This sample 11 day (10 nights) itinerary covers several of Italy's highlights from Rome northwards: Tuscany, Cinque Terre & Venice. The services we provide as part of our comprehensive packages include accommodations, train tickets, in-city transfers (airport & train station), long-distance sightseeing transfers, and city tours. 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 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 arrival, we will provide you with a local SIM that you can use to reach your local JayWay contact (who you will meet in person) 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 firsthand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambience.
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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
Castellina in Chianti
Monterosso Al Mare
Venice
package excludes:
- Flights from and to your home country.
- 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
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 destination-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.3 Nights in Rome
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.
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.
Day 2
Day 2 - Your First Full Day in Rome

Golf Cart Around Rome Private Tour
Explore Rome effortlessly with a private golf cart tour, a comfortable and eco-friendly way to see the city. Glide through the streets with your private guide, visiting iconic landmarks like the Colosseum, Pantheon, and Trevi Fountain while hearing fascinating stories. Venture off the beaten path to hidden gems like the keyhole and the Pyramid of Cestius, adding unique stops to your adventure. This personalized tour lets you cover more ground, take breaks when needed, and fully immerse yourself in Rome’s history and charm.
Relive Ancient Rome
Discover the origins of Rome by visiting the iconic Colosseum and the Roman Forum, where you can immerse yourself in the grandeur of Ancient Rome. A private guide can share the fascinating history behind the Colosseum’s construction and its subsequent evolution, followed by a tour of the Roman Forum, the heart of Roman political life. Alternatively, we can arrange a group tour with a reputable company; please note that the Colosseum occasionally adjusts its tour schedules or order, both of which offer a deeper understanding of this ancient city's incredible legacy.

Premium Colosseum, Roman Forum and Palatine Hill Group Tour
Explore the captivating tales of lions, gladiators, and emperors on a comprehensive journey through Ancient Rome. Skip the lines and enjoy express entry to the Colosseum, Roman Forum, and Palatine Hill. With an expert guide leading a small group of no more than 15 individuals, immerse yourself in an intimate and enjoyable tour of these three iconic sites, delving into the rich history of Ancient Rome.

Colosseum and Roman Forum Private Tour
Explore the Roman Forum, where your guide will bring ancient temples, theaters, and political landmarks to life with fascinating stories. Ascend Palatine Hill to hear captivating tales of luxury and opulence while surrounded by peaceful ruins. Enjoy priority access to the Colosseum and use VR glasses to visualize its gladiatorial battles and ancient grandeur. This private tour offers personalized storytelling and an unforgettable journey through Rome’s iconic past.

Gladiator's Gate Special Access Colosseum Group Tour
On this tour, you will enter the Colosseum like a gladiator, venturing through its ancient corridors and entering via the Gladiator’s Gate. You will hear captivating tales of emperors and ruthless crowds, then ascend to explore the Colosseum's first and second levels with your guide. You will conclude your adventure with a captivating tour of Palatine Hill and the Roman Forum, where history comes alive amidst the ancient ruins.
Day 3
Day 3 - Your Second Full Day in Rome
Gourmet Experiences
There's no better way to explore Italian cuisine than by taking gourmet tours, which will give you a deep cultural experience. You can learn how to make gelato and tiramisu, enjoy a luxury gourmet dinner with a wine tasting in a private cellar, or be part of a small group food crawl. Choose any of these experiences, and we guarantee you'll want more.

Guided Group Wine & Food Pairing Dinner Near the Pantheon
This 2.5-hour tour and degustation is perfect for foodies. You'll start with an aperitif as you soak up the atmosphere. Then you'll head for dinner, enjoying sumptuous Roman specialties while you get the special treatment from the owners of the restaurant. We can't think of a better way to enjoy a Roman dinner!

