Greek Islands Volcanic Wine Tour: Santorini, Milos & Sifnos

Your private Greek Islands wine tour begins in Athens, with a private transfer from the airport or your Athens hotel to the port of Piraeus. Board your ferry to Sifnos (tickets included) and watch the mainland dissolve into open Aegean water as the islands emerge on the horizon.

On arrival in Sifnos, meet your driver for private transfer to Hotel Niriedes, a tranquil seaside property styled in traditional Cycladic whitewash. Relax this evening with a three-course welcome dinner combined with island wine. This is your first taste of what Sifnos has been cooking in clay vessels and wood-fired ovens for centuries.

After breakfast, embrace your creative side with an immersion in one of the Cyclades’ oldest artistic traditions. Sifnos once supplied pottery to the entire Mediterranean. The island’s craftsmen became so synonymous with the trade that a potter anywhere in the Cyclades was simply called a Sifnios, regardless of where he was born.

This morning visit a working studio where the wheel still turns the way it has for centuries. Your private pottery workshop traces every stage of production: the fire-resistant local clay that made Sifnian ceramics uniquely suited to cooking vessels, the techniques for throwing and glazing, the wood-fired kiln. 

After this morning’s pottery workshop, the afternoon is free to relax and explore the island at your own pace.

Start your day by visiting a working family farm, walking the kitchen garden where the herbs and vegetables for your cooking class grow in the rocky soil. Your hosts will demonstrate five traditional recipes, chosen for what each represents in Sifnian food culture. 

Depending on the season, recipes might include Revithada, a chickpea dish soaked overnight, then slow-baked in a sealed clay pot for six hours; mastelo, lamb marinated in red wine and dill, rested on a grid of vine twigs inside its clay vessel and slow-roasted for hours; Mizithropita, the island’s honey-sweet cheese pie. 

Enjoy a farmhouse lunch to follow, paired with Greek wines.

The remainder of your day is free to relax and explore on your own. 

Enjoy a final breakfast by the sea in Sifnos before your private transfer to the ferry port.

The fast ferry crossing from Sifnos to Milos takes about 45 minutes (tickets included).

Meet your driver on arrival to the port of Adamas in Milos for private transfer to the 4-star Santa Maria Village Resort & Spa.

Relax and enjoy the rest of the day at leisure until your included welcome dinner this evening (wines purchased locally).

Milos is one of five active centers of volcanic activity in Greece. The island emerged from the Aegean floor roughly 3 million years ago as a series of eruptions built it from the seabed up. As a result, Milos is geologically rich in volcanic stone. 

Before the invention of bronze, Milos was the main source of obsidian (volcanic glass) that Neolithic traders exported throughout the Eastern Mediterranean. The ancient Miliotes were the first people in the Aegean to mine and trade on a regional scale. Your private Milos geology tour travels deep into the past, tracing the island’s volcanic formations through colorful landscapes and 10,000 years of mining history.

Understanding the island’s volcanic soil will also help inform your appreciation of local viticulture during tomorrow’s Milos wine tasting.

Today’s experience lasts about 5 hours, during which a light lunch is included (wines purchased locally).

The remainder of the afternoon is free to relax at the hotel, go to the beach, and explore independently. 

Compared with Santorini, Milos is not a significant wine producing Greek island, but it does have one of the most ingenious wineries in the Cyclades. This small production family winery near Pollonia cultivates indigenous Cycladic grape varietals Assyrtiko, Monemvasia, Malagouzia. Mavrotragano, Aidani, Mandilaria, Savatiano and Roditi in small plots next to a naturally formed volcanic cave. The cave’s constant temperature year round allows for natural thermal regulation during vinification and aging. 

Begin your visit with a guided walk through the vineyards, learning the family’s techniques for growing vines in Milos’s arid conditions, then continue to the winery where you’ll discover the family’s process of vinification and aging inside a volcanic cave.

Your private tasting will include eight different wines, a local grappa, local cheeses and other local products. 

The rest of your day is free to relax and enjoy the island.

Meet your driver in the hotel lobby this morning for transfer to the ferry in Adamas (fast ferry tickets included). 

Relax on board the ferry for the approximately two-hour journey to Santorini. As the island comes into view, the visual contrast between the deep blue Aegean Sea and white-washed houses show why Santorini is one of the most photogenic of all the Greek islands. 

What remains of Santorini today is one semi-circular half of an ancient volcano that blew itself apart during a massive eruption in approximately 1,600 BC. Its cone collapsed into an undersea caldera, creating the dramatic westward-facing cliffs that bless Santorini with its famous Aegean sunsets.  

On arrival in Santorini, meet your driver for private transfer to the 4-star El Greco Resort & Spa, located within walking distance of Fira and the caldera rim. Settle in and spend the rest of the day at your leisure. Dinner tonight is under your own arrangement. We will be happy to make recommendations and assist you with reservations. 

Winemaking on Santorini dates back more than 4,000 years. Key to the success of Santorini vineyards is the kouloura — vines trained into a low, spiral shaped basket close to the ground. The kouloures are a centuries-old solution to the island’s two most relentless forces: the Meltemi winds and the summer sun. The grapes (usually Assyrtiko) grow inside the basket, protected from the wind and sun by the vine’s own canopy. The vine’s roots reach deep through volcanic ash and pumice, sometimes 30 feet down, searching for water. 

Your private Santorini wine tour visits two or three distinct wineries selected for their commitment to indigenous varietals, and for how their wines express the island’s unique volcanic terroir. Your private Santorini wine tastings will showcase a selection of styles from across the island, including Santorini’s famous Vinsanto. Local cheese and olive pairings are included, along with lunch at one of the wineries or a local restaurant. 

Return to your hotel in the late afternoon and enjoy the rest of the day to relax. We will be happy to suggest restaurants in Fira and assist you with reservations. 

Today is yours to explore more of Santorini at your own pace before tonight’s farewell sunset cruise.

Depart on a sailing catamaran in the late afternoon, when the Aegean light turns amber and the caldera walls begin to glow. Sail to the volcanic islet of Nea Kameni, the active center of the caldera, where you’ll be able to swim in the sea and the hot springs.

Enjoy a BBQ dinner on board, served with Santorini wines, as you watch the sun set over the Aegean. 

Savor a final morning on the island before checkout and private transfer to Santorini airport or ferry port. 

If you’re not ready for the adventure to end, ask us about extensions. Nearby options include wine tours on Crete, mainland Greece, Italy, Croatia, and Turkey.