
Pizza
Pizza is one of Italy's most famous and beloved foods. It features a thin, crispy crust topped with...
Italy, nestled in southern Europe, is a treasure trove of ancient history, world-renowned art, and natural beauty. From the ruins of Rome to the romantic canals of Venice, each city offers stories that span centuries.
September brings pleasant weather—warm days and cool evenings, ideal for exploring. With a high budget, you can enjoy private vineyard tours in Tuscany, luxe stays on the Amalfi Coast, and Michelin-star dining. Traveling with friends, savor Italy’s vibrant nightlife, chic shopping, and unforgettable landscapes together.
Customized for these preferences:
Travel StyleTravelling with friends
Dates04-18 September 2025
BudgetHigh budget
AccommodationHotel, apartment or house, resort, villa, homestay
Interests and Activities:
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Location
Southern Europe
Currency
Euro (EUR)
Religion
Roman Catholicism
Population
58,958,000
Language
Italian, regional languages
Electricity
230V, 50Hz, Type C/F/L
Time zone
UTCCET (UTC+1)
Country code
+39
Internet access
Widespread, fast, affordable
Climate
Mediterranean, alpine in north
Language:
Italian
hello
goodbye
yes
no
how much
please
thank you
excuse me
Most travelers reach Italy by flying, with major airports in Rome, Milan, and Venice welcoming international flights from around the world. For those already in Europe, high-speed trains like the Frecciarossa and Eurostar provide comfortable, quick journeys from cities such as Paris, Zurich, and Munich. Private chauffeur services and luxury train options can add extra comfort for groups of friends with a higher budget.
You can also arrive by boat via luxury cruises docking in coastal cities like Venice and Naples, or charter a private yacht for a unique entry. September weather is usually pleasant, making all these travel methods reliable, and peak summer crowds have eased, so you’ll enjoy a smoother travel experience. Consider pre-booking VIP airport transfers and private tours for the most seamless and stylish trip.
Italy enjoys a Mediterranean climate, with hot, dry summers, mild and wet winters, and pleasant springs and autumns. Northern regions get colder in winter and can see snow in the Alps, while southern areas remain warmer year-round. Coastal areas are generally milder than inland regions.
From September 4 to September 18, expect comfortable temperatures—usually between 20–28°C (68–82°F)—with cooler evenings and a chance of brief rain showers, especially in the north. Extreme weather is rare, though occasional storms are possible. This time of year is perfect for outdoor adventures, sightseeing, lively nightlife, harvest season gastronomy, arts events, and cultural festivals across the country.
Italy is famous for its regional specialties—think Roman carbonara, Florentine steak, Sicilian arancini, and gelato everywhere. Key local drinks include espresso and aperitivi like Aperol Spritz. For fine dining, try Osteria Francescana (Modena), La Pergola (Rome), or Il Luogo di Aimo e Nadia (Milan). Milan and Florence also offer lively rooftop bars and chic wine cellars.
Tipping isn’t mandatory; service (coperto) is often included, but leaving small change for excellent service is appreciated. Reserve in advance at renowned spots. Dietary needs are increasingly catered for, though gluten-free and vegan options are more common in larger cities. Enjoy long, leisurely meals—food is a celebrated, social experience in Italy.
Pizza
Pizza is one of Italy's most famous and beloved foods. It features a thin, crispy crust topped with...
Lasagna
Lasagna is a classic Italian pasta dish consisting of layers of wide flat pasta, rich tomato sauce, creamy...
Risotto
Risotto is a creamy and comforting Italian rice dish cooked with broth until it reaches a velvety consistency....
Tiramisu
Tiramisu is a luscious and decadent Italian dessert made from layers of coffee-soaked ladyfingers, creamy mascarpone cheese, and...
Ossobuco
Ossobuco is a traditional Milanese dish featuring braised veal shanks cooked with white wine, broth, and aromatic vegetables....
Italy’s best stays for friends on a high budget include five-star hotels like Rome’s Hotel de Russie or Milan’s Mandarin Oriental, both luxurious and centrally located. For a more authentic vibe, choose elegant villas in Tuscany, such as Villa Cora, or modern apartments in Florence’s Santo Spirito neighborhood—both ideal for groups.
Resorts along the Amalfi Coast (Le Sirenuse or Belmond Hotel Caruso) offer unmatched scenery and top amenities, while Lake Como's private villas and Venice’s palatial hotels are also exceptional. Use booking platforms like Booking.com, Plum Guide, or Airbnb Luxe for high-end options. For September 4–18, book early as it’s still high season in many popular Italian destinations.
Begin your Italian adventure by settling into your new surroundings, exploring vibrant city streets, and immersing yourself in local culture with your friends.
Start your Italian adventure by strolling through the charming cobblestone streets of Trastevere in Rome. Enjoy lively piazzas, artisan shops, and street performers—a perfect way to soak up the local culture with friends.
Delight in a curated wine tasting at one of Rome’s famous enotecas. Sample regional varieties and learn about Italian wine traditions with your friends, while savoring delicious local antipasti.
Unwind after your journey with aperitivo on a panoramic rooftop overlooking Rome’s skyline. Enjoy signature Italian cocktails and nibbles as you take in stunning sunset views with your group.
