Greece Sailing Adventure: Cyclades Islands

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Has very high quality customer experiences and demonstrated commitment to responsible travel practices. read more
4.6 . Excellent
94%
Travel Style: Array Relaxed
Physical Level: All or most of day hiking or biking, hills included. Moderate
Lodging Level: Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels. Value (3*)
10 days
From: $ 2,357 $ 236 / day
Checking price

Overview

Highlights (Bullets)

  • A Santorini sunset around the caldera is a sight to behold. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs and watch as day turns to night in the most stunning of ways.
  • Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.
  • Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life. This is island living, Greek style.
  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village – a couple of the many experiences to be had around the Cyclades.
  • No Greek island adventure is complete without a stop in Mykonos. Embrace your hedonistic side with its boutique culture and nightlife or relax on one of the many beaches dotted along the coast.

Short Description

Fulfil your dreams of sailing the Greek Islands on a ten-day seafaring adventure around the renowned Cyclades. Setting off from Santorini, cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos. Throw in some freshly caught seafood, local wines and a laidback way of life, and you’re set to drift and roll to the patterns of the ocean. Cool off with regular swims in the Aegean’s turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places. Trust us – it’s all smooth sailing from here.

Style Small ship cruise
See all the highlights and popular spots on a classic tour.
Itinerary Focus Classic Highlights
Mid-range budget with accommodations ranging from comfortable lodges, guesthouses, and homestays to three star hotels.
Lodging Level Value (3*)
Flight & Transport Inclusions All internal ground transport
Start City Santorini
End City Santorini

Destinations

Greece

Attractions & Cities Visited

Mykonos Santorini

Activities & Interests

Sailing

Age Requirement

15-99

No single supplement
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Itinerary

Day 1 Santorini – Ios

Welcome to Greece! Meet your skipper and shipmates at Cafe Spartakos at 1pm at Athinios Port Santorini and take a private boat transfer over to the island of Thirasia where you will board your yacht. If you’ve got time, why not consider arriving a couple of days early to enjoy Santorini. Check out the range of restaurants, shops and bars in the island's capital, Thira. An absolute must is to take a walk along the caldera's rim to Firostefani, Imerovigli and Oia. This is a particularly memorable experience at sunset, but make sure you leave plenty of time so you aren't walking in darkness. Santorini's volcanic beaches are another must-see. After your welcome meeting, set sail (approximately 5 hours) through Santorini’s caldera, cruising across the Aegean Sea to drop anchor at the island of Ios via Manganari Beach. Check out Hora's shops, restaurants and bars – a short walk from the harbour in Ios – which all come alive in the evenings. Please note depending on the weather conditions and berthing availability for our yachts, we might cross from Santorini to Ios by Ferry. This will mean you will arrive at Ios in the afternoon providing you with more free time to explore this beautiful Island.

Day 2 Amorgos

Sail to the rugged island of Amorgos (approximately 4 hours). This is the stunning location of Luc Bresson's film, 'The Big Blue'. Stop for a swim at Paradisi Beach before continuing along the coast to the port of Katapola. The restaurants, cafes and bars along the waterfront are an excellent place to relax and enjoy views of classic Cycladic windmills and an old Venetian castle. You might like to explore the ancient Minoan Settlement or drive up to the spectacular 11th-century monastery, Moni Hozoviotissis, for beautiful views of the Aegean Sea. Also worth a visit is the village of Hora, sitting high up in the rocky mountainside. Stroll through the labyrinth of stone laneways and Byzantine churches surrounding the town square. The Amorgos Archaeological Collection is housed nearby in Gavros Tower.

Day 3 Small Cyclades

Cast off and sail to the Small Cyclades this morning (approximately 4 hours). This group of islands boast quaint fishing villages, clear waters and beautiful beaches. While all of these islands once harboured communities in ancient times, the middle ages saw this reduced to just pirates and goats. Today, only Koufonisia, Iraklia, Schinoussa and Donousa have permanent residents, with the largest population said to be around 300. In the evening, perhaps sample fresh seafood in a waterfront taverna and sit back to enjoy the peace of the Mediterranean.

Day 4 Naxos

Today you'll make your way to the largest Cycladic island of Naxos. There’s the option of taking a day trip around the island, but you can always stay behind and relax. The island’s best beaches are to the south, where water sports are also on offer. Perhaps hike up to the old Roman Catholic neighbourhood of Kastro, where winding laneways, mansions and churches all retain a medieval feel. While here, stop by the Roman Catholic Cathedral in the square, and the nearby Archaeological Museum which is housed in the former Jesuit School of Commerce. Take an optional trip to the countryside to observe rural life, see one of the oldest temples in Greece and enjoy lunch in the hills at a family tavern. Get a taste of the local brew with a shot of Kitron (best described as a lemon liquor). In the evenings, indulge in the vibrant nightlife of Hora.

Day 5-6 Syros

Sail to the island of Syros (approximately 4 hours), 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. Perhaps 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 culture in the capital of Syros and the Cyclades, Ermoupoli, and check out the magnificent town hall in the main square.

Day 7 Mykonos

In the morning, raise anchor and set off on a short cruise (approximately 3 hours) to an island packed with beauty and glamour, Mykonos. With a history of around 5000 years, the island is said to be named after Apollo's grandson. It was also the mythological base for a deadly battle between Zeus and the Titans, their giant petrified bodies forming the rocks of the island. Browse the chic galleries and boutiques in town, examine the unique architecture of the Church of Panagia Paraportiani or relax on one of the island’s white beaches. In the evening, perhaps wander down to Little Venice, where colourful wooden balconies hang precariously over the sea – the ideal spot to sit back with a cocktail and enjoy an Aegean sunset. Afterwards, join in the fun of Mykonos’ notorious nightlife.

