View from the top of a cliff in Santorini
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Operated by Intrepid Travel

Sail Greece: Santorini to Mykonos

From
CAD 1,733
Duration
8 days
Countries
Greece
Activity
moderate
Group size
Max 11
Rating
4.8 · 137 reviewsvia Intrepid Travel

The adventure

Dreaming of crystal-clear waters, whitewashed villages, historical ruins, lively Greek culture and deliciously fresh cuisine straight from the sea? Then sail from Santorini to Mykonos on this eight-day boat trip in Greece. Spend blissed-out days under sun drenched skies enjoying the best of the Greek Islands, including Santorini, Ios, Amorgos, the Small Cyclades, Naxos and Mykonos. Watch the sunset, explore olive groves, feast on fresh food and wine and fall asleep to the gentle rocking of your yacht every night.

At a glance

Duration
8 days
Route
Santorini → Mykonos
Countries
Greece
Activity level
moderate
Style
Beach & Islands, Culture & History, Cycling, Food & Drink, Sailing & Marine
Group size
Max 11
Ages
15+
Flights
Not included
Solo travellers
Welcome

Day by day

Charming coastal town with hills and sea under a cloudy sky.
Your journey through

Greece

Day 1Santorini – IosKalimera! Welcome to Greece. You’ll meet your skipper at 1 pm at Cafe Spartakos, where your adventure will immediately begin. If you arrive in Santorini early (and it’s recommended that you do), maybe check out the local restaurants, shops and bars in Fira or walk along the caldera's rim to Firostefani, Imerovigli and Oia for sunset. Santorini's volcanic beaches are another must-see. Check out Red Beach or the black beaches of Perissa, Vlhada, Perivolos and Agios Georgios. The first port of call is the local supermarket to buy supplies as a group. The starter pack will include provisions for some breakfasts, lunches and/or snacks. If you have any special dietary requirements, please make sure you notify your agent at the time of booking so they can accommodate your requests. Then, board a ferry from Santorini to Ios and walk the short distance to your yacht – your home for the next seven nights. When you’ve settled in, check out the nearby sandy beaches on Ios or head to Hora's shops, restaurants and bars (a short walk from the harbour), which all come alive in the evening. Your skipper can suggest the best bar to watch the sun go down as you get to know your new travelling companions.
A breathtaking sunset view of a cruise ship near the island of Santorini, Greece.Santorini
Kalimera! Welcome to Greece. You’ll meet your skipper at 1 pm at Cafe Spartakos, where your adventure will immediately begin. If you arrive in Santorini early (and it’s recommended that you do), maybe check out the local restaurants, shops and bars in Fira or walk along the caldera's rim to Firostefani, Imerovigli and Oia for sunset. Santorini's volcanic beaches are another must-see. Check out Red Beach or the black beaches of Perissa, Vlhada, Perivolos and Agios Georgios. The first port of call is the local supermarket to buy supplies as a group. The starter pack will include provisions for some breakfasts, lunches and/or snacks. If you have any special dietary requirements, please make sure you notify your agent at the time of booking so they can accommodate your requests. Then, board a ferry from Santorini to Ios and walk the short distance to your yacht – your home for the next seven nights. When you’ve settled in, check out the nearby sandy beaches on Ios or head to Hora's shops, restaurants and bars (a short walk from the harbour), which all come alive in the evening. Your skipper can suggest the best bar to watch the sun go down as you get to know your new travelling companions.
Map showing Santorini
Day 2AmorgosVisit the mountainous island of Amorgos today, known for Luc Bresson's film 'The Big Blue.' Amorgos has evidence of society as far back as 4000 BC! At Katapola, the island's main port, you'll see classic Cycladic architecture with windmills and an old Venetian castle. Stroll the waterfront, explore the ancient Minoan settlement or visit the village of Hora (Amorgos town), which sits high on the rocky mountainside. Maybe drive up to the 11th-century monastery, Moni Hozoviotissis, gripping the cliff face with views across the Aegean Sea.
Aerial view of Panagia Hozoviotissa Monastery on Amorgos Island at sunset, featuring stunning coastal cliffs.Amorgos
Visit the mountainous island of Amorgos today, known for Luc Bresson's film 'The Big Blue.' Amorgos has evidence of society as far back as 4000 BC! At Katapola, the island's main port, you'll see classic Cycladic architecture with windmills and an old Venetian castle. Stroll the waterfront, explore the ancient Minoan settlement or visit the village of Hora (Amorgos town), which sits high on the rocky mountainside. Maybe drive up to the 11th-century monastery, Moni Hozoviotissis, gripping the cliff face with views across the Aegean Sea.
Map showing Amorgos
Day 3Small CycladesOver the next two days, you’ll sail to the Small Cyclades, where only Koufonisia, Iraklia and Schinousa have permanent residents. Here, you'll discover clear waters, small beaches, friendly locals and sleepy tavernas all built around the fishing villages. When you dock, you can explore the town and maybe sample some fresh seafood in a waterfront taverna – a great way to take in the sights and sounds of the Mediterranean. Watch the amazing sunsets from the boat or the shores and soak up the atmosphere!
A picturesque church sits atop a hill in Oia, Greece, under a bright blue sky.Small Cyclades
Over the next two days, you’ll sail to the Small Cyclades, where only Koufonisia, Iraklia and Schinousa have permanent residents. Here, you'll discover clear waters, small beaches, friendly locals and sleepy tavernas all built around the fishing villages. When you dock, you can explore the town and maybe sample some fresh seafood in a waterfront taverna – a great way to take in the sights and sounds of the Mediterranean. Watch the amazing sunsets from the boat or the shores and soak up the atmosphere!
