Why Cypress Tours to Italy?

Check out our tours and get ready for an unforgettable experience!

Santorini and Italy’s “Heel”

Santorini and Italy’s “Heel”

History and beauty, land and sea, food and wine – wrapped up in two countries on your bucket list. Santorin, Greece, and Italy’s Apulia Region: olive oil, wine, trulli houses and the most coastline of any Italian region.

From Venice to Viareggio

From Venice to Viareggio

This adventure explores the north of Italy’s boot, from Venice on the east coast to the Cinque Terre on the west cost. Wine estates, beach towns, truffle hunting and balsamic vinegar of Modena – so many flavors to enjoy!

Summer in Tuscany and Palio Horse Race

Summer in Tuscany and Palio Horse Race

This unique trip to Tuscany includes the centuries-old celebration on August 16: the Palio horse race! We will have exclusive balcony seats above the crowd and celebrate in Siena in the days leading up to the event.

Have It All! Wine Country and the Amalfi Coast

Have It All! Wine Country and the Amalfi Coast

This 11-day tour combines the medieval mystique and Etruscan caves of Orvieto with the serene and scenic Amalfi Coast. We’ll dine in a cave, visit wineries, make gnocchi and spend a day on the sea in our private boat.

local Italian man holding a bottle of wine and presenting it to a table

Custom Package Options

Let’s design your custom turn-key travel experience together! My network of professionals will treat you like family and help you experience Italy’s highlights and hidden gems like a local.

boy holding flag for flag throwing ceremony

Holidays and Festivals

Every village in Italy has a patron saint, and they celebrate that saint in a big way at least once year. There are holidays and festivals somewhere every month. Let me know what interests you, and we’ll make a plan!

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