10 BEST Italy Small Group Trips & Tours 2025/2026

Italy Small Group Tours: Highlights Of Italy

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Highlights of Italy

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How long does it take to fall in love? In a country where history spills from world-class museums and tiny osterias serve up life-changing pasta recipes, eight days might just be enough (but if you have more time, why not extend your adventure?). On this trip, you’ll begin winding your way through the canals of Venice, hiking through the scenic Cinque Terre, soaking up beauty and history of Florence and finishing up in the piazzas of Rome. With plenty of free time for independent exploration and the freedom to discover Italy's history and culture at your own pace, there's no better way to see this popular pocket of Europe.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Hostel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Liguria, Cinque Te

Rome, Venice, Liguria, Cinque Terre and Liguria, Florence

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Duration8 days

From

USD 1,995

USD 1,548

Saving

USD 447

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Best of Italy

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The enduring phrase ‘la dolce vita’ (the good life) truly captures the essence of Italy. On this trip, you’ll spend 14 days discovering the heart of all things Italian on a culturally rich adventure from the piazzas of Rome to the canals of Venice. Discover the Tuscan countryside on a leisurely cycle along Lucca’s Serchio River, peer into Pisa, take to the trails of the Cinque Terre for some stunning coastal views and walk the Portofino Peninsula with its glamourous residents. With time spent wine tasting in rural villages, cruising along Lake Como and relaxing along canals in Venice, you’ll soon understand why Italy remains in the hearts of all who visit.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Asti, Lake Como, F

Rome, Venice, Asti, Lake Como, Florence, Lucca, Liguria

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Duration14 days

From

USD 4,690

USD 3,867

Saving

USD 823

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Rome to Amalfi

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If you want a short trip packed with diversity, this eight-day adventure through southern Italy is perfect for you. Acquaint yourself with Italy's 'Eternal City' (Rome) and get up close and personal with a still active volcano in Naples before witnessing the aftermath of a volcanic eruption in Pompeii. Soak up the sunshine in the coastal town of Sorrento and explore the beautiful Amalfi Coast. This trip promises a blend of history, trekking and culinary delights — a taste of la dolce vita awaits.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Hut

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Amalfi Coast & Campania, P

Rome, Amalfi Coast & Campania, Pompeii, Sorrento, Amalfi

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Duration8 days

From

USD 2,460

USD 2,148

Saving

USD 312

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Small Group Tour of Sicily: Highlights

4.8

(6 reviews )

Trip customizable

Best price guaranteed

We had a wonderful day together with Alfredo. Alfredo was the best guide ever!! He was excellent and was so fluent in english, he told us many interesting stories. He is an expert in Sicilian history and culture. he was both singing and dancing for us-we enjoyed it a lot. But most of all, he was such a service minded and understanding person. For example we were come minutes late in the morning and then we enjoyed the tour at the winery so much that we caused a delay in Alfredo's schedule but he was so humble and understanding. We highly recommend it to everyone travelling to Sicily.

Food toursWine tasting tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Palermo, Catania, Sicily, Taormi

Palermo, Catania, Sicily, Taormina, Syracuse

Duration8 days

From

USD 2,908

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Amalfi Coast Walking - Agriturismo

4.8

(92 reviews )

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A great way to explore the Amalfi coast... the people and the places!

Walking toursFood tours

Tour Type

Small Group Tour

Accommodation

Resort, Villa, Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Naples, San Lazzaro, Amalfi, Capri

Duration8 days

From

USD 2,070

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Tuscany Walking and Wine

4.9

(10 reviews )

No booking fees

Best price guaranteed

Want to explore Tuscany without a rushed itinerary? Want a small group? Want to hike to wineries and hill towns? Stay in interesting hotels that are hundreds of years old? A wine and food buff? Then this is for you. I had a great time on this trip. Had a full day in Sienna and a nice orientation tour of Florence (I spent a few extra days) Plus to get to visit lesser known towns that the big companies overlook. My favorite was Pienza. A nice little town that also had my favorite hotel and great places to eat. And yes, we tasted wonderful Italian wines, as well as the best cold cuts and cheeses I’ve ever tasted. And did I also mention hiking to wineries and hill towns? Wonderful sights, with spectacular views. One hike it rained towards the end, but that didn’t dampen our spirits.

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Florence, Pisa, San Gimignano, T

Florence, Pisa, San Gimignano, Tuscany, Pienza, Montalcino

Duration8 days

From

USD 2,830

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Italy Small Group Tours: Explore Southern Italy

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Explore Southern Italy

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Take off on an unforgettable journey down Italy’s rarely visited heel, getting to know another side of this beautiful country. See the beauty of Amalfi, unwind in style among the sophisticates of Trani and tour the Roman ruins, baroque churches and whitewashed alleyways of Lecce. Wander among the peculiarly shaped houses of Alberobello, wander the hillside dwellings of Matera and discover the Old Town’s life surrounding Bari's Basilica di San Nicola. Head down and say ciao to Italy’s southernmost slice of the Adriatic.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Bari, Amalfi Coast & Campania, A

Bari, Amalfi Coast & Campania, Amalfi, Trani, Lecce, Alberobello, Matera

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Duration10 days

From

USD 2,790

USD 2,300

Saving

USD 490

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Classical Sicily

4.5

(13 reviews )

No booking fees

Best price guaranteed

Excellent itinerary, competent and resourceful leader, good guides, comfortable transport.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Syracuse, Sicily, Syracusa, Trap

Syracuse, Sicily, Syracusa, Trapani, Palermo, Giardini Naxos, Taormina

Duration8 days

From

USD 2,830

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Cinque Terre: Hike, Bike & Kayak

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Explore a surreal region of Italy that looks straight out of a postcard (only better) with this eight-day multi-active trip. The houses are painted in multi-coloured shades, the sea is brighter than the sky, and the sun beams down brightly – welcome to the Cinque Terre. This jewel of Europe changes with the light of the day and is best explored on foot, on a bike or on a kayak. On this trip, you’ll witness natural beauty on all three! Cycle past olive groves, hike to medieval monuments, kayak to sandy beaches and refuel your energy every afternoon with cocktails and carbs. This is living!