Map showing Small Cyclades
Day 4Amorgos to Small Cyclades
Amorgos to Small Cyclades
Map showing Amorgos to Small Cyclades
Day 5NaxosContinue to Naxos today for more beaches, small villages and the fragrant olive groves of Hora (the capital). This place has a mythological history and the Old Town is perfect for a stroll. Follow a pathway up to the impressive Venetian Kastro where mansions, monuments and churches all retain their medieval spirit in a mass of winding laneways. Stop by the old Roman Catholic Cathedral in the square, and the nearby Archaeological Museum, housed in the former Jesuit School of Commerce. Maybe head into the countryside to see the local rural life, visit one of the oldest temples in Greece and chill out in the hills with lunch at a family tavern. Perhaps taste the heady local brew of Kitron (a lemon liquor) and top it off with a walk along the beach.
Captivating coastal view of Naxos Town with bright blue waters under a clear summer sky.Naxos
Continue to Naxos today for more beaches, small villages and the fragrant olive groves of Hora (the capital). This place has a mythological history and the Old Town is perfect for a stroll. Follow a pathway up to the impressive Venetian Kastro where mansions, monuments and churches all retain their medieval spirit in a mass of winding laneways. Stop by the old Roman Catholic Cathedral in the square, and the nearby Archaeological Museum, housed in the former Jesuit School of Commerce. Maybe head into the countryside to see the local rural life, visit one of the oldest temples in Greece and chill out in the hills with lunch at a family tavern. Perhaps taste the heady local brew of Kitron (a lemon liquor) and top it off with a walk along the beach.
Map showing Naxos
Day 6SyrosSail to the island of Syros, dropping by the Bay of Gaidharos along the way for a swim. Known for its relaxed atmosphere and neo-classical architecture, Syros’ neutral role during the Greek Revolution made it a safe haven for the persecuted. You can catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleyways (the views of the Aegean are stunning from up here!). Sample authentic Greek food and soak up the culture in Ermoupoli, the capital. Tonight, maybe immerse yourself in local island life with an optional group dinner at a neighbourhood family's home. Tuck into some homemade cuisine made with fresh, seasonal ingredients and enjoy the views from the seafront.
Beautiful pastel-colored buildings on Syros island coastline at dusk.Syros
Sail to the island of Syros, dropping by the Bay of Gaidharos along the way for a swim. Known for its relaxed atmosphere and neo-classical architecture, Syros’ neutral role during the Greek Revolution made it a safe haven for the persecuted. You can catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleyways (the views of the Aegean are stunning from up here!). Sample authentic Greek food and soak up the culture in Ermoupoli, the capital. Tonight, maybe immerse yourself in local island life with an optional group dinner at a neighbourhood family's home. Tuck into some homemade cuisine made with fresh, seasonal ingredients and enjoy the views from the seafront.
Map showing Syros
Day 7MykonosLifting anchor, set off on a short sail to Mykonos, arriving in the late afternoon. This classic Mediterranean island boasts white-washed architecture and narrow streets and laneways perfect for exploring. The hum of the nightlife, cafes, restaurants, galleries and boutiques give way to the island's best sandy beaches. Soak in the atmosphere by joining fellow sun-seekers and partygoers on the beach or take a daytrip to the sacred island of Delos – the birthplace of Apollo and Artemis. Little Venice has colourful wooden balconies that hang precariously over the sea, and this is the perfect spot to sit back with a cocktail and enjoy an Aegean sunset.
Charming white buildings and vibrant boats in Mykonos harbor on a sunny summer day.Mykonos
Lifting anchor, set off on a short sail to Mykonos, arriving in the late afternoon. This classic Mediterranean island boasts white-washed architecture and narrow streets and laneways perfect for exploring. The hum of the nightlife, cafes, restaurants, galleries and boutiques give way to the island's best sandy beaches. Soak in the atmosphere by joining fellow sun-seekers and partygoers on the beach or take a daytrip to the sacred island of Delos – the birthplace of Apollo and Artemis. Little Venice has colourful wooden balconies that hang precariously over the sea, and this is the perfect spot to sit back with a cocktail and enjoy an Aegean sunset.
Map showing Mykonos
Day 8MykonosYour trip ends today at around 10 am this morning on Mykonos. There are no activities planned, but it’s recommended you book an extra night of accommodation so you have plenty of time to explore and soak up the beauty of this famed island. If you need help booking a few extra days, just get in touch with your booking agent ahead of time.
Explore the picturesque Agios Nikolaos Church by the sea on a sunny day in Mykonos, Greece.Mykonos
Your trip ends today at around 10 am this morning on Mykonos. There are no activities planned, but it’s recommended you book an extra night of accommodation so you have plenty of time to explore and soak up the beauty of this famed island. If you need help booking a few extra days, just get in touch with your booking agent ahead of time.
Map showing Mykonos

Traveller reviews

4.8

Based on 137 reviews · via Intrepid Travel

Discover Greece

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Upcoming departures

DatesPrice / personAvailability
23 Jun 202630 Jun 2026CAD 2,146On requestBook my trip
23 Jun 202630 Jun 2026CAD 2,290On requestBook my trip
23 Jun 202630 Jun 2026CAD 2,290On requestBook my trip
27 Jun 20264 Jul 2026CAD 1,733Only a few spotsBook my trip
27 Jun 20264 Jul 2026CAD 2,527On requestBook my trip
27 Jun 20264 Jul 2026CAD 1,936On requestBook my trip
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