
Introduction
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.
Personalised guide
Travelling with friends · 4–18 Sep · High budget · Hotel, apartment or house, resort, villa, homestay

Itinerary for Italy · September 2025
Itinerary
Italy · September 2025
Viewing Day 1 · Fri 5 Sep. Numbered pins match today's itinerary stops; purple markers are recommended experiences. Click a pin for details.Pins match today's stops. Purple pins are experiences.
- 1Start 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.
- 2
Wine Tasting at a Historic Enoteca
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. - 3
Aperitivo on a Rooftop Terrace
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.
Recommended experience

Ponza, boat trip on board the Zannone 1954
5.0 (186 reviews)
The tour is totally customizable. Guests can choose the embarkation point (Ponza Island), the departure and return times and, compatibly with the weather conditions, the entire itinerary. On request it is possible to obtain local wines, fresh fruit and champagne served on board.
From €1,200 EUR
per person
Key Facts
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
ciao (chow)goodbye
arrivederci (ah-ree-veh-dehr-chee)yes
sì (see)no
no (noh)how much
quanto costa? (kwan-toh koh-sta)please
per favore (pehr fa-vo-ray)thank you
grazie (grah-tsee-eh)excuse me
mi scusi (mee skoo-zee)
Logistics
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.
Weather
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.
Food & Drink
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....
Accommodation
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.
Attractions

Rome Fiat 500 Vintage tour
Free transportation with Fiat 500 behind photo points. Don't lose the opportunity to live the best moment of your life, enjoy beautiful photos with a classic Fiat 500, a true icon of Italian automotive history, with over 60 years of charm and character. Book your Rome Vintage photo experience with the Fiat 500, enjoy the superb and fascinating locations of city with a roman photographer. We will happily take photos of you and your companions. In the middle of the experience, a special break in a famous "gelateria" for a tasty gelato or if you prefer a breakfast with "cornetto e cappuccino". Book now and get ready for an experience that will leave you with cherished memories for years to come.
From €119 EUR

Games & Treasures Hunts Tour in Rome
Enjoy our 2 hours fun tour in Rome! We will discover the highlights of the city center while playing a family game: your guide will be asking to solve quizes and questions for points and prizes. You and the kids will get entertained and engaged throughout the whole experience.
From €115 EUR

Rome Hotel to Civitavecchia Cruise Ship Port Private Transfer
No need to wait around for your ride since your professional chauffeur will already be waiting for you when you leave your accommodation. Transfer Chauffeurs only speak the local language (Italian) or very basic English. All our vehicles and drivers have the necessary professional license and security clearance to access the cruise port for the best and easiest way to get to and from Civitavecchia. The maximum number of passengers a large van can accommodate is 8. This size of vehicle is the largest permissible for accessing city centers and the cruise port of Civitavecchia. Luggage Capacity: 1-2 Passengers - up to 2 suitcases and 2 small carryons 3-6 Passengers - up to 6 suitcases and 6 small carryons 7-8 Passengers - up to 8 suitcases and 8 small carryons Necessary Information to book your transfer: - Pick up time - Hotel Name and Address in Rome - Ship Name - Embarkation Time **Booking requests that are incomplete cannot be processed.
From €335 EUR

Civitavecchia Cruise Ship to Rome PrivateTransfer
No need for you to walk anywhere because unlike taxis, trains, or buses, we have permission to enter the port area so our clients have the privilege of being picked up right by their ship. All our vehicles and drivers have the necessary professional license and security clearance to access the cruise port. The maximum number of passengers a large van can accommodate is 8. This size of vehicle is the largest permissible for accessing city centers and the cruise port of Civitavecchia. Luggage Capacity: 1-2 Passengers - up to 2 suitcases and 2 small carryons 3-6 Passengers - up to 6 suitcases and 6 small carryons 7-8 Passengers - up to 8 suitcases and 8 small carryons Necessary Information to book your transfer: - Pick Up Time - Ship Name - Hotel Name and Address **Booking requests that are incomplete cannot be processed.
From €335 EUR

