Tuscany Fly & Drive


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NOTE: If you would like to travel on a departure date not shown, please see our new 
Tuscany Fly and Drive Getaway with flexible departure dates


Featuring Base yourself in the medieval hill town of San Gimignano then tour the wine region of Tuscany independently; car rental, flights & hotel included
Style Independent PackageThese un-escorted packages have no set schedule or guides, so you have the freedom and flexibility to explore on your own from your centrally-located hotel. More of these packages
Freedom to explore at your own pace; unescorted
Departures Scheduled Dates
Price Includes
  • Flights
  • Rental Car
  • Hotel
  • Round-trip flights from New York (JFK) or Newark (EWR), to Milan Malpensa (MXP) including fuel surcharges and taxes and fees
  • 7 day car rental: Manual Transmission Fiat Panda or similar. Unlimited mileage, Third Party Liability, Collision Damage Waiver (CDW), Theft Protection (TP), Vehicle License Fee, Location/Airport fees, and local taxes (VAT)
  • 6 nights accommodations in a First Class Hotel
  • Breakfast daily
  • Exciting excursions in and outside of San Gimignano
  • Upgrade to other car categories
Highlights San Gimignano, Italy plus 7 day car rental.
Departs New York City (NYC); other gateways on request (flight schedule)
Themes History & CultureFamily Friendly
What to Expect This leisurely-paced, independent tour requires minimal walking and is suitable for most levels of physical fitness. This tour does not include a tour guide or escort.

Prepare for your trip Already booked? Find everything you need to know before you go, including information about passport & visa requirements, flights, luggage, and more.

Tuscany Fly & Drive tour itinerary Visit a true Etruscan Gem, San Gimignano on this Tuscany tour package. This small walled medieval hill town in the heart of Tuscany, also known as the Town of Fine Towers, is famous for its unique architecture and unforgettable skyline. Driving your own rental car you will be able to explore Tuscany at your own pace. You may choose to explore the preserved tower houses of San Gimignano or visit the many nearby quaint towns bathed for centuries in the nourishing Tuscan sun. Enjoy wine in the Chianti region, art and history in nearby Florence, or a relaxing spa treatment in Montecatini Terme. You will find the options are endless when driving in and around Tuscany.

Dates, Prices & Options

Departure Dates & Prices

NOTE: Need to travel on a date not listed below? Please see our new 
Tuscany Fly and Drive Getaway with flexible departure dates

Flights & Departure Cities

Note: NYC departures will be from either JFK or EWR based upon availability when you make your reservation. Your flight itinerary showing which airport that you are departing from will be emailed to you in 24-48 hours.

Rental Cars

Drivers must be at least 23 years of age with a driver's license and International Driver's Permit valid for at least 1 year after departure date. See other Terms & Conditions that apply to your rental car.

CREDIT CARD DEPOSIT REQUIRED. Upon arrival in Italy, you must have €800 to €1,600 available credit, depending on your vehicle type, to hold as deposit for the duration of the rental. The credit card must be a non-electric card with embossed number registration and name. We highly recommend that you have at least €2000 credit available to cover these and other holds that could be imposed on your card. These funds will not be available for your use.

Car Upgrades: weekly supplement per vehicle


Low Season

Apr 1 - Jun 13, 2016

Oct 1, 2016 - Mar 31, 2017

High Season

Jun 14 - Sep 30, 2016

Economy Manual - Fiat Panda or similar (B-EBMR)
Compact Manual - Fiat 500L or similar (D-CDMR)
Intermediate Manual - Ford C-Max or similar (E-IDMR)
Intermediate Automatic - Opel Insignia or similar (R-IFAR)
Fullsize Minivan Automatic - Ford Galaxy or similar (L-FVAR)
Premium Minivan Manual - Opel Vivaro or similar (H-PVMR)
To upgrade your vehicle, please enter the desired car type into the comments field during your booking, or contact us after booking. We will amend your balance due accordingly. Let us know if you are sharing this vehicle with any passengers not on your reservation. For more details, please see Rental Cars.
Included Car
Fiat Panda

Economy Manual - Fiat Panda or similar

  • Group Code – B
  • ACRISS Code – EBMR
  • 2-4 doors / 4 seats
Upgrade Rental Cars
Fiat 500-L

Compact Manual - Fiat 500-L or similar

  • Group Code – D
  • ACRISS Code – CDMR
  • 2-4 doors / 4 seats
Ford C-Max

Intermediate Manual - Ford C-Max or similar

  • Group Code – E
  • ACRISS Code – IDMR
  • 4 doors / 5 seats
Opel Insignia

Intermediate Automatic - BMW 3-Series or similar

  • Group Code – R
  • ACRISS Code – IFAR
  • 4 doors / 5 seats
Ford Galaxy

Fullsize Automatic - Ford Galaxy (7-seater) or similar †

  • Group Code – L
  • CRISS Code – FVAR
  • 4 doors / 7 seats
Opel Vivaro

Premium Manual - Opel Vivaro (9-seater) or similar †

  • Group Code – H
  • ACRISS Code – PVMR
  • 4 doors / 9 seats

† For these vehicles, driver must be at least 25 years of age with a driver's license valid for at least 3 years after departure date.


