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2 Week Tours to Italy

Looking to explore Italy for 2 weeks? Then choose from our range of rail journeys, guided coach and small group tours with 9 of the best tour operators to Italy. June, August and September are the most popular months to travel to Italy and we have 458 departures available.
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15 trips (458 trip Departures)
14 Day Italy's Best with Cosmos
Tour
 (39)

14 Days Rome to Rome
Operated By: Cosmos
Departures: Mar 2026 to Dec 2027
Trip Styles: Coach, Scenic
Visit: Italy, Switzerland
Black Friday Sale
Single Supplement Waiver
Exclusive Savings
From
US$3,061
Save 388
Per Person
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14 Day Country Roads of Southern Italy & Sicily with Insight Vacations
Tour
 (8)

14 Days Rome to Palermo
Operated By: Insight Vacations
Departures: Apr 2026 to Oct 2027
Trip Styles: Coach, Scenic
Visit: Italy, Sicily
Sign Up Savings
Best of Summer Sale
Exclusive Savings
From
US$4,473
Save 1,075
Per Person
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14 Day Sicily in Depth with 6-Day Malta Option with Insight Vacations
Tour
 (6)

14 Days Palermo to Malta
Operated By: Insight Vacations
Departures: Apr 2026 to Oct 2027
Trip Styles: Coach, Scenic
Visit: Sicily, Malta
Sign Up Savings
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From
US$5,140
Save 394
Per Person
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14 Day Highlights of Sicily & Southern Italy with Globus
Tour
 (5)

14 Days Rome to Palermo
Operated By: Globus
Departures: Jun 2026 to Nov 2027
Trip Styles: Coach, Scenic
Visit: Italy, Sicily
Exclusive Savings
From
US$3,983
Save 374
Per Person
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14 Day Ultimate Italy with G Adventures
Tour
 (3)

14 Days Rome to Venice
Operated By: G Adventures
Departures: May 2026 to Nov 2027
Trip Styles: Adventure, Small Group, Rail
Visit: Italy
Exclusive Savings
From
US$3,685
Save 129
Per Person
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14 Day Highlights of Sicily with G Adventures
Tour
 (2)

14 Days Palermo to Palermo
Operated By: G Adventures
Departures: Apr 2026 to Oct 2027
Trip Styles: Adventure, Small Group
Visit: Sicily
G's February Sale
Exclusive Savings
From
US$3,726
Save 793
Per Person
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14 Day Italy: Pasta & Piazzas with Topdeck
Tour
 (2)

14 Days Rome to Rome
Operated By: Topdeck
Departures: May 2026 to Oct 2026
Trip Styles: Small Group, Rail, 18-30's, Scenic
Visit: Italy
Exclusive Savings
From
US$2,793
Save 250
Per Person
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14 Day Best of Italy with Intrepid Travel
Tour
 (1)

14 Days Rome to Venice
Operated By: Intrepid Travel
Departures: Apr 2026 to Nov 2027
Trip Styles: Adventure, Small Group, Rail
Visit: Italy
Exclusive Savings
From
US$4,828
Save 795
Per Person
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14 Day Sicily in Depth with 6-Day Malta Option (Winter) with Insight Vacations
Tour

14 Days Palermo to Malta
Operated By: Insight Vacations
Departures: Mar 2026 to Mar 2027
Trip Styles: Coach, Winter, Scenic
Visit: Sicily, Malta
Sign Up Savings
Exclusive Savings
From
US$4,098
Save 877
Per Person
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14 Day Sicily in Depth with 6-Day Malta Option (Small Group) with Insight Vacations
Tour

14 Days Palermo to Malta
Operated By: Insight Vacations
Departures: Jul 2026 to Aug 2026
Trip Styles: Coach, Small Group, Scenic
Visit: Sicily, Malta
Sign Up Savings
Exclusive Savings
From
US$6,033
Save 396
Per Person
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14 Day Journeys: Iconic Italy with G Adventures
Tour

14 Days Venice to Rome
Operated By: G Adventures
Departures: Apr 2026 to Oct 2027
Trip Styles: Adventure, Small Group
Visit: Italy
G's February Sale
Exclusive Savings
From
US$5,853
Save 1,246
Per Person
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14 Day Classic Italy (Small Group) with Tauck
Tour

14 Days Sorrento to Venice
Operated By: Tauck
Departures: Jun 2026 to Oct 2026
Trip Styles: Coach, Small Group, Scenic
Visit: Italy
From
US$12,490
Per Person
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14 Day Venice to Rome by Rail with Sorrento & the Amalfi Coast with Explore Worldwide
Tour

14 Days Venice to Sorrento
Operated By: Explore Worldwide
Departures: Apr 2026 to Oct 2026
Trip Styles: Adventure, Small Group, Rail
Visit: Italy
Exclusive Savings
From
US$5,325
Save 177
Per Person
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14 Day Italy Escape with Adriatic Cruise with Travelmarvel
Tour + Cruise

14 Days Rome to Dubrovnik
Operated By: Travelmarvel
Ship: MV Princess Eleganza
Departure: 17 June 2026
Visit: Italy, Slovenia, Croatia
Exclusive Savings
Inside
-
Oceanview
$7,007
Balcony
-
Suite
-
From
US$7,007
Save 133
Per Person
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14 Day Classic Italy with Tauck
Tour

14 Days Sorrento to Venice
Operated By: Tauck
Departures: Apr 2026 to Oct 2026
Trip Styles: Coach, Scenic
Visit: Italy
From
US$11,890
Per Person
View Trip
Results: 15 results

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Italy & Sicily

All Italy Tours Northern Italy Tours Sicily Tours Southern Italy Tours Tuscany Tours

Travel Styles

18-30's Tours Active Adventures Coach Tours Cycling Tours Family Holidays Food & Wine Tours Luxury Tours Rail Journeys Small Group Tours Walking & Hiking Tours Winter Tours & Trips

Trip Lengths

10 Day 2 Week 7 Day

Departure Months

March April May June July August September October November December January February

Popular Italy Operators

APT Italy Tours CIE Italy Tours Collette Italy Tours Cosmos Italy Tours Costsaver Italy Tours Exodus Italy Tours Explore's Italy Tours G Adventures Italy Tours Globus Italy Tours Insight Vacations Italy Tours Intrepid Italy Tours Trafalgar Italy Tours

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