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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Accommodations

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.

15% OFF TODAY

Europe Explorer - May 2026

4.8

(42 reviews )

No booking fees

Best price guaranteed

This was my first trip to Europe and I could not imagine experiencing it any better than on the 18 day EX tour. Although we only scratched the surface of many places it gave a wonderful perspective for places I want to come back to for further exploration. We covered a lot of ground in 18 days and made unforgettable memories. I was expecting to see beautiful things and have great experience but the relationships that formed within our group were an unexpected, and delightful, surprise. I'm so thankful I choose to do this tour and have recommended to all of my friends. I will definitely do another Expat tour when I'm able. Disclaimer; This is not a trip for those who want to kick back and relax. It was very active with many early mornings, late night and non-stop adventure days.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Paris, Amsterdam, Rome, Venice

Paris, Amsterdam, Rome, Venice, Lauterbrunnen, Black Forest, Toulouse, Barcelona, Avignon, Nice, Tuscany

15% OFF TODAY

Duration18 days

From

USD 4,100

USD 3,475

Saving

USD 625

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Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - May 2026

No booking fees

Best price guaranteed

On a journey through the less-traveled country roads of Umbria and Tuscany, discover another side to the Italy you love. Stroll Assisi’s old city, and explore the Umbrian hill town of Spoleto, where the gilded façade of the cathedral rivals with the silvery sheen of the olive trees. Visit Florence, the “Cradle of the Renaissance.” In Siena, stand inside one of Tuscany’s most ancient piazzas. Admire the famous towers of San Gimignano and hunt for truffles in the Umbrian countryside. Delight in regional specialties and Italian wine with every dinner. Feel like a local as you discover the marvels of wine, cuisine, culture, and history.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Tuscany, Chianti, Umbria

Rome, Tuscany, Chianti, Umbria, Pienza

Duration11 days

From

USD 3,749

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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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25% OFF TODAY

La Dolce Vita - 11 days - May 2026

No booking fees

Best price guaranteed

COACH TOUR: Take in the best of Italy on this 11-day journey from Rome, looping through Florence, Venice, and the sun-drenched south. Explore ancient ruins in Pompeii, cruise the canals of Venice, and marvel at the Vatican’s artistic treasures. Sip Tuscan wine in Montepulciano, discover Renaissance Florence, and see Pisa’s famous Leaning Tower. In the south, enjoy a formal dinner in Sorrento and a day trip to the glamorous island of Capri. With guided tours, scenic drives and plenty of local flavours, this trip blends history, culture and coastlines—perfect for anyone wanting a deep dive into Italy’s many highlights.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Sorrento, Florence, Bologn

Rome, Sorrento, Florence, Bologna, Venice, Tuscany, Naples, Capri

25% OFF TODAY

Duration11 days

From

USD 3,465

USD 2,599

Saving

USD 866

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25% OFF TODAY

Italian Expresso - 5 days - May 2026

No booking fees

Best price guaranteed

COACH TOUR: Explore the best of central Italy on this five-day journey from Rome to Venice, with scenic stops in Florence, Bologna and the Tuscan countryside. Visit Assisi and Siena en route to Florence, where Renaissance treasures and Tuscan cuisine await. Wander Bologna’s historic streets and enjoy a street food tasting before heading to Venice for gondolas, cicchetti and grand architecture. Wrap up with wine and views in hilltop Montepulciano before returning to Rome. With guided sightseeing, regional flavours and iconic landmarks throughout, this compact adventure is perfect for travellers keen to experience Italy’s cultural heart in style.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Tuscany, Florence, Bologna

Rome, Tuscany, Florence, Bologna, Venice

25% OFF TODAY

Duration5 days

From

USD 1,475

USD 1,106

Saving

USD 369

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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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Rome & Live Like a Local in a Tuscan Villa - May 2026

Trip customizable

Best price guaranteed

Experience Italy like never before with a stay at the historic Villa Casagrande, where rolling vineyards, timeless villages, and authentic Italian living await. This immersive journey blends comfort and culture—enjoy guided tours of Florence and San Gimignano, hands-on cooking classes, wine tastings, and free time to unwind in the villa’s gardens or by the pool. More than a tour, it’s your chance to live like a local in the heart of Tuscany from Rome

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Tuscany, Lucca, San Gimignano

Duration9 days

From

USD 2,332

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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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Super Sales

Tuscan Escape - May 2026

(4 reviews )

No booking fees

Best price guaranteed

Great trip overall. The day trip were great. I wish the hotel was near a town or close to restaurants, but overall very great trip

Chill outLocal culture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Tuscany, Florence, Lucca

Rome, Tuscany, Florence, Lucca, Montalcino

Duration7 days

From

USD 1,325

USD 1,285

Saving

USD 40

View Tour

All Tuscany Tours in May 2026

Page 2 of 26 Trips in Tuscany during May 2026 with 1,315 Reviews

Get a customized trip to Tuscany in May 2026

Page 2 of 26 Trips in Tuscany during May 2026 with 1,315 Reviews

Europe Explorer - May 2026

Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - May 2026

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

Italy: Tuscany and Umbria Vineyard Walks - May 2026

La Dolce Vita - 11 days - May 2026

Italian Expresso - 5 days - May 2026

Amsterdam to Rome - May 2026

Mediterranean Coastal Journey Spain, France & Italy - May 2026

Rome & Live Like a Local in a Tuscan Villa - May 2026

Tuscan Treats - May 2026

Italian Indulgence - May 2026

Tuscan Escape - May 2026

Europe

Asia

South America

Africa

North America

Oceania

Polar

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

All Tuscany Tours in May 2026

Page 2 of 26 Trips in Tuscany during May 2026 with 1,315 Reviews

Get a customized trip to Tuscany in May 2026

Page 2 of 26 Trips in Tuscany during May 2026 with 1,315 Reviews