When it comes to a destination as diverse as Italy, it takes more than one trip to get a real taste of the country's multiple faces. Yet, this two-week itinerary covers a lot of ground. Starting in Rome, this trip introduces you to the charms of the Eternal City before you surrender to the beauty of the Amalfi Coast in Sorrento. Your 14-day trip ends in Eastern Sicily where you'll take your time exploring some of the most spectacular and authentic towns in Southern Italy: Taormina, Ragusa, and Siracusa.
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, a valuable source of 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 with data 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 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.
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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
Sorrento
Taormina
Ragusa
Siracusa
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.

Welcome to Rome - Group City Stroll with Gelato Tasting
Join an intimate Rome walking tour designed to acquaint you with the Eternal City at the outset of your journey. Explore the foremost attractions while savoring a delightful gelato tasting experience. Wander through the Pantheon, Trevi Fountain, Spanish Steps, Piazza Navona, and encounter remnants of Ancient Roman history along this leisurely excursion, limited to just 15 fellow travelers.
Day 2
Day 2 - Your First Full Day in Rome

Premium Colosseum, Roman Forum and Palatine Hill Group Tour
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.
First Time in Rome
There are many aspects to Rome's history and it's easy to be overwhelmed by this most spectacular of cities. If it's your first time in Rome you're probably wondering where to start. Our recommendation is to take a bike tour, which enables you to cover more ground and get a sense of the city's geography. Sites like the Colosseum, Roman Forum, and the Vatican all deserve a little longer time and we'll add suggestions for visiting those into your subsequent days in the Eternal City. If biking around the city doesn't appeal, we can offer the same tour but using a golf cart as your means of conveyance.

E-bike Along the Appian Way Private Tour
Uniquely discover Rome with this bike tour along the ancient Appian Way on a comfortable electric bike. Pass through Porta Appia with your English-speaking guide and explore landmarks like the Caracalla Baths, ancient tombs, and important churches. Ride past the Catacombs and the Circus of Maxentius while learning fascinating stories of Roman history. This e-bike adventure combines ease, history, and priceless relics for an unforgettable experience.

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

Vatican Early Morning Small Group Tour
Your semi-private early morning Vatican tour begins near the entrance of the Vatican Museums, where you will meet your expert guide. Explore the Pinecone Courtyard, Octagonal Courtyard, and galleries filled with masterpieces, including the Laocoön, Apollo Belvedere, and the Belvedere Torso. Visit the Sistine Chapel, where you can admire Michelangelo’s breathtaking ceiling frescoes and “The Last Judgement” before the crowds arrive. The tour continues through the Raphael Rooms and St. Peter’s Basilica, where you will see Michelangelo’s Pietà, Bernini’s Baldacchino, and the grandeur of Piazza San Pietro.
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 4
Day 4 - Traveling to Sorrento by Train
Today you're off to the beautiful Amalfi Coast. The fastest and most economical way to get there is to take a 1-hour train from Rome to Naples and then have our driver pick you up from the train station to take you directly to your accommodations in Sorrento. We've included standard class tickets in your package but an upgrade to a higher class is possible for an extra fee. The whole journey should take approximately 2 hours.
You can upgrade your transfer

Sorrento by Private Transfer with a Stop in Pompeii (Guided Tour and Entrances Included)
Upgrade for an additional cost
3 Nights in Sorrento
3 Nights in Sorrento


3 Nights in Sorrento
The genteel resort town of Sorrento on the southern end of the Bay of Naples is clearly designed for comfort. Complete with a solid portfolio of three to five star hotels, plenty of restaurants and gelaterias it's a typical slice of the Italian riviera. It makes for an easily accessible and affordable base for boat trips to Capri, a visit to Naples, Pompeii and Vesuvius or a jaunt to the other side of the Sorrentine peninsula to the Amalfi Coast. In Sorrento itself you'll enjoy all the advantages of a small town with a sizeable year-round population and a cosy Centro Storico packed with bars, antique shops, churches and grand old palazzos.
The genteel resort town of Sorrento on the southern end of the Bay of Naples is clearly designed for comfort. Complete with a solid portfolio of three to five star hotels, plenty of restaurants and gelaterias it's a typical slice of the Italian riviera. It makes for an easily accessible and affordable base for boat trips to Capri, a visit to Naples, Pompeii and Vesuvius or a jaunt to the other side of the Sorrentine peninsula to the Amalfi Coast. In Sorrento itself you'll enjoy all the advantages of a small town with a sizeable year-round population and a cosy Centro Storico packed with bars, antique shops, churches and grand old palazzos.
Day 4
Day 4 - Arrival in Sorrento
Our driver will take you to your accommodation in Sorrento.
Indulge alla Sorrentino
Even though limoncello is the most famous product in this area, there are many other foods and specialties to try in Sorrento and the Amalfi Coast. Some of the most famous are Provolone del Monaco di Sorrento, a sort of semi-hard cow's milk cheese that has a smooth texture and mild smoky flavor, which goes great with local wine. The tomatoes here are also very special. There are many different varieties, and each is rich in flavor. They all taste excellent when they are sliced thick and topped with extra virgin olive oil, basil, and a dash of salt for a perfect bruschetta. Of course, the list wouldn't be complete without mozzarella! There are many places to try this famous cheese, but our favorite is the Caseificio Apreda Francesco, a traditional producer with many delicious varieties.

