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Italy Tours Starting In May 2027

If you're looking at joining a tour to Italy in May 2027, we have 36 unique rail journeys, guided coach and small group tours with 1,913 departures from the world's leading tour operators departing in May.
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Departures (May 2027)
< April 2027 June 2027 >
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24 Days
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36 Tours (1,913 Tour Departures)
14 Day Best of Italy with Intrepid Travel
Tour
 (1)

14 Days Rome to Venice
Operated By: Intrepid Travel
Departures: Jul 2025 to Oct 2027
Trip Styles: Adventure, Small Group, Rail
Countries Visited: Italy
Exclusive Deal
Save (per person) 1,024
From (per person) 3,716
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12 Day Italian Vistas with Collette
Tour
 (1)

12 Days Rome to Stresa
Operated By: Collette
Departures: Jul 2025 to Jun 2027
Trip Styles: Coach, Scenic
Countries Visited: Italy
Latest Offer
Save (per person) 401
From (per person) 3,879
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8 Day Italy: Highlights of Sicily with Intrepid Travel
Tour
 (1)

8 Days Catania to Palermo
Operated By: Intrepid Travel
Departures: Jul 2025 to Nov 2027
Trip Styles: Adventure, Small Group
Countries Visited: Sicily
Exclusive Deal
Save (per person) 566
From (per person) 2,264
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11 Day Old World Sicily & Malta with Collette
Tour
 (1)

11 Days Sliema to Taormina
Operated By: Collette
Departures: Sep 2025 to Jun 2027
Trip Styles: Coach, Small Group, Scenic
Countries Visited: Sicily, Malta
Last Minute DealLatest Offer
Save (per person) 472
From (per person) 3,527
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13 Day Sicily and Its Isles with Collette
Tour
 (1)

13 Days Palermo to Taormina
Operated By: Collette
Departures: Sep 2025 to Jun 2027
Trip Styles: Coach, Small Group, Scenic
Countries Visited: Sicily
Exclusive Savings
Save (per person) 112
From (per person) 4,801
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13 or 12 Day Southern Italy & Sicily with Collette
Tour
 (1)

13 or 12 Days Palermo to Rome
Operated By: Collette
Departures: Aug 2025 to Jun 2027
Trip Styles: Coach, Scenic
Countries Visited: Sicily, Italy
Last Minute DealLatest Offer
Save (per person) 512
From (per person) 3,879
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8 Day Spotlight on Northern Italy with Collette
Tour
 (1)

8 Days Treviso to Treviso
Operated By: Collette
Departures: Sep 2025 to Jun 2027
Trip Styles: Coach, Scenic
Countries Visited: Italy
Latest Offer
Save (per person) 232
From (per person) 2,521
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8 Day Spotlight on Tuscany with Collette
Tour
 (1)

8 Days Montecatini Terme to Montecatini Terme
Operated By: Collette
Departures: Jul 2025 to Jun 2027
Trip Styles: Coach, Scenic
Countries Visited: Italy
Last Minute DealLatest Offer
Save (per person) 332
From (per person) 2,230
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8 Day Italy Real Food Adventure with Intrepid Travel
Tour

8 Days Venice to Rome
Operated By: Intrepid Travel
Departures: Jul 2025 to Oct 2027
Trip Styles: Adventure, Small Group, Rail, Food & Wine
Countries Visited: Italy
Exclusive Deal
Save (per person) 905
From (per person) 2,510
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23 Day Rome to Sicily with Intrepid Travel
Tour

23 Days Rome to Palermo
Operated By: Intrepid Travel
Departures: Aug 2025 to Oct 2027
Trip Styles: Adventure, Small Group
Countries Visited: Italy, Sicily
Exclusive Savings
Save (per person) 184
From (per person) 7,850
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8 Day Rome to Amalfi with Intrepid Travel
Tour

8 Days Rome to Minori
Operated By: Intrepid Travel
Departures: Jul 2025 to Oct 2027
Trip Styles: Adventure, Small Group, Rail
Countries Visited: Italy
Exclusive Deal
Save (per person) 736
From (per person) 1,694
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8 Day Amalfi Coast: Hike & Kayak with Intrepid Travel
Tour

8 Days Naples to Amalfi
Operated By: Intrepid Travel
Departures: Jul 2025 to Oct 2027
Trip Styles: Adventure, Small Group, Kayaking, Walking & Hiking
Countries Visited: Italy
Exclusive Deal
Save (per person) 274
From (per person) 2,462
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10 Day Essential Italy with Intrepid Travel
Tour

10 Days Venice to Rome
Operated By: Intrepid Travel
Departures: Jul 2025 to Oct 2027
Trip Styles: Adventure, Small Group, Rail, 18-30's
Countries Visited: Italy
Exclusive Deal
Save (per person) 581
From (per person) 1,744
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8 Day Highlights of Italy with Intrepid Travel
Tour

8 Days Venice to Rome
Operated By: Intrepid Travel
Departures: Jul 2025 to Nov 2027
Trip Styles: Adventure, Small Group, Rail
Countries Visited: Italy
Exclusive Deal
Save (per person) 532
From (per person) 1,519
View Trip
8 Day Hiking in the Dolomites with Intrepid Travel
Tour

8 Days Venice to Venice
Operated By: Intrepid Travel
Departures: Jul 2025 to Sep 2027
Trip Styles: Adventure, Small Group, Walking & Hiking
Countries Visited: Italy
Exclusive Deal
Save (per person) 1,082
From (per person) 2,964
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10 Day Italy Experience with Intrepid Travel
Tour

