10 Best Italy Multiday Tours in September 2026

Southern Italy And Sicily - September 2026

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Southern Italy and Sicily - September 2026

4.4

(108 reviews )

No booking fees

Best price guaranteed

All the options were excellent. The local guides walked at a slow pace giving us time to take pictures. Our guide Alfonso and our driver Tito were great. We would take a tour with them anytime

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Pompeii, Rome, Sorrento, Palermo

Pompeii, Rome, Sorrento, Palermo, Capri, Taormina, Agrigento

15% OFF TODAY

Duration10 days

From

USD 3,575

USD 3,051

Saving

USD 524

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Best of Italy: Tuscany, Cinque Terre & The Amalfi Coast - September 2026

(4 reviews )

No booking fees

Best price guaranteed

Great adventure, great guide in Shallal, we'd love to have her on our next adventure! Can say nothing but good things, except perhaps to schedule during a cooler time of year but that is not anything you can change!. We did notice the group dynamic changed when 4 people ended their first week with our group and 4 new people joined our group for the 2nd week. We were more of a team with the first group we had and that was really nice and a good selling point for small group tours like yours. For our next tour we'll be looking only at small group tours.

Local culture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Naples, Amalfi Coast &

Florence, Naples, Amalfi Coast & Campania, Cinque Terre, Castellina In Chianti, Sorrento

Duration13 days

From

USD 3,749

USD 3,637

Saving

USD 112

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Italy Bellissimo - September 2026

4.7

(228 reviews )

No booking fees

Best price guaranteed

Amazing variety of experiences, excellent tour guide and local specialists. I also loved that Trafalgar supports local artists and family run farms. A highlight for me was the Make Travel Matter experience with the weavers.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Capri, Assisi, Venice, Montecatini Terme

Duration11 days

From

USD 3,305

USD 3,206

Saving

USD 99

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Jewels of Italy and Milan by Rail - September 2026

(1 review )

Trip customizable

Best price guaranteed

I’ve always loved Italy, but doing it by rail added a special touch. Over eight days, we hit Rome, Florence, Venice, and wrapped up in Milan, all by high-speed train. The pace worked perfectly for me (I’m 58), with fresh city arrivals each morning and comfortable hotels each night The highlights: a hop-on hop-off loop in Rome hit the Colosseum, Pantheon, Trevi Fountain , an optional wine tasting tour that I booked in Florence and Venice’s gondola ride. Everything flowed perfectly well..no dragging suitcases or missed trains. For travelers in our age bracket, this tour blends comfort, culture, and hassle-free travel. If you want Italy’s treasures without the planning headache, this rail tour delivers in a big way.

City sightseeingTrain tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Venice

Duration8 days

From

USD 1,417

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7% OFF TODAY

Italia Amore Mio - Venice To Milan - September 2026

4.9

(34 reviews )

No booking fees

Best price guaranteed

5/5. Using this service for your upcoming trip to Italy is highly recommended! The entire procedure went quite well. The drivers, guides, and tours they arranged for us were all wonderful, helpful. All of our questions received prompt responses from Sinan and Alex. I couldn't imagine returning to Italy without making use of this tour company once more! We had an amazing time!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

6-80 yrs

Operated in

english

Destinations

Venice, Pompeii, Florence, Perug

Venice, Pompeii, Florence, Perugia, Rome

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Duration8 days

From

USD 3,390

USD 3,149

Saving

USD 241

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Amalfi Coast Dream - Small-Group Tour - September 2026

(1 review )

Trip customizable

Best price guaranteed

Received excellent service and suggestions for a tour we planned for our son and daughter when they toured the Amalfi Coast in August. Hotels were all in great locations close to the action and all excellent 4 or 5 star. Would definitely use or recommend the tour operator to friends or family.

Countryside and village visits

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Sorrent

Amalfi Coast & Campania, Sorrento, Campania, Rome

Duration4 days

From

USD 1,434

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European Trail - September 2026

(1 review )

No booking fees

Best price guaranteed

This tour was so much fun. Learnt a lot, met a lot of new friends, and had a ton of fun. Would highly recommend this tour, and to travel through Europe in general.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Hostel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Paris, London, Amsterdam, Berlin

Paris, London, Amsterdam, Berlin, Prague, Vienna, Krakow, Budapest, Ljubljana, Venice, Rome, Florence, Swiss Alps

Duration23 days

From

USD 2,795

USD 2,711

Saving

USD 84

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Jewels of Italy by Rail - September 2026

(1 review )

Trip customizable

Best price guaranteed

Three of us girlfriends decided it was time for an Italian cultural recharge, and we picked the rail tour to hit the highlights with ease. We explored Rome and saw the Coloseum as we opted for an optional tour. Florence was also beautiful. Venice was pure magic. Our shared gondola ride under the Bridge of Sighs (with just six in the gondola) felt cozy and unforgettable . We spent afternoons discovering boutique shops and colorful squares. For us, this tour struck the perfect balance. Relaxed evenings with wine and laughter. The train travel was a breeze, everything was well-coordinated.

