Accessible Italy

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Price
from $6,100
Duration
10 days
Destinations
Rome, Castellina in Chianti, Florence, Milan

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Route for Rome, Castellina in Chianti, Florence, Milan tour

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.

Itinerary

  1. Day 1 Arrival 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.
    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.
  2. Day 2 Your First Full Day in Rome

    Golf Cart Around Rome Private Tour

    Golf Cart Around Rome Private Tour

    The Private Rome Golf Cart Tour sounds like an incredible way to explore the Eternal City! It offers a unique and comfortable way to experience Rome's iconic sites while learning about its fascinating history. Riding in an eco-friendly golf cart not only allows for convenience but also minimizes the physical strain of touring the city on foot. With a knowledgeable guide at the helm, travelers can make the most of their time by efficiently navigating through Rome's streets while uncovering hidden gems and significant landmarks. The personalized nature of a private tour ensures that visitors can pause for photos, take in the sights, or even enjoy a quick refreshment break, enhancing the overall experience. This blend of culture, history, and fun promises an engaging and enriching adventure through one of the world's most captivating cities!
    • Activity Level : Easy
    • Duration : 3 hours

    Included in your vacation package price

    Colosseum Express - Semi Private Tour

    Colosseum Express - Semi Private Tour

    Step into the footsteps of the ancient Roman gladiators as you pass through the Gladiators Gate and enter the Arena Floor on this guided semi private Colosseum tour. Enjoy skip the line access and discover the most iconic monument of the ancient world with exclusive entry to the Arena Floor on this express experience.
    • Activity Level : Light
    • Duration : 1 hour

    Included in your vacation package price

    Gelato, Espresso and Tiramisu Group Walking Tour

    Gelato, Espresso and Tiramisu Group Walking Tour

    This 2.5-hour tour will be a sweet indulgence! Meet your small group at Piazza della Minerva at the statue of the elephant, 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 hours

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

    Contemporary Figurative Art at the Dorothy Circus Gallery

    Contemporary Figurative Art at the Dorothy Circus Gallery

    If you're a fan of art but need a break from Rome's historic art scene, then you'll love the Dorothy Circus Gallery, the first exhibition of its kind in Rome dedicated to contemporary figurative art. The gallery showcases a diverse mix of internationally renowned and emerging artists specializing in painting, sculpture, photography, and street art, chosen for their captivating visual styles and intriguing connections to Pop iconography, New Surrealism, and Magic Realism. If you're looking for a whimsical escape on a rainy or hot day, then this is for you!
    Opening hours: Tuesday to Saturday - 11:30 -18:30 Sundays and Mondays - closed

    Suggestion to explore on your own

  3. Day 3 Your Second Full Day in Rome

    Vatican Museums and Sistine Chapel Private Tour

    Vatican Museums and Sistine Chapel Private Tour

    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

    Included in your vacation package price

    Roman Retail Therapy

    Roman Retail Therapy

    Milan might be Italy's fashion capital, but that is debatable, something you'll surely discover when visiting Rome if you're a big shopper! Whether you're looking for high-end, big-name designers, searching for something handmade by a local, or on the hunt for antiques, Rome can cater to all shopping needs. "Via del Corso" is Rome's main clothes shopping street with offerings for every budget, while the famous "Via dei Condotti", leading to the Spanish Steps, is known for its high-end brand name shops such as Gucci and Dolce e Gabbana. For handmade objects, whether leather products or jewelry, the Monti neighborhood near the Colosseum is filled with charming boutique shops of all sorts. For antiques, get lost in the streets near the Pantheon and near Via di Ripetta; you'll find antique shops dotted everywhere.
    You'll also find other shopping suggestions on your Guest Page, or you can ask your local Destination Expert.

    Suggestion to explore on your own

  4. Day 4 Traveling to Castellina in Chianti by Private Transfer / Arrival in Castellina in Chianti

    Castellina in Chianti by Private Transfer with a stop in Orvieto
    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.
    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.
    Your driver will bring you to your accommodation in Castellina center or in the scenic countryside nearby, depending on your choice of accommodation.

    Our recommendation for Tuscany: The region is very authentic, charming and most of the best hotels are located in the countryside and not in the towns. If you want to go visit a winery or get dinner somewhere outside of the hotel, we recommend ensuring you have some tours booked in advance, as it can be a bit of a challenge to get transportation if you want to explore on your own.There are only a few taxis and they are quite expensive. For this reason, for clients who prefer to explore on their own and not hire a tour, we recommend considering a rental car if you are comfortable with driving in Italy. If you're interested, please let us know and we can suggest the best way to include it in your itinerary and provide you with the price difference.
    A Night in the Medieval Citadel

    A Night in the Medieval Citadel

    Stroll around the Medieval Citadel of Castellina at the end of the day and enjoy the peace all around you. Walking through its alleys and tiny streets will be like jumping into the past. End your evening jaunt of Castellina with a delicious dinner and wine in one of the best restaurants in town. Our favorite is Taverna Squarcialupi, which has a terrace overlooking the surrounding hills.

