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Italian Classics for Cassidy & Sam's Wedding

11 Days / 10 Nights

Ravello, Naples, Rome, Florence, Venice

as seen in
Travel and LeisureFodorsUSA TodayNew York TimesNational GeographicWashington PostVogue

Begin your Italian adventure with the celebration of Sam & Cassidy's marriage in Ravello before heading off to explore Italy's quintessential cities, the holy trinity of Rome, Florence, and Venice. Rome, fresh from its Jubilee year glow-up is first up. Take your pick of ancient Rome's archeological sites, the Vatican, or the beating heart of the Eternal City itself. From Rome you're headed to Italy's art gallery, Florence. Florence is also the perfect base for exploring the Tuscan countryside. Your final stop is Venice, the floating city. A place so magical you won't believe it until you arrive.

We'll take care of all the accommodations, logistics, arrange the included excursions, and be with you every step if the way. By booking through Cassidy & Sam's page you'll also get a $100 discount off the package price AND a Michelin-starred lunch during your trip.

One of our team members in Italy 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 two countries offer, including things to see and do and other inside tips from restaurant recommendations to tipping advice. Upon request, we will provide you with an eSIM with data that you can use to reach your local JayWay contact (whom you will meet in person) throughout your trip. In all of our destinations, we offer a variety of memorable 3- to 5-star accommodation options, including boutique hotels and charming B&Bs. With our firsthand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambiance.

Route for Ravello, Naples, Rome, Florence, Venice tour

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2 Nights in Ravello

2 Nights in Ravello

3 days in Ravello

2 Nights in Ravello

With its beautiful villas, enchanting gardens and spectacular sea views, Ravello epitomizes everything that makes the Amalfi Coast unique. Throughout the centuries, aristocrats and rich merchants have called Ravello home, leaving their mark and defining the quaint town's identity up to this day with the gorgeous mansions and palaces they built. Unsurprisingly, Ravello has always been a popular destination for artists, writers, and musicians, too, as all this beauty is truly inspiring. It's the same beauty that draws modern-day explorers to this bijou hilltop town on the Amalfi Coast which promises an unforgettable escape in a setting of unfathomable charm.

With its beautiful villas, enchanting gardens and spectacular sea views, Ravello epitomizes everything that makes the Amalfi Coast unique. Throughout the centuries, aristocrats and rich merchants have called Ravello home, leaving their mark and defining the quaint town's identity up to this day with the gorgeous mansions and palaces they built. Unsurprisingly, Ravello has always been a popular destination for artists, writers, and musicians, too, as all this beauty is truly inspiring. It's the same beauty that draws modern-day explorers to this bijou hilltop town on the Amalfi Coast which promises an unforgettable escape in a setting of unfathomable charm.

Day 1

Day 1 - Arrival in Ravello

Upon arrival at Naples Airport, your driver will greet you and take you to your accommodation in Ravello. The journey will take approximately one hour and fifteen minutes, depending on the time of day, weather, and traffic conditions.

Welcome Dinner

Suggestion to explore on your own

This evening, you’ll enjoy a special welcome dinner hosted by Cassidy and Sam — the perfect chance to relax, mingle, and kick off the celebrations together.

Day 2

Day 2 - Your First Full Day in Ravello

Wedding Day

Suggestion to explore on your own

Today, we celebrate Cassidy and Sam’s big day! Enjoy a beautiful ceremony followed by an unforgettable reception filled with food, music, and dancing.

Day 3

Day 3 - Traveling to Rome by Private Transfer & Train, via Naples

Today, it is time to leave Ravello and head to Naples. Our driver will pick you up from your accommodations in Ravello and take you there directly. The drive will take around one hour and fifteen minutes, but there can be more discoveries along the way. For an extra fee, we can arrange for a stop in Pompeii, or our recommendation, the much less crowded but just as interesting Herculaneum, part of the same UNESCO listing as Pompeii. A visit to the surface of the crater of Vesuvius is another option en route.

