Italian Highlights

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Price
from $5,700
Duration
11 days
Destinations
Rome, Castellina in Chianti, Monterosso Al Mare, Venice

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Route for Rome, Castellina in Chianti, Monterosso Al Mare, Venice tour

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.

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

    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.
    • Activity Level : Easy
    • Duration : 3 hours

    Included in your vacation package price

    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.

    Suggested activities for an additional cost, depending on your choice

    Premium Colosseum, Roman Forum and Palatine Hill Group Tour

    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.
    • Activity Level : Moderate
    • Duration : 3 hours

    Suggested activities for an additional cost, depending on your choice

    Colosseum and Roman Forum Private Tour

    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.
    • Activity Level : Light
    • Duration : 3 hours

    Suggested activities for an additional cost, depending on your choice

    Gladiator's Gate Special Access Colosseum Group Tour

    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.
    • Activity Level : Moderate
    • Duration : 3 hours 15 minutes

    Suggested activities for an additional cost, depending on your choice

  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.

    Suggested activities for an additional cost, depending on your choice

    Guided Group Wine & Food Pairing Dinner Near the Pantheon

    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!
    • Activity Level : Easy
    • Duration : 2 hours 30 minutes

    Suggested activities for an additional cost, depending on your choice

    Group Food Tour - Campo de' Fiori, Jewish Ghetto, Trastevere

    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.
    Just so you know, this tour includes approximately 3.5 km (2.17 miles) of walking.
    • Activity Level : Light
    • Duration : 3 hours 30 minutes

    Suggested activities for an additional cost, depending on your choice

    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.

    Suggested activities for an additional cost, depending on your choice

    The Complete Vatican Group Tour with Vatican Museums and Sistine Chapel

    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.

    • Activity Level : Light
    • Duration : 3 hours 30 minutes

    Suggested activities for an additional cost, depending on your choice

    Vatican Highlights Private Guided Tour

    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.
    • Activity Level : Light
    • Duration : 3 hours 15 minutes

    Suggested activities for an additional cost, depending on your choice

  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 take you directly to your accommodations in the center of Castellina or the scenic countryside nearby, depending on your choice of accommodations.

    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 would like to 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 our guests who prefer to explore on their own and not book a tour, we recommend considering a rental car if you are comfortable 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 any cost differences.
    Stroll Through History

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

    Private Chianti Vespa Tour with Lunch and Wine Tasting from Castellina in Chianti

    Private Chianti Vespa Tour with Lunch and Wine Tasting from Castellina in Chianti

    Hop on a classic Vespa and ride through the heart of Tuscany, leaving the crowds behind as you follow the legendary Chiantigiana road between Florence and Siena. You’ll cruise past rolling hills, medieval villages, and breathtaking viewpoints, stopping along the way to soak in the scenery and atmosphere. The journey includes visits to top Chianti wineries, where you discover the art of winemaking and enjoy tastings in a stunning countryside setting. Stylish, relaxed, and unforgettable, this is Tuscany experienced as a true lifestyle, not just a tour.
    • Activity Level : Moderate
    • Duration : 5 hours

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

    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 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.
    • Activity Level : Light
    • Duration : 7 hours

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

  6. Day 6 Traveling to Monterosso Al Mare by Private Transfer / Arrival in Monterosso Al Mare

    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.
    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.
    Your driver will bring you straight to your accommodation at Monterosso Al Mare.
  7. Day 7 Your First Full Day in Monterosso Al Mare

    Cinque Terre Private Hiking Tour

    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.
    • Activity Level : Strenuous
    • Duration : 6 hours

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

    Cinque Terre Group Boat Cruise at Sunset with Dinner on Board

    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.
    • Activity Level : Easy
    • Duration : 3 hours

    Included in your vacation package price

  8. Day 8 Your Second Full Day in Monterosso Al Mare

    Visit Portofino and Private Tour of Genoa

    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.
    • Activity Level : Light
    • Duration : 9 hours

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

    Swim in Splendid Waters

    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!

