10 Best Italy Multiday Tours in September 2026

Sardinian Splendours: A 7-Day Small Group Tour - September 2026

Trip customizable

Best price guaranteed

Discover the heart and soul of Sardinia on this 7-day small group journey, from historic Cagliari to the luxurious Costa Smeralda—featuring vibrant cities, traditional shepherds’ feasts, ancient Nuragic sites, and breathtaking coastal views. Along the way, explore hilltop villages, immerse yourself in Sardinian culture, and savor the island’s rich culinary heritage with local food and wine experiences. With handpicked accommodations, seamless transportation, and expert local guides, this tour offers an unforgettable blend of authenticity, comfort, and discovery

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Cagliari, Olbia, Alghero

Duration7 days

From

USD 2,420

View Tour

Super Sales

Premium Walking & Hiking on Italy's Amalfi Coast - September 2026

No booking fees

Best price guaranteed

Lace up your hiking boots and set your sights towards the spectacular Mediterranean horizon. This seven-day Premium walking and hiking trip on the Amalfi Coast features the best of the short hikes in the area, and is a nature-lover’s dream! Walk the crater rim of the Mount Vesuvius volcano, say Buongiorno to local farmers along the Pathway of the Gods, take in sweeping panoramic views from the Path of the Lemons, and catch a ferry to the glamorous island of Capri. Then, visit Pompeii to explore the preserved ruins and learn about the history of the area. Spend two nights in in a clifftop hotel, soak up sunsets, eat your weight in delicious Italian food (carbs, anyone?) and get active in one of the most beautiful parts of Italy, if not the world.

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Naples, Capri, Sentiero Degli De

Naples, Capri, Sentiero Degli Dei, Amalfi

Duration7 days

From

USD 5,460

USD 5,296

Saving

USD 164

View Tour

Upgraded - Walking Italy: Rome & Umbria - September 2026

(2 reviews )

No booking fees

Best price guaranteed

Discover the historical wonders of Rome and the picturesque landscapes of Umbria on this week-long walking holiday. Explore charming hill towns, stunning basilicas, Orvieto's cathedral and caves, and Rome's ancient landmarks. Montefalco and Assisi - Leisurely and moderate grade walks to charming hill towns with breath-taking Umbrian views Orvieto - Enchanting town with a magnificent cathedral, underground caves, and wine-tasting Rome - Ancient landmarks like the Colosseum and Roman Forum, plus delicious Italian cuisine Upgraded range - Immerse yourself in Umbria's beautiful countryside with our hand-picked Premium accommodations

Walking toursCity sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Rome, Colosseum, Umbria, Montefa

Rome, Colosseum, Umbria, Montefalco, Assisi, Spoleto, Orvieto

Duration8 days

From

USD 4,010

View Tour

A Taste of Sicily - Palermo to Syracuse - September 2026

4.9

(9 reviews )

No booking fees

Best price guaranteed

Wonderful week on Sicily. The overnight stay on the farm was definitely the highlight and the tour provided a great opportunity to explore the island. Our guide Fabio was great

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Palermo, Monreale, Agrigento, Mo

Palermo, Monreale, Agrigento, Modica, Syracuse, Ortygia, Catania

Duration8 days

From

USD 3,050

View Tour

Amalfi Coast Walking - Hotel Risorgimento - September 2026

4.7

(48 reviews )

No booking fees

Best price guaranteed

Our guide Matteo made the holiday for us. His knowledge, humour and care of the group was exceptional, making sure every one of us had a memorable holiday. Thoroughly enjoyed the itinerary with a good balance between harder & easier days. Hotel staff were very attentive. Lovely friendly group too. Thank you all.

City sightseeingWalkingBeach

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Naples, San Lazzaro, Capri

Duration8 days

From

USD 2,070

View Tour

A Taste of Tuscany - Hilltop Towns and Vineyards - September 2026

4.9

(9 reviews )

No booking fees

Best price guaranteed

Trip was excellent. Tour Guide, Gus, was fantastic, very knowledgeable, great communicator, and made sure all of our needs were met. Food and wine tour could not have been better. Never really liked many wines but the tastings proved me wrong. The agricultural farms were great and the food fresh and abundant. Villages were quaint. Castle was very interesting - 34 generations living in it and continuously running a vineyard and producing wine since 1141 is unbelievable! Looking into another food tour in another country. Gave accommodations less rating because hotels were in old buildings and they made due with space available: 1) First 2 nights in Hotel Bologna, the room was very, very small and had 2 twin beds aligned in tandem against one wall - would not have fit any other way, 2) Hotel Le Cisterna, last 3 nights, walls were so thin we could hear every word people next door said.

