A Dream Italian Honeymoon

  • Travel and Leisure
  • Fodors
  • USA Today
  • New York Times
  • National Geographic
  • Washington Post
  • Vogue
Price
from $5,050
Duration
10 days
Destinations
Rome, Castellina in Chianti, Florence, Venice

Get a price estimate for this trip

Month of travel
Month of travel
No. of travelers
No. of travelers
Accommodation level
Accommodation level
Route for Rome, Castellina in Chianti, Florence, Venice tour

Where could be more perfect for your first trip as a married couple than Italy? Start off with some time in Rome. Even if you've been before, the Eternal City always has something more to see. A private driver will whisk you to Tuscany, stopping along the way at medieval Orvieto for lunch. Take some time to relax at your hotel or farmhouse's pool. The final stop is La Serenissima – Venice! But on the way you'll have a day in Florence with a private guide to show you the city's sights and take you to the legendary Uffizi and Accademia galleries. All of our tours are custom, and this is just a sample meant to give an idea for 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 card or eSIM 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.
    Roman Holiday in Love

    Roman Holiday in Love

    There are many ways to make your stay in Rome even more romantic. For a little light exercise along with your romance, head to the artificial lake in the Villa Borghese Gardens. For just a few euros, you and your beloved can go to the water and circumnavigate the impressive Temple of Asclepius, which sits on the island in the middle. Enjoy a spa treatment themed after some Italian classic wines. Choose from the grand Brunello di Montalcino or a bubbly Prosecco experience, as well as a tasting of the fruit of the vine itself. That theme runs all the way through your two-hour treatment, from grape seed scrubs to scented bubbles. Let your local Destination Expert know when you'd like to schedule your visit, and we'll make a reservation directly at the spa, located right in the heart of Rome, by the Pantheon.

    Suggestion to explore on your own

  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

    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

  3. Day 3 Your Second Full Day in Rome

    Roman Retail Therapy

    Roman Retail Therapy

    While Milan is often referred to as Italy’s fashion capital, Rome offers a diverse shopping experience that rivals any other city. Visitors can find everything from luxury designer boutiques to unique handmade items and antiques. Via del Corso is Rome’s main shopping street, catering to all budgets with a wide selection of clothing stores. For high-end fashion, Via dei Condotti, near the Spanish Steps, is home to prestigious brands such as Gucci and Dolce & Gabbana. The Monti neighborhood, located near the Colosseum, is renowned for its artisanal leather goods and jewelry boutiques. Antique shops are concentrated around the Pantheon and Via di Ripetta. Additional tips are available on your Guest Page or from your local Destination Expert.

    Suggestion to explore on your own

    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

    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 Your Second Full Day in Castellina in Chianti

    Explore Chianti's Hills on Foot and Wheels

    Explore Chianti's Hills on Foot and Wheels

    The rolling hills around Castellina offer many possibilities for splendid short or day-long trips. Your accommodations and the local tourist office, which are located on the main street close to Palazzo Squarcialupi, will offer plenty of suggestions and maps for hiking and cycling. On the edge of the village is a Vespa and Cinquecento (vintage Fiat car) rental company, should you want to indulge in a little nostalgic exploration of the surroundings in style.

    Suggestion to explore on your own

  7. Day 7 Traveling to Venice by Private Transfer & Train, via Florence / Day Stop in Florence / Arrival in Venice

    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 to the main railway station Santa Maria Novella, from where you will continue your journey.
    Florence City Private Walking Tour

    Florence City Private Walking Tour

    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

    Included in your vacation package price

    Your time in Florence has drawn to a close but there's plenty more Italian splendor ahead of you as you push north to the magnificent maritime city of Venice. We have included standard class train tickets for the high-speed train service which takes around two hours. An upgrade to a higher class is possible at an extra cost. We'll arrange for our driver to pick you up from your accommodations and take you to Florence Train Station.
    Upgrade to Venice by Private Transfer with a stop in Modena

    You can upgrade your transfer

    Venice by Private Transfer with a stop in Modena

    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.

