Upcoming Tours – 2025

This tentative list is based on requests and early planning for 2025. If you have an idea, let me know!

April – Sicily, the Beautiful Crossroads of Culture and History 

Mt. Etna, Arab architecture, Greek ruins and a confluence of cultures that bring you unparalleled food, wine and travel experiences. Sicily is Italy…but it isn’t. We’ll stay in a former palace and former castle on the south and west sides so we can enjoy boat tours, volcanic wines, cannoli and more.

April — Santorini, Greece and Italy’s Apulia Region  

We will soak up the splendor of Santorini before hopping over to the heel of the boot. We’ll enjoy the traditional foods and wines of both areas, tour the dramatic coastlines by boat, and visit the olive-tree capital of Italy. More than 60 million trees in Apulia, where we’ll wander through ancient olive groves – some as old as 3,000 years!

May —  History and Beauty: Rome, Lake Como and Venice

We will enjoy the beauty and richness of North Italy’s gems: at the foot of the Alps, we will visit Lake Como and get acquainted the beautiful village of Menaggio. Then we’ll cross the top of the boot by highspeed train to spend time in the “floating city” of Venice. We’ll dine on the traditional foods of these regions, see spectacular views from mountain tops and bell towers, and spend some time on the water – lake and lagoon!

May – Athens and Santorini Greece (FULL)

This custom trip will explore ancient Greece, from the coastal views of Santorini in the Cyclades islands to Athens and its rich history and ruins. We’ll soak up art and architecture, history and culture and taste our way through this magnificent country.

June — Rome and the Amalfi Coast (FULL)

We’ll visit ancient Rome and Pompeii for our history fix and then spend several days at our seaside estate for some R&R. Seafood, local wines and a day on our private boat to Capri make this a very popular trip!

August –  Palio horse race in Siena! (FULL)

This unique trip to Tuscany in the summer 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. In addition to staying in the heart of Siena, we’ll also spend part of our time at a country estate near San Casciano – allowing us two different and very special “home bases.”

September — Lake Como and the Italian Alps

We will enjoy the beauty and richness of North Italy’s gems: the Italian Alps and Lake Como. We’ll dine on the traditional foods of these regions, see spectacular views from Mont Blanc (France) and make our way over to Lake Como to see villas, vineyards and a bit of Switzerland.

September – Turin, Italy and Normandy, France

What a collection of history and culture. Turin boasts not only the famous Shroud, but it’s also the birthplace of the global Slow Food movement . We will wine and dine our way through Piedmont and then to France, traveling through the glorious Alps by train. We’ll make our way to the Normandy area to walk the steps of brave WWII soldiers and experience the many cultural offerings in this beautiful corner of France.

September — Fall in Tuscany: colorful Chianti and the Riviera

If your image of Italy includes cypress trees, red tile roofs, wine and pasta, this is your trip. We’ll spend half our time in the Chianti countryside at a beautiful villa and half in a beach town on the Ligurian Sea. We’ll visit gems like Siena and Lucca, join a truffle hunter and his dog in the woods, and cook alongside a world-class chef in his convent-turned-cooking school.

October — Lisbon, Portugal (FULL)

This informal tour will be recon together: discovering history and culture of this western-most country of mainland Europe. I will book tours and transfers and we will vet them together as we refine this ideal visit for future travelers. Seafood, wines and the Portuguese language will provide new opportunities, especially for previous Italy travelers.

Send me a note if you have a request or itinerary idea! lynette@cypresstours.net

In an ancient olive grove of 2,000-year-old trees in Apulia, the “heel of the boot.”