Wine tasting toursFood tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Pisa, Pienza, Siena, Chianti, Vo

Pisa, Pienza, Siena, Chianti, Volterra, San Gimignano

Duration8 days

From

USD 3,040

View Tour

Venice to Rome by Rail + Sorrento and the Amalfi Coast - September 2026

(1 review )

No booking fees

Best price guaranteed

Traverse Italy by train, taking in the sights and delights of the country's most iconic cities. Explore the canals of Venice by boat and on foot, wander the food markets of Bologna and marvel at the sumptuous architecture of Florence. Immerse yourself in the vibrant street life and famous sights of charismatic Rome before heading to the sun-drenched region of Campania to explore the colourful Amalfi Coast, legendary ruins of Pompeii and mighty Mount Vesuvius towering over the Bay of Naples. Rome - Spend two days in the Italian capital with time to explore the ancient Colosseum and Roman Forum. Capri and Sorrento Peninsula - Witness la dolce vita in cliff-top Sorrento, with an optional visit to Capri. Amalfi Coast - Walk the Path of the Lemons, soaking in the enchanting coastal views along the way.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Venice, Sorrento, Maiori, Amalfi

Venice, Sorrento, Maiori, Amalfi, Bologna, Pisa, Rome, Naples

Duration14 days

From

USD 5,260

View Tour

Venice to Rome by Rail - September 2026

(1 review )

No booking fees

Best price guaranteed

My 1st time in Europe! Our tour leader Paris Bermuda was so organized and genuinely very pleasant and sweet. The stops along the way were fascinating, picturesque and so much fun! Wonderful history and stunning buildings! Recommended highly!

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Rome, Venice, Bologna, Florence

Rome, Venice, Bologna, Florence, Pisa

Duration7 days

From

USD 2,970

View Tour

Rome, Sorrento and the Amalfi Coast - September 2026

4.3

(15 reviews )

No booking fees

Best price guaranteed

Accommodations were always very nice and the itinerary was amazing. Our Explore Leader, Manny, was the Best! She was so informative, set up special group meals where we could attend if we wanted to. She had amazing knowledge of everywhere we went and had such a great sense of humor. Our group was small and we all got along so well and much of this is attributed to Manny. Thank You! I look forward to traveling with your company again.

City sightseeingBeach

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Rome, Sorrento, Naples, Maiori

Rome, Sorrento, Naples, Maiori, Amalfi

Duration8 days

From

USD 2,970

View Tour

Super Sales

Simply Italy Reunion 35 to 45 - September 2026

No booking fees

Best price guaranteed

Welcome to 15 days of pure Italian travel immersion with your squad of awesome 35-45 year old travellers. Covering Rome, Florence, Milan, Venice and beyond, this one brings you the blissful best of this soul-stirring country. Explore Rome's historical highlights, travel through the streets of Michelangelo's Florence, indulge in some authentic pasta on the Amalfi Coast. Stop by to see the stooping slopes of Sorrento in the breezy winter or the picture perfect Positano for your summery soul. And that's just an aperitivo. Beauty, romance and all the pasta you can fit in; the good life just got even better. That's amore!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Naples, Amalfi Coast, Flor

Rome, Naples, Amalfi Coast, Florence, Cinque Terre, Milan, Venice

Duration15 days

From

USD 3,035

USD 2,944

Saving

USD 91

View Tour

Super Sales

Journeys: Northern Italy, Venice to Florence - September 2026

(4 reviews )

No booking fees

Best price guaranteed

Amazing. Tour guide made the trip worth while!