Day 8 Sifnos

Set sail for the island of Sifnos, known for its production of high quality ceramics. The island's bare hills belie fertile valleys of wild juniper, terraced olive groves and almond trees. The beach in the main port of Kamares is one of the best on the island and the ideal place to swim. Wander among the whitewashed houses, churches and chapels of the village of Apollonia, which is the capital of Sifnos. The Museum of Popular Art displays old photographs, textiles, costumes and pots. Climb up the headland to enjoy panoramic ocean views and see the medieval architecture of the fortress of Kastro.

Day 9 Folegandros

Sail towards the tranquil island of Folegandros this morning. Named after the son of a former King of Crete, Folegandros has suffered a long history of colonisation and occupation like many of the surrounding islands. In the port of Karavostasis, the pebbly beach or a waterfront taverna are nice places to relax. Take a stroll through the island’s capital of Hora, one of the oldest villages in the Cyclades. The area in and around the Kastro is the most striking. In the evening wander up the hill to the pretty Church of the Panagia, an excellent vantage point to view the sunset.

Day 10 Santorini

Bid farewell to the open water as you sail back through the caldera from Folegandros and drop anchor at Thirasia Island at about 9.30 am. Take a 10.30 am private boat transfer to Athinios Port, Santorini, arriving at about 11 am. With no other activities planned for today, your adventure ends on arrival in Santorini. Your skipper can assist with organising a taxi to drop you off at your hotel or Santorini International Airport.

Availability

Checking price
Price From $ 2,357
Price Per Day: $ 236 per day
Checking price
Start DateFinish DateBase PriceAvailability 
May-06-2023May-15-2023$ 2,3578 spots left Reserve
May-16-2023May-25-2023$ 2,5072 spots left Reserve
May-23-2023Jun-01-2023$ 2,357Sold Out Reserve
May-26-2023Jun-04-2023$ 2,3579 spots left Reserve
Jun-05-2023Jun-14-2023$ 2,3575 spots left Reserve
Jun-15-2023Jun-24-2023$ 2,4425 spots left Reserve
Jun-16-2023Jun-25-2023$ 2,4875 spots left Reserve
Jun-25-2023Jul-04-2023$ 2,44210 spots left Reserve
Jul-05-2023Jul-14-2023$ 2,4674 spots left Reserve
Jul-09-2023Jul-18-2023$ 2,44211 spots left Reserve
Jul-15-2023Jul-24-2023$ 2,5329 spots left Reserve
Jul-25-2023Aug-03-2023$ 2,5775 spots left Reserve
Aug-01-2023Aug-10-2023$ 2,53210 spots left Reserve
Aug-04-2023Aug-13-2023$ 2,53211 spots left Reserve
Aug-14-2023Aug-23-2023$ 2,53210 spots left Reserve
Aug-24-2023Sep-02-2023$ 2,5326 spots left Reserve
Aug-25-2023Sep-03-2023$ 2,53211 spots left Reserve
Sep-03-2023Sep-12-2023$ 2,5124 spots left Reserve
Sep-13-2023Sep-22-2023$ 2,4428 spots left Reserve
Sep-17-2023Sep-26-2023$ 2,3579 spots left Reserve
Sep-23-2023Oct-02-2023$ 2,35711 spots left Reserve
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4,186 Intrepid Travel Travel Reviews & Ratings

94%
4.6 out of 5 (100+ reviews)
Excellent 3,164
Great 667
Average 132
Disappointing 66
Terrible 157
Value
4.6
Guide
4.6
Activities
4.6
Lodging
4.6
Transportation
4.6
Meals
4.6

Greece Sailing Adventure: Cyclades Islands

The trip met all expectations, was a

5.0
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Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
The trip met all expectations, was a lovely, pleasant experience, the skipper was knowledgeable and competent.

I picked this trip due to the

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
I picked this trip due to the itinerary of seeing numerous islands in a short time, and I had the freedom to be able to do that, getting to most islands by early afternoon.
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It's a very unique trip I have

5.0
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Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
It's a very unique trip I have ever done. Small group is nice, and it's more relax.

Great trip leader, brand new boat

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
Great trip leader, brand new boat

I was very pleased with everything.Besides it

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
I was very pleased with everything.Besides it is the 2nd time I travel with intrepid

Intrepid continues to provide an authentic yet

5.0
Details
Value5.0
Guide5.0
Activities5.0
Lodging5.0
Transportation5.0
Meals5.0
Intrepid continues to provide an authentic yet affordable experience. My kind of travel.

Details

Flight & Transport Inclusions

All internal ground transport Boat

Group Size

Small Group - 24 max

Maximum Number of People in Group: 11

Accommodations

Overnight boat (9 nights)

Guides

On this trip you will be accompanied by one of our skippers. Your skipper's role involves taking charge of the sailing, the safety of the vessel and safety for all passengers on board. Skippers all hold a Yacht Master Offshore license or higher and have completed an intense training and review process before sailing with us. They are also fully qualified in CPR and First Aid. The aim of the skipper is also to take the hassle out of your travels by organizing the overall operation and smooth-running of the trip, managing trip logistics and coordinating the kitty (where applicable). Your skipper will provide information on the places you are travelling through, offer suggestions for things to do and see, recommend great local eating venues and introduce you to our local friends. While not being guides in the traditional sense you can expect skippers to have a broad general knowledge of the places visited on the trip, including historical, cultural, religious and social aspects.

Age Notes :

Min. Age: 15

Max Age: 99

Additional Information

Finish point

  • Cafe Spartakos
  • Athinios Port
  • Santorini
  • GREECE

Trip ID#:

intrepid-ZSRV

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