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A Dream Italian Honeymoon

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 Serenissim – 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 in the region will be available to you during and leading up to the 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 cell phone that you can use to contact our employee (who you will meet in person) throughout your trip. In all of our destinations, we offer a variety of memorable 3-5 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.

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

Suggestion to explore on your own

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 man-made lake in the Villa Borghese Gardens. For just a few euros you and your beloved can take to the water and circumnavigate the impressive Temple of Asclepius that 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, and 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 JayWay contact know when you'd like to schedule your visit and we'll make a reservation directly with the spa, located right in the heart of Rome by the Pantheon.

Day 2

Day 2 - Your First Full Day in Rome

Focus on Ancient Rome

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

Rome's origin story unfolds when you visit the Colosseum and the adjacent Roman Forum. Hear about life in ancient Rome and soak in the grandeur of these testaments to a lost civilisation. We can arrange for a private guide to explain how the Colosseum was built and what happened to it in the years since. Afterwards the tour proceeds to the Roman Forum, the center of political life of the city and ultimately the Empire, finding out the different purposes of the buildings whose columns and porticos still stand today.


Activity Level : Moderate
Duration : 3 Hours

Day 3

Day 3 - Your Second Full Day in Rome

Couples Pampering: Brunello or Prosecco Spa

Suggestion to explore on your own

What better way to spend an afternoon in Rome with your loved one than enjoying a spa treatment themed after some Italian classic wines. Choose from the grand Brunello di Montalcino or a bubbly Prosecco experience and as well as a tasting of the fruit of the vine itself that theme runs all the way through your 2 hour treatment, from grape seed scrubs to scented bubbles. Let your local JayWay contact know when you'd like to have your visit scheduled and we'll make a reservation directly with the spa, located right in the heart of Rome by the Pantheon.

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.

We also offer the following excursions in Rome

4 Day Private Gourmet Tour - Guide and Driver
Light4 Days
Colosseum, Roman Forum and Palatine Hill Group Tour
Moderate3 Hours
Cooking Class in the Jewish District Group Tour
Easy3 hours
Eating in the Monti Neighborhood: A Pizza Tour Close to the Colosseum
Light2.5 hours

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 bring you to your accommodation in the Tuscan countryside.

Tasting Dinner in Castellina in Chianti

Taverna Squarcialupi in the small hilltop town of Castellina in Chianti is one of our favorite restaurants in the area, Mauro the maitre will take great care of you as you sit down to enjoy a specially created tasting menu based on the chef's signature dishes using quality local ingredients and with seasonal variations.


Activity Level : Easy
Duration : 1.5 hours

Day 5

Day 5 - Your First Full Day in Castellina in Chianti

Montalcino, Montepulciano and Pienza

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

Spend a day exploring the Tuscan countryside south of Siena, with a couple of winery visits in the the renowned denominations of Montalcino, famous for its Brunellos and Montepulciano, known for its Vino Nobile wines. Between the two you'll find Pienza, an idyllic Tuscan village synonymous with Pecorino cheese. With all these gastronomic delights you're bound to have a delicious day. If you'd prefer not to do the driving we can arrange for a private driver to take you around and open a few doors in places that are even more authentic.


Activity Level : Light
Duration : 7 hours

Day 6

Day 6 - Your Second Full Day in Castellina in Chianti

San Gimignano

Suggestion to explore on your own

"Medieval Manhattan" is how we like to describe San Gimignano. A Tuscan hilltop town with a difference, there are just 14 towers remaining but they still do enough to help you imagine what it must have looked like in its heyday. The towers were built by wealthy merchant families, keen to expand their palazzos but only able to build skywards, confined as they were by the town's walls. As well as climbing Torre Grossa the other main draw to this UNESCO World Heritage Site is the 15th century Duomo, a church painted with impressive frescoes. We can arrange for a driver to take you there or you could self-drive in a rental car or even by hiring a Vespa for the day.

Day 7

Day 7 - Traveling to Florence by Private Transfer & Train

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 accommodation to transfer you to the capital of the Tuscany region, Florence. The journey will take between 45 and 90 minutes depending on where in Tuscany you choose to stay.

We also offer the following excursions in Castellina in Chianti

Private Cooking Class with Professional Chef in Castellina in Chianti
Light3 hours
Siena Half-day Private Tour from Castellina
Moderate4 hours
Siena and San Gimignano Full-day Private Tour from Castellina
Moderate8 hours
Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Castellina in Chianti
Light7 hours

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 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 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 Santa Maria Novella station where you can store your luggage until later in the day while you take your tour.

The Best of Florence in a Day

Included in your vacation package price.

An experienced private guide will spend most of the day with you, combining guided visits to the Accademia to see Michaelangelo's famous David, the Uffizi Gallery to admire the must-see works of the Renaissance and a walking tour of the historical center. After the Accademia visit in the morning you'll have a lunch break , then continue the walking tour to the Uffizi visit, where your tour ends.


