Sail Greece: Mykonos to Santorini - 8 Days



Who is this trip for
Genders
- Female56%
- Male44%
Average age
Start / End
- Mykonos
- Firá
Physical rating
Group size
1 - 11Meals included
0Highlights
- Visit the chic waterfront bars that line the beaches of Mykonos, serving authentic Greek food and cocktails as the sun goes down. This is a great place to eat well and relax!
- Explore the 11th-century monastery of Moni Hozoviotissis, wedged between the dramatic cliffs of Amorgos.
- Head away from the tourist trail to the remote Small Cyclades islands, chock-full of tavernas serving fresh seafood and small villages to explore.
- Hop between paradise islands in the iconic Cyclades by yacht – is there any better way? Swim in the Aegean Sea off the side of the boat and let the waves rock you to sleep each night.
- Watch the sunset from the coast or the deck every night and if you’re game, get up early for sunrise – where better to seize the day than on the sea?
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Summary
Move between the boat, the beach and inviting Greek villages on this relaxing eight-day sailing adventure between Mykonos and Santorini. Spend your days swimming in turquoise waters, lazing on white-sand beaches, sampling mouth-watering local cuisine and exploring coastal villages steeped in history, mythology and beauty. Visit the beautiful islands of Amorgos, Naxos, Small Cyclades and Ios, watch a host of spectacular sunsets and enjoy Greek hospitality before returning to the boat to be rocked gently to sleep at night.
Itinerary
Day 1
Mykonos
Kalimera! Welcome to Greece. Your adventure begins with a welcome meeting at 4 pm at a restaurant called De-Tox Café located at Marina Tourlos. The first port of call is the local supermarket to buy supplies for your trip 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 us at the time of booking so we can accommodate your requests. Before or after the meeting, maybe head out to explore Mykonos or unwind on one of the island’s sandy beaches. Perhaps visit the Church of Panagia Paraportiani or browse the galleries, restaurants and boutiques. Tonight, why not grab your fellow travellers and wander down to Little Venice to enjoy a cocktail by the water at sunset.
Day 2
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 Sea are stunning from up here!). Maybe sample some authentic Greek food and soak up the culture in the capital 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.
Day 3
Naxos
Make your way across the glistening water to Naxos – home to beautiful beaches, fragrant olive groves and the villages of Hora, the capital of Naxos. As the largest Cycladic Island, Naxos also has one of the most colourful mythological histories. The Old Town areas of Hora are perfect for a stroll and some nightlife. Visit the impressive Venetian Kastro, where mansions, monuments and churches all retain their medieval spirit in the winding laneways. Stop by the old Roman Catholic Cathedral in the square, and the nearby Archaeological Museum which is housed in the former Jesuit School of Commerce. The massive Portara stands as the gateway to the unfinished Temple of Apollo on the islet of Palatia, just to the north of the marina. You can also head into the countryside to see local rural life, visit one of the oldest temples in Greece, then chill out in the hills with lunch at a family tavern. Get a taste of the local brew with a shot of Kitron (best described as a lemon liquor) and top it off with a wander along the beach.
Day 4
Small Cyclades
Sail to the Small Cyclades, where only Koufonisia, Iraklia, Schinousa and Donousa have permanent residents. Here, you'll discover clear waters, great beaches, friendly locals and sleepy tavernas all built around the fishing villages. Over the next two days you can explore the towns, maybe sampling some fresh seafood in a waterfront taverna – the perfect way to take in the delights of the Mediterranean. Watch the sunset on the board or on the shores of the sea and get to know your fellow travellers as you sail.
Day 5
Small Cyclades
Sail to the Small Cyclades, where only Koufonisia, Iraklia, Schinousa and Donousa have permanent residents. Here, you'll discover clear waters, great beaches, friendly locals and sleepy tavernas all built around the fishing villages. Over the next two days you can explore the towns, maybe sampling some fresh seafood in a waterfront taverna – the perfect way to take in the delights of the Mediterranean. Watch the sunset on the board or on the shores of the sea and get to know your fellow travellers as you sail.
Day 6
Amorgos
Visit the rugged mountainous island of Amorgos is known for Luc Bresson's film 'The Big Blue.' Amorgos has a history of colonisation and occupation with evidence of a functioning society back as far 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, which was built gripping the cliff face. Soak up the panoramic views across the Aegean Sea and find a good spot for sunset.
Day 7
Ios
Continue to Ios – this island has been inhabited since the early Cycladic times, proudly claiming to be the burial place of epic Greek poet Homer. Ios is home to many gorgeous beaches and is known for the preservation of its classic cube houses, which are packed around the laneways of Hora. A short walk from the harbour are Hora's shops, restaurants, nightclubs, bars and cafes. If you’re seeking a more authentic taste of the Old Town, explore during the day while the masses are beachside. The popular beaches of Gialos and Milopotas are also lively at night with a range of water sports on offer during the day. Valmas, Kolitzani and Tsamaria are all options if you're looking for something a little quieter. Sunset views can be enjoyed from the hill where Panagia Gremiotissa (the Church of the Virgin) sits. The distinctive single palm tree next to the church makes it an icon you can always see from throughout town.
Day 8
Santorini
This morning, catch the ferry from Ios to Santorini to arrive at Athinios Port by 12 pm. If you plan to depart today, make sure your flight doesn’t depart Santorini until after 4 pm. Your skipper can assist with organising a taxi to drop you off at your hotel or Santorini Airport. It’s recommend booking a couple of extra night's accommodation to see all the sights that Santorini has to offer – if you do have the time to extend your adventure, just get in touch with your booking agent ahead of time.
What's Included
Accommodation
Overnight boat (7 nights)
Meals
Breakfasts: 0, Lunches: 0, Dinners: 0
Vegetarian options are available on all meals throughout the adventure.
Vegetarian options availableLocal Guide
GuidedThis adventure is led by a local guide throughout. The main language of this adventure is English. Please contact us for other languages available.
Wifi
Wifi is available during the adventure. In some areas and / or accommodation / transport Wifi may be free.
Dates & Prices
Aug 25
from £1,153Sep 25
from £1,098Oct 25
from £1,133May 26
from £1,323Jun 26
from £1,323Jul 26
from £1,323Aug 26
from £1,323Sep 26
from £1,323Oct 26
from £1,323
- Save 2%Tue 23 Sep 2025 > Tue 30 Sep 2025Guaranteed Departure4 spaces of 11 left£1,525£1,494
- Save 22%Sat 27 Sep 2025 > Sat 4 Oct 20256+ spaces of 11 left£1,400Best offer£1,098
Customer reviews & ratings
We had a fantastic sailing trip from Mykonos to Santorini with Intrepid. Niko was such a safe and reliable skipper who showed us a great time whilst sailing between the islands. We would highly recommend this trip to anyone who would like to experience a genuine sailing experience in the Greek islands.
Rohan Jul, 2025 VerifiedI thoroughly recommend this sailing adventure it is the only way to see the islands ! On the sea with an experienced skipper bring your sense of freedom and enjoy the company of new friends. Single travels do not worry - you will make new travel buddies.
Lisa Jul, 2025 Verified
Essential trip information
Our Important Notes and Packing List cover all essentials, from necessary equipment to inclusions, ensuring you're fully equipped and informed for this extraordinary adventure and more.
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