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Experienced Traveler Trips in Italy

Discover Italy through the eyes of experienced travelers with over 260 carefully curated tours. Featuring in-depth cultural experiences, authentic local connections, and sophisticated itineraries designed for discerning travelers, rated by more than 6,200 experienced adventurers.

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Experienced Traveler Trips in Italy

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Showing 1 - 10 of 272 results

Duration

1 day26 days

Day Tour
Multiday Tour

Departures

June 2026
July 2026
August 2026
September 2026
October 2026

Price

USD 45USD 16,582

Budget Tours
Luxury Tours

Tour Types

Group Tours
Small Group Tours
Solo-friendly Group Tours
Solo-only Group Tours
Private Tours

Activities

Cultural, religious and historic sites
City sightseeing
Trekking and Hiking
Art and architecture
Walking tours

Physical Rating

relaxed
easy
moderate
challenging

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Destinations

Rome
Venice
Florence
Naples
Sorrento

Start & End Location

Guide Types

Guided Tours
Self Guided Tours
Partially Guided Tours

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Design a fully customized Italy trip with a local travel expert who understands what experienced travelers seek. From immersive cultural experiences and curated stays to flexible pacing and exclusive access.

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Physical Rating

relaxed
easy
moderate
challenging

Departures

June 2026
July 2026
August 2026
September 2026
October 2026

Tour Types

Group Tours
Small Group Tours
Solo-friendly Group Tours
Solo-only Group Tours
Private Tours

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Activities

Cultural, religious and historic sites
City sightseeing
Trekking and Hiking
Art and architecture
Walking tours

Duration

1 day26 days

Day Tour
Multiday Tour

Guide Types

Guided Tours
Self Guided Tours
Partially Guided Tours

Destinations

Rome
Venice
Florence
Naples
Sorrento

Page 26 of 272 Experienced Travelers Trips in Italy with 6,223 Reviews

Siena City & Duomo Walking Tour

Trip customizable

Best price guaranteed

Meet your guide in front of the church of San Domenico in Siena, easy to find even if you are arriving from out of town with your own car, as there...

Walking tours

Tour Type

Group Tour

Age Range

2-79 yrs

Operated in

english

Destinations

Siena

Duration2 hours

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Summer Super Sales

Small Group San Gimignano & Volterra Tour from Siena

Trip customizable

Best price guaranteed

Our trip starts with a drive towards San Gimignano. On our way, we stop for a walk in the fortress of Monteriggioni, a medieval and perfectly prese...

Cultural, religious and historic sites

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Age Range

5-79 yrs

Operated in

english

Destinations

Siena, Tuscany

Duration8 hours

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Summer Super Sales

Small Group Chianti and Castles Wine Tour from Siena

Trip customizable

Best price guaranteed

Our first stop is under the walls of the Castello di Brolio, here we have time for taking pictures and getting an up close look at the vineyards. I...

Farm and plantation visits

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Age Range

5-79 yrs

Operated in

english

Destinations

Siena, Chianti

Duration8 hours

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Summer Super Sales

Small Group Chianti & San Gimignano Sunset Wine Tour

Trip customizable

Best price guaranteed

Meet your guide in front of the church of San Domenico in Siena at 2:30pm, easy to find even if you are arriving from out of town with your own car...

Beer and drinks tasting

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Age Range

5-79 yrs

Operated in

english

Destinations

Siena, Tuscany, Chianti

Duration8 hours

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Summer Super Sales

Best Of Southern Italy

Trip customizable

Best price guaranteed

Set off on a sensory journey through Italy’s storied south with the "Best Of Southern Italy" tour, a relaxed, self-guided exploration perfect for t...

Cultural, religious and historic sites

Tour Type

Independent TourTypically a private tour undertaken by one or two travelers

Accommodation

Hotel, Resort, Villa

Age Range

8-99 yrs

Operated in

English

Destinations

Naples, Sorrento, Minori

Duration9 days

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Summer Super Sales

E-Bike Chianti Tour from Siena with Winery Lunch

Trip customizable

Best price guaranteed

Join us for a unique tour exploring the beautiful Chianti region of Tuscany by electric bike. These bikes make biking in Tuscany, one of the world’...

Bicycle tours

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Age Range

13-79 yrs

Operated in

english

Destinations

Siena

Duration6 hours

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Summer Super Sales

Iconic Rome and Amalfi

Trip customizable

Best price guaranteed

Imagine cruising scenic highways from Rome to the sun-soaked Amalfi Coast—this 6-day self-drive sightseeing tour invites experienced travelers to e...

City sightseeing

Tour Type

Independent TourTypically a private tour undertaken by one or two travelers

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Amalfi Coast & Campania, Amalfi

Duration6 days

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Summer Super Sales

Absolute Italy by Rail

Trip customizable

Best price guaranteed

Let the rails guide you through Italy’s most iconic cities on the "Absolute Italy by Rail" tour package—a 12-day independent trip curated for trave...

Train tours

Tour Type

Independent TourTypically a private tour undertaken by one or two travelers

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Florence, Venice, La Spezi

Rome, Florence, Venice, La Spezia, Milan

Duration12 days

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Summer Super Sales

Mediterranean New Year's Eve - Naples, the Amalfi Coast and Sicily (port-to-port package)

No booking fees

Best price guaranteed

To celebrate the New Year, embark on a festive cruise to the heart of the most beautiful ports of call in southern Italy and Sicily. Between Naples...

Cruise

Tour Type

Cruise Tour

Accommodation

Ship Cabin, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Naples, Milazzo, Messina, Vibo M

Naples, Milazzo, Messina, Vibo Marina, Salerno

Duration8 days

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Summer Super Sales

Christmas Traditions and Mediterranean Treasures - Naples, the Amalfi Coast and Sicily (port-to-port package)

No booking fees

Best price guaranteed

As Christmas approaches, let yourself be carried away on a cruise to the heart of the most beautiful ports of call in southern Italy and Sicily. Fr...

Cruise

Tour Type

Cruise Tour

Accommodation

Ship Cabin, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Naples, Milazzo, Messina, Vibo M

Naples, Milazzo, Messina, Vibo Marina, Salerno

Duration8 days

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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

Hi there

Experienced Traveler Trips in Italy

Experienced Traveler Trips in Italy

Build a personalized Italy trip for mature travelers?

Page 26 of 272 Experienced Travelers Trips in Italy with 6,223 Reviews

Page 26 of 272 Experienced Travelers Trips in Italy with 6,223 Reviews