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Venice, Cinque Terre

Duration7 days

From

USD 2,999

USD 2,909

Saving

USD 90

View Tour

A Taste of Italy: 8 Days - Classic - September 2026

Trip customizable

Best price guaranteed

Like a creamy gelato or hot espresso, one taste of Italy can linger for a lifetime. Travelling from the Eternal City of Rome and up through the hazy hills of Tuscany, you’ll spend eight days sampling the best of Assisi, Siena, Florence, Bologna, Venice, and Montepulciano. Catch the spirit of La Vita Bella as you explore elegant Florentine piazzas, rummage through handcrafted artisanal treasures, sip world-class wines, and float down intimate Venetian canals

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice

Duration8 days

From

USD 1,524

View Tour

27% OFF TODAY

Super Sales

European Escapade - September 2026

4.9

(27 reviews )

No booking fees

Best price guaranteed

Loved the whole experience- visited all the best countries in Europe, tasted wines, spirits and other European alcohol In cheapest prices. It’s not suitable for asians with dark skin and if you’re over 34 yrs old unless you have a thick skin to not give any reaction to the comments some people make as a joke- only because they are white and still young. Not sure what they are so proud about in those moments. Other than that I enjoyed my time with rest of them. The price was on discount- I had to add on some extra adventures which worth it. Honestly 24 days is finished so quickly. Recommend to all the people who like explore Europe more in less time in cheaper price. Great work contiki, I am on my second one now- in Thailand, this group of approx 30 people is much better than European escapades (just my personal experience).

City sightseeing

Tour Type

Group Tour

Accommodation

Hostel, Hotel, Resort, Guest House

Age Range

18-35 yrs

Operated in

english

Destinations

London, Paris, Lucerne, Lyon, Ba

London, Paris, Lucerne, Lyon, Barcelona, French Riviera, Florence, Rome, Venice, Vienna, Munich, Prague, Berlin, Amsterdam, Beaujolais

27% OFF TODAY

Duration24 days

From

USD 4,232

USD 3,079

Saving

USD 1,153

View Tour

Super Sales

Hike the Tour du Mont Blanc - September 2026

No booking fees

Best price guaranteed

Uncover the Alps in all their glory as you spend eight days hiking the iconic Tour du Mont Blanc. Following a circuit route from Chamonix in France, come face to face with dizzying peaks, glittering lakes and rolling pastures, passing through Switzerland and Italy on the way. Each day ends in charming accommodation, and your luggage will be transported for you to lighten the load. With a highly qualified International Mountain Leader as your guide who will not only ensure your safety, but also show you what makes this part of the world so special, you can focus on the gorgeous natural scenery!

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Lodge

Age Range

15-99 yrs

Operated in

english

Destinations

Chamonix, Argentiere, Champex, C

Chamonix, Argentiere, Champex, Courmayeur, Les Chapieux, Les Contamines-Montjoie

Duration8 days

From

USD 4,485

USD 4,350

Saving

USD 135

View Tour

Combine Italy in September with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Italy

View Tours

Alternatively, explore tours that are exclusively just Italy and Spain, Germany and Italy or France and Italy.

All Italy Tours in September 2026

Page 17 of 306 Trips in Italy during September 2026 with 6,444 Reviews

See Italy tours by duration

Sardinian Splendours: A 7-Day Small Group Tour - September 2026

Premium Walking & Hiking on Italy's Amalfi Coast - September 2026

Upgraded - Walking Italy: Rome & Umbria - September 2026

A Taste of Sicily - Palermo to Syracuse - September 2026

Amalfi Coast Walking - Hotel Risorgimento - September 2026

A Taste of Tuscany - Hilltop Towns and Vineyards - September 2026

Venice to Rome by Rail + Sorrento and the Amalfi Coast - September 2026

Venice to Rome by Rail - September 2026

Rome, Sorrento and the Amalfi Coast - September 2026

Simply Italy Reunion 35 to 45 - September 2026

Journeys: Northern Italy, Venice to Florence - September 2026

A Taste of Italy: 8 Days - Classic - September 2026

European Escapade - September 2026

Hike the Tour du Mont Blanc - September 2026

Page 17 of 306 Trips in Italy during September 2026 with 6,444 Reviews

Combine Italy in September with Nearby Countries for an Unforgettable Trip

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Italy Tours in September 2026

Page 17 of 306 Trips in Italy during September 2026 with 6,444 Reviews

See Italy tours by duration

Page 17 of 306 Trips in Italy during September 2026 with 6,444 Reviews