Group Food Tour - Campo de' Fiori, Jewish Ghetto, Trastevere
Food lovers, here's your chance to experience Rome’s enchanting squares and neighborhoods while tasting your way through some of the city’s best shops, restaurants, and markets, discovering the secrets of Italian cuisine. Meet your friendly, local expert food connoisseur in the city center, and get ready to stroll through a number of neighborhoods to visit the most famous food markets, groceries, coffee shops, ice cream shops, and restaurants. Taste some of the delicious food and wines the city is famous for, including pizza bianca, mortadella, gelato, and supplì. From fried artichokes or zucchini flowers in the Jewish ghetto to spices and vegetables in Campo de Fiori, you'll ignite your senses and burn some calories while you enjoy walking amongst the beauty around you.
A Visit to Rome's Unique Sovereign State - Vatican City
The striking dome of St. Peter's Basilica is an unmistakable landmark in Rome, dominating the city’s skyline and often being the first sight upon arriving by plane. Vatican City, an independent sovereign state surrounded by stone walls, serves as the spiritual and administrative heart of the Roman Catholic Church and is an essential destination during any visit to Rome. For an enriching experience, we recommend combining a tour of the Vatican Museums with a visit to St. Peter's Basilica. We offer private, group, and small group tours, each providing exclusive insights into this remarkable destination.

The Complete Vatican Group Tour with Vatican Museums and Sistine Chapel
For an in-depth exploration of Rome's iconic highlights, this guided tour with an expert is a must. Discover the Sistine Chapel, Vatican Museums, and beyond—an immersive Vatican journey. Skip the lines and delve into these remarkable buildings and their artistic treasures with your private guide, gaining insights into their rich history and profound significance.

Vatican Highlights Private Guided Tour
Discover the Vatican's wonders on a private guided tour tailored to your pace, including the Vatican Museums, Sistine Chapel, and St. Peter’s Basilica. Skip the long lines with the VIP entrance and dive straight into the Papal Palace’s treasures. Admire masterpieces like the Laocoon and Apollo Belvedere as your guide shares their fascinating histories in the scenic courtyard. End your journey with awe-inspiring visits to Michelangelo’s Sistine Chapel and the grandeur of St. Peter’s Basilica.
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.

2 Nights in Castellina in Chianti
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.
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 take you directly to your accommodations in the center of Castellina or the scenic countryside nearby, depending on your choice of accommodations.
Stroll Through History
Nestled in the heart of the Chianti Classico region, Castellina in Chianti offers a delightful blend of history, culture, and gastronomy. Explore the town's ancient Etruscan roots at the Montecalvario Tomb and stroll along the Via delle Volte, a charming medieval walkway with stunning views of the countryside. Visit the Rocca di Castellina, a historic fortress with a panoramic tower, and enjoy wine tastings at local wineries celebrating the famed Chianti Classico. With its quaint streets and inviting atmosphere, you will fall in love with Castellina Tuscany's timeless beauty.

Day 5
Day 5 - Your First Full Day in Castellina in Chianti

Siena Half-Day Private Tour from Castellina
There's no better way to explore the beautiful city of Siena than with a private local guide. A half-day trip is the perfect amount of time for this excursion. You'll tour the city and see the most impressive buildings and monuments while your guide fills you in on the history and most interesting stories from the city's past. This being Italy, there are plenty of opportunities for delicious local cuisine. Your guide will give you suggestions on the best local places where you can stop on your own to enjoy a typical, Sienese lunch. To conclude this five-hour excursion you'll be driven back to you accommodation.

Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Castellina in Chianti
This excursion 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 for an extra fee. 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.
Day 6
Day 6 - Traveling to Monterosso Al Mare by Private Transfer
It's time to head to the coast! We will arrange for a driver to pick you up from your accommodations in Tuscany and transfer you to the Cinque Terre area. The drive from Tuscany to Cinque Terre takes around 3 hours without stops but for an additional fee, we can arrange a stop on the way for you. For anyone with a love of motoring or chocolate, the town of Pontedera offers up the choice of the Amedei chocolate factory or the Piaggio museum. Even if you haven’t heard of Piaggio you’ll certainly have seen a few of their signature Vespas during your time in Italy but they started out as an aeronautics company. Alternatively, if you didn’t take a day trip to Pisa while in Tuscany then this is your chance. Although most just stop to gawp at the leaning tower, the Duomo and Baptistery are worth your time.
3 Nights in Monterosso Al Mare
3 Nights in Monterosso Al Mare