    Venice - The Ultimate Romantic Getaway and a City for Lovers

    Venice is considered one of the most romantic cities in the world due to its enchanting atmosphere, timeless beauty, and unique setting. Its winding canals, picturesque bridges, and narrow alleyways create an intimate and serene backdrop, perfect for strolling hand-in-hand with a loved one. The city’s rich history, stunning architecture, and art-filled piazzas exude a sense of timeless elegance, while gondola rides through the canals offer a peaceful and romantic experience. Whether enjoying a candle-lit dinner in a hidden courtyard or admiring the sunset over the Grand Canal, Venice's charm effortlessly evokes romance at every turn.

    Suggestion to explore on your own

  8. Day 8 Your First Full Day in Venice

    Private Gondola Ride

    Private Gondola Ride

    A gondola ride is the most iconic and romantic way to experience Venice. Glide through enchanting canals, gently rocked by the water. Admire grand palaces, historic bridges, and hidden corners only visible from the water. Let your gondolier take you through breathtaking views and timeless beauty.
    • Activity Level : Easy
    • Duration : 25 minutes

    Included in your vacation package price

    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

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

  9. Day 9 Your Second Full Day in Venice

    Murano and Burano

    Central Venice is amazing, but sometimes it's good to get out of the center and see something different. We recommend venturing away from the usual path and embarking on a boat journey to traverse the water and discover two captivating islands. Murano boasts charming architecture similar to Venice, but its primary allure lies in the remarkable glassblowers. You can witness their ongoing creations at numerous factories and showrooms throughout the island. On the other hand, Burano, like the rest of the islands in Venice, is a delightful destination comprised of smaller interconnected islands via numerous bridges. The island immediately captivates visitors with its vividly painted houses, radiating a unique and vibrant energy. Predominantly inhabited by artists, Burano offers an inviting environment for exploration and discovery. Whether you prefer a group boat excursion or a private one, we can arrange tours to enhance your experience.

    Suggested activities for an additional cost, depending on your choice

    Premium Lagoon Group Tour with Murano Glass Blowing, Burano & St. Erasmo Winery

    Premium Lagoon Group Tour with Murano Glass Blowing, Burano & St. Erasmo Winery

    Apart from Venice itself, the Venetian Lagoon is dotted with tiny gems of islands and this incredible tour shows you around the charms of the two most known among them: Murano and Burano. In the company of your small group, you'll enjoy a relaxing ride on a private boat and be amazed by a private glassmaking demonstration within the walls of a beautiful old church.
    • Activity Level : Light
    • Duration : 4 hours 15 minutes

    Suggested activities for an additional cost, depending on your choice

    Grand Canal Private Tour with Stops at Murano and Burano

    Grand Canal Private Tour with Stops at Murano and Burano

    Explore Venice by water with a private boat tour along the Grand Canal, led by a knowledgeable crew sharing insights into the city's history and legends. Immerse yourself in Venetian culture by visiting Murano for a mesmerizing glass-blowing demonstration and Burano to experience its vibrant, colorful streets.
    • Activity Level : Light
    • Duration : 4 hours

    Suggested activities for an additional cost, depending on your choice

  10. Day 10 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.

  • Colosseum and Roman Forum Private Tour

    Activity level : Light
    Duration : 3 hours

  • 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

  • Gladiator's Gate Special Access Colosseum Group Tour

    Activity level : Moderate
    Duration : 3 hours 15 minutes

  • 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

  • Premium Colosseum, Roman Forum and Palatine Hill Group Tour

    Activity level : Moderate
    Duration : 3 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, Florence 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
    3 nights accommodation in Castellina in Chianti
    3 nights accommodation in Venice
  • Breakfast (hotels only)
  • Rome Fiumicino Airport Transfer
    Rome - Castellina in Chianti Private Transfer with a stop in Orvieto
    Castellina - Florence Private Transfer
    Florence Train Station Transfer
    Venice Private Water Taxi Santa Lucia Train Station Transfer
    Venice Marco Polo Airport Transfer
  • Florence - Venice Standard Class Train Tickets
  • Golf Cart Around Rome Private Tour
    Florence City Private Walking Tour
    Private Gondola Ride

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

4.9122 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

Get your personalized itinerary based on this trip.

Chat with us

Unlock Your Custom Trip Plan

Where would you like to go? Choose one or more. Hold Ctrl (Cmd on a Mac) to select several.

We will contact you within 1 working day to discuss your requirements and prepare a truly customized trip plan for you.

©2026 JayWay Travel Inc.