Top 10 Holidays in Italy to Take in 2026 – Prices from €999pp
From the Italian Lakes to the Amalfi Coast, Cinque Terre to Puglia, I’ve got 10 great holidays in Italy, including city breaks, multi-centre options, and escorted tours.
I’ve been very fortunate to travel to many wonderful places over the years, but my holidays in Italy stand out among the very best. Few countries inspire quite like Italy. From stunning lakes and golden beaches to vibrant cities and charming hilltop towns, Italy has it all. But with all this plus 58 UNESCO World Heritage Sites and world-famous cuisine, how do you decide where to holiday in Italy?
That’s where I come in! I’ve handpicked a selection of Tropical Sky’s luxury Italy holidays that are designed to let you experience La Dolce Vita in style! I love that every option – whether it’s gliding into Venice by water-taxi or enjoying city breaks by first-class rail, comes with transfers included, making multi-centre holidays in Italy completely stress-free.
From single-destination stays that let you explore at your own pace, to fully guided escorted tours with exclusive dining experiences, I’ve got holidays in Italy to suit all travel styles.
These are just a small sample of the many holidays in Italy that Tropical Sky offer. Durations, dates, cities and hotels can be changed, and they can also curate bespoke Italian holidays to suit you. Tropical Sky can be contacted online, by phone, or you can visit their Customer Lounge in Dublin if you prefer to book your dream holiday to Italy in person.
1. Puglia: Flights, 4 Star Hotel & Transfers, 7 Nights from €999pp
With five UNESCO World Heritage Sites, gorgeous beaches and some of Italy’s prettiest towns, Puglia needs be on your bucket list. I took a short break there a few years ago and would love to return to see more.
For this Puglia holiday Tropical Sky have selected the top-rated Hotel Monte Sarago, which is just 10 minutes walk from the whitewashed town of Ostuni – also known as the ‘White City’. This is a super base to explore Puglia’s dramatic towns and villages, and is only 35 minutes drive from Brindisi.
The hotel’s central location means you don’t need to hire a car, however, I strongly suggest you do! The charming town of Alberobello looks straight out of a movie set, while the historic city of Lecce, the picturesque village of Locorotondo, and the stunning seaside town of Polignano a Mare are also must-see destinations in Puglia.
As well Puglia’s highlights, I highly recommend you visit the ancient city of Matera, which is located in neighbouring Basilicata. Matera is one of the most remarkable cities I have been to. It is a UNESCO-World Heritage city that has been inhabited for over 9000 years. Matera is guaranteed to take your breath away – and I’m sure the entire region of Puglia will too.
Read: Three towns you must visit in Puglia
Price of €999 per person includes flights and a seven-night stay in the Hotel Monte Sarago on a bed and breakfast basis. Price is based on May 2026 departure from Dublin but many more dates are available.
2. Rome & Sorrento: Flights, 4 Star Hotels & All Transfers, 7 Nights from €1779pp
Is there a better holiday combination than Rome and Sorrento? I don’t think so! This iconic twin-centre Italian holiday gives you the chance to explore one of the world’s greatest cities, along with the captivating Amalfi Coast, with all transfers seamlessly arranged.
Your trip begins with three nights in the top-rated 4 Star Guardian Hotel in Rome, which is close to Rome’s historic centre and its top attractions. There are ancient wonders at every corner including the Colosseum, Pantheon and Trevi Fountain, and make sure to pre book a tour of the Vatican and the Sistine Chapel. I truly believe Rome is a city that everyone should see at least once in their lifetime.
Read: Top 10 things to do in Rome and restaurant recommendations
You will then be transferred by private car to Termini train station and given first-class tickets to Naples where you will be met for a private transfer to the Art Hotel Gran Paradiso in Sorrento, your home for the next four nights.
The Amalfi Coast is one of Italy’s most captivating destinations, and the lively resort of Sorrento is one of the best places to stay. Marvel at the pastel-painted houses of Positano and the hill top town of Ravello, and take a boat trip to the Isle of Capri.
