Journey through the Mediterranean’s most storied islands—Sicily, Cyprus, and Crete—on a richly layered exploration of history, landscapes, and living traditions. From ancient civilizations and UNESCO World Heritage sites to coastal villages and vibrant historic cities, this journey blends cultural depth with striking natural beauty.

Travel by ferry, private vehicle, and short flights as you explore archaeological treasures, medieval citadels, and seaside communities shaped by centuries of maritime exchange. Along the way, expert local guides bring each destination to life, while a balanced pace allows time for independent discovery, regional cuisine, and memorable Mediterranean moments.

May 8-June 3 and October 3-29, 2027

To book this tour click "See Availability." A calendar pops up showing the first date of the tour. Click the date of the tour to continue to the booking page. If you want a future date, use the arrow on the top right to move forward on the calendar to view additional dates. Prices listed are in USD. To see the price in your currency, at the top of the booking page there is a drop-down menu, click that to select your country and it will convert the price to your currency. You can pay in your own currency.

Trip pricing is contingent upon a minimum of four (4) participants and is subject to adjustment should this minimum not be met.

• Walk through Sicily’s great ancient civilizations, from the Greek theaters of Siracusa and Segesta to the Valley of the Temples in Agrigento and the vast ruins of Selinunte.

• Marvel at UNESCO treasures, including the Villa Romana del Casale’s world-renowned mosaics and Palermo’s Arab-Norman masterpieces.

• Experience Sicily’s diverse cultural influences, from Mazara del Vallo’s North African Kasbah to Monreale’s glittering Byzantine mosaics.

• Visit Nicosia, the world’s last divided capital, crossing between the Republic of Cyprus and Northern Cyprus

• Exclusive visit to the Turkish Republic of Northern Cyprus

• Visit Omodos & Kalopanayiotis Rural Villages in Cyprus

• Rethymno, one of the most historical and picturesque towns on Crete.

• Explore Crete’s Minoan heritage, including historic towns and rugged coastal scenery

• Accommodations with breakfast. 4-5*.

• Accompanying guides (different ones for each country)

• Arrival & Departure Transfers on tour dates

• AC Transport van or minibus depending on group size

• Entrance Fees

• In Cyprus & Crete: 13 lunches, 2 dinners based on min 4 people

• Cooking lesson in a traditional family home in Chania

• Flight ticket Chania-Athens

• International airfare

• Tourist tax (if any)

• Tips to drivers, guides, and hotel porters

• Meals for group size less than 4 people

• Flight ticket Catania-Larnaca

• Flight ticket Larnaca-Heraklion