Capri, Tuscany & Rome for Cassidy & Sam's Wedding

12 Days / 11 Nights

Ravello, Capri, Naples, Florence, Castellina in Chianti, Rome

Average Guest Rating 5.0 / 5

as seen in

Begin your Italian adventure with the celebration of Sam & Cassidy's marriage in Ravello before heading off to arguably Italy's most stylish island, Capri. Window shop the designer boutiques and visit the famous blue grotto in between enjoying your hotel's amenities. A change of pace sees you next in Castellina, a picturesque hilltop town in Chianti, Tuscany. Perfect for sampling the region's wines, and visiting the magnificent city of Siena. Your final stop is 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.
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.

Enquire About This Trip

Tell us the month of travel, how many travelers and what star level accommodation you'd like to stay in.
We'll put together a customized trip plan for you based on this itinerary.

Sending ...

Thank you!

Thank you for your interest in taking a trip based on this itinerary. One of our expert travel advisors will be in touch soon to start tailoring it precisely to your preferences.

Ooops!?

Something went wrong at our end, please try again in a moment.

2 Nights 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.

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 Capri by Private Transfer

Today, it's time to travel to the beautiful island of Capri. Our driver will pick you up from your accommodations in Ravello and take you to Sorrento, which is around one hour away. From there, you'll enjoy a forty-five-minute ride by hydrofoil to Capri. There are also ferries from Positano, but from our experience, they are unreliable (less frequent, not guaranteed departures), so we recommend taking the hydrofoil from Sorrento. Please note that two pieces of luggage per person are included in this transfer, and additional luggage costs around $15 per piece.

Capri By Private Transfer with Car to Sorrento & Hydrofoil

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

3 Nights in Capri

3 Nights in Capri

The island of Capri, located in the Bay of Naples, draws millions of visitors a year, many staying for just a few hours to visit the famous grottos. Arriving at the workaday port area is just the first part of your journey. A ride in one of the island's signature convertible taxis will take you closer to your hotel, either in the town of Capri on top of one of the island's two hills or Anacapri on the other. The rest of the journey will involve some walking or using a porter service with a smaller vehicle. The narrow lanes and steps of the town aren't car-friendly! The main reasons to stay on Capri are the views from your hotel room balcony or terrace and to enjoy the atmosphere in the evening after the crowds have left, which is what makes Capri a honeymooners' favorite.

Day 3

Day 3 - Arrival in Capri

Upon your arrival to Capri port, you will be greated by our assistant who will take you to your accommodation by taxi. In case your hotel will be in in the pedestrian only zone, you will be dropped of at Piazza Umberto and the assistant will walk you to the hotel.

Sunset Views for Dinner

Suggestion to explore on your own

Enjoy Capri's town center in the evening when most of the crowds have cleared and the island quiets down. Stroll around the main square, "La Piazzetta" and the tiny streets around it. You could choose to enjoy a drink and a snack at one of the cafés overlooking the Mediterranean Sea, such as Capri Garden Bar or Capri Rooftop, with their magical views at sunset. We also suggest going out to dinner at one of the local restaurants with a view, such as Verginiello, and ending your night with a gelato, just like the locals do.

Day 4

Day 4 - Your First Full Day in Capri

3-Hour Private Boat Excursion Around the Island of Capri

Included in your vacation package price.

On this classic Capri island tour, you'll explore the renowned Blue Grotto, Green Grotto, White Grotto, Faraglioni rocks, Marina Piccola, and Punta Carena Lighthouse. Guided by an experienced skipper, you'll uncover hidden secrets and marvel at the stunning coastline. Dive into the crystal-clear waters for a refreshing swim, promising a day of relaxation and rejuvenation. Get set for an unforgettable adventure discovering the wonders of Capri!

Activity Level : Light

Duration : 3 hours

Enjoy a Drink at the Lively Piazzetta Square

Suggestion to explore on your own

While in Capri, we highly suggest doing as the locals do: enjoy an Italian-style "aperitivo" (aperitif), consisting of your drink of choice and some local snacks, on the island's most famous square known as "La Piazzetta". This bustling location is a hot spot at all hours of the day, but if you want a chance to spot VIPs and celebrities who frequent the square after a day on their yachts, the best time to enjoy an aperitivo at one of the outdoor tables is between 7:00 PM and 9:00 PM. You'll get to live a bit of the high life and perhaps, who knows, get to take a selfie with someone famous! And, even if you don't see any familiar faces, you'll still get a taste of living "la dolce vita" - the sweet life.

