina in Chianti, Poggibonsi, Monteriggioni and so much more.
Amalfi Town is a jewel of a seaside resort that has an ideal climate, breathtaking views and unique natural beauty, plus the most vibrant, typical Italian atmosphere. Its cluster of white buildings amble up the hillside from the water rather than clinging vertically to it like the other towns in the area, making it a bit easier to walk around. The city starts at the water's edge with a pretty promenade along the Mediterranean and a marina full of colorful boats. The focal point of the historic center is the Piazza del Duomo, in front of the striking cathedral. The piazza offers sidewalk cafes and elegant shops.
Visit and explore the Piazza del Duomo and the cathedral, the Emerald Grotto at Cape Conca as well as the Convento di San Francesco and so much more.
Naples reputation as the most vibrant city in Italy can be a double-edged sword, explaining why some tourists love it and others hate it outright. As far as Italian cliches go, Naples seems to encapsulate them all, from the home of pizza and gelato to mandolin playing musicians. Nonetheless, the charm of Naples resides in its narrow streets, ancient churches, street markets, cafes, bars and restaurants, all contributing to the cacophony of sounds and images embodying the spirit of the Italian South.
Visit and discover the Ancient Ruins of Pompeii, Climb Mount Vesuvius, sail to the Island of Capri, explore the Nativity Markets, visit the National Archaeological Museum, the Secret Underground World and the San Gennaro Catacombs, visit the Ruins of Herculaneum, enjoy the Piazzas of the city, and so much more.