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Southern Italy Tours Starting In May 2026

If you're looking at joining a tour through Southern Italy in May 2026, we have 21 unique guided tours and small group adventures with 597 departures from the world's leading tour operators departing in May.
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Departures (May 2026)
< April 2026 June 2026 >
Duration
7 Days
14 Days
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$1,500pp
$12,040pp
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21 Tours (597 Tour Departures)
14 Day Country Roads of Southern Italy & Sicily with Insight Vacations
Tour
 (7)

14 Days Rome to Palermo
Operated By: Insight Vacations
Departures: Apr 2025 to Oct 2026
Trip Styles: Coach, Scenic
Countries Visited: Italy, Sicily
Last Minute DealToday's Deal
Save (per person) 545
From (per person) 5,325
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14 Day Highlights of Sicily & Southern Italy with Globus
Tour
 (5)

14 Days Rome to Palermo
Operated By: Globus
Departures: Mar 2025 to Nov 2026
Trip Styles: Coach, Scenic
Countries Visited: Italy, Sicily
Your Wow Starts Now
Save (per person) 500
From (per person) 3,799
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9 Day Country Roads of Southern Italy with Insight Vacations
Tour
 (2)

9 Days Rome to Rome
Operated By: Insight Vacations
Departures: Apr 2025 to Sep 2026
Trip Styles: Coach, Scenic
Countries Visited: Italy
Last Minute DealToday's Deal
Save (per person) 529
From (per person) 3,350
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10 Day Southern Italy and Sicily with Trafalgar
Tour
 (2)

10 Days Rome to Palermo
Operated By: Trafalgar
Departures: Apr 2025 to Oct 2026
Trip Styles: Coach, Scenic
Countries Visited: Italy, Sicily
Today's DealLast Minute Deal
Save (per person) 551
From (per person) 3,850
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7 Day Exploring the Amalfi Coast with G Adventures
Tour
 (1)

7 Days Naples to Naples
Operated By: G Adventures
Departures: Mar 2025 to Nov 2026
Trip Styles: Adventure, Small Group, Walking & Hiking
Countries Visited: Italy
Last Minute Offer
Save (per person) 277
From (per person) 1,572
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8 Day Highlights of Puglia with Explore!
Tour
 (1)

8 Days Bari to Lecce
Operated By: Explore!
Departures: May 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Off The Beaten Track
Countries Visited: Italy
From (per person) 2,560
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8 Day Local Living Italy - Amalfi Coast with G Adventures
Tour
 (1)

8 Days Naples to Naples
Operated By: G Adventures
Departures: Apr 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Walking & Hiking
Countries Visited: Italy
From (per person) 2,299
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12 Day Southern Italy & Sicily with Collette
Tour
 (1)

12 Days Palermo to Rome
Operated By: Collette
Departures: Apr 2025 to May 2026
Trip Styles: Coach, Scenic
Countries Visited: Sicily, Italy
Latest Offer
Save (per person) 300
From (per person) 3,699
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8 Day Italy Coast to Coast by E-bike: Puglia to Amalfi Coast with Exodus Adventure Travels
Tour

8 Days Monopoli to Sorrento
Departures: May 2025 to Sep 2026
Trip Styles: Adventure, Small Group, Cycling
Countries Visited: Italy
From (per person) 4,350
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8 Day Gourmet Puglia with Cosmos
Tour

8 Days Bari to Martina Franca
Operated By: Cosmos
Departures: May 2025 to Oct 2026
Trip Styles: Coach, Scenic
Countries Visited: Italy
Exclusive Deal
Save (per person) 150
From (per person) 2,079
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8 Day A Taste of Italy - Walking in Puglia with Explore!
Tour

8 Days Altamura to Monopoli
Operated By: Explore!
Departures: May 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Food & Wine, Walking & Hiking
Countries Visited: Italy
Exclusive Deal
Save (per person) 360
From (per person) 2,350
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8 Day Walking in Puglia & Matera with Exodus Adventure Travels
Tour

8 Days Alberobello to Matera
Departures: Mar 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Walking & Hiking
Countries Visited: Italy
From (per person) 2,400
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8 Day Cycling Puglia & Matera with Exodus Adventure Travels
Tour

8 Days Matera to Lecce
Departures: Apr 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Cycling
Countries Visited: Italy
From (per person) 2,700
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8 Day Highlights of the Amalfi Coast with Exodus Adventure Travels
Tour

8 Days Agerola to Agerola
Departures: Mar 2025 to Dec 2026
Trip Styles: Small Group, Scenic
Countries Visited: Italy
From (per person) 2,400
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8 Day Cycle Puglia with Explore!
Tour

8 Days Altamura to Monopoli
Operated By: Explore!
Departures: Apr 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Cycling, Walking & Hiking
Countries Visited: Italy
Exclusive DealSolo Traveller Offer
Save (per person) 410
From (per person) 2,490
View Trip
8 Day Walking the Amalfi Coast with Exodus Adventure Travels
Tour

8 Days Agerola to Agerola
Departures: Mar 2025 to Dec 2026
Trip Styles: Adventure, Small Group, Walking & Hiking
Countries Visited: Italy
From (per person) 2,175
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8 Day Puglia: Discover the Heel of Italy with Exodus Adventure Travels
Tour

8 Days Matera to Lecce
Departures: Mar 2025 to Oct 2026
Trip Styles: Small Group, Scenic
Countries Visited: Italy
From (per person) 2,695
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13 Day Italy: Amalfi Coast to Puglia with Collette
Tour

13 Days Naples to Alberobello
Operated By: Collette
Departures: Apr 2025 to May 2026
Trip Styles: Coach, Small Group, Scenic
Countries Visited: Italy
From (per person) 4,599
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9 Day Hidden Treasures of Southern Italy with Globus
New ReleaseTour

9 Days Naples to Alberobello
Operated By: Globus
Departures: May 2025 to Oct 2026
Trip Styles: Coach, Scenic
Countries Visited: Italy
Your Wow Starts Now
Save (per person) 150
From (per person) 2,489
View Trip
8 Day Amalfi Coast Family Adventure with Exodus Adventure Travels
Tour

8 Days Agerola to Agerola
Departures: Mar 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Family, Walking & Hiking
Countries Visited: Italy
From (per person) 2,550
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9 Day Rome & Amalfi Coast with Collette
Tour

9 Days Rome to Amalfi
Operated By: Collette
Departures: Apr 2025 to May 2026
Trip Styles: Coach, Scenic
Countries Visited: Italy
Last Minute DealLatest Offer
Save (per person) 400
From (per person) 3,499
View Trip
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