10 Best Tuscany Multiday Tours in May 2026

Get a customized trip to Tuscany in May 2026

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

Alessandra GalassiTravel Expert in Italy
Danilo CataniaTravel Expert in Italy
Enrico Maria MalacarneTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Simon H.Travel Expert in Belgium, France, Italy & Switzerland

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Super Sales

Italy: Florence to Rome, Walking the Vineyards of Tuscany and Umbria - May 2026

(4 reviews )

No booking fees

Best price guaranteed

I loved my trip with G Adventures to Italy! The hiking, visits to wineries and delicious food made it a memorable trip. I would love to return to Italy with G Adventures again!

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-100 yrs

Operated in

english

Destinations

Rome, Florence, Tuscany, Umbria

Duration10 days

From

USD 4,999

USD 4,849

Saving

USD 150

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Super Sales

Italy: Tuscany and Umbria Vineyard Walks - May 2026

(8 reviews )

No booking fees

Best price guaranteed

An amazing holiday, an exceptional CEO and a lovely group of people in a truly beautiful part of Italy. I wish I could do it all over again!!

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-100 yrs

Operated in

english

Destinations

Rome, Florence, Tuscany, Umbria

Duration8 days

From

USD 3,999

USD 3,879

Saving

USD 120

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15% OFF TODAY

Amsterdam to Rome - May 2026

4.4

(7 reviews )

No booking fees

Best price guaranteed

Overall it was a great vacation. The tour leader (Matt) was professional, knowledgeable and funny. The coach driver (Alex) was great too. They worked well together and gave a constant calm feeling to our group. Our leaders had a few obstacles to overcome and they handled them without us ever needed to worry. A few suggestions from Matt made our trip even better. We ate with different people each night, we rotated seats and made friends for a life time. Life changing experience.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Paris, Rome, Toulouse, Barcelona

Paris, Rome, Toulouse, Barcelona, Avignon, Monaco, Tuscany, Amsterdam

15% OFF TODAY

Duration11 days

From

USD 2,660

USD 2,255

Saving

USD 405

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Mediterranean Coastal Journey Spain, France & Italy - May 2026

No booking fees

Best price guaranteed

Venture along the glittering Mediterranean coast on an immersive journey connecting the Spanish, French and Italian Rivieras. Taste your way along the Mediterranean coast sampling traditional Catalan specialties in a 17th-century farmhouse, flavorful Provençal cuisine in Marseille, and traditional focaccia in Genoa. Enjoy the iconic must-sees and venture to gems off the beaten path, like the rolling hills of the Tuscan countryside. Take a step into the culture and meet the locals. From chameleonic Barcelona to sun-kissed Nice; from glamorous Monaco to the rolling hills of the Chianti countryside, find your dream Mediterranean journey.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Barcelona, Tuscany, Nice, Genoa

Barcelona, Tuscany, Nice, Genoa, San Gimignano, Costa Brava, Figueres, Marseille

Duration16 days

From

USD 5,499

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5% OFF TODAY

Tuscan Treats - May 2026

4.7

(128 reviews )

No booking fees

Best price guaranteed

Back Roads Tuscan Treats was an amazing trip. We stayed in some beautiful towns such as Lucca & Pienza. Our guide Francesca was wonderful, very friendly and organised. Thank you Back Roads

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Florence, Lucca, Volterra, Pienz

Florence, Lucca, Volterra, Pienza, Tuscany

5% OFF TODAY

Duration8 days

From

USD 2,579

USD 2,450

Saving

USD 129

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Italian Indulgence - May 2026

4.7

(256 reviews )

No booking fees

Best price guaranteed

Excellent tour of Italy. Such a beautiful country! Our tour guide and driver were excellent as well. WE were very happy with our accommodations. We covered about 3200 kms. and visited many great cities, town, and villages. We liked the culture, food, and scenery. The Italian people are very gracious and happy to see visitors.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Venice, Lake Maggiore, Son

Rome, Venice, Lake Maggiore, Sondrio, Trento, Perugia, Tuscany, Lucca, Portofino, Langhe

Duration13 days

From

USD 5,119

USD 4,919

Saving

USD 200

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Flavours of Tuscany & Cinque Terre - May 2026

Trip customizable

Best price guaranteed

Experience the best of Italy with this 8-day tour, staying in Rome, Florence, and the charming Monterosso al Mare. Explore Rome’s rich history with a 24-hour Hop-On Hop-Off ticket. Enjoy a scenic half-day tour from Florence to the Chianti region, complete with wine and olive oil tastings. Discover the stunning beauty of Cinque Terre with a 48-hour Train Card. Your journey includes a private airport transfer in Rome and high-speed train travel between cities, offering the perfect balance of guided tours and independent exploration

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Tuscany, Montero

Rome, Florence, Tuscany, Monterosso, Cinque Terre

Duration8 days

From

USD 1,355

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All Tuscany Tours in May 2026

Page 2 of 21 Trips in Tuscany during May 2026 with 1,016 Reviews

Get a customized trip to Tuscany in May 2026

Page 2 of 21 Trips in Tuscany during May 2026 with 1,016 Reviews

Italy: Florence to Rome, Walking the Vineyards of Tuscany and Umbria - May 2026