    Suggestion to explore on your own

  9. Day 9 Traveling to Venice by Train / Arrival in Venice

    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.
    Upgrade to Venice by Private Transfer

    You can upgrade your transfer

    Venice by Private Transfer

    Upgrade for an additional cost

    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.
    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.
  10. Day 10 Your First Full Day in Venice

    First Time in Venice Private Tour

    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.
    • Activity Level : Light
    • Duration : 3 hours

    Included in your vacation package price

    Doge's Palace Group Tour

    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.
    • Activity Level : Light
    • Duration : 1 hour 15 minutes

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

    Venice Street Food and Rialto Market Group Tour

    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).
    • Activity Level : Light
    • Duration : 3 hours

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

  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.

Ideas to customize your trip further

  • After Hours Santa Maria Maggiore and Terraces Small Group Tour

    Activity level : Light
    Duration : 1 hour

  • Baroque Masterpieces - Borghese Gallery Small Group Tour

    Activity level : Light
    Duration : 2 hours

  • Cappuccino and Tiramisu Italian Breakfast Group Cooking Class

    Activity level : Light
    Duration : 1 hour 30 minutes

  • Colosseum Express - Semi Private Tour

    Activity level : Light
    Duration : 1 hour

  • Colosseum Private Family Tour for Kids

    Activity level : Light
    Duration : 2 hours 30 minutes.

  • E-bike Along the Appian Way Private Tour

    Activity level : Moderate
    Duration : 3 hours

  • Early Entrance Small Group Colosseum & Roman Forum Tour with Special Arena Access

