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All Italy Tours in May 2026

Planning for a trip to Italy during May? We offer 120 tour packages to Italy departing in May 2026 that have 1,100 customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Italy on your May holiday.

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All Italy Tours in May 2026

May 2026 Jun 2026 Jul 2026 Aug 2026 Sep 2026 Oct 2026 Nov 2026 Dec 2026 Jan 2027 Feb 2027 Mar 2027

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Showing 1 - 10 of 16 results

Duration

1 day24 days

Day Tour
Multiday Tour

Price

USD 31USD 6,990

Budget Tours
Luxury Tours

Tour Types

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

Age

Young Travelers (Age 18-39)Mature Travelers (Age 40-59)Senior Travelers (Age 60+)

Activities

Walking tours
Explorer
Trekking and Hiking
Bicycle tours
Cultural, religious and historic sites

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
Florence
Venice
Naples
Siena

Start & End Location

Guide Types

Guided Tours
Self Guided Tours
Partially Guided Tours

Discounts

Discounted Tours
Last Minute Deals

See Italy tours by duration

May 2026 Jun 2026 Jul 2026 Aug 2026 Sep 2026 Oct 2026 Nov 2026 Dec 2026 Jan 2027 Feb 2027 Mar 2027

Duration

1 day24 days

Day Tour
Multiday Tour

Tour Types

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

Activities

Walking tours
Explorer
Trekking and Hiking
Bicycle tours
Cultural, religious and historic sites

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
Florence
Venice
Naples
Siena

Guide Types

Guided Tours
Self Guided Tours
Partially Guided Tours

Get a customized trip to Italy in May 2026

Plan a multi-country or regional adventure across Italy in May 2026, with help from a local expert.

Alessandra GalassiTravel Expert in Italy
Danilo CataniaTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy

Start planning your Trip

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Start & End Location

Price

USD 31USD 6,990

Budget Tours
Luxury Tours

Page 2 of 16 Trips in Italy during May 2026 with 131 Reviews

Cycle the Via Francigena - Parma to Siena - May 2026

(1 review )

No booking fees

Best price guaranteed

Excellent trip - the bike was great - all hotels also very good with good breakfasts. Was very impressed with the logistics - no dramas!

Bicycle toursSightseeing Tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Siena, Parma, Aulla, Massa, Lucc

Siena, Parma, Aulla, Massa, Lucca, San Miniato Alto, San Gimignano

Duration9 days

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Ancient Venetian Empire by Bike - May 2026

4.3

(7 reviews )

No booking fees

Best price guaranteed

Well organised, professional, easy to follow, and certainly the way to do and/or organise a cycling holiday.

Bicycle tours

Tour Type

Private Tour

Accommodation

Hotel, Resort

Age Range

18-99 yrs

Operated in

english

Destinations

Venice, Porec, Caorle, Portogrua

Venice, Porec, Caorle, Portogruaro, Aquileia, Trieste, Portoroz

Duration8 days

View Tour

Paestum & the Cilento National Park - May 2026

Trip customizable

Best price guaranteed

Experience the authentic side of southern Italy as you cycle through the serene Cilento National Park and the ancient site of Paestum on this nine-...

Bicycle tours

Tour Type

Private Tour

Accommodation

Hotel, Resort

Age Range

18-99 yrs

Operated in

English

Destinations

Amalfi Coast & Campania, Paestum

Amalfi Coast & Campania, Paestum, San Marco, La Petrosa, Piaggine

Duration9 days

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Tuscany Cycle for Families - May 2026

(1 review )

No booking fees

Best price guaranteed

Families keen to explore Tuscan treasures will love the Tuscany Cycle for Families trip, an eight-day self-guided cycling holiday from Pisa to Flor...

Bicycle tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Pisa, Empoli, San Giuli

Tuscany, Pisa, Empoli, San Giuliano Terme, Lucca, Vinci, Florence

Duration8 days

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Upcoming Departures

May 30

Jun 06

Upcoming Departures

May 30

May 31

Upcoming Departures

May 28

May 29

Cycling Lake Garda by e-bike - May 2026

No booking fees

Best price guaranteed

It's no surprise that Lake Garda is northern Italy's most popular destination. Full of beauty and history, lush green hills frame the clear waters...

Bicycle tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

12-99 yrs

Operated in

english

Destinations

Lake Garda, Bardolino, Borghetto

Lake Garda, Bardolino, Borghetto, Lombardy & the Lakes, Sirmione, Mantua

Duration7 days

View Tour

Upcoming Departures

May 31

Jun 01

Upcoming Departures

May 30

May 31

Page 2 of 16 Trips in Italy during May 2026 with 131 Reviews

E-Bike Chianti Tour from Siena with Winery Lunch - May 2026

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

View Tour

Upcoming Departures

May 30

8 seats remaining

Jun 03

8 seats remaining

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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

All Italy Tours in May 2026

All Italy Tours in May 2026

See Italy tours by duration

Get a customized trip to Italy in May 2026

Page 2 of 16 Trips in Italy during May 2026 with 131 Reviews

Cycle the Via Francigena - Parma to Siena - May 2026

Ancient Venetian Empire by Bike - May 2026

Paestum & the Cilento National Park - May 2026

Tuscany Cycle for Families - May 2026

Cycling Lake Garda by e-bike - May 2026

Page 2 of 16 Trips in Italy during May 2026 with 131 Reviews

E-Bike Chianti Tour from Siena with Winery Lunch - May 2026