10 Days Venice to Rome
Operated By: Intrepid Travel
Departures: Jul 2025 to Nov 2027
Trip Styles: Adventure, Small Group, Rail
Countries Visited: Italy
Exclusive Deal
Save (per person) 1,276
From (per person) 3,539
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11 Day Best of Italy with Collette
Tour

11 Days Venice to Rome
Operated By: Collette
Departures: Sep 2025 to Jun 2027
Trip Styles: Coach, Small Group, Scenic
Countries Visited: Italy
Latest Offer
Save (per person) 596
From (per person) 3,919
View Trip
10 Day Tuscan & Umbrian Countryside with Collette
Tour

10 Days Rome to Tuscany
Operated By: Collette
Departures: Oct 2025 to Jun 2027
Trip Styles: Coach, Small Group, Off The Beaten Track, Scenic
Countries Visited: Italy
Exclusive Savings
Save (per person) 88
From (per person) 3,527
View Trip
10 Day Explore Southern Italy with Intrepid Travel
Tour

10 Days Amalfi to Bari
Operated By: Intrepid Travel
Departures: Jul 2025 to Oct 2027
Trip Styles: Adventure, Small Group
Countries Visited: Italy
Exclusive Deal
Save (per person) 402
From (per person) 2,278
View Trip
8 Day Cinque Terre: Hike, Bike & Kayak with Intrepid Travel
Tour

8 Days Levanto to Genoa
Operated By: Intrepid Travel
Departures: Aug 2025 to Sep 2027
Trip Styles: Adventure, Small Group, Cycling, Kayaking, Walking & Hiking
Countries Visited: Italy
Exclusive Deal
Save (per person) 714
From (per person) 2,141
View Trip
8 Day Tuscany, Lake Maggiore & the Italian Riviera with Collette
Tour

8 Days Lake Maggiore to Tuscany or Turin to Tuscany
Operated By: Collette
Departures: Oct 2025 to Jun 2027
Trip Styles: Coach, Scenic
Countries Visited: Italy
Latest Offer
Save (per person) 240
From (per person) 2,521
View Trip
8 Day Cycle Tuscany with Intrepid Travel
Tour

8 Days Florence to Pisa
Operated By: Intrepid Travel
Departures: Jul 2025 to Oct 2027
Trip Styles: Adventure, Small Group, Cycling
Countries Visited: Italy
Exclusive Deal
Save (per person) 706
From (per person) 2,119
View Trip
8 Day Premium Puglia with Intrepid Travel
Tour

8 Days Bari to Naples
Operated By: Intrepid Travel
Departures: Jul 2025 to Oct 2027
Trip Styles: Adventure, Small Group
Countries Visited: Italy
Exclusive Deal
Save (per person) 1,043
From (per person) 3,787
View Trip
8 Day Highlights of Italy in Winter with Intrepid Travel
Tour

8 Days Rome to Venice
Operated By: Intrepid Travel
Departures: Nov 2025 to Dec 2027
Trip Styles: Adventure, Small Group, Rail, Winter
Countries Visited: Italy
Exclusive Savings
Save (per person) 61
From (per person) 2,636
View Trip
17 Day Premium Sicily and Tuscany with Intrepid Travel
Tour

17 Days Palermo to Venice
Operated By: Intrepid Travel
Departures: Aug 2025 to Sep 2027
Trip Styles: Adventure, Small Group
Countries Visited: Italy, Sicily
Exclusive Deal
Save (per person) 2,401
From (per person) 8,714
View Trip
10 Day Premium Sicily with Intrepid Travel
Tour

10 Days Palermo to Catania
Operated By: Intrepid Travel
Departures: Aug 2025 to Nov 2027
Trip Styles: Adventure, Small Group
Countries Visited: Sicily
Exclusive Deal
Save (per person) 1,342
From (per person) 4,794
View Trip
24 Day Premium Sicily and Italy in Depth with Intrepid Travel
Tour

24 Days Palermo to Venice
Operated By: Intrepid Travel
Departures: Aug 2025 to Aug 2027
Trip Styles: Adventure, Small Group, Rail
Countries Visited: Italy, Sicily
Exclusive Savings
Save (per person) 356
From (per person) 15,915
View Trip
17 Day Premium Sicily and Puglia with Intrepid Travel
Tour

17 Days Palermo to Naples
Operated By: Intrepid Travel
Departures: Aug 2025 to Oct 2027
Trip Styles: Adventure, Small Group
Countries Visited: Italy, Sicily
Exclusive Savings
Save (per person) 238
From (per person) 10,780
View Trip
9 Day Italy: Highlights of Calabria with Intrepid Travel
Tour

9 Days Naples to Catania
Operated By: Intrepid Travel
Departures: Aug 2025 to Oct 2027
Trip Styles: Adventure, Small Group, Rail
Countries Visited: Italy, Sicily
Exclusive Deal
Save (per person) 789
From (per person) 2,366
View Trip
15 Day Premium Italy in Depth with Intrepid Travel
Tour

15 Days Bari to Venice
Operated By: Intrepid Travel
Departures: Jul 2025 to Oct 2027
Trip Styles: Adventure, Small Group, Rail
Countries Visited: Italy
Exclusive Deal
Save (per person) 2,078
From (per person) 7,542
View Trip
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