    Activity level : Light
    Duration : 3 hours

  • Early Risers Small Group Tour with Pantheon & Breakfast

    Activity level : Light
    Duration : 2 hours 30 minutes

  • Family Fun Private Walking Tour - History, Games, and Delicacies

    Activity level : Moderate
    Duration : 3 hours

  • Gelato, Espresso and Tiramisu Group Walking Tour

    Activity level : Light
    Duration : 2 hours

  • Golf Cart Evening Small Group Tour with Drinks

    Activity level : Easy
    Duration : 3 hours

  • Group Cooking Class in the Jewish District

    Activity level : Easy
    Duration : 2.5 hours

  • Group Gelato & Tiramisu Class in a Professional Kitchen

    Activity level : Light
    Duration : 2 hours

  • Last Entry Colosseum, Arena Access & Rooftop Aperitif Private Tour

    Activity level : Light
    Duration : 3 hours 15 minutes

  • Magical Rome at Night Private Tour by Car

    Activity level : Easy
    Duration : 3 hours

  • Orvieto and Civita di Bagnoregio Private Day trip from Rome

    Activity level : Moderate
    Duration : 9 hours

  • Pasta-Making with a Local Chef Group Class

    Activity level : Easy
    Duration : 3 hours

  • Pizza & Ice-Cream Fiat 500 Private Tour For Families

    Activity level : Easy
    Duration : 3 hours

  • Pompeii Day Trip and Amalfi Coast Drive Group Tour

    Activity level : Moderate
    Duration : 13 hours

  • Pristine Sistine Early Entrance Group Vatican Tour

    Activity level : Light
    Duration : 4 hours

  • Pristine Sistine at Closing Time: Late Entry Group Vatican Tour

    Activity level : Light
    Duration : 3 hours

  • Private Appian Way Golf Cart Tour with Lunch

    Activity level : Easy
    Duration : 5 hours

  • Private Day Trip to Bomarzo & Orvieto from Rome

    Activity level : Moderate
    Duration : 8 hours

  • Private Fiat 500 Tour with Aperol Spritz

    Activity level : Easy
    Duration : 3 hours

  • Private Golf Cart Tour of Rome by Night with Drinks

    Activity level : Easy
    Duration : 3 hours

  • Private Tour of Castel Sant’Angelo

    Activity level : Light
    Duration : 2 hours

  • Private Walking Tour of Rome with Highlights and Gelato Tasting

    Activity level : Moderate
    Duration : 2 hours

  • Roman Private Aperitivo Experience

    Activity level : Light
    Duration : 2 hours

  • Rome City Center Highlights Group E-bike Tour

    Activity level : Moderate
    Duration : 4 hours

  • Rome E-Bike Group Tour with Street Food and Market Visit

    Activity level : Moderate
    Duration : 3 hours 30 minutes

  • Rome Highlights VIP Private Tour

    Activity level : Moderate
    Duration : 9 hours 15 minutes

  • Rome Major Basilicas Private Tour

    Activity level : Easy
    Duration : 3 hours

  • Rome Off-the-Beaten Path Private Tour with Visit of Castel Sant'Angelo

    Activity level : Moderate
    Duration : 3 hours

  • Rome Pizza Making Class

    Activity level : Light
    Duration : 2 hours 30 minutes

  • Rome Three Major Basilicas Small Group Tour

    Activity level : Light
    Duration : 3 hours

  • Rome by Night E-Bike Group Tour

    Activity level : Moderate
    Duration : 2 hours 30 minutes

  • Rome in A Day Group Tour

    Activity level : Moderate
    Duration : 7 hours 30 minutes

  • Rome’s Crypts & Catacombs Family Private Tour

    Activity level : Light
    Duration : 2 hours 30 minites

  • San Clemente, Roman Houses and Baths of Caracalla Private Tour

    Activity level : Moderate
    Duration : 3 hours

  • Seven Sips of Italy: A Private Wine Journey

    Activity level : Light
    Duration : 2 hours

  • Small Group Day Trip to Naples and Pompeii

    Activity level : Moderate
    Duration : 9 hours

  • St. Peter's Basilica Small Group Tour with Dome and Crypt Visit

    Activity level : Moderate
    Duration : 2 hours 30 minutes

  • Sunset Pizza Group Tour in Monti

    Activity level : Moderate
    Duration : 2 hours

  • Testaccio District Street Food Group Tour

    Activity level : Light
    Duration : 3 hours 30 minutes

  • The Great Beauty Rooftop Aperitif and Opera at Sunset

    Activity level : Easy
    Duration : 2 hours

  • Tivoli Villas & Gardens Private Tour

    Activity level : Light
    Duration : 7 hours

  • Traditional Jewish Roman Dinner Group Experience

    Activity level : Light
    Duration : 2 hours

  • Trastevere & Jewish Ghetto Private Tour of Rome

    Activity level : Light
    Duration : 2 hours

  • Trastevere Tasting Private Experience

    Activity level : Light
    Duration : 2 hours 30 minutes

  • Underground Rome Catacombs with Aqueducts and Appian Way Group Walking Tour

    Activity level : Light
    Duration : 3 hours 15 minutes

  • VIP Vatican Key Master's Group Tour

    Activity level : Light
    Duration : 2 hours

  • Vatican Early Morning Private Tour

    Activity level : Light
    Duration : 3 hours 30 minutes

  • Vatican Early Morning Small Group Tour

    Activity level : Light
    Duration : 3 hours 30 minutes

  • Vatican Museums and Colosseum Combo Full Day Private Tour

    Activity level : Moderate
    Duration : 8 hours

  • Vatican Night Private Tour

    Activity level : Light
    Duration : 2 hours 30 minutes

  • Vatican, Sistine Chapel and St. Peter’s Basilica Private Family Tour

    Activity level : Light
    Duration : 2 hours 30 minutes

  • Vespa Sidecar Group Tour

    Activity level : Moderate
    Duration : 3 hours

  • Vespa Sidecar Private Tour

    Activity level : Moderate
    Duration : 3 hours

Rome, Castellina in Chianti, Monterosso Al Mare and Venice

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
    3 nights accommodation in Monterosso Al Mare
    2 nights accommodation in Venice
  • Breakfast (hotels only)
  • Rome Fiumicino Airport Transfer
    Rome - Castellina in Chianti Private Transfer with a stop in Orvieto
    Castellina - Monterosso Private Transfer
    Venice Private Water Taxi Santa Lucia Train Station Transfer
    Venice Marco Polo Airport Transfer
  • Monterosso - Venice Standard Class Train Tickets
  • Golf Cart Around Rome Private Tour
    Cinque Terre Group Boat Cruise at Sunset with Dinner on Board
    First Time in Venice Private Tour

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

4.993 reviews

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

Review by Jill, Aidan & Gabriel
The JayWay team was exceptional. I have not used travel agents in many years by planning trips for our family, but I highly recommend JayWay for families that are busy or just want a smooth plan. The hotels, travel tickets within Italy all, tours all exceeded expectations.

- Jill, Aidan & Gabriel - New York

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