Accessible Italy

10 Days / 9 Nights

Rome, Castellina in Chianti, Florence, Milan

Average Guest Rating 4.9 / 5

Exploring Italy with restricted mobility might seem like a challenge, but we've carefully crafted this itinerary to meet the needs of people with impaired mobility or those who wish to enjoy comfortable traveling with less emphasis on walking tours.
The main attractions of Rome, Tuscany, Florence, and Milan are the key parts of our itinerary, and they are all easy to reach thanks to the unique transportation that we use in each city. You will tour Rome with a Golf Cart, we will take you for a cooking class in Tuscany with a private car, and you'll see Milan in style, from the passenger seat of a vintage Fiat while charming Florence will be explored on foot, but entirely adjusted to your pace. A combination of selected activities enables diversity and a great sense of Italian culture.
The services that we include as a part of our comprehensive travel package include accessible accommodation, city tours, themed tours, and day tours provided with various transportation as well as the connection between destinations. To enable easy access to all our destinations you will be traveling with private transportation between destinations giving you the possibility to enjoy beautiful views and potentially add some interesting stops along the route.
In addition to the tours included we can arrange a number of excursions based on your own interests. All of our tours are custom, and this is just a sample meant to give an idea of what our trips are like, and the opportunities our destinations provide.
One of our team members in the region will be available to you leading up to and during your trip to answer any questions and arrange additional local services. You will receive access to your Guest Page, with its information on the best these destinations have to offer, including things to see and do, and other inside tips from restaurant recommendations to tipping advice. Upon your arrival, we will provide you with a local SIM that you can use to reach your local JayWay contact throughout your trip. In all of our destinations, we offer a variety of memorable 3-5 star accommodation options, including boutique hotels, charming B&Bs, and spacious apartments. With our first-hand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambience.

3 Nights in Rome

3 Nights in Rome

The capital of Italy is a vibrant, energetic and stylish city. While thoroughly modern in sensibility, Rome is also home to some of the world’s most important works of classic art and architecture. This city has been an epicenter for culture, politics and religion for more than 2,500 years. From the Spanish Steps to the Vatican, there are more than enough sights to keep even the most active tourists busy and even somewhere as popular as Rome you can find places just off the tourist trail and bustling with locals. But it’s also nice to slow down and enjoy Rome’s famous cafes and restaurants, which can be just as beguiling as the buildings. Lounge with an espresso on the Campo de Fiori and watch the changing light on the fountains and the facades. Visit the Vatican and explore some of the world’s most beautiful churches. Rome really comes alive at night, when restaurants and wine bars bring a renewed vitality to the city. You’ll also have opportunities for day trips to local vineyards, olive groves, and other places producing regional delicacies. No matter what your interests, or what kind of holiday you’re looking for, Rome will be an enjoyable destination.

Day 1

Day 1 - Arrival in Rome

After you land at Rome's Fiumicino airport you will be met in the arrivals hall by a driver holding a sign with your name on. The journey to your accommodation in the center of Rome should take around an hour.

Our representative will then meet with you to answer any questions you have and to get you settled for the rest of your trip.

Gelato, Espresso and Tiramisu Group Walking Tour

Please ask your travel advisor for the cost to add this to your package

This 2.5-hour tour will be a sweet indulgence! Meet your small group at Piazza della Minerva, and get ready to taste the best coffee, gelato and tiramisu in Rome! Combining Italy’s famous coffee with desserts that have become world-famous, this personalized tour will take you through lovely neighborhoods.

Activity Level : Light

Duration : 2.5 hours

Day 2

Day 2 - Your First Full Day in Rome

Private Rome Golf Cart Tour

Included in your vacation package price.

The Private Rome Golf Cart Tour is designed to allow you to see the city without putting miles on your feet. Enjoy seeing the most important sites and hidden gems in an eco-friendly, comfortable golf cart on this private tour. Your private tour guide will chauffeur you around the Eternal City quickly and efficiently while sharing with you the rich history and exciting stories that have built up Rome. Your Rome Golf Cart Tour is a private tour that allows you to maximize your time in the Eternal City and gives you the opportunity to stop and snap a photo or enjoy a short coffee or gelato break if you wish (not included). Come enjoy a tour mixed with culture, history, and fun!

Activity Level : Easy

Duration : 3 hours

Art Markets

Suggestion to explore on your own

If you want to do something different you can spend your Sunday morning in Rome strolling markets. Spread along the Tiber in northern Rome, the Ponte Milvio Antique and Art Market is perfect for a Sunday stroll. If you want to escape Rome's crowds, explore this market and enjoy the river's breezes and the shade of surrounding trees. Just a few minutes from the Colosseum, in the colorful and traditional neighborhood of Monti, the weekend Mercato Monti market is the temporary home of many talented local artists. Here, you can find anything vintage or design, from clothing and jewelry to colorful takes on classic Frida Kahlo prints.