Day 5
Day 5 - Your First Full Day in Sorrento

Group Boat Excursion to the Amalfi Coast
Today you'll be exploring the wonders of the Amalfi coast by boat. You'll meet your experienced skipper at the harbor and set out for this full-day tour. Along the way you'll have a chance to see some of the natural wonders of the area as well as interesting historical landmarks. There's simply no better way to get to know the fascinating geography and culture of this region of Italy. Be sure to bring your camera!
Day 6
Day 6 - Your Second Full Day in Sorrento
Bagni Salvatore
Enjoy a dip in the sea and soak up the sun at this unique swimming structure in Sorrento. Three ample tiers have been turned into a relaxing haven where you can rent beach chairs and umbrellas and spend the whole day enjoying the warm sun and swimming in the crystal-clear sea. There is a series of sunbathing platforms on the stone piers, with direct access into the sea via ladders, which makes the area all the more unique with its views of Roman ruins. The historic setting makes for a picturesque place to spend an afternoon with everything you need, including a bar and restaurant for refreshments and meals.


Group Boat Excursion to Capri
Experience the beauty of Capri on a full-day excursion starting from the Sorrento port. Sail along the picturesque Sorrento coastline and marvel at iconic landmarks like the Green Cave, the White Cave, and Faraglioni Rocks. Enjoy stops for refreshing swims in crystal-clear waters and explore Capri and Anacapri during four hours of free time, discovering charming spots like Piazza Umberto I. Conclude your unforgettable journey with a return to the Sorrento port, having savored the essence of "la bella vita".
Day 7
Day 7 - Traveling to Taormina by Airplane

3 Nights in Taormina
3 Nights in Taormina



3 Nights in Taormina
Taormina is the most famous destination in Sicily, hosting actors and actresses in an atmosphere of glamor, luxury, and seaside relaxation. We recommend visiting the fascinating Greek theater, nestled in a splendid location with spectacular views of scenic beaches and the snow-capped volcanic Mt. Etna. Then take time for a walk among the picturesque medieval streets and go shopping for local handicrafts, which include coral, lace, ceramics, and sweets.
Taormina is the most famous destination in Sicily, hosting actors and actresses in an atmosphere of glamor, luxury, and seaside relaxation. We recommend visiting the fascinating Greek theater, nestled in a splendid location with spectacular views of scenic beaches and the snow-capped volcanic Mt. Etna. Then take time for a walk among the picturesque medieval streets and go shopping for local handicrafts, which include coral, lace, ceramics, and sweets.
Day 7
Day 7 - Arrival in Taormina
Upon arrival at Catania Fontanarossa Airport, your driver will be waiting for you in the arrivals hall to take you directly to Taormina, a 40 minute drive.

Taormina at Sunset Small Group Walking Tour
Admire Taormina in a whole new light with a small group sunset walking tour. You'll experience the unique relaxed atmosphere of the most famous Sicilian resort on this 2.5-hour walking tour, strolling down its magic medieval streets lit with romantic lights. Enjoy the charming scents of citrus and fresh seafood in the air, beautiful sounds of music played on the vivid streets, hear from your guide about the history and culture of Taormina and Sicily itself, and see the important sights. You will end your sunset tour on the terrace of one of the best restaurants in the very heart of Taormina with a distinctive view of smoking Etna and illuminated Ionian coastline. You will be offered a glass of Aperol Spritz or wine of your choice, accompanied by light appetizers.
Day 8
Day 8 - Your First Full Day in Taormina

Etna Countryside Food and Wine Small Group Tour
On this full-day tour, you will journey through Sicilian villages, learning about culture and traditions. At a family winery, you will indulge in prosecco and wine tastings paired with local delicacies. Then, you will relax at a historic farmhouse with scenic views, savoring more wine and traditional dishes. At a final stop, you will conclude your experience with a taste of authentic local liquors.
Day 9
Day 9 - Your Second Full Day in Taormina
City Center Highlights and Shopping
Being such a small town, Taormina offers the perfect opportunity to enjoy a nice afternoon of walking and shopping. The whole center is a pedestrian area, which will allow you to walk around and explore the city on your own easily. Corso Umberto is the main walking street that crosses the whole center of Taormina. Here you will find many luxury boutiques, clothes shops, and jewelers (which gave the town the nickname "the Sicilian Saint Tropez"), as well as grocery stores, restaurants, and some cafes and bars where you can sit and relax, have a cup of coffee or, in the late afternoon, a nice aperitivo overlooking the sea from above.