3 Nights in Monterosso Al Mare
As the northern-most of the Cinque Terre villages, Monterosso-al-Mare (literally the red mountain by the sea) is the most accessible of five. Road, rail and ferry links, and a wide choice of hotels make this an excellent base for visiting all the other villages and neighboring towns as well. This choice and accessibility comes at a price – it is the least pretty of the five. Yet that will hardly seem to matter when you're looking out to sea, or hiking the steep trail to Vernazza, the next village. Monterosso has the largest and best equipped beach of all the Cinque Terre villages so if some sun worship is on your vacation agenda, this is the perfect spot. As well as the opportunity to hike in the Cinque Terre national park between some of the villages you can also take the regular trains or if seas allow, the ferry service to the other villages. Private and boat day trips provide another way to admire the villages from their most natural aspect, the sea.
As the northern-most of the Cinque Terre villages, Monterosso-al-Mare (literally the red mountain by the sea) is the most accessible of five. Road, rail and ferry links, and a wide choice of hotels make this an excellent base for visiting all the other villages and neighboring towns as well. This choice and accessibility comes at a price – it is the least pretty of the five. Yet that will hardly seem to matter when you're looking out to sea, or hiking the steep trail to Vernazza, the next village. Monterosso has the largest and best equipped beach of all the Cinque Terre villages so if some sun worship is on your vacation agenda, this is the perfect spot. As well as the opportunity to hike in the Cinque Terre national park between some of the villages you can also take the regular trains or if seas allow, the ferry service to the other villages. Private and boat day trips provide another way to admire the villages from their most natural aspect, the sea.
Day 6
Day 6 - Arrival in Monterosso Al Mare
Your driver will bring you straight to your accommodation at Monterosso Al Mare.
Day 7
Day 7 - Your First Full Day in Monterosso Al Mare

Hiking Trails in Cinque Terre
Hiking in Cinque Terre is demanding but rewarding, only for people in good physical condition and equipped with good hiking boots, comfortable outfits, a sun hat, sunscreen, and extra water. The Monterosso to Vernazza leg takes around 3 hours, and the same for Vernazza to Corniglia. Note that the scenic and easy walk "Via dell’Amore" (the love road) between Riomaggiore and Manarola is interrupted and won’t be restored soon.

Cinque Terre Group Boat Cruise at Sunset with Dinner on Board
Experience an unforgettable journey along the stunning Cinque Terre coastline, capturing breathtaking views of all five villages from a comfortable boat. Indulge in a refreshing swim or snorkeling adventure in enchanting bays and savor a sumptuous aperitif with complimentary drinks and local delicacies as you watch the sunset. All this will create unforgettable memories of Italy's picturesque coastline.
Day 8
Day 8 - Your Second Full Day in Monterosso Al Mare

Portofino and Camogli, the Jewels of Liguria
If you have a few days to enjoy the area, we recommend visiting Santa Margherita Ligure, a renowned coastal destination. This place offers easy access to Cinque Terre by train, and it's very close to picturesque Camogli and the VIP-tourism hamlet of Portofino, which is the quintessential image of the Italian Riviera. From Camogli, a regular boat takes you to the magnificent medieval Abbey of San Fruttuoso, which is only reachable by sea and offers great swimming opportunities. The whole area is part of the protected natural reserve of Portofino Promontory, which is ideal for hiking, sailing, and scuba diving. You can easily explore the area with an experienced local driver in conjunction with a visit to Genoa's famous aquarium.
Swim in Splendid Waters
If you like swimming, you have more than a few options on the coast. In warmer weather, we definitely recommend the tiny harbors of Vernazza and Riomaggiore. The only equipped beach nearby is in Monterosso, and this one is suitable for families as well. So grab your towel and suncream and maybe a focaccia and a drink or gelato. As usual, the best suggestion is to follow the locals!