Day 1: Depart USA/Overnight Flight

  • Board your overnight flight for Milan

Day 2: Milan/San Gimignano

Accommodations: 5 nights Hotel Sovestro, San Gimignano

  • Arrive in Milan and collect your rental car
  • Make your way to your hotel in San Gimignano (approx. 4.5-5 hours)
  • Balance of the day at leisure

San GimignanoFull Day Itinerary: Arrive in Milan and collect your rental car. Start your adventure making your way to your hotel in San Gimignano (approx. 4.5 - 5 hours). Enjoy the balance of the day to relax and unwind and enjoy the facilities of the hotel. Or venture out for your first exploration of the small medieval town. Your hotel is conveniently located outside of the walled city of San Gimignano giving you a fantastic view of the surrounding region.

Days 3-6: San Gimignano

Included meals: Breakfast.

  • Enjoy 5 days at leisure

Full Day Itinerary: Enjoy 5 days of leisure in picturesque Tuscany. Choose which cities and villages to explore as you drive through the cinematic landscapes of the region and experience its rich cultural history.

Day 7: San Gimignano/Milan

Accommodations: 1 night Crowne Plaza Milan-Malpensa Airport Hotel or similar. Included meals: Breakfast.

  • Make your way to your hotel in Milan

Full Day Itinerary: After breakfast, make your way to your hotel in Milan. Take advantage of the hotel’s facilities or head in to town for last minute shopping and exploration.

Day 8: Milan/USA

Included meals: Breakfast.

  • Drive to the airport to return your rental car and check in for your return flight to the USA

Suggested Sightseeing

GenoaGenoa. Venture northwest to Genoa, the capital of the Liguria region and sixth largest city in Italy. Genoa has earned its nickname, "La Superba" (The Proud One), from its glorious past and impressive landmarks. A portion of its old town was added to the list of UNESCO World Heritage Sites in 2006. You may choose to visit the Lanterna (a 117 m high lighthouse), the ancient seaside district of Boccadassa, the Aquarium of Genoa (the largest in Italy), or delight in the local cuisine.

Vernazza, Cinque TerreCinque Terre. From Genoa, Cinque Terre is about a 1.5 hour drive, and from San Gimignano, under 3 hours. Cinque Terre is perched on the rugged Italian coast and west of the City of La Spezia, known as The Five Lands because it includes five villages, Manarola, Vernazza, Monterosso al Mare, Corniglia, and Riomaggiore. The Five Lands, coastline, and the surrounding hillsides comprise the Cinque Terre National Park, a UNESCO World Heritage Site. Cars cannot reach the villages, but they are connected by footpaths, boats, and trains. Enjoy the spectacular seaside views, bountiful seafood, and lack of corporate development which allows an authentic Ligurian experience.

Tower of PisaPisa. Drive about 1.5 hours northwest from San Gimignano to Pisa, a city whose main attraction's reputation precedes it. Located on the mouth of the River Arno, Pisa is the capital city of the Province of Pisa and the world renowned for the Piazza del Duomo (a UNESCO World Heritage Site) which contains the Leaning Tower, the Duomo, the Bapistry, and the monumental cemetery of Campo Santo. Although, the city is best known for the Leaning Tower, it also has over 20 other historic churches, palaces and scenic bridges. Experience the city of Pisa at your own pace, and enjoy the many historical sites that it has to offer.

Florence panoramaFlorence. Venture north for approximately 1 hour to Florence, the capital of the Tuscany region and birthplace of the Renaissance. Once a center of medieval European trade and finance, Florence has experienced a turbulent history featuring at once architectural and artistic wonders and periods of rule by the Medici family and many religious and political revolutions. Immerse yourself in its history and visit the historical center of Florence (a UNESCO World Heritage Site) including Santa del Fiore, more popularly known as The Duomo, with its dome built by Filippo Brunellshi, the Campanile, the Baptistery, Piazza della Signoria and its Fountain of Neptune, the Uffizi Gallery, and of course The Accademia Gallery, home of the original statue of David by Michelangelo.

Piazza del Campo, SienaSiena. Drive a little under 1 hour southeast to the city of Siena from San Gimignano. The capital of the province of Siena, it is the historic center and a UNESCO World Heritage site. A city famous for its art and cuisine, you may want to visit one the many museums and restaurants that dot the city, illuminating its culture and heritage. You may want to visit the Siena Cathedral and admire a great example of Italian Romanesque-Gothic architecture, the Museo dell'Opera del Duomo containing the Maestà and other works by Sienese masters, the Piazza del Campo housing the Palazzo Pubblico and the Torre del Mangia, or enjoy the world of fashion as Siena has easy access to locally produced luxury goods.


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Terrific packages at excellent prices.

Cheryl Levinson

Before You Book

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Prepare for
your trip

Find everything you need to know before you go, including how to pay your balance due, and information about passport & visa requirements, flights, packing & luggage, and more.