10 Best Florence Multiday Tours in May 2026

Halloween Super Sales

France, Switzerland, and Italy by Rail - May 2026

No booking fees

Best price guaranteed

Make tracks to embark on a 23-day adventure encompassing France, Switzerland and Italy. Using trains as your primary means of moving about, you’ll get started in the City of Lights before moving into Lausanne and Lucerne, with their UNESCO World Heritage-listed vineyard terraces and views of the Alps. Then it’s into Italy, where you’ll have plenty of free time to explore Rome before heading north to the Tuscan countryside, Cinque Terre, the Portofino Peninsula and more. Best of all, you’ll do with the comforts of rail transport and an expert local leader showing you the way.

ExplorerTrain tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Paris, Venice, Rome, Florence, L

Paris, Venice, Rome, Florence, Lucca, La Spezia, Asti, Lake Como, Lausanne, Lucerne, Bellinzona, Ticino Valley Natural Park

Duration23 days

From

USD 10,145

USD 9,841

Saving

USD 304

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Best Of Italy By Train - 11 Days - May 2026

18% OFF TODAY

Halloween Super Sales

Best of Italy by Train - 11 days - May 2026

No booking fees

Best price guaranteed

Travel from Venice to Rome using Italy's high speed rail network on this 11-day escorted group tour. Enjoy a guided walking tour and gondola ride in the Canal City before moving on to Florence, Cradle of the Renaissance. Venture to Tuscany to see the historic walls of Siena and the medieval towers of San Gimignano, and take in the ancient ruins of Pompeii. Stay for three nights in charming Sorrento, with an included day trip to Capri and an Amalfi Coast cruise. End in Rome, with a guided walking tour and included tickets to the Hop-On Hop-Off bus tour service, plus a farewell group dinner in Trastevere.

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Venice, Florence, Sorrento

18% OFF TODAY

Duration11 days

From

USD 4,555

USD 3,756

Saving

USD 799

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18% OFF TODAY

Halloween Super Sales

Highlights of Italy - May 2026

No booking fees

Best price guaranteed

Check off every bucket list dream on this highlight-packed adventure through the heart of Italy. Stand in awe of Rome’s ancient history as you explore landmarks that have shaped the world, then lose yourself in Florence’s Renaissance art and architecture that redefined creativity. Walk along Venice’s iconic canals, where every turn feels like a scene from a romantic postcard. And just when you think it can’t get better, indulge in Montepulciano’s rich culinary traditions and savor its world-renowned wines. From timeless history to indulgent flavors, this life-changing journey will leave you longing for just one more taste of Italy’s magic.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Venice, Montepulciano, Florence

18% OFF TODAY

Duration9 days

From

USD 2,489

USD 2,052

Saving

USD 437

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Halloween Super Sales

Solo-ish Italy - May 2026

(4 reviews )

No booking fees

Best price guaranteed

Wonderful community feel amongst travelers. A wonderful introduction to Italy, kudos to you guys for putting this together. Planning and logistics on this level is impressive. Would highly recommend, just not when Alive is CEO

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-100 yrs

Operated in

english

Destinations

Florence, Venice, Cinque Terre

Florence, Venice, Cinque Terre, Lake Como

Duration9 days

From

USD 2,699

USD 2,618

Saving

USD 81

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Halloween Super Sales

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 1,362

USD 1,321

Saving

USD 41

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Halloween Super Sales

Irresistible Italy: Rome to Venice - May 2026

Trip customizable

Best price guaranteed

Unveil Italy’s splendor with a 12-day journey through Rome, Florence, La Spezia, Milan, and Venice. Indulge in a wine tasting in Chianti, a private transfer from Rome’s airport, and captivating guided tours of the Colosseum, Roman Forum, and Pompeii. Discover Tuscany’s charm on a coach tour, revel in the scenic Cinque Terre with a 48-hour Train Card and embrace the elegance of Lake Como with unlimited boat trips. Savor a gondola ride in Venice and glide through high-speed train adventures across Italy’s iconic landscapes

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Colosseu

Rome, Florence, Venice, Colosseum, La Spezia, Cinque Terre, Milan, Lake Como

Duration12 days

From

USD 3,126

USD 3,033

Saving

USD 94

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Halloween Super Sales

Essence of Italy: Rome, Sorrento, and Venice - May 2026

Trip customizable

Best price guaranteed

Begin your journey with a private transfer from Rome's airport to your hotel, followed by a half-day guided small group tour of the Colosseum and Roman Forum. Travel by high-speed train to Naples, where you'll enjoy a private transfer to Sorrento with a 2-hour stop to explore Pompeii. In Sorrento, take an excursion to the enchanting Capri Island, including a visit to the Blue Grotto. Continue to Florence via high-speed train, and immerse yourself in the city's rich history. Conclude your Italian adventure in Venice, with a gondola ride through its picturesque canals

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Sorrento

Rome, Florence, Venice, Sorrento, Capri

Duration9 days

From

USD 2,868

USD 2,782

Saving

USD 86

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Halloween Super Sales

Fantasia Italiana - May 2026

Trip customizable

Best price guaranteed

Travelling from eternal Rome and up through the hazy hills of Tuscany, you’ll spend five days sampling the best of Assisi, Siena, Florence, Bologna, Venice, and Montepulciano. Catch the spirit of La Vita Bella as you explore elegant Florentine piazzas, rummage through handcrafted artisanal treasures, sip world-class wines, and float down intimate Venetian canals. Experience a taste of Italy with us!