Private Walk Through the Jewish Ghetto in Rome
Discover the beauty, mystery and history of the world’s oldest Jewish Ghetto and find the hidden treasures of Rome that most tourists never see. This tour of the more local side of Rome has you meet your friendly, expert guide in Piazza Venezia at the North side of Trajan's Column before you head into the famous Jewish Ghetto or Jewish Quarter. Discover one of the oldest and still functioning parts of Rome as your guide brings this area to life.
Private Capri Escape: Full-Day Boat Tour from Sorrento
A relaxing day on board, pampered by our attentive staff. Our skipper will let you see the isle of Capri from a unique point of view. An exclusive service for you, your family and friends, to celebrate special events and to make your holiday in Italy unforgettable. most glamorous island of Italy. Book your private boat tour now.
From $1484 USD
Rome’s Festive Sights And Christmas Lights
Ah, we love Christmas time, don’t you? And you get to spend it in Rome with one of our hosts who will take you on a journey through the festive Eternal City! You could stop by the spectacular Nativity scenes at St Peter’s Square and Piazza del Popolo before perusing the stalls of the Christmas market in the Piazza Navona. Feast on classic Christmas treats like pandoro or panettone, soak up the atmosphere and get cozy amongst the Christmas lights and festive garlands draped across a piazza. Within 24 hours after booking you'll receive a short questionnaire about your personality and interests. Based on your responses, you'll be assigned a like-minded host. Your host will communicate with you directly to suggest an itinerary to help you discover what makes the city unique. You will also agree on a meeting time and place. Your itinerary is flexible, so during the experience, you can always change your mind about what you want to do
From $143 USD
World War II History Private Walking Tour of Florence
Enjoy this customized tour that is paced to suit your needs and interests as we explore Florence's contemporary history and discover the people and events that shaped Italy's participation in World War II. See the Ponte Vecchio, the Pitti Palace, and more. Learn interesting details about Italy during World War II. Highlights: - Explore Florence with the WWII History Expert Guide - Walk through the areas that were the most damaged by the war - Learn about Italy’s involvement in World War II - Hear the true story of Benito Mussolini and fascism in Italy - Enjoy a private tour tailored to your pace, needs and interests We will explore Florence with the WWII History Expert Guide, then walk through the areas that were the most damaged by the war. You will learn about Italy’s involvement in World War II and hear the true story of Benito Mussolini and fascism in Italy.
From $195 USD
Private Amalfi Coast Tour in a Apreamare 38ft DIAMOND Boat
A relaxing day on board, pampered by our attentive staff. Our skipper will let you see the isle of Capri from a unique point of view. An exclusive service for you, your family and friends, to celebrate special events and to make your holiday in Italy unforgettable.
From $2670 USD
Sea, Volcano and History: Giardini Naxos, Isolabella, Etna and Taormina
this tour gives you the unique opportunity to enjoy the best Sicily can offer: the amazing sea, beaches, the volcano, the marine reserve of Isolabella and the pearl of the ionia sea that's Taormina
From $227 USD
Naples Orientation Private Walking Tour
Meet your private guide and discover Naples on an orientation walking tour from the cruise terminal or from your hotel in town. We will visit the Old historic Centre and the Royal City. If you like walking, we can also visit the Seaside. The tour will focus on the History, Art, and Urban Structure of Naples, and we will also discover the life of the Neapolitans and the street food. Naples is a fascinating crossroads of people and history. It was founded by the Greeks and then ruled by many different nations – Romans, Byzantine, Germans, Normans, French, Spanish, and Austrians. Each of these nations left an indelible sign of their presence, not only in the monuments of the city but also in its language, customs, traditions, food, way of life. Your private guide will be there to point you out to the main historical information but also to introduce you to some local delicacies and to the spirit of this bustling city. The tour is customizable and private.
From $406 USD
Private Capri Day Tour from Sorrento on a 38ft Motorboat
A relaxing day on board, pampered by our attentive staff. Our skipper will let you see the isle of Capri from a unique point of view. An exclusive service for you, your family and friends, to celebrate special events and to make your holiday in Italy unforgettable.
From $2374 USD
Capri & Positano from Sorrento - Full Day with Classic Gozzo 38ft
A relaxing day on board, pampered by our attentive staff. Our skipper will let you see the isle of Capri from a unique point of view. An exclusive service for you, your family and friends, to celebrate special events and to make your holiday in Italy unforgettable.
From $2670 USD
Tales Of Pirates, Legends and Secret Gardens on Lake Como
A walk that is a long story, full of curiosity and memories of events almost forgotten. We explore the upper part of the western shore of the Lake, a land of partisans, the stage of the epilogue of Mussolini’s life, castles inhabited by freshwater pirates, breathtaking landscapes, ancient legends, and a mysterious and enchanted garden. Places almost ignored even by locals but hiding some pearls of extraordinary beauty.
From $261 USD
Private Amalfi Coast Tour in a ROMAR BERMUDA Boat
A relaxing day on board, pampered by our attentive staff. Our skipper will let you see the Amalfi coast from a unique point of view. An exclusive service for you, your family and friends, to celebrate special events and to make your holiday in Italy unforgettable.
From $1187 USD
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