Day 10
Day 10 - Traveling to Ragusa by Private Transfer
Today you'll be saying "a dopo" to Taormina and leaving the coast behind, to explore inland Sicily. A driver will pick you up from your accommodation and drive you for two and a half hours, first between Mt Etna and the sea as you go along the coast, and then into the hills and valleys that lead to Ragusa. If you would like to make more of a day of it, your local JayWay contact can arrange for a stop along the way, for an extra fee. If you're into street food, an early start and a stop (maybe even for a guided tour) at the bustling central market of Catania is a must. Should decorative arts be more your thing, then Caltagirone, famed for its hand-painted ceramics, is just a small detour. Upon arriving at Ragusa, your driver will leave you at your accommodations in atmospheric Ragusa Ibla.

2 Nights in Ragusa
2 Nights in Ragusa



2 Nights in Ragusa
There are two Ragusas (three if you count Dubrovnik, once also known by that name). Ragusa Ibla and Ragusa Superiore. Ragusa Ibla is the one you've seen in pictures and maybe the Inspector Montalbano books and TV series. Before the 1693 Sicily earthquake, the town of Ragusa was located on the site of the current Ragusa Superiore. After that was destroyed, a new town was built on the slightly lower neighboring hill, in the late Baroque style fashionable at the time. This is the town known as Ragusa Ibla. It's one of eight towns that make up the "Late Baroque Towns of the Noto Valley" UNESCO World Heritage listing. Fast forward to modern day, when a new town was built on the ruins of the original, and this is Ragusa Superiore, where most locals live. The rabbit warren of narrow streets and alleyways of Ibla is in stark contrast to those of Superiore. Superiore is a great place to avail yourself of all the conveniences of a modern town, as well as some excellent restaurants where you'll be the only foreigner, it doesn't have the same magic that Ragusa Ibla enjoys.
There are two Ragusas (three if you count Dubrovnik, once also known by that name). Ragusa Ibla and Ragusa Superiore. Ragusa Ibla is the one you've seen in pictures and maybe the Inspector Montalbano books and TV series. Before the 1693 Sicily earthquake, the town of Ragusa was located on the site of the current Ragusa Superiore. After that was destroyed, a new town was built on the slightly lower neighboring hill, in the late Baroque style fashionable at the time. This is the town known as Ragusa Ibla. It's one of eight towns that make up the "Late Baroque Towns of the Noto Valley" UNESCO World Heritage listing. Fast forward to modern day, when a new town was built on the ruins of the original, and this is Ragusa Superiore, where most locals live. The rabbit warren of narrow streets and alleyways of Ibla is in stark contrast to those of Superiore. Superiore is a great place to avail yourself of all the conveniences of a modern town, as well as some excellent restaurants where you'll be the only foreigner, it doesn't have the same magic that Ragusa Ibla enjoys.
Day 10
Day 10 - Arrival in Ragusa
Your driver will bring you as close as possible to your accommodation located in the historic center of Ragusa Ibla.
Granita and Walk
You have just arrived in Ragusa and settled in your hotel, and now you have a couple of hours to explore the city on your own. Where to go, where to start? Our suggestion is to walk around the city center a little bit and stop at Caffè Italia in Piazza San Giovanni and refresh with a lovely granita (a semi-frozen dessert made from sugar and water and offered in various flavors). This is the best place to try it in Ragusa, where their go-to flavors are coffee and pistachio. If you add some fresh whipped cream on top, then it's just a dream!