Dorothy Circus Gallery

Suggestion to explore on your own

If you love pop surrealism, you’ll definitely enjoy the Dorothy Circus Gallery's exhibitions. This was the first art gallery in Rome to specialize in the genre, but this gallery also features an art bookshop well-stocked with monographs, limited edition prints, and artsy toys.

Day 3

Day 3 - Your Second Full Day in Rome

Vatican Museums and Sistine Chapel Private Tour

Included in your vacation package price.

On this special excursion you'll be seeing one of the most impressive highlights in Rome: the Vatican. You'll skip the lines and have your own private guide to explain the history and significance of this amazing building and the works of art it contains. On this 3-hour excursion you'll be astounded by the wonderful spiritual and artistic experience that you'll have upon visiting this historic and religious site.

Activity Level : Light

Duration : 4 hours

Roman Retail Therapy

Suggestion to explore on your own

Milan might be Italy's fashion capital but that doesn't mean Rome's devoid of places to shop for anything from an accessory to a full outfit. Whether you're looking for high-end big name designers or searching for something one-of-a-kind by an up and coming local, Rome can cater to both needs. You'll find plentiful shopping suggestions in your Guest Page once you book.

Day 4

Day 4 - Traveling to Castellina in Chianti by Private Transfer

It's time to bid arrivederci to the eternal city as you're headed for the hills of Tuscany, one of the loveliest parts of Italy. Your driver will pick you up from your accommodation in Rome and you will head north on the highway, taking a small detour at around halfway, to visit UNESCO-listed Orvieto, a medieval gem famed for its gothic cathedral and stunning frescoes. You'll have a couple of hours of free time here to sight-see before continuing your journey to your accommodation in Tuscany. The journey till the first stop takes about 2 hours. After your stop in Orvieto you will continue your way to Castellina in Chianti. The whole journey takes around 6 hours. Please note that this is a non guided transfer.

Castellina in Chianti by Private Transfer with a stop in Orvieto

2 Nights in Castellina in Chianti

2 Nights in Castellina in Chianti

We have chosen Castellina as one of our key destinations in Tuscany as this small town or large village offers all the facilities most visitors need while allowing them to enjoy the countryside location as well. Public transport is limited so you will definitely need a driver or rental car while you're here. On the edge of a village is a Vespa and Cinquecento (vintage Fiat car) rental company, should you want to indulge in a little nostalgic exploration of the surroundings. Close by you'll find San Gimignano, a 'medieval Manhattan' well worthy of a day trip and the walled town of Monteriggioni is even closer.

Day 4

Day 4 - Arrival in Castellina in Chianti

Your driver will bring you to your accommodation in Castellina center or in the scenic countryside nearby, depending on your choice of accommodation.

Private Cooking Class with Professional Chef in Castellina in Chianti

Included in your vacation package price.

This three-hour cooking class is perfect for pasta lovers. With an expert Italian chef you'll learn the secrets of world-class cuisine, then sit down to eat what you've prepared. And it all takes place in a professional kitchen in the gorgeous hills of Chianti. What could be better?

Activity Level : Light

Duration : 3 hours

Day 5

Day 5 - Your First Full Day in Castellina in Chianti

Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Castellina in Chianti

Included in your vacation package price.

This tour has been designed to give you a taste of authentic Tuscany. You'll be driven through the beautiful countryside south of Siena, where you'll have the possibility to stop for some wine tasting. Your first stop, Montalcino, is famous for its Brunellos. You'll also visit Montepulciano, which is known for its Vino Nobile wines. Please let us know if you wish to visit a winery so we can book it for you.

Activity Level : Light

Duration : 7 hours

Stroll Through History

A relaxed stroll around Castellina feels like a trip back in time. Start from "La Rocca," the mighty fortress where the Chianti League faced the threat of its archenemy, nearby Siena. Located in the main square, its fourteenth century tower offers splendid views of the Chianti landscape. Also worth seeing is the Monternano Castle, and the Archaeological Museum of Chianti inside the fortress. In the historical center of Via Ferruccio, you will find many restaurants, boutiques, shops, and historical buildings, such as Palazzo Squarcialupi and Palazzo Banciardi.