Naples by Private Transfer
We also offer the following excursions in Ravello

Amalfi Coast Private Day Trip from Ravello
Moderate8 hours
Pompeii Private Day Trip with Cooking Class and Wine Tasting on Mount Vesuvius from Ravello
Moderate8 hours
Pompeii and Mount Vesuvius Private Day Trip from Ravello
Moderate8 hours
Private Boat Day Trip to Amalfi Coast from Ravello
Moderate11 hours, including transportation to and from Ravello

Day Stop in Naples

Day Stop in Naples

1 days in Naples

Day Stop in Naples

To call Naples rough around the edges would be quite the understatement. Yet amidst the chaos and beneath the grime is one of Italy's true gems. It's the third-largest city in the country, home to over three million people. An important port city for all the civilizations that have existed there, Naples is the original melting pot. Founded as Neapolis (literally "new city") by the Greeks in the 7th century B.C., Naples has many layers of history for you to discover.

To call Naples rough around the edges would be quite the understatement. Yet amidst the chaos and beneath the grime is one of Italy's true gems. It's the third-largest city in the country, home to over three million people. An important port city for all the civilizations that have existed there, Naples is the original melting pot. Founded as Neapolis (literally "new city") by the Greeks in the 7th century B.C., Naples has many layers of history for you to discover.

Day 3 - Day Stop in Naples

Day 3 - Day Stop in Naples

Today you're off to magnificent Rome. We've included a standard class tickets on one of the many high-speed train services, but an upgrade to a higher class is possible for an extra fee. The journey time is a little over an hour.

You can upgrade your transfer

Upgrade to Rome by Private Transfer with a stop at Pompeii

Rome by Private Transfer with a stop at Pompeii

Upgrade for an additional cost

3 Nights in Rome

3 Nights in Rome

4 days 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 3

Day 3 - Arrival in Rome

Upon arriving to Roma Termini train station, we'll arrange for our driver to pick you up from the terminal and take you to your centrally located accommodation.

Experience Rome’s Authentic Aperitivo Culture

Suggestion to explore on your own

For an authentic Italian experience, enjoy an "aperitivo"—the Italian equivalent of happy hour. Typically held from 6:30 PM to 8:00 PM, locals gather to sip spritz, prosecco, wine, or beer, accompanied by light snacks before dinner. Offerings range from simple nibbles, such as olives and chips, to more substantial dishes, including small pizzas, sandwiches, and pasta salads. Popular spots for an aperitivo include Freni e Frizioni in Trastevere, Doppiozeroo in Ostiense, and Rec23 in Testaccio, with additional options available along the Tiber River during the summer months.

Experience Rome’s Authentic Aperitivo Culture

Day 4

Day 4 - Your First Full Day in Rome

Rome in A Day Group Tour

Rome in A Day Group Tour

Included in your vacation package price.

Experience the highlights of Rome, encompassing the Vatican Museums, Colosseum, and the iconic landmarks of the historic center (Pantheon, Trevi Fountain, and Piazza Navona). Relish a seamless and enjoyable day as we arrange a private transfer from the historic center to the Vatican, ensuring a hassle-free experience. Benefit from skip-the-line access at every site you explore, including the Vatican and Colosseum. This exclusive group tour in Rome uniquely combines tickets for these two renowned attractions, along with private group transfers between each site.


Activity Level : Moderate
Duration : 7 hours 30 minutes

Day 5

Day 5 - Your Second Full Day in Rome

Guided Group Wine & Food Pairing Dinner Near the Pantheon

Guided Group Wine & Food Pairing Dinner Near the Pantheon

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

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

The Best Views of Rome for Great Selfies

Suggestion to explore on your own

Rome’s seven hills offer scenic walks, hidden historical gems, and the chance to enjoy an aperitivo with locals, all while capturing the perfect selfie. Snap a stunning photo from the viewpoint of Gianicolo Hill or the "Garden of the Oranges," where the city’s monuments provide a breathtaking backdrop. For a romantic touch, wander the sun-dappled paths leading to the Pincio Terrace in Villa Borghese, offering the best view of Saint Peter’s Basilica and Piazza del Popolo. These iconic spots are ideal for photography, ensuring you leave with unforgettable snapshots of Rome’s beauty and charm.

The Best Views of Rome for Great Selfies

Day 6

Day 6 - Traveling to Florence by Train

Today it's time to bid arriverderci to the Eternal City. You're headed to Italy's art palace, Florence. The high speed train service gets you there in just over an hour and a half. We've included standard class tickets in your package but can upgrade these to business class for an extra fee. We will also arrange for a driver to take you to Roma Termini station in plenty of time for your departing train.