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Cinque Terre and Liguria, Levant

Cinque Terre and Liguria, Levanto, Santa Margherita

Duration8 days

From

USD 2,855

USD 2,769

Saving

USD 86

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Local Living Italy—Amalfi Coast

(8 reviews )

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I thoroughly enjoyed my local experience tour. I was able to complete all the hikes offered. A good number of my fellow travelers were not able to do the hikes. It seemed their understanding of the physical requirements was not good. Perhaps more or clearer information on physical fitness requirements would help(?…).

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Guest House

Age Range

12-100 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Naples

Amalfi Coast & Campania, Naples, Furore

Duration8 days

From

USD 2,399

USD 2,327

Saving

USD 72

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Italy Small Group Tours: Highlights Of Italy In Winter

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Highlights of Italy in Winter

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While most associate Italy with a piercing, orange-hued summer, the mild winters make the country the perfect place to visit during the off season! On this eight-day trip, you’ll see all the iconic spots with far fewer tourists crowding the squares and clogging up the lines. Take in the crumbling ruins of Rome, the renaissance beauty of Florence and the canals of 15th century Venice and grab your classic photo of the Leaning Tower in Pisa. With the cold mornings and afternoon espressos, you’ll have all the more reason to tuck into all the delicious local cuisine, glasses of vino and cheeky desserts, too – ah Italia!

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence, Bologna

27% OFF TODAY

Duration8 days

From

USD 2,710

USD 1,972

Saving

USD 738

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Rome to Sicily

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Starting in Italy's 'Eternal City' of Rome, this epic adventure will take you through the Amalfi coastline to Calabria and Sicily over 23 days. Learn about the catastrophic fate of Pompeii, soak up the sunshine in the coastal town of Sorrento and explore the beautiful Amalfi Coast, before heading south to Calabria – a hidden gem for those who stray off Italy’s beaten path. Continue to bustling Sicily, with the volcanic valleys of Mt. Etna, the timeworn streets of Syracuse, the Baroque wonders of Ragusa, the ruins of the Valley of Temples and the rich anti-Mafia history of Palermo. Starring dramatic cliffside villages, clear waters and delicious seafood, this is a chance to experience the highlights of southern Italy.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Guest House, Resort, Hut

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Palermo, Lazio, Civita, Tr

Rome, Palermo, Lazio, Civita, Tropea, Reggio Calabria, Catania, Siracusa, Pompeii, Agrigento, Marsala, Sorrento, Amalfi

Duration23 days

From

USD 7,770

USD 7,537

Saving

USD 233

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Rome to Southern Italy

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This 17-day adventure around Italy takes in some of the most ancient sites in European history and shows you the lesser-known countryside, too. With a local by your side, you’ll explore the bustling streets of Rome, then travel through beautiful countryside past villas, vineyards and rolling hills as you visit historical sites like Pompeii, Lecce and the Sassi dwellings in Matera. There’s plenty of free time available to explore the area and take in the sites at your own pace, whether you want to indulge in food and wine or enjoy local experiences.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa, Hut

Age Range

15-99 yrs

Operated in

english

Destinations

Bari, Rome, Trani, Lecce, Albero

Bari, Rome, Trani, Lecce, Alberobello, Matera, Pompeii, Sorrento, Amalfi Coast & Campania

Duration17 days

From

USD 5,235

USD 5,078

Saving

USD 157

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Madrid to Rome

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Lose yourself in three of Europe's most enchanting countries on this 22-day adventure from Barcelona to Rome. Discover Provencal food and world-class wines as you wander through Europe’s high rollers in the French Riviera, and feast on beautiful sights in the cliff-top towns of Cinque Terre. Then, travel in the footsteps of Gaudi and Picasso and taste those local drops and plates of tapas. See flamenco in Seville, explore the grandeur of Alhambra Palace in Granada and visit Sagrada Familia – the largest unfinished Catholic church in the world.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Guest House

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Lake Como, Venice, Gubbio

Rome, Lake Como, Venice, Gubbio, Assisi, Umbria, Florence, Lucca, La Spezia, Asti

Duration22 days

From

USD 8,480

USD 8,226

Saving

USD 254

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All Italy Small Group Trips

19 Small Group Trips in Italy with 201 Reviews

19 Small Group Trips in Italy with 201 Reviews

Highlights of Italy

Best of Italy

Rome to Amalfi

Small Group Tour of Sicily: Highlights

Amalfi Coast Walking - Agriturismo

Tuscany Walking and Wine

Explore Southern Italy

Classical Sicily

Cinque Terre: Hike, Bike & Kayak

Local Living Italy—Amalfi Coast

Highlights of Italy in Winter

Rome to Sicily

Rome to Southern Italy

Madrid to Rome

Europe

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Adventure and sport

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All Italy Small Group Trips

19 Small Group Trips in Italy with 201 Reviews

19 Small Group Trips in Italy with 201 Reviews