Activity Level : Moderate
Duration : 6 hours

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. As your accommodation may be within easy walking distance of the station we haven't included a train station transfer. If needed your hotel reception can easily book a taxi for you a reasonable rate.

You can upgrade your transfer

Private Transfer to Venice

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 your hotel in the city.

Day 8

Day 8 - Your First Full Day in Venice

Introducing Venice: A Private Tour

Included in your vacation package price.

Venice is a magical city, and today you’ll discover the best it has to offer, with a private three-hour tour with your own personal guide. You’ll get a feel for the layout of the city and appreciate some of its legendary landmarks. After being picked up at your accommodation, you’ll head toward the elegant Piazza San Marco, which is enclosed by buildings from the ancient republic. The shining gold of the Byzantine St. Mark church is sure to impress you. Later you’ll wind your way through the Castello district, including the large campo Santa Maria Formosa. Before reaching the famous Rialto bridge you’ll stop by the square of San Giovanni e Paolo and the Marco Polo House. From the top of the bridge you’ll be able to take in the wonders of the Grand Canal. At this point you’ll be right in the market, which is a lovely place to enjoy a glass of wine along with local recipes. Here you’ll conclude your tour in true Italian style.


Activity Level : Light
Duration : 3 hours

Day 9

Day 9 - Your Second Full Day in Venice

Cicchetti and Wine Group Tour of Venice

Included in your vacation package price.

Take your taste buds on a delicious adventure with this tour of Venice's Bacari wine bars and their famous cicchetti dishes. These small tapas-style dishes are ideal for teaming with Italian wine, so tour the city's famous bars and try everything from fried olives to wedges of cheesy polenta. With the chance to learn about the history along the way, this is one Venice tour no food lover can miss. This three-hour tour is a pure delight for all your senses. You'll love it!


Activity Level : Easy
Duration : 2.5 hours

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.

We also offer the following excursions in Venice

Dolomites and Cortina d'Ampezzo Private Car Tour
Moderate9 hours
Grand Canal Boat Group Tour
Easy1 hour
Group Walking Tour of Venice
Light1.5 hour
Medieval Towns and Prosecco Tasting Private Tour
Moderate9 hours

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

3 Nights Accommodation
Breakfast (hotels only)
Rome Fiumicino Airport Transfer
Rome Fiumicino Airport Transfer
Rome - Tuscany Private Transfer with a stop in Orvieto

Castellina in Chianti

3 Nights Accommodation
Breakfast (hotels only)
Tuscany - Florence Private Transfer

Florence

Florence in a Day Private Tour
Florence - Venice Standard Class Train Tickets

Venice

3 Nights Accommodation
Breakfast (hotels only)
Venice Water Taxi Santa Lucia Train Station Transfer
First Time in Venice Private Tour
Cicchetti and Wine Group Tour of Venice
Venice Water Taxi Marco Polo Airport Transfer
The package excludes:

  • 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.
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 Europe-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
Our local staff are at your service throughout your journey via the local prepaid cellphone which we provide.
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.

Glowing Reviews from Our Guests

4.9 / 5

Average of our Guest's Ratings of vacation packages including these destinations

Megan & Jason

Missouri

JayWay Travel turned our dream honeymoon into reality. From help with the accommodations, transfers between cities, daily excursions and so much more, we had the best time. We can’t wait to go on another JayWay vacation.

JayWay Travel turned our dream honeymoon into reality. From help with the accommodations, transfers between cities, daily excursions and so much more, we had the best time. We can’t wait to go on another JayWay vacation.

Year : 2019
Visited : Italy, Croatia
Itinerary : Castellina in Chianti, Rome, Dubrovnik, Hvar, Split
Rating :
4.8 / 5
Year : 2019
Visited : Italy, Croatia
Itinerary : Castellina in Chianti, Rome, Dubrovnik, Hvar, Split
Rating :
4.8 / 5

Mike & Kirsten

Nebraska

JayWay Travel is a company that will take most of the hassles of planning an international trip. From budgeting, preplanning ideas and execution. JayWay Travel help build the trip that you want instead of following someone else's itinerary.

JayWay Travel is a company that will take most of the hassles of planning an international trip. From budgeting, preplanning ideas and execution. JayWay Travel help build the trip that you want instead of following someone else's itinerary.

Year : 2019
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :
5 / 5
Year : 2019
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :
5 / 5

James & Jan

Texas

JayWay Travel plans your trip down to the smallest detail according to your wishes. Big time travel without the big group.

JayWay Travel plans your trip down to the smallest detail according to your wishes. Big time travel without the big group.

Year : 2019
Visited : Italy, Slovenia, Croatia
Itinerary : Rome, Castellina in Chianti, Florence, Venice, Ljubljana, Rovinj, Zadar, Split, Korcula, Dubrovnik, Rome
Rating :
5 / 5
Year : 2019
Visited : Italy, Slovenia, Croatia
Itinerary : Rome, Castellina in Chianti, Florence, Venice, Ljubljana, Rovinj, Zadar, Split, Korcula, Dubrovnik, Rome
Rating :
5 / 5

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