Upcoming Tours – 2024

Tentative dates and destinations below. More information to come. If you have a request, let me know! We have time to tweak this schedule:

April 30 – May 10 NEW! Santorini and Italy’s “Heel” (FULL)

History and beauty, land and sea, food and wine – wrapped up in two countries on your bucket list. We’ll start on the island of Santorini for beaches, wine and gyros. From there we’ll hop across to Bari, Italy, and enjoy all that the heel of Italy’s boot has to offer: olive oil, wine, trulli houses and the most coastline of any Italian region.

May 11 – 22 – Rome, Amalfi Coast and Santorini (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. We’ll hop over to Santorini, Greece to wrap up this magical tour. Seafood, local wines and a day on our private boat to Capri make this a very popular trip!

May 24 – June 3 — Tuscany, Rome and the Amalfi Coast (FULL)

We’ll enjoy the Chianti wine country at our villa surrounded by vineyards and we’ll explore Tuscan gems like Florence, Siena and Panzano. We’ll experience Eternal City and take in must-sees like the Vatican and Colosseum and also get off the beaten path! We’ll finish with time on serene Amalfi Coast – boats, Capri and Limoncello.

June 1-15 – Florence, Rome and on to Greece (FULL)

Similar to the first trip of the season, we’ll visit Rome and Florence and then hop over to Santorini. – and Athens. We’ll soak up art and architecture, history and culture and compare wines from Italy and Greece.

Aug 27–Sept 7 Lake Como and the Italian Alps (FULL)

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 7-17 – The North and The South: Lake Como and Apulia (FULL)

We will soak up the splendor and differences of Italy’s spectacular north and south! From the Italian Alps and Lake Como down to the heel of the boot. We’ll enjoy the traditional foods and wines of both regions, tour Lake Como by boat to see the incredible villas and views, 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!

September 19-29 — Fall in Tuscany: colorful Chianti and the Riviera (FULL)

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.

Sept 28–Oct 8 – Sicily, the Beautiful Crossroads of Culture and History (FULL)

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.

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

With Luca and truffle dog, Giotto, after a successful truffle hunt!