Day 6

Day 6 - Traveling to Florence by Private Transfer

It's time to leave the Tuscan countryside behind but you're not going too far. We will arrange for a driver to meet you at your accommodations to transfer you to the capital of the Tuscany region, Florence. The journey will take about 1 hour. If you'd like to make a day of out it, for an additional fee we can arrange some stops on the way in the Tuscan hills.

2 Nights in Florence

2 Nights in Florence

Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci's works are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.

Day 6

Day 6 - Arrival in Florence

Upon reaching Florence your driver will take you as close as possible to your accommodation. As the city has several pedestrian only areas so you may need to walk a short way to your accommodation, depending on its location.

Florence City Private Walking Tour

Included in your vacation package price.

Sometimes Florence feels like an outdoor museum. There's so much to see in every direction, it can be a little overwhelming. That's why this three-hour city walking tour is so great: in a short time you'll explore the most important bridges, alleys, medieval markets and Renaissance palaces, so you can appreciate the best of this unique city. You'll be picked up from you accommodation and your guide will lead you through the city streets.

Activity Level : Moderate

Duration : 3 Hours

Day 7

Day 7 - Your First Full Day in Florence

Accademia Gallery Private Tour

Included in your vacation package price.

This tour of the Academia Gallery is a great way to experience the rich artistic culture and history of Florence. You'll meet your guide at your hotel, then walk for an hour in the beautiful Florence city centre and then to the gallery. The statue of David is definitely the most famous work on display, but it's certainly not the only thing worth seeing. Have your questions at the ready!

Activity Level : Light

Duration : 3 hours

Boared in Florence

Suggestion to explore on your own

Being the heart of Tuscany, Florence offers a true feast for the tastebuds, including but not limited to the pecorino Toscano cheese made from sheep's milk, wild boar in many variations, homemade pasta, and of course some amazing wine. However, one of the most famous Florentine dishes is Fiorentina steak, so we suggest to start with this one. Beloved by locals and applauded by tourists, Trattoria da Mario is the absolute best place to try it. For some great steak and equally good other options, there are many excellent restaurants in this city, including our favorites Trattioria ZaZa, Buca Lupi, and La Giostra.

Day 8

Day 8 - Traveling to Milan by Private Transfer

Today you'll be traveling to Milan. Your driver will pick you up at your accommodations at the agreed-upon time. The trip takes about 3.5 hours. For an additional fee, we can arrange a stop in Bologna on the way.

2 Nights in Milan

2 Nights in Milan

Italy’s fashion and business hub, Milan fizzes with energy. But don't let the city's professional side fool you: this is a place that prides itself on history and culture, and the locals always seems to be having a good time. Milan's signature building is the Duomo, an imposing Gothic cathedral that sits in the heart of this former Roman capital. The combination of its size and beauty make it a must-see sight. You can also look forward to elegant evenings at the legendary La Scala opera, charming cafes and restaurants, great shopping opportunities, and breathtaking art and architecture. Home to Da Vinci's Last Supper, Milan is also rich in art galleries, from the old masters to contemporary art. This being Italy, you'll find delicious cuisine here too, and the "aperitivo" is one of the most interesting traditions of Milan gastronomy. At many of the city's cafes and bars in the early evening you can pay a slightly higher price for a drink and get your pick from a free buffet. It's one of the best ways to experience the different flavors of Milanese cooking. The compact city center means that one or two days should be enough to satisfy your curiosity.

Day 8

Day 8 - Arrival in Milan

Your driver will take you to your accommodation in the center of Milan.

Gourmet Delicacies and Street Food Favorites

Please ask your travel advisor for the cost to add this to your package

The bustling streets of downtown Milan are the ideal setting for all sorts of foodie experiences: from tasty snacks for always-on-the-run businessmen, to sweet treats in traditional bakeries. There are a couple of Milanese favorites you will run into on most menus. A cotoletta alla Milanese, essentially a veal schnitzel, or a much more indulgent veal ossobuco often accompanied with a saffron risotto. Then there are the reinvigorating spirits and premium wines. All of this and more can be discovered with our street food tour, led by an experienced and entertaining local guide.

Activity Level : Light

Duration : 3 hours

Day 9

Day 9 - Your First Full Day in Milan

Milan City Center Private Tour with Fiat 500

Best of Milan Private Tour in a Vintage Fiat 500

Included in your vacation package price.

This unique tour gives you the chance to explore Milan in the driver's seat of a vintage Fiat 500. Over the course of two hours you'll cruise the streets and explore some of the most notable squares and architecture in the city. There will be several stops for photos and you'll get a real feel for the unique atmosphere of this charming, romantic destination.