There are so many beautiful places to explore, and that’s on top of a coastline packed with ancient sites and surrounded by turquoise seas. You may wish to extend your stay in Sorrento, simply talk to the team in Tropical Sky and they will arrange it for you.
Price of €1779 per person includes flights, 1st class train tickets, all transfers, and seven-night hotel stays on a bed and breakfast basis. Price is based on May 2026 departure from Dublin but many more dates are available.
3. Sorrento & Capri: Flights, 4 Star Hotels & All Transfers, 8 Nights from €1939pp
This twin-centre holiday is my idea of heaven! Your holiday begins with five days in Sorrento, the perfect base for exploring the Amalfi Coast. You’ll stay at the 4-star Art Hotel Paradiso, which overlooks the Bay of Naples and offers easy access to Sorrento’s vibrant centre. Then it’s on to Capri, where you’ll experience the island at its most magical, being able to wander its pretty streets when the day-trippers have gone.
You will be staying at the highly rated Hotel Syrene, which is located on the famous Via Camerelle and just five minutes walk from Capri’s iconic Piazetta. Shop till you drop at its designer boutiques, take a boat trip to the Blue Grotto, hike to its famous viewing points or simply spend the day people watching – Capri is the place to just relax and watch the world go by.
Like all of Tropical Sky’s package holidays in Italy, all transfers are arranged for you. At the end of your stay, a return ferry and private transfer will take you back to Naples Airport.
Price of €1939 per person includes flights, ferry tickets, all transfers and eight-night hotel stays on a bed and breakfast basis. Price is based on May 2026 departure from Dublin or Shannon but many more dates are available.
4. Lake Garda & Verona: Flights, 4 Star Hotels & All Transfers, 7 Nights from €1499pp
Italy’s largest lake, Lake Garda, is a long-standing favourite with Irish holidaymakers, offering more than 50 picturesque villages and historic towns to discover. Its location is also ideal for visiting nearby Verona, famed for its grand Roman amphitheatre and Juliet’s legendary balcony.
This wonderful Italy holiday lets you experience both, beginning with a three-night stay in Verona, followed by four nights on the shores of Lake Garda.
In Verona, you’ll spend three nights at the highly rated NH Collection Palazzo Verona, one of the best hotels in Verona, before enjoying private transfers to Lake Garda. There, you can choose between two top-rated properties: the elegant Palazzo del Garda in Desenzano, or the Olivi Hotel & Natural Spa in Sirmione – one of my favourite towns on the lake.
All transfers, including private airport transfers are included for your convenience, but if you prefer to take car hire, or wish to extend your stay in Lake Garda, talk to the team in Tropical Sky and they will arrange it for you.
Price of €1499 per person includes flights, all transfers and seven-night hotel stays on a bed and breakfast basis. Price is based on May 2026 departure from Dublin but many more dates are available.
5. Lake Como & Milan: Flights, 4 Star Hotels & All Transfers from €2429pp
Lake Como has been the destination of choice for celebrities for many years, so why not join them with this seven-night holiday that includes a three-night stay in Milan, followed by four nights in this stunning part of Italy.
The 4 Star Worldhotel Cristoforo Colombo will be your home in Milan which is ideally located to explore Milan’s top attractions and fashion district. Marvel at the iconic Duomo, shop till you drop, and pay a visit to the famous QC Terme Spa, known for its beautiful pools and relaxing atmosphere.
You will then enjoy a private transfer to Lake Como to the top-rated 4 Star Hilton Lake Como. Located on the lake shore and boasting a rooftop pool and spa, this has super onsite amenities and offers easy access to Lake Como’s pretty villages and nearby town.
Price of €2429 per person includes flights, all transfers and seven-night hotel stays on a bed and breakfast basis. Price is based on May 2026 departure from Dublin but many more dates are available.
6. Sicily & Vulcano: Flights, 5 Star Hotels & All Transfers from €2629pp
Channel your inner White Lotus with this luxurious twin-centre escape combining Sicily and the island of Vulcano. Begin with four nights in a beautifully restored 19th-century Sicilian villa, now the elegant 5-star Donna Carmela Resort & Lodges.