You can upgrade your transfer

Upgrade to Florence by Private Transfer with a Stop in Assisi

Florence by Private Transfer with a Stop in Assisi

Upgrade for an additional cost
We also offer the following excursions in Rome

After Hours Santa Maria Maggiore and Terraces Small Group Tour
Light1 hour
Baroque Masterpieces - Borghese Gallery Small Group Tour
Light2 hours
Colosseum and Roman Forum Private Tour
Light3 hours
E-bike Along the Appian Way Private Tour
Moderate3 hours

3 Nights in Florence

3 Nights in Florence

4 days in Florence

3 Nights 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 6

Day 6 - Arrival in Florence

Upon arriving to Florence's main station, Santa Maria Novella, we'll arrange for our driver to pick you up from the train station and take you to your centrally located accommodation.

An Unforgettable First Night in Florence

Suggestion to explore on your own

On your first night in Florence, take a leisurely evening stroll along the Arno River, soaking in the views of the illuminated Ponte Vecchio and the historic center. Enjoy a delicious dinner at a traditional trattoria, where you can savor classic Florentine dishes like bistecca alla fiorentina or ribollita. Afterward, head to Piazza della Signoria to admire the statues and the grandeur of the Palazzo Vecchio. End the evening with a gelato at Gelateria Edoardo, Florence is famed for its high-quality, organic ingredients, while taking in the grandeur of the suggestively lit Duomo.

An Unforgettable First Night in Florence

Day 7

Day 7 - Your First Full Day in Florence

The Tuscan Gems - Siena, San Gimignano and the Tuscan Countryside Group Tour

The Tuscan Gems - Siena, San Gimignano and the Tuscan Countryside Group Tour

Included in your vacation package price.

See the highlights of Siena through the eyes of a local guide, admire the marvelous Tuscan landscape, taste genuine regional food (like assorted cold cuts, cured ham, salami, cheeses and bruschetta) paired with great wines, and finish your day relaxing in the hilltop village of San Gimignano, with its vertiginous medieval tower homes.


Activity Level : Moderate
Duration : 10 hours

Day 8

Day 8 - Your Second Full Day in Florence

Florence City Private Walking Tour

Florence City Private Walking Tour

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

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

Uffizi Gallery Private Tour

Discover Da Vinci’s Florence

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

Leonardo da Vinci, one of history’s greatest minds, was born just outside Florence, and the Da Vinci Museum (https://leonardointeractivemuseum.com/en/) in the city offers a unique opportunity to explore his genius. Located in the heart of Florence, the museum features a hands-on exhibition of intricate wooden machines based on Leonardo's own drawings. For those seeking to immerse themselves in Renaissance art, the Uffizi Gallery houses several of da Vinci’s masterpieces, making it an essential stop on any Florence itinerary. We recommend experiencing these iconic sites with a private tour for a deeper understanding of da Vinci's contributions to art and science.


Activity Level : Light
Duration : 3 hours

Day 9

Day 9 - Traveling to Venice by Train

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

Upgrade to Venice by Private Transfer with a stop in Modena

Venice by Private Transfer with a stop in Modena

Upgrade for an additional cost
We also offer the following excursions in Florence

Best of Florence Group Walking Tour
Light3 hours
Chianti Small Group E-Bike Tour with Lunch and Tastings
Light6 hours
Chianti Wine & Dine - Group Tour with Dinner in a Vineyard
Moderate6 hours 30 minutes
Cinque Terre Group Day Trip
Light12 hours

2 Nights in Venice

2 Nights in Venice

3 days in Venice

2 Nights in Venice

Venice is a legendary city with a charm and atmosphere all its own. The city was constructed on more than 100 islands connected by a series of canals, most of which are lined with gorgeous palaces, beautiful churches, and all sorts of impressive architecture. While the city isn’t huge, it is packed with pedestrian-only streets and quaint, winding alleys that will keep you exploring for days. The city is very popular with tourists year-round, so you certainly won’t be the only travelers walking through the streets with camera in hand. This being Italy, the cuisine in Venice is delicious, and we can especially recommend the Cicchetti of Venice tour. Cicchetti are Venetian tapas, and this tour will introduce you to some of the city’s most iconic eateries and its most delicious recipes. If it’s your first time in Venice, we can organize a tour to show you all the most important sites. And since no trip to the city of canals is complete without a boat ride, we offer a number of ways for you to get a new point of view of the city and its magnificent architecture. It’s easy to while away your time in Venice, discovering new secrets around every corner.