Train toursSightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice

Duration7 days

From

USD 1,154

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Local Living Italy—sorrento - September 2026

27% OFF TODAY

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Local Living Italy—Sorrento - September 2026

(4 reviews )

No booking fees

Best price guaranteed

This was a bucket list trip for me and I highly recommend this tour. It exceeded my expectations. Looking forward to more G Adventures!

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa, Guest House

Age Range

12-100 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Naples

Amalfi Coast & Campania, Naples, Sorrento

27% OFF TODAY

Duration7 days

From

USD 2,199

USD 1,600

Saving

USD 599

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Grand Italy & Sicily - September 2026

4.7

(77 reviews )

No booking fees

Best price guaranteed

It covers so many areas in Italy We got exposed to so much history and culture

Wine tasting tours

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Palermo, Sorrento, Capri

Rome, Palermo, Sorrento, Capri, Alberobello, Giardini Naxos, Santa Margherita, Portofino, Lake Maggiore, Venice, Florence

15% OFF TODAY

Duration17 days

From

USD 8,250

USD 6,993

Saving

USD 1,257

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Southern Italy - September 2026

4.8

(40 reviews )

No booking fees

Best price guaranteed

This trip is for you if you're searching for delicious food, helpful guidance, and entertaining company! Excellent use of ten days! As a solo traveler, I really appreciated having my own room because at some other companies, you have to share a room with a stranger. Alessandro was an excellent guide who added much enjoyment to the trip.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english, spanish, portuguese

Destinations

Rome, Taormina, Sorrento, Palerm

Rome, Taormina, Sorrento, Palermo, Agrigento, Ragusa

Duration11 days

From

USD 4,450

USD 4,317

Saving

USD 134

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25% OFF TODAY

Italian Expresso - 5 days - September 2026

No booking fees

Best price guaranteed

COACH TOUR: Explore the best of central Italy on this five-day journey from Rome to Venice, with scenic stops in Florence, Bologna and the Tuscan countryside. Visit Assisi and Siena en route to Florence, where Renaissance treasures and Tuscan cuisine await. Wander Bologna’s historic streets and enjoy a street food tasting before heading to Venice for gondolas, cicchetti and grand architecture. Wrap up with wine and views in hilltop Montepulciano before returning to Rome. With guided sightseeing, regional flavours and iconic landmarks throughout, this compact adventure is perfect for travellers keen to experience Italy’s cultural heart in style.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Tuscany, Florence, Bologna

Rome, Tuscany, Florence, Bologna, Venice

25% OFF TODAY

Duration5 days

From

USD 1,475

USD 1,106

Saving

USD 369

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Northern Italy Family Holiday - September 2026

No booking fees

Best price guaranteed

Explore the delights of Italy on a family-focused cultural exploration of the best sights and finest food that Italy has to offer on this eight-day tour of the country’s best. Get exploring in the winding canal maze of Venice, dip your toes in the ocean by the beautiful Cinque Terre coastline, make and taste authentic Italian pesto, savour delicious Tuscan cuisine, get the perfect snap of the Learning Tower of Pisa and try as much gelato as you can (how many flavours can the kids try before you leave?). There’s something for all ages in Italy as you whisk through Venice to Rome on this family escapade – now that’s amore!

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Cinque Terre and L

Rome, Venice, Cinque Terre and Liguria, Pisa

Duration8 days

From

USD 3,295

USD 3,196

Saving

USD 99

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Country Roads Of Northern Italy - September 2026

14% OFF TODAY

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Country Roads of Northern Italy - September 2026

4.5

(48 reviews )

No booking fees

Best price guaranteed

Keep the flexibility of the add on activities.

AdventureCity sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Trento, Lake Maggiore

14% OFF TODAY

Duration10 days

From

USD 4,450

USD 3,841

Saving

USD 609

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Combine Italy in September with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Italy

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

All Italy Tours in September 2026

Page 8 of 326 Trips in Italy during September 2026 with 6,326 Reviews

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Southern Italy and Sicily - September 2026

Best of Italy: Tuscany, Cinque Terre & The Amalfi Coast - September 2026

Italy Bellissimo - September 2026

Jewels of Italy and Milan by Rail - September 2026

Italia Amore Mio - Venice To Milan - September 2026

Amalfi Coast Dream - Small-Group Tour - September 2026

European Trail - September 2026

Jewels of Italy by Rail - September 2026

Local Living Italy—Sorrento - September 2026

Grand Italy & Sicily - September 2026

Southern Italy - September 2026

Italian Expresso - 5 days - September 2026

Northern Italy Family Holiday - September 2026

Country Roads of Northern Italy - September 2026

Page 8 of 326 Trips in Italy during September 2026 with 6,326 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 8 of 326 Trips in Italy during September 2026 with 6,326 Reviews

See Italy tours by duration

Page 8 of 326 Trips in Italy during September 2026 with 6,326 Reviews