Make time to visit the nearby hilltop town of Taormina, where The White Lotus was filmed, it is only 30 minutes away. I stayed in this beautiful town many years ago and loved it. If time allows excursions to Syracuse and Mount Etna are also worthwhile – or book a sailing trip to the crystal clear waters of the Aeolian islands.
From Sicily, enjoy a private transfer to the port before a scenic hydrofoil ride carries you to Vulcano, where you will spend three nights at the 5-star Therasia Resort Sea & Spa. With its breathtaking views, world-class dining, ( there are two Michelin-starred restaurants here ) and stunning sunsets, it’s the perfect finale to your Italian adventure.
Price of €2629 per person includes flights, ferry tickets, all transfers and seven-night hotel stays on a bed and breakfast basis. Price is based on May 2026 departure from Dublin but many more dates are available.
7. Venice, Florence & Rome: Flights, 4 Star Hotels & All Transfers, 9 Nights from €1649pp
This amazing Italy holiday takes you to three of Italy’s most iconic cities – Venice, Florence, and Rome, on one epic trip. Enjoy three nights in top-rated hotels in each city, with private transfers, water taxis, and 1st-class rail tickets all seamlessly arranged for you.
Your adventure begins in Venice, staying right on the Grand Canal. Arrive in style with a water taxi from the airport, then spend your days exploring St. Mark’s Square, gliding along the canals by gondola, and wandering through the city’s maze of narrow streets. Venice is a city like no other, making it the perfect starting point for your Italian holiday.
Read: Top 10 things to do in Venice
From Venice, a water taxi will take you to the station for your 1st-class rail journey to Florence, where you will check into the top rated 4-star Palazzo Lorenzo Hotel Boutique & Spa. Ideally located near Florence’s top attractions, this stylish hotel is the perfect base for discovering the city’s treasures.
Admire the magnificent Duomo, stroll across the famous Ponte Vecchio, and lose yourself in the masterpieces of the Uffizi Gallery – home to one of the world’s greatest art collections.
Finally, continue by 1st-class rail to Rome for your three-night stay at the highly-rated 4-star Guardian Hotel. Close to the historic centre, it’s the ideal base for exploring the Eternal City. With landmarks like the Colosseum, Pantheon, Trevi Fountain, and Vatican City just waiting to be discovered, Rome is the grand finale to this extraordinary train journey through Italy.
Read: Top 10 things to do in Rome and restaurant recommendations
Price of €1649 per person includes flights, 1st class train tickets, all transfers and nine-night hotel stays on a bed and breakfast basis. Price is based on March 2026 departure from Dublin or Cork, but many more dates are available.
8. Florence & Tuscany Coast: Flights, 4 Star Hotels & All Transfers, 7 Nights from €1739pp
Tuscany is one of my favourite regions in Italy. As well as the stunning cities of Florence and Siena and it’s medieval walled towns, scenic drives through Tuscany’s rolling hills are an attraction in itself. This twin-centre holiday combines a three-night stay in the Tuscan capital with a relaxing beach stay.
Florence is Tuscany’s capital city and when walking around it, you get the feeling that it deserves to be! Most people visit Tuscany to see its rolling hills and hilltop towns, but I firmly believe that in order to fully experience Tuscany, you need to see its extraordinary capital.
Florence is the home of the Renaissance and has one of the largest collections of art in the world. From its Uffizi Gallery to the spectacular Duomo, Michelangelo’s David to the iconic Ponte Vecchio, Florence has stunning architecture and is packed with sculptures, paintings and statues.
After three days in this great city you will enjoy a private transfer to the Tuscan coast, where you will stay at another top-rated hotel, the Versilia Lido UNA Esperienze, which boasts its own private beach, and is close to the seaside town of Viareggio.
I suggest extending your stay to explore Tuscany’s stunning countryside and spectacular walled towns – talk to the team in Tropical Sky and they will arrange it for you.