Day 11
Day 11 - Your First Full Day in Ragusa

Ancient, Baroque, and Fascist Architecture Private Tour

Aperitivo on a Boat
Ragusa is a small city but with a lot to offer. If you have visited everything and are looking for a fun activity, we highly suggest taking a boat trip—maybe pair it with an aperitivo or a wine tasting!
Day 12
Day 12 - Traveling to Siracusa by Private Transfer

2 Nights in Siracusa
2 Nights in Siracusa



2 Nights in Siracusa
With a history stretching back 27 centuries, there's a lot to see and do both in and around Siracusa (also known as Syracuse). While the main, relatively modern, town of Siracusa itself isn't so impressive, the tiny island of Ortigia, occupying less than half a square mile, is the real thing. It's still a functioning town in its own right, with over 3,000 inhabitants, but is also UNESCO-listed. This is where you'll spend much of your time and where you'll stay. The Greeks found plenty to like when they set up home in what they first called Neapolis (new city), and by the 5th century BC it rivaled Athens itself in population. Although it is the hometown of Archimedes (who built extraordinary machines to defend the city from Roman besiegers) and the location of several ancient Greek ruins (and some Roman ones too), many come here to admire the Baroque architecture you'll find around the town. Like many places in Sicily, at the crossroads of so many empires and dominions, there are traces to be found of each of the civilizations that passed through Siracusa.
With a history stretching back 27 centuries, there's a lot to see and do both in and around Siracusa (also known as Syracuse). While the main, relatively modern, town of Siracusa itself isn't so impressive, the tiny island of Ortigia, occupying less than half a square mile, is the real thing. It's still a functioning town in its own right, with over 3,000 inhabitants, but is also UNESCO-listed. This is where you'll spend much of your time and where you'll stay. The Greeks found plenty to like when they set up home in what they first called Neapolis (new city), and by the 5th century BC it rivaled Athens itself in population. Although it is the hometown of Archimedes (who built extraordinary machines to defend the city from Roman besiegers) and the location of several ancient Greek ruins (and some Roman ones too), many come here to admire the Baroque architecture you'll find around the town. Like many places in Sicily, at the crossroads of so many empires and dominions, there are traces to be found of each of the civilizations that passed through Siracusa.
Day 12
Day 12 - Arrival in Siracusa
Your driver will bring you as close as possible to your accommodation located in the historic center of Siracusa, on the splendid island of Ortigia.
First Night in Ortigia
As your first night in the city, whether you have already explored the place a little bit, or you have a walking tour scheduled for the next day, the thing you want to start with is the island of Ortigia. It's the real "city center" of Siracusa and it's an all pedestrian area, therefore it's usually quite nice to walk around. The historical center is rich in restaurants, pubs, and bars. We suggest to start with some pizza and, maybe, a beer in the area of Molo Sant'Antonio (basically at the entrance of the island) and then cross Ponte Umberto into Via Cavour and Piazzetta San Rocco to enjoy a nice bar with a view or in the main street and have another beer or a glass of delicious Sicilian wine.

Day 13
Day 13 - Your First Full Day in Siracusa

Ortigia Private Walking Tour
This walking tour with an expert local guide will show you the most fascinating areas in the city and teach you more about the history and culture here. From cathedrals to the best cafes, your guide will show you everything. You'll even learn about the city's most famous son, the inventor Archimedes. Your guide is friendly and knowledgeable and will answer all your questions. You'll be picked up from your accommodation and dropped off there at the end of the tour.

Siracusa Cooking Class Group Tour
You're in for a delicious day with this excursion. You'll discover tasty traditional Sicilian recipes with an expert cook, starting from the exploration of the lively and colorful food market and finishing with a social meal of the goodies you've prepared. The whole experience lasts about 5 hours and will give you a new point of view on Sicilian gastronomy and hospitality.
Day 14
Day 14 - Departure Day
It's time to depart sensational Sicily. Say a fond "arrivederci" to Siracusa as you head north to Catania airport for your departing flight. The jounrey should take a little under an hour.
Glowing Reviews from Our Guests
Average of our Guest's Ratings of tour packages including these destinations

I could not recommend this company enough. Everything was professional and seamless. We really felt like all of our needs were met and everything was thought of.
– Alyssa & Darren, New York
Visited : Italy
Itinerary : Rome, Sorrento, Naples, Taormina, Palermo
Rating :

Highly recommend JayWay for anyone who is looking to have their own adventure but needs help in planning and executing. The flexible and professional approach is what sold us from the beginning. This photo was in a restaurant in Ortigia recommended by our guide Marco. Great meal and so much fun with the staff. Wonderful experience. Great way to celebrate 50 years together!
– Marylee & Frank, Massachusetts
Visited : Italy
Itinerary : Catania, Siracusa, Ragusa, Agrigento, Palermo, Taormina, Catania, Rome
Rating :

Jayway structured our entire 2 week trip to Sicily. it was one of the most wonderful travel experiences we have ever had. All of our expectations were achieved.
– Joe, Sharon, Mark & Lorraine, New York
Visited : Italy
Itinerary : Milan, Palermo, Agrigento, Ragusa, Siracusa, Taormina, Milan
Rating :