Venice is a legendary city with a charm and atmosphere all its own. The city was constructed on more than 100 islands connected by a series of canals, most of which are lined with gorgeous palaces, beautiful churches, and all sorts of impressive architecture. While the city isn’t huge, it is packed with pedestrian-only streets and quaint, winding alleys that will keep you exploring for days. The city is very popular with tourists year-round, so you certainly won’t be the only travelers walking through the streets with camera in hand. This being Italy, the cuisine in Venice is delicious, and we can especially recommend the Cicchetti of Venice tour. Cicchetti are Venetian tapas, and this tour will introduce you to some of the city’s most iconic eateries and its most delicious recipes. If it’s your first time in Venice, we can organize a tour to show you all the most important sites. And since no trip to the city of canals is complete without a boat ride, we offer a number of ways for you to get a new point of view of the city and its magnificent architecture. It’s easy to while away your time in Venice, discovering new secrets around every corner.

Day 9

Day 9 - Arrival in Venice

Start your Venetian experience off in style by arriving in a private water taxi. We'll arrange a transfer by boat from Santa Lucia train station to the closest possible point to your hotel in Venice. Please note that porter assistance from the water taxi to the hotel is not included but can be arranged at extra charge.

Welcome to Venice!

Suggestion to explore on your own

Make the most of your first night in Venice with an unforgettable introduction to this magical city. Whether you prefer a relaxing start or an active evening, Venice offers something for every mood. Savor an aperitif overlooking the Grand Canal at Erbaria, where charming bars with outdoor seating set the scene, followed by a delightful dinner in one of the Rialto area’s renowned restaurants. For those eager to explore, take a scenic stroll along the Zattere to Punta della Dogana for breathtaking views of San Marco and the Grand Canal, then cross the water by traghetto to complete your enchanting first evening in Venice.

Welcome to Venice!

Day 10

Day 10 - Your First Full Day in Venice

First Time in Venice Private Tour

First Time in Venice Private Tour

Included in your vacation package price.

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

Venice - An Open Art Museum

Suggestion to explore on your own

Venice is often described as an open-air art museum, where every turn reveals a blend of history, architecture, and artistic brilliance. The city’s crown jewel, St. Mark’s Basilica, impresses with its Byzantine mosaics, while the Doge’s Palace showcases Gothic elegance. Beyond these landmarks, visitors will find ornate palazzi lining the Grand Canal, richly decorated churches, and hidden squares adorned with sculptures and frescoes. Even a simple stroll along its winding alleyways or crossing its graceful bridges feels like moving through a vast canvas that has inspired artists for centuries. With world-class museums, galleries, and the beauty of daily life, Venice offers an endless celebration of art in every form.

Venice - An Open Art Museum

Day 11

Day 11 - Departure Day

It's time to bid arrivederci to Venice but you'll get a good last look at the city as your private water taxi captain takes you to the airport for your departing flight. Your private boat will dock at the closest possible point to your hotel.

We also offer the following excursions in Venice

Ancient Crafts & Artisans' Workshops Tour
Light3 hours
Authentic Murano Glass Factory Private Tour
Light2 hours
Create Your Own Carnival Mask Private Experience
Easy3 hours
Doge's Palace Group Tour
Light1 hour 15 minutes

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.

Ravello

2 Nights Accommodation
Breakfast (hotels only)
Naples Airport - Ravello Private Transfer
Ravello - Naples Private Transfer

Naples

Naples - Rome Standard Class Train Tickets

Rome

3 Nights Accommodation
Breakfast (hotels only)
Rome Train Station Transfer
Rome in A Day Group Tour
Rome Train Station Transfer
Rome - Florence Standard Class Train Tickets

Florence

3 Nights Accommodation
Breakfast (hotels only)
Florence Train Station Transfer
The Tuscan Gems - Siena, San Gimignano and the Tuscan Countryside Group Tour
Florence Train Station Transfer
Florence - Venice Standard Class Train Tickets

Venice

2 Nights Accommodation
Breakfast (hotels only)
Venice Private Water Taxi Santa Lucia Train Station Transfer
Assistance at S. Lucia Train Station
First Time in Venice Private Tour
Venice Marco Polo Airport Transfer

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

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.