Day 5

Day 5 - Your Second Full Day in Capri

The Heart of Capri and Anacapri Private Walking Tour

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

Enjoy this exclusive private tour to experience the highlights of Capri and Anacapri with an experienced local guide and discover the best attractions of the island. You will start from “La Piazzetta”, the iconic center of Capri village, followed by a walk through the medieval neighborhood of Sant'Anna and Via Camerelle, which is famous for its fashion boutiques. You will then continue toward the Gardens of Augustus with its amazing view of the Faraglioni Rocks and the Marina Piccola Bay. It is then time for a panoramic ride towards Anacapri in a private convertible to visit Villa San Michele, which is so full of history. You'll then be taken by a chairlift ride to Mount Solaro and experience the enchanting 360-degree view of the Gulf of Naples and the Amalfi Coast. With this tour, you will see the best of the beautiful island and understand why it is the destination point with the rich and famous, so don't forget to bring your camera!

Activity Level : Light

Duration : 3 Hours

Exploring Capri's Ancient Past

Suggestion to explore on your own

Villa Jovis, the former residence of Emperor Tiberius, is one of Capri’s most significant archaeological sites and a rewarding destination for history enthusiasts. Located on the island’s eastern cliffs, it offers sweeping views of the sea and coastline. Visitors can reach the villa by taking a scenic 45-minute walk from Capri town, following well-marked paths through gardens and quiet lanes. The ruins feature original Roman walls, arches, and cisterns, offering insight into imperial architecture and daily life. Its dramatic setting and historical importance make Villa Jovis a fascinating stop for those exploring Capri’s ancient past.

Day 6

Day 6 - Traveling to Florence by Private Transfer & Train, via Naples

Today you'll leave to Naples. First, our driver will pick you up from your accommodation in Capri and take you to the Capri port from where you'll enjoy a 45 minute ride (approximately) by Hydrofoil. Upon your arrival to the Naples port, a driver will wait for you and will drive you to Naples city. Please note that 2 pieces of luggage per person are included on this transfer, additional luggage costs around $15 per piece.

We also offer the following excursions in Capri

Capri Private Walking Food Tour

Light2 hours

Capri Private Walking Tour

Light3 hours

Natural Arch Private Guided Hiking Tour

Moderate3 hours

Romantic Sunset Private Boat Tour with Aperitif

Light2 hours

Day Stop 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.

Day 6 - Day Stop in Naples

Today you're headed for one of Italy's cultural highlights of Italy, Florence, capital of Tuscany. The journey by high speed train takes around three hours and there are trains throughout the day. We've included standard class tickets in your package but an upgrade to a higher class is possible for an extra fee. We also arrange a driver to take you to the station in plenty of time to get to your train.

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.

Day 6 - Day Stop in Florence

It's time to leave a hustle and bustle of Florence and head for the hills. We will arrange for a driver to pick you up at the train station in Florence and transfer you through the scenic countryside to Castellina in Chianti. The drive will take about 1 hour.

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.

Day 6

Day 6 - 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.

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.

A Night in the Medieval Citadel

Suggestion to explore on your own

Stroll around the Medieval Citadel of Castellina at the end of the day and enjoy the peace all around you. Walking through its alleys and tiny streets will be like jumping into the past. End your evening jaunt of Castellina with a delicious dinner and wine in one of the best restaurants in town. Our favorite is Taverna Squarcialupi, which has a terrace overlooking the surrounding hills.

Day 7

Day 7 - Your First Full Day in Castellina in Chianti

Off-Road Tuscan Wine Private Tour

Included in your vacation package price.

Explore Chianti's backroads and wineries from a vintage Land Rover, one of the best ways to experience the region's picturesque landscapes and architecture. This tour offers an opportunity to taste wine, honey, and olive oil, showcasing the region's renowned red wines and various sub-regions. Engage in conversations with winery owners while savoring a delightful meal, discovering the finest offerings of the area.

Activity Level : Moderate

Duration : 6 hours

Day 8

Day 8 - Your Second Full Day in Castellina in Chianti

Explore the Timeless Beauty of Siena with Ease

Suggested activities for an additional cost, depending on your choice

Siena, a city renowned for its medieval charm, stunning architecture, and rich history, is located about 30 minutes by car from Castellina in Chianti. Known for the magnificent Piazza del Campo, where the famous Palio horse race takes place, and the striking Siena Cathedral, the city is a must-visit for those exploring Tuscany. We can arrange a private transfer and guided tour, offering you the opportunity to fully immerse yourself in Siena’s artistic treasures, vibrant atmosphere, and culinary delights without the hassle of transportation. Discover this enchanting city at your own pace with our expert-guided experience tailored to your preferences.

