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.
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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
Florence
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.
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.

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.
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.
Day 3
Day 3 - Your Second Full Day in Rome
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.

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.

3 Nights in Castellina in Chianti
3 Nights in Castellina in Chianti


3 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

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 - Your Second Full Day in Castellina in Chianti
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.

Day 7
Day 7 - Traveling to Venice by Private Transfer & Train, via Florence
It's time to leave the Tuscan countryside behind but you're not going too far. We will arrange for a driver to meet you at your accommodations to transfer you to the capital of the Tuscany region, Florence. The journey will take about 1 hour. If you'd like to make a day of out it, for an additional fee we can arrange some stops on the way in the Tuscan hills.
Day Stop in Florence
Day Stop in Florence



Day Stop in Florence
Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci's works are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.
Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci's works are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.
Day 7 - Day Stop in Florence
Day 7 - Day Stop in Florence
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
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.
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.
You can upgrade your transfer

Venice by Private Transfer with a stop in Modena
Upgrade for an additional cost
3 Nights in Venice
3 Nights in Venice



3 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 7
Day 7 - 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.
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.
Day 8
Day 8 - Your First Full Day in Venice

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.

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.
Day 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.

Premium Lagoon Group Tour with Murano Glass Blowing and Burano
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.

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.
Day 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.
Glowing Reviews from Our Guests
Average of our Guest's Ratings of tour packages including these destinations

The whole trip was so well done 👍. Cost versus quality was right on
– David, Donna, Daniela, BRIAN, Rose, Jason & Dana, West Virginia
Visited : Italy
Itinerary : Rome, Florence, Venice
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Jayway listened to what I was asking for in our experience. The trip was seamless, we felt very blessed.
– Kevin, Lisa, Jacob & Angelyna, California
Visited : Italy
Itinerary : Sorrento, Rome, Venice
Rating :

Our needs and expectations were exceeded in every area. We have been sharing with many friends and colleagues about your amazing level of service. We will recommend JayWay highly and Will use your services again if/when we travel to Europe again.
– Ed & Susan, Colorado
Visited : Italy
Itinerary : Venice, Rome, Sorrento
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