Upon arrival in Santorini, you’ll be greeted at the airport and transported to our luxurious villa overlooking the iconic caldera. Take some time to relax and soak in the views of the Aegean Sea. In the evening, we’ll gather for a welcome dinner at a local taverna, enjoying authentic Greek dishes and getting to know each other as we kick off our retreat. The night will be spent relaxing and settling into your new home for the next few days.

Meals: Dinner at surprise restaurant included

Stay: Santorini Villa with Caldera Views

We’ll start the day with a little four-wheeler tour around the island, taking in Santorini’s famous blue-domed churches and postcard-perfect landscapes. We’ll stop in quaint villages like Pyrgos and explore some hidden gems, taking in panoramic views along the way. After lunch, we’ll have a relaxing afternoon by the pool before embarking on a private sunset catamaran cruise. We’ll sail along the caldera, stopping to swim in the volcanic hot springs, and enjoy a freshly prepared Greek dinner as we watch the sun set over the water.

Meals: Breakfast, Dinner (onboard the catamaran)

Stay: Santorini Villa

Start your day at your own pace, whether you want to explore the local shops, grab a coffee with a view, or relax by the villa’s pool. In the afternoon, we’ll head to the picture-perfect village of Oia for a private wine tasting tour at a local winery, where we’ll sample Santorini’s famous wines made from indigenous grapes. Afterward, we’ll stroll through the streets of Oia, visiting scenic viewpoints and artisan shops, before watching the world-renowned Oia sunset. The evening is free for you to explore the island’s nightlife or enjoy a quiet dinner with friends.

Meals: Breakfast provided

Stay: Santorini Villa

In the morning, we’ll ferry to the beautiful island of Milos, known for its stunning coastline and laid-back vibe. After checking into our seaside accommodations, we’ll set sail on a private boat tour of the island. You’ll get to swim in the crystal-clear waters, explore hidden coves, and discover the famous Kleftiko sea caves. We’ll end the day with dinner at a beachfront restaurant, watching the sun dip into the horizon while enjoying fresh seafood and local cuisine.

Meals: Breakfast, Dinner

Stay: Milos Seaside Hotel

Today, we’ll explore some of the most unique and picturesque beaches in Greece. Our first stop will be the otherworldly Sarakiniko Beach, with its striking white rock formations and turquoise waters. From there, we’ll visit Firiplaka and Tsigrado beaches, where we’ll spend the day snorkeling, sunbathing, and soaking up the island’s relaxed atmosphere. In the evening, we’ll enjoy a group dinner at a local taverna, savoring traditional Greek dishes while sharing stories from the day.

Meals: Breakfast, Dinner

Stay: Milos Seaside Hotel

After breakfast, we’ll ferry to the stunning island of Kefalonia, where we’ll settle into our villa in the charming harbor village of Fiskardo. In the afternoon, we’ll explore the village’s colorful streets, stopping for coffee and local pastries along the way. The evening will be spent enjoying a sunset dinner overlooking Fiskardo’s peaceful harbor, where we can watch the boats drift in while indulging in Mediterranean flavors.

Meals: Breakfast, Dinner

Stay: Kefalonia Villa

Our last full day of the retreat will be filled with adventure as we explore the natural wonders of Kefalonia. We’ll start with a visit to the iconic Myrtos Beach, often voted one of the most beautiful beaches in the world. Next, we’ll visit the enchanting Melissani Cave, where we’ll take a boat ride through its shimmering underground lake. In the evening, we’ll gather for a farewell dinner at a local taverna, celebrating the unforgettable week we’ve shared together.

Meals: Breakfast, Dinner

Stay: Kefalonia Villa

After breakfast, it’s time to say goodbye to Greece. We’ll provide transportation to the airport, but for those extending their stay, we’re happy to provide recommendations for further exploring Kefalonia or the nearby islands.

Meals: Breakfast