Siena Half-Day Private Tour from Castellina

Suggested activities for an additional cost, depending on your choice

There's no better way to explore the beautiful city of Siena than with a private local guide. A half-day trip is the perfect amount of time for this excursion. You'll tour the city and see the most impressive buildings and monuments while your guide fills you in on the history and most interesting stories from the city's past. This being Italy, there are plenty of opportunities for delicious local cuisine. Your guide will give you suggestions on the best local places where you can stop on your own to enjoy a typical, Sienese lunch. To conclude this five-hour excursion you'll be driven back to you accommodation.

Activity Level : Moderate

Duration : 4 hours

Siena and San Gimignano Full-day Private Tour from Castellina

Suggested activities for an additional cost, depending on your choice

This full-day tour is simply fantastic. Start with a two-hour guided tour of Siena, then you'll have an hour to enjoy lunch on your own. After the lunch break, you'll continue your journey to San Gimignano, where you will have a two-hour guided tour. The journey to San Gimignano takes about one hour. After your visit in San Gimignano your driver will take you to your accommodation.

Activity Level : Moderate

Duration : 8 hours

Day 9

Day 9 - Traveling to Rome by Private Transfer

It's time to leave the hills of Tuscany and head to the eternal city, Rome. Your driver will pick you up from your accommodation in Tuscany and you will head south, 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 Rome.

Rome by Private Transfer with a stop in Orvieto

We also offer the following excursions in Castellina in Chianti

Private Cooking Class with Professional Chef in Castellina in Chianti

Light3 hours

Private Day Trip to Florence

Light8 hours

Truffle Hunt and Wine Tasting Private Tour

Moderate5 hours

Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Castellina in Chianti

Light7 hours

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.

Day 9

Day 9 - Arrival in Rome

Upon reaching Rome your driver will drop you directly at your accommodation in the center of the city.

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 10

Day 10 - Your First Full Day in Rome

Premium Colosseum, Roman Forum and Palatine Hill Group Tour

Included in your vacation package price.

Explore the captivating tales of lions, gladiators, and emperors on a comprehensive journey through Ancient Rome. Skip the lines and enjoy express entry to the Colosseum, Roman Forum, and Palatine Hill. With an expert guide leading a small group of no more than 15 individuals, immerse yourself in an intimate and enjoyable tour of these three iconic sites, delving into the rich history of Ancient Rome.

Activity Level : Moderate

Duration : 3 hours

Gelato, Espresso and Tiramisu Group Walking Tour

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

This 2.5-hour tour will be a sweet indulgence! Meet your small group at Piazza della Minerva at the statue of the elephant, and get ready to taste the best coffee, gelato, and tiramisu in Rome! Combining Italy’s famous coffee with desserts that have become world-famous, this personalized tour will take you through lovely neighborhoods.

Activity Level : Light

Duration : 2 hours

Day 11

Day 11 - Your Second Full Day in Rome

The Complete Vatican Group Tour with Vatican Museums and Sistine Chapel

Included in your vacation package price.

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

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 12

Day 12 - Departure Day

A driver will pick you up at your Rome accommodation and drop you off at Rome's Fiumicino Airport for your departing flight.

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

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 - Capri Private Transfer with Car and Hydrofoil

Capri

3 Nights Accommodation

Breakfast (hotels only)

Capri Port Private Transfer

3-Hour Private Boat Excursion Around the Island of Capri

Capri - Naples Private Transfer with Car and Hydrofoil

Naples

Naples Port - Train Station Transfer

Naples - Florence Standard Class Train Tickets

Florence

Florence Train Station - Castellina Private Transfer

Castellina in Chianti

3 Nights Accommodation

Breakfast (hotels only)

Off-Road Tuscan Wine Private Tour

Castellina - Rome Private Transfer with a stop in Orvieto

Rome

3 Nights Accommodation

Breakfast (hotels only)

Premium Colosseum, Roman Forum and Palatine Hill Group Tour

The Complete Vatican Group Tour with Vatican Museums and Sistine Chapel

Rome Fiumicino 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.

Glowing Reviews from Our Guests

5.0 / 5

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

Review by Allen, Margaret, Michael, Angela, Denise & Donald

Exactly what we were looking for. Solid advice in the planning process. Amazing support throughout our trip

– Allen, Margaret, Michael, Angela, Denise & Donald, Connecticut

Year : 2025
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Sorrento, Rome
Rating :

5 / 5

Traveling to a foreign country can be nerve-wracking but JayWay made sure we were well taken care of and (mostly) worry-free. They make excellent recommendations for hotels and activities.

– Janice, Mark, Max & Natalie, Ohio

Year : 2025
Visited : Italy
Itinerary : Florence, Rome, Sorrento, Naples
Rating :

5 / 5

JayWay make a bespoke trip the best without exceeding your budget!

– Lynn & Evan, California

Year : 2025
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :

5 / 5