    Suggestion to explore on your own

  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

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

    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

    Included in your vacation package price

    Stroll Through History

    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. In the historical center of Via Ferruccio, you will find many restaurants, boutiques, shops, and historical buildings, such as Palazzo Squarcialupi and Palazzo Banciardi.
  6. Day 6 Traveling to Florence by Private Transfer / Arrival in Florence

    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.
    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.
    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.
    An Unforgettable First Night in Florence

    A Different View on Florence

    Enjoy a relaxing stroll through Florence city center, walk by the famous Duomo and the bell tower, Piazza della Signoria and continue to Ponte Vecchio, the famous old bridge from there you can enjoy a great view of the city on both sides of the river. End your night on a rooftop bar, Sesto on Arno is a great option, where you can enjoy your drink while admiring the city from above.

    Suggestion to explore on your own

  7. Day 7 Your First Full Day in Florence

    Florence Walking and David Visit Private Tour

    Florence Walking and Accademia Gallery Private Tour

    With this tour you'll make the most of your time in Florence: you'll be picked up at your accommodation by your guide, who will lead you through the city streets. You'll explore the most important bridges, alleys, medieval markets and Renaissance palaces, so you can appreciate the best of this unique city. Together, you will then reach the Academia 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 : Moderate
    • Duration : 3 hours

    Included in your vacation package price

    Florence’s Iconic Dishes - A Taste of Tradition

    Boared in Florence

    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.

    Suggestion to explore on your own

  8. Day 8 Traveling to Milan by Private Transfer / Arrival in Milan

    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.
    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.
    Your driver will take you to your accommodation in the center of Milan.
    Milan's Hidden Gems

    Milan's Hidden Gems

    Enjoy a day filled with exploration in Milan, venturing off the beaten paths to unveil the city's enchanting hidden gems. Discover the unique charm of Villa Invernizzi and its real flamingos, or immerse yourself in the vibrant neighborhood affectionately known as the "Rainbow Block" between Via Abraham Lincoln and Via Benjamin Franklin. Explore the modern allure of Piazza Gae Aulenti, where contemporary skyscrapers and shops surround a chic square adorned with fountains and colorful night lights. Milan's secrets await, promising a day of delightful surprises beyond the usual tourist trails.

    Suggestion to explore on your own

  9. Day 9 Your First Full Day in Milan

    Milan City Center Private Tour in a Fiat 500

    Milan City Center Private Tour with Fiat 500

    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 architecture and sites in the city in one of Italy's most iconic vehicles. There will be several stops for photos ,and you'll get a real feel for the unique atmosphere of this charming, romantic city.
    • Activity Level : Light
    • Duration : 2 hours

    Included in your vacation package price

    Leonardo da Vinci and his Milanese Masterpieces

    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.

    Suggestion to explore on your own

  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.

Rome, Castellina in Chianti, Florence and Milan

What's Included in your trip

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.

Included

  • 3 nights accommodation in Rome
    2 nights accommodation in Castellina in Chianti
    2 nights accommodation in Florence
    2 nights accommodation in Milan
  • Breakfast (hotels only)
  • Rome Fiumicino Airport Transfer
    Rome - Castellina in Chianti Private Transfer with a stop in Orvieto
    Castellina - Florence Private Transfer
    Florence - Milan City Private Transfer
    Milan Malpensa Airport Transfer
  • Golf Cart Around Rome Private Tour
    Colosseum Express - Semi Private Tour
    Vatican Museums and Sistine Chapel Private Tour
    Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Castellina in Chianti
    Florence Walking and Accademia Gallery Private Tour
    Milan City Center Private Tour with Fiat 500

What's excluded in your package

  • Local city taxes in Italy. These need to be paid at your hotels in cash; we are unable to pay them in advance for you. City tax is charged per person per night and varies by destination and accommodation level.
  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

Glowing Reviews From Our Guests

4.9105 reviews

Review by Wendy Toyama
I felt cared for by the local guides at JayWay. As a women traveling on my own, safety is a priority so this reassured me and my family. I also appreciated the way they listened to my needs, desires and dreams to craft an experience that was inspiring, restorative and memorable.

- Wendy Toyama - Illinois

Review by Bella & Dallas
I would highly recommend JayWay travel. They made it so easy, and we truly could just enjoy the trip and not stress about anything. Everything went so smoothly, they were so helpful and communicated so well with us!

- Bella & Dallas - Texas

Review by Alex & Halie
It was so easy to plan a trip with JayWay and we had the best time!

- Alex & Halie - Pennsylvania

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