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice

Duration5 days

From

USD 1,003

USD 973

Saving

USD 30

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Halloween Super Sales

A Taste of Italy: 8 Days - Classic - May 2026

Trip customizable

Best price guaranteed

Like a creamy gelato or hot espresso, one taste of Italy can linger for a lifetime. Travelling from the Eternal City of Rome and up through the hazy hills of Tuscany, you’ll spend eight days sampling the best of Assisi, Siena, Florence, Bologna, Venice, and Montepulciano. Catch the spirit of La Vita Bella as you explore elegant Florentine piazzas, rummage through handcrafted artisanal treasures, sip world-class wines, and float down intimate Venetian canals

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice

Duration8 days

From

USD 1,527

USD 1,481

Saving

USD 46

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Tuscan Adventure: Rome To Florence - May 2026

22% OFF TODAY

Halloween Super Sales

Tuscan Adventure: Rome to Florence - May 2026

(4 reviews )

No booking fees

Best price guaranteed

It was great and I am really glad I did it through a travel company, because planning it on my own would have taken so much time that i probably wouldn't be able to go.

Explorer

Tour Type

Small Group Tour

Accommodation

Villa, Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Florence, Montepulciano

22% OFF TODAY

Duration7 days

From

USD 1,849

USD 1,435

Saving

USD 414

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Best Of Northern Italy: Florence To Venice - May 2026

18% OFF TODAY

Halloween Super Sales

Best of Northern Italy: Florence to Venice - May 2026

(4 reviews )

No booking fees

Best price guaranteed

The overall experience was a lot of fun. We were busy the entire time, and with the great organization managed to see a whole lot of Northern Italy within such a small amount of time. We were very nicely taken care of by our CEO. She was extremely responsive and helpful when any questions came her way, and she absolutely loved when people asked questions about Italy and it's storied history. Great trip!

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Venice, Cinque Terre

Florence, Venice, Cinque Terre, Lake Como

18% OFF TODAY

Duration8 days

From

USD 1,999

USD 1,648

Saving

USD 351

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Halloween Super Sales

Rome Florence Venice and Milan by Rail - May 2026

Trip customizable

Best price guaranteed

This tour will take you on a memorable train ride across the major touristic cities of Italy. You’ll begin by exploring Rome, with stunning feats of civilization, modern and age-old alike. Colosseum, Navona Square, Pantheon, Spain Square, and Trevi Fountain are a few places that you can visit. The next place where you’ll take a train would be Florence. History, art, countryside, and delicious food are the gist of what this capital city of Tuscany has in store for you. Accademia and Uffizi Galleries are a must-visit. After Florence, The City of Water, Venice, awaits your arrival. Though the journey to Venice via rail is gorgeous, the city itself has its charm. Riding into a gondola through the Grand Canal and being mesmerized by the city’s beauty should be on your list. In addition, take a walking tour covering St Mark’s Square, Doge's Palace, Bell Tower, etc. Finally, we are at the last city of this train tour—Milan. An epitome of great fashion and design, Milan is a heart stealer. Apart from the latest cultural trends, you can even get a slice of history by visiting the Milan Cathedral. Also, ensure not to miss Leonardo Da Vinci’s stupefying Cenacolo, the Last Supper, which is one of the most famous artworks in the world. This train journey is one of the most popular Italy travel packages, offering a comprehensive tour of Italy's iconic cities.

Explorer

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Milan, Rome, Florence, Venice

Duration9 days

From

USD 1,102

USD 1,069

Saving

USD 33

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Rome To Venice Express - 4 Days - May 2026

18% OFF TODAY

Halloween Super Sales

Rome to Venice Express - 4 days - May 2026

No booking fees

Best price guaranteed

COACH TOUR: Travel from Rome to Venice on this 4-day express tour. Explore the medieval town of Assisi and UNESCO-listed Siena. Take in the highlights of Florence, 'Cradle of the Renaissance' and enjoy free time to further explore at your own pace. In Bologna, see the historic sites and embark on a street food experience before arriving in the Canal City of Venice.

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Venice, Florence

18% OFF TODAY

Duration4 days

From

USD 1,355

USD 1,117

Saving

USD 238

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Halloween Super Sales

Journeys: Northern Italy, Venice to Florence - May 2026

(4 reviews )

No booking fees

Best price guaranteed

Amazing. Tour guide made the trip worth while!

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Venice, Cinque Terre

Duration7 days

From

USD 3,099

USD 3,006

Saving

USD 93

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All Florence Tours in May 2026

Page 3 of 44 Trips in Florence during May 2026 with 155 Reviews

Get a customized trip to Florence in May 2026

Page 3 of 44 Trips in Florence during May 2026 with 155 Reviews

France, Switzerland, and Italy by Rail - May 2026

Best of Italy by Train - 11 days - May 2026

Highlights of Italy - May 2026

Solo-ish Italy - May 2026

Flavours of Tuscany & Cinque Terre - May 2026

Irresistible Italy: Rome to Venice - May 2026

Essence of Italy: Rome, Sorrento, and Venice - May 2026

Fantasia Italiana - May 2026

A Taste of Italy: 8 Days - Classic - May 2026

Tuscan Adventure: Rome to Florence - May 2026

Best of Northern Italy: Florence to Venice - May 2026

Rome Florence Venice and Milan by Rail - May 2026

Rome to Venice Express - 4 days - May 2026

Journeys: Northern Italy, Venice to Florence - 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 Florence Tours in May 2026

Page 3 of 44 Trips in Florence during May 2026 with 155 Reviews

Get a customized trip to Florence in May 2026

Page 3 of 44 Trips in Florence during May 2026 with 155 Reviews