Read: The best places to visit in Tuscany
Price of €1739 per person includes flights, all transfers and seven-night hotel stays on a bed and breakfast basis. Price is based on June 2026 departure from Dublin or Cork but many more dates are available.
Holidays in Italy – Escorted Tours
9. Escorted Tour of Cinque Terre, Milan, Parma & Italian Lakes: Flights, Hotels, Tours & Selected Meals, 7 Nights from €2329
This elegant escorted journey of Northern Italy combines the cities of Milan, Parma and Genoa with the stunning Cinque Terre region and Lake Maggiore. There are exceptional experiences included as well as guided tours with local specialists, and a Tour Director throughout.
This trip begins with a two-night stay in Milan, Italy’s fashion capital, where you’ll explore iconic landmarks like the Duomo, La Scala Opera House, and the Galleria, with time for optional visits to Lake Como.
The next stop is a two-night stay in Parma, a haven for food lovers. You’ll enjoy authentic tastings at a prosciutto factory and a family-run Parmigiano Reggiano caseificio, plus a guided city tour through its Roman and medieval past.
Next, discover the magic of the Cinque Terre, where pastel-coloured villages are built into cliffs above the Ligurian Sea. This is one of Italy’s most beautiful coastlines – I spent some time here recently and it is one of those places that does live up to the picture perfect images you see online. I have no doubt that the scenic boat ride and free time in Monterosso will make the Cinque Terre a highlight of the trip.
The adventure continues in Genoa, with a guided stroll along UNESCO-listed Via Garibaldi before spending your last two nights on the shores of Lake Maggiore at the highly-rated Hotel Simplon Baveno. Here, you will have time to relax or enjoy optional excursions, but not before finishing off this amazing trip by sailing across the lake to the secluded Isola dei Pescatori for a special Be My Guest dinner experience.
With top-rated hotels, tours with local specialists, and superb food and cultural experiences, this tour blends Italy’s glamour, history, and natural beauty into one seamless journey.
Price of €2329 per person includes flights, travel by luxury coach, seven-night hotel stays on a bed and breakfast basis, guided tours and excursions, three evening meals, and professional tour conductor throughout. Price is based on July 2026 departure but many more dates are available.
10. Escorted Tour – Colours of Sicily: Flights, Hotels, Tours & Selected Meals from €2779pp
This incredible journey through Sicily begins in Palermo, a lively city where Arab, Norman, and Italian influences shine through its markets, piazzas, and architecture. After exploring the city and nearby Monreale, you’ll set off to uncover Sicily’s rich history and vibrant towns.
In Marsala, learn about the ancient salt pans and savour the region’s famous wines, before heading to Agrigento’s Valley of the Temples, one of the world’s most remarkable Greek archaeological sites. Continue on to Ragusa and the Baroque beauty of Modica, where chocolate-making traditions reveal a slice of Sicilian heritage.
Next, step back in time in Syracuse, with treasures waiting on the island of Ortigia. From there, the tour takes you to Catania and the ancient hill town of Taormina, complete with the Teatro di Taormina. This gorgeous town is one of my favourite places in Sicily and is the location where the famous White Lotus was filmed.
The trip concludes with free time to soak up Taormina at your own pace, but you can also opt for excursions to Mount Etna and the hilltop village of Savoca, famously featured in The Godfather. A special Be My Guest dinner rounds off the adventure, with authentic Sicilian hospitality and cuisine.
Price of €2779 per person includes flights, travel by luxury coach, eight-night hotel stays on a bed and breakfast basis, guided tours and excursions, four evening meals, and professional tour conductor throughout. Price is based on June 2026 departure but many more dates are available.
I hope these holiday packages in Italy will inspire you to plan a trip to this captivating country soon. This is just a small sample of the many Italy holidays that Tropical Sky offer. They can tailor make the perfect trip to suit your requirements by phone, at their Customer Lounge in Dublin, or you can submit an enquiry online.
While every effort was made to ensure accuracy, prices, attractions and activities are subject to change. This post was sponsored by Tropical Sky.