Day 9
Day 9 - Traveling to Venice by Train
It's a day of traveling from Coast to Coast today, from the Ligurian coast to the Adriatic. We'll book you standard class tickets from Monterosso Al Mare to Venice. Depending on where you're staying, you'll need to change trains at least once, in Milano Centrale. An upgrade to a higher class is possible for an extra fee. The whole journey takes around 6 hours. If necessary your hotel will be able to arrange a taxi to the train station.
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Venice by Private Transfer
Upgrade for an additional cost
2 Nights in Venice
2 Nights in Venice



2 Nights in Venice
Venice is a legendary city with a charm and atmosphere all its own. The city was constructed on more than 100 islands connected by a series of canals, most of which are lined with gorgeous palaces, beautiful churches, and all sorts of impressive architecture. While the city isn’t huge, it is packed with pedestrian-only streets and quaint, winding alleys that will keep you exploring for days. The city is very popular with tourists year-round, so you certainly won’t be the only travelers walking through the streets with camera in hand. This being Italy, the cuisine in Venice is delicious, and we can especially recommend the Cicchetti of Venice tour. Cicchetti are Venetian tapas, and this tour will introduce you to some of the city’s most iconic eateries and its most delicious recipes. If it’s your first time in Venice, we can organize a tour to show you all the most important sites. And since no trip to the city of canals is complete without a boat ride, we offer a number of ways for you to get a new point of view of the city and its magnificent architecture. It’s easy to while away your time in Venice, discovering new secrets around every corner.
Venice is a legendary city with a charm and atmosphere all its own. The city was constructed on more than 100 islands connected by a series of canals, most of which are lined with gorgeous palaces, beautiful churches, and all sorts of impressive architecture. While the city isn’t huge, it is packed with pedestrian-only streets and quaint, winding alleys that will keep you exploring for days. The city is very popular with tourists year-round, so you certainly won’t be the only travelers walking through the streets with camera in hand. This being Italy, the cuisine in Venice is delicious, and we can especially recommend the Cicchetti of Venice tour. Cicchetti are Venetian tapas, and this tour will introduce you to some of the city’s most iconic eateries and its most delicious recipes. If it’s your first time in Venice, we can organize a tour to show you all the most important sites. And since no trip to the city of canals is complete without a boat ride, we offer a number of ways for you to get a new point of view of the city and its magnificent architecture. It’s easy to while away your time in Venice, discovering new secrets around every corner.
Day 9
Day 9 - Arrival in Venice
Start your Venetian experience off in style by arriving in a private water taxi. We'll arrange a transfer by boat from Santa Lucia train station to the closest possible point to your hotel in Venice. Please note that porter assistance from the water taxi to the hotel is not included but can be arranged at extra charge.
Day 10
Day 10 - Your First Full Day in Venice

First Time in Venice Private Tour
Discover Venice with this unique walking tour, which unfolds through the elegant Piazza San Marco, surrounded by the governmental buildings of the ancient Republic. You'll see the beautiful Saint Mark church, then stroll through the Castello district including the large campo Santa Maria Formosa. The square of San Giovanni e Paolo will be your next stop. Before reaching Rialto you'll pass by the Marco Polo house. From the top of the famous Rialto bridge you'll encounter all the splendours of the Grand Canal.

In the Footsteps of the Doges
The Doge’s Palace, an architectural masterpiece of Venetian Gothic design, stands proudly beside St. Mark’s Basilica in the heart of Piazza San Marco. Once the residence of the Doge, the elected ruler of Venice, this grand palace also served as the seat of government and the center of political life during the city’s height as a maritime power. Since opening as a museum in 1923, it has welcomed visitors to admire its opulent halls adorned with masterpieces by artists such as Tintoretto and Veronese. Highlights include the ornate Golden Staircase, the vast Council Chamber, and the infamous Bridge of Sighs connecting to the old prison. A visit offers an unforgettable journey into Venice’s rich political, artistic, and architectural heritage.

Venetian Tapas and Wine Tours
You're in Italy, so good food isn't too far away if you know where to look. One of our favorite ways to get to know a city is by taking a food tour. We can highly recommend taking part in these small group tours and getting your culinary bearings set with an afternoon sampling cicchetti (Venetian tapas), accompanied by wine at Venice's best Bacari (traditional wine bars).
Day 11
Day 11 - Departure Day
It's time to bid arrivederci to Venice but you'll get a good last look at the city as your private water taxi captain takes you to the airport for your departing flight. Your private boat will dock at the closest possible point to your hotel.
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