Rome: Trevi Fountain Photoshoot, Private & Early Morning
Unlike ordinary photoshoots, we provide a fully personalised session tailored to your style, whether you're celebrating a honeymoon, proposal, engagement, anniversary, or solo adventure. Your professional photographer will guide you through natural poses, ensuring you feel confident & relaxed. Beyond the Trevi, we explore picturesque cobblestone streets, charming piazzas & secret corners, creating a variety of breathtaking shots that tell a unique story. With expert composition & lighting techniques, every moment is captured beautifully. Why Choose This Photoshoot? ✔ Private & Exclusive – No rushing, just relaxed moments ✔ Best Light & Atmosphere – Capture Rome at its quietest & most magical time ✔ Hidden Gems – Discover charming locations beyond the usual tourist spots ✔ Professional Quality – High-end photography with fast editing ✔ Customisation Available – Add locations like the Spanish Steps or Colosseum. Book now & turn your Roman holiday into an unforgettable visual story!
From €55 EUR

Rome at Sunrise Walking Tour: Pantheon Trevi Fountain & Breakfast
Experience the many iconic sites of Rome in the quiet beauty of the morning light and with the least possible amount of crowds. With an expert guide, embark on a journey through the Eternal City for fabulous photos of site such as the Pantheon, Trevi Fountain, Spanish Steps, Piazza Navona and more! You will also experience a delicious Italian breakfast amidst the beautiful backdrop of the Roman streets. Enjoy this wonderful and comprehensive tour of the heart of Rome in the intimate atmosphere of our truly small group of 6 people max. Or, for a truly personalized experience, book your very own Private tour! Both options are available. Please note: Tours booked on the first Sunday of the month or on national holidays will not include Pantheon entry.
From €129 EUR

Professional Lab Pasta Experience
In 4 years of activity in our pasta shop, me and Angelo, we have received many nominations: in the prestigious "Gambero Rosso" guide since 2017 and among the beest 10 pasta factories in Rome. In Italy, the "pastificio" is a place where fresh pasta is made and sold to those who want to cook it at home. We have been inspired by the pasta that our grandmother made in the kitchen when we were child. It was a very special pasta and today we made our dream come true because we re proud to teach, right inside our "EX pastificio", the old Italian method for making pasta to hundreds of people who want to learn how to eat healthy pasta according to the true Italian tradition thus transmitting all the love and passion of our families. Today we dedicate all ourselves to organizing cooking classes of great value to teach how to make fresh artisan pasta in a simple and effective way, thus managing to make all the recipes of the lesson at home.
From €64 EUR

Unique Rome by Night, Photo Tour and Workshop Under the Stars
This is the only photo tour to collect exclusively amazing five-star reviews. That is because my priority is always QUALITY over quantity, providing friendly, expert, and undivided attention to my customers. You will tour Rome with a true professional Photographer during a photo workshop designed to give you the best experience of Rome by Night while capturing its most iconic locations. You'll learn: Light & Exposure: Master long exposures, light balance, and the use of natural and artificial light at night. Camera Settings: guidance of manual mode, ISO control, white balance, aperture, and shutter speed. Composition: Learn to frame compelling shots using leading lines, symmetry, foreground interest, and layering. Coaching: Real-time constructive and friendly feedback and guidance as you shoot. iPhone users are also welcome. Optional Photo Review: Submit your images for detailed critique and tips for improvement. Check our photos and 5-star reviews. You will look no further.
From €180 EUR

The Very Best Tour of Rome
Get the best Rome in limo private tours by locals, from the epic scenes that rocked the Colosseum to the incredible works of Michelangelo and Bernini commissioned by the Popes. Top Tour of Italy, with professional english speaking driving guides and the latest comfortable a/c Mercedes vehicles, is specialized in realizing the tour you want and optimizing your time to make the experience one of a kind.
From €381 EUR

Private Tour - Capitoline Museums
Discover with us the oldest European public collection of antiquities created by Pope Sixtus IV at the end of the XV century! At the beginning or at the end of your holiday, this Museum will help you to make all the pieces of the old roman history fit together and you can't miss the incredible view over the Roman Rorum from the Museum. Some of the masterpieces of the Museum: • Capitoline Square • Main Courtyard (Colossus of Constantine) • Main Staircase (panels of Marcus Aurelius and Hadrian) • Room of Orazi and Curiazi & Room of the Captains (XVI Century frescoes, Bernini's and Algardi's masterpieces) • Ancient Roman bronze sculptures • Room of the She Wolf • Medusa's Head (Bernini) • Marcus Aurelius Exedra • Archaeological Ruins of the ancient Capitoline Temple of Juppiter • Collection of the Roman Horti (monumental gardens of noblemen) • Tabularium (Roman Forum view) • Low courtyard of the New Palace (Marforio Fountain)
From €130 EUR
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