Itinerary
- Day 1
Santorini
Meet your skipper and crew at Cafe Spartakos in Athinios Port at 1 pm, then board your yacht for the week. Before setting sail, you can walk around Thira to get a feel for the island, check out the volcanic beaches, or stroll along the caldera's rim. Later you'll head to Ios port where you'll have free time to find beaches and wander through the town's shops and restaurants.
Optional Activities
- Arrive early to explore Santorini's restaurants, shops and bars
- Visit volcanic beaches
- Walk along the caldera's rim to Firostefani, Imerovigli and Oia
- Explore Ios beaches
- Browse Hora's shops, restaurants and bars
Landmarks Athinios Port Thira Firostefani Imerovigli Oia Ios Port 
- Day 2
Ios to Amorgos
Your yacht sails to Amorgos, the island where 'The Big Blue' was filmed. You'll stop at Paradisi Beach for a swim, then dock at Katapola port. From there, check out waterfront restaurants with views of Cycladic windmills and a Venetian castle, or head inland to find ancient Minoan sites, an 11th-century monastery perched with Aegean views, the mountain village of Hora, and the Amorgos Archaeological Collection.
Optional Activities
- Swim at Paradisi Beach
- Explore Katapola waterfront restaurants, cafes and bars
- Visit the ancient Minoan Settlement
- Visit Moni Hozoviotissis monastery (11th-century)
- Explore the village of Hora
- Visit Amorgos Archaeological Collection in Gavros Tower
Landmarks Amorgos Paradisi Beach Katapola Moni Hozoviotissis Hora Gavros Tower 
- Day 3
Small Cyclades
This morning you sail to the Small Cyclades, a group of islands with small fishing villages and crystal-clear waters. Only four islands have year-round residents: Koufonisia, Iraklia, Schinoussa, and Donousa. Spend the day relaxing and swimming at beautiful beaches. By evening, head to a waterfront taverna for fresh seafood while you take in the quiet of the Mediterranean.
Optional Activities
- Swim and relax on the islands' beaches
- Explore fishing villages
- Sample fresh seafood at waterfront taverna
Landmarks Koufonisia Iraklia Schinoussa Donousa - Day 4
Naxos
You arrive at Naxos, the largest Cycladic island, and have options for how to spend your time. Take an optional island tour or stay aboard to relax. If you go ashore, head to southern beaches for water sports, hike up to the medieval Kastro neighborhood with its narrow lanes and churches, visit the Roman Catholic Cathedral and Archaeological Museum, or join an optional countryside trip to see rural villages, ancient temples, and have lunch at a family taverna. Later, try local Kitron liquor.
Optional Activities
- Day trip around Naxos
- Visit southern beaches
- Try water sports
- Hike to Kastro neighborhood
- Visit Roman Catholic Cathedral
- Visit Archaeological Museum
- Optional countryside trip to observe rural life and ancient temples
- Lunch at family tavern in the hills
- Taste local Kitron (lemon liquor)
Landmarks Kastro Roman Catholic Cathedral Archaeological Museum 
- Day 5
Syros
Your yacht sails to Syros, stopping at Bay of Gaidharos for a swim. The island has a relaxed vibe and neo-classical buildings from its time as a safe haven during the Greek Revolution. Explore the fortress-like village of Ano Syros with its stone archways and Aegean views, or head to the capital Ermoupoli to find authentic Greek food and local culture. In the evening, consider joining an optional group dinner at a neighborhood family's home with homemade food and seafront views.
Optional Activities
- Swim at Bay of Gaidharos
- Bus trip to Ano Syros village
- Explore stone archways and narrow alleys
- Sample authentic Greek food and culture in Ermoupoli
- Visit town hall in main square
- Optional group dinner at neighborhood family's home
Landmarks Bay of Gaidharos Ano Syros Ermoupoli 
- Day 6
Syros
You have the day on Syros to move at your own pace. Relax on the yacht, return to places you liked, or find new spots to check out around the island.
- Day 7
Mykonos
Today you head to Mykonos, an island with about 5,000 years of history. Browse galleries and boutiques, see the distinctive Church of Panagia Paraportiani, or relax on white sand beaches. As evening comes, walk over to Little Venice where colorful wooden balconies hang over the sea and order a sunset cocktail before heading out to experience the island's famous nightlife.
Optional Activities
- Browse galleries and boutiques
- Visit Church of Panagia Paraportiani
- Relax on white beaches
- Visit Little Venice
- Enjoy sunset cocktails at Little Venice
- Experience Mykonos nightlife
Landmarks Church of Panagia Paraportiani Little Venice 
- Day 8
Sifnos
You set sail for Sifnos, well-known for producing high-quality ceramics. The landscape has bare hills mixed with fertile valleys of wild juniper, terraced olive groves, and almond trees. Swim at Kamares beach, walk through whitewashed houses and churches in the capital Apollonia, visit the Museum of Popular Art, and climb the headland for panoramic ocean views and medieval Kastro fortress architecture.
Optional Activities
- Swim at Kamares beach
- Explore Apollonia village
- Visit Museum of Popular Art
- Climb headland for panoramic ocean views
- Visit medieval fortress of Kastro
Landmarks Kamares Apollonia Museum of Popular Art Kastro - Day 9
Folegandros
Your yacht sails toward Folegandros, a quiet island with a long history of settlement. Relax at the pebbly Karavostasis beach or sit at waterfront tavernas. Take a stroll through Hora, one of the oldest villages in the Cyclades, and check out the striking Kastro area. In the evening, climb up to the Church of the Panagia for a great spot to watch the sunset.
Optional Activities
- Relax at Karavostasis pebbly beach
- Dine at waterfront tavernas
- Explore Hora village
- Visit Kastro area
- Visit Church of the Panagia for sunset views
Landmarks Karavostasis Hora Kastro Church of the Panagia - Day 10
Return to Santorini
Your sailing adventure ends today. You catch the ferry from Ios back to Santorini, arriving at Athinios Port just before noon. Your skipper can help arrange a taxi to your hotel or Santorini International Airport if you need one.
Optional Activities
- Extend your stay in Santorini
Landmarks Athinios Port