Activity Level : Light

Duration : 2 hours

Leonardo da Vinci and his Milanese Masterpieces

Suggestion to explore on your own

Leonardo da Vinci spent many years in Milan, where some of his works are still kept. Start at the Pinacoteca Ambrosiana, a treasure chest that displays "The Portrait of a Musician" and "The Atlantic Codex." You can see "The Last Supper" in the Convent of Santa Maria delle Grazie. Tickets are very hard to get, and the official website is sold out a year in advance. We recommend booking a tour with our expert local guide, which includes the entrance ticket.

Day 10

Day 10 - Departure Day

We will arrange for a driver to transfer you to Milan's main international airport, Malpensa, in plenty of time for your flight.

What's Included

Here are all the services provided as part of your complete vacation package. See what every JayWay trip includes.
Please let us know if you'd like to upgrade any transfers or add any additional tours or excursions to your itinerary.

Rome

3 Nights Accommodation

Breakfast (hotels only)

Rome Fiumicino Airport Transfer

Private Rome Golf Cart Tour

Vatican Museums and Sistine Chapel Private Tour

Rome - Castellina in Chianti Private Transfer with a stop in Orvieto

Castellina in Chianti

2 Nights Accommodation

Breakfast (hotels only)

Transfer to/from Taverna Squarcialupi

Private Cooking Class with Professional Chef in Castellina in Chianti

Transfer to/from Taverna Squarcialupi

Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Castellina in Chianti

Castellina - Florence Private Transfer

Florence

2 Nights Accommodation

Breakfast (hotels only)

Florence City Private Walking Tour

Accademia Gallery Private Tour

Florence - Milan Private Transfer

Milan

2 Nights Accommodation

Breakfast (hotels only)

Best of Milan Private Tour in a Vintage Fiat 500

Milan Malpensa Airport Transfer

package excludes:

Flights to and from Europe.
Tips for Tour Guides, Drivers and Local Reps.
Meals (other than breakfast if included in room rate and meals listed as included in food tours and excursions, unless explicitly stated otherwise).
Parking fees for your Rental Car (if you are booking one with us) unless otherwise indicated. Some hotels provide free parking facilities.
Travel Insurance. See the insurance link on our website

Benefits of Traveling with JayWay

A JayWay vacation is more than the sum of its parts. Our team work tirelessly to ensure your experience is memorable for all the right reasons. Your trip is personalized to maximize your enjoyment. You're taken care of every step of the way.

A Travel Advisor who speaks your language

We will make sure that all your requirements and interests are taken into account in preparing your itinerary.

A totally tailored itinerary for your vacation

Your trip is customized for you by an experienced trip planner and an expert on the region.

A choice of hand-picked hotels and excursions

We've personally inspected and tested all the hotels and local tour providers we work with to ensure quality.

Detailed pre-trip preparation to make the most of every day

Your Europe-based Tour Manager will be in touch by email and phone a month before you arrive to finalize timings.

On-trip Concierge Service to smooth out any bumps in the road

Your tour manager is at your service throughout your journey. We'll provide a local SIM so you can stay connected.

Personalized Guest Page to make sure you're not missing out

Packed with detailed information and recommendations curated by locals on the best things to do, see and eat.

Glowing Reviews from Our Guests

4.9 / 5

Average of our Guest's Ratings of vacation packages including these destinations

Ali, Marguerite, Paula & Amy

New Jersey

JayWay was easy to work with, had great ideas and were very responsive. We always felt taken care of and their contacts are top-notch!

Year : 2023
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Rome
Rating :

4.8 / 5

Tammy & Rhonda

Virginia

It was an amazing experience. Extremely organized and well-planned and executed trip.

Year : 2023
Visited : Greece, Italy, France
Itinerary : Athens, Santorini, Rome, Florence, Venice, Paris
Rating :

5 / 5

Jordan & Kevin

Delaware

JayWay truly goes the extra mile to remove the stress associated with travel. We felt completely taken care of with and that JayWay had our best interests in mind. That allowed us to just sit back and enjoy the ride.

Year : 2023
Visited : Italy
Itinerary : Venice, Florence, Rome, Sorrento
Rating :

5 / 5

Get an Instant Price Estimate

Choose the month of travel, how many travelers and what star level accommodation you'd like to stay in, then get an instant price estimate.

Once you’ve done that you can request a tailor-made itinerary based on this by entering just a few more details.

Per Person Package Price from^*

Sending ...

Thank you!

Thank you for your interest in taking a trip based on this itinerary. One of our expert travel advisors will be in touch soon to start tailoring it precisely to your preferences.

Ooops!?

Something went wrong at our end, please try again in a moment.