Greece Sailing Adventure: Cyclades Islands

Intrepid Travel · 10 days
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
Greece Sailing Adventure: Cyclades Islands
10 Days
From AUD $2880
Trip Type
Group Tour
Activity Level
Average

Rating


(20 reviews)

Greece Sailing Adventure: Cyclades Islands

Greece Sailing Adventure: Cyclades Islands

Intrepid Travel · 10 days
Duration

10 days

Tour Type

Group Tour

Accommodations

Moderate

Physical Rating

Average

Guide Language

English

Experience Overview

Sail through the gorgeous Greek Islands on a ten-day seafaring adventure around the Cyclades. Setting off from Santorini, you’ll cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos.

Highlights

  • 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.
  • Walk along the volcanic rim of Santorini, past white villages that cling to cliffs and watch as day turns to night during sunset at the caldera – this is a memory you’ll bring home!
  • 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.
  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village.
  • Visit Mykonos for the quintessential Greek Islands experience. Embrace your hedonistic side with the boutique culture and nightlife or relax on one of the many beaches dotted along the coast.

Trip Details

Duration

10 days

Transportation

Boat

Tour Type

Group Tour

Guide Language

English

Starts

Santorini – Ios, Greece

Finishes

Santorini, Greece

Accommodations

Moderate

Travel Style

SailVentures

Physical Rating

Average

Itinerary

1
Day 1: Santorini – Ios
Kalimera! Welcome to Greece. Your adventure begins in Santorini, where you’ll meet your skipper and fellow travellers at Cafe Spartakos at 1 pm at Athinios Port. If you’ve got time, consider arriving a couple of days early to see all that Santorini has to offer. There’s heaps of amazing restaurants, shops and bars in the island's capital, Thira, not to mention some of the most beautiful beaches and landscapes. Check out the volcanic beaches or take a walk along the caldera's rim to Firostefani, Imerovigli and Oia – this walk is also recommended at sunset, especially! After meeting your crew, you’ll board your yacht – your home for the next seven nights. You’ll sail to Ios’ port, where you’ll have some free time to explore the nearby beaches or check out Hora's shops, restaurants and bars – it’s all accessible within a short walk from the harbour.

Accommodation:

  • Overnight boat (Number of Nights: 1)
2
Day 2: Amorgos
Sail to the rugged island of Amorgos. 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 11th-century monastery, Moni Hozoviotissis, for beautiful views of the Aegean Sea. Maybe head to 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.

Accommodation:

  • Overnight boat (Number of Nights: 1)
3
Day 3: Small Cyclades
Cast off and sail to the Small Cyclades this morning. This group of islands are home to some small fishing villages as well as beautifully clear waters and beaches. While all these islands once harboured communities, 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, maybe sample some fresh seafood in a waterfront taverna and sit back to enjoy the peace of the Mediterranean.

Accommodation:

  • Overnight boat (Number of Nights: 1)
4
Day 4: Naxos
Today you'll make your way to the largest Cycladic Island of Naxos. There’s the option of taking a daytrip 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. Maybe 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, 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 have lunch in the hills at a family tavern. Tonight, taste the local brew with a shot of Kitron (lemon liquor).

Accommodation:

  • Overnight boat (Number of Nights: 1)
5
Day 5-6: Syros
Sail to the island of Syros, dropping by the Bay of Gaidharos 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. Over the next two days, maybe catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleys (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 town hall in the main square. At night, 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.

Accommodation:

  • Overnight boat (Number of Nights: 2)
6
Day 7: Mykonos
Head to Mykonos today – 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 galleries and boutiques in town, see the unique architecture of the Church of Panagia Paraportiani or relax on one of the island’s white beaches. Tonight, maybe wander down to Little Venice, where colourful wooden balconies hang precariously over the sea – this is the ideal spot to sit back with a cocktail and enjoy the Aegean sunset. After, join the fun of Mykonos’ notorious nightlife.

Accommodation:

  • Overnight boat (Number of Nights: 1)
7
Day 8: Sifnos
Set sail for the island of Sifnos, known for its production of high-quality ceramics. The island's bare hills contrast the 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 – the capital of Sifnos. The Museum of Popular Art displays old photographs, textiles, costumes and pots. Climb up the headland for panoramic ocean views and see the medieval architecture of the fortress of Kastro.

Accommodation:

  • Overnight boat (Number of Nights: 1)
8
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 waterfront tavernas 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, maybe wander up the hill to the Church of the Panagia – an excellent vantage point to view the sunset.

Accommodation:

  • Overnight boat (Number of Nights: 1)
9
Day 10: Santorini
Bid farewell to the open water as you catch the ferry back from Ios to Santorini, arriving back at Athinios Port just before 12 pm. With no other activities planned, your adventure ends today in Santorini. Your skipper can assist with organising a taxi to drop you off at your hotel or Santorini International Airport. If you would like to extend you stay, just get in touch with your booking agent ahead of time.
Exclusions
  • Flights to and from origin and destinations
  • Airport transfers (arrival and departure)
  • Anything else not explicitly listed in tour inclusions
  • Recommended gratuities/tipping
  • Optional activities/tours
  • Personal expenses
  • Travel insurance
  • Visas, meals and beverages not stated in the list of inclusions.
Important Information
Meals

When meals are not included, your tour leader (where available) will be happy to help with restaurant recommendations, bookings, and directions. Please let us know if you have any dietary needs or preferences. We willdo our best to accommodate these, though we cannot guarantee that every request can be met.

Luggage

You are responsible for your personal belongings throughout the tour. You will need to carry your own bags between the vehicle and your hotel room. Drivers will assist with loading and unloading luggage from the vehicle.

Mobility

Travellers requiring wheelchair access should contact our sales and service team, who can make enquiries on your behalf.

Fitness Level

This tour requires an Average level of fitness. Activities are paced gently and include leisure time. You may be expected to join guided walks of up to one hour, navigate short stairways and mild inclines, and manage your own luggage. You should also be able to board and exit all transport without assistance.

Travellers are expected to be self-sufficient and capable of handling all aspects of their journey. Please discuss your circumstances and support needs with your booking agent to confirm this trip is suitable.

If you are unsure, we recommend consulting your doctor before booking or travelling. (Note: I assume each tour has a different description depending on level of fitness required).

Sightseeing

If a planned site visit is unavailable due to changes in operating hours or holiday closures, the itinerary may be altered, or a comparable activity will be substituted where possible and subject to availability.

Visas

Visa conditions can change. Once you receive your travel documents, check with the relevant embassy, consulate, or immigration office of your destination for the latest information.

  • It is your responsibility to ensure you have the correct and valid travel documents and to comply with all entry requirements.
  • Non-Australian citizens must also confirm visa and identification requirements with the appropriate consulate or visa agency.
  • Certain occupations (for example, journalists, government officials, or those working in charities) may face additional restrictions when applying for visas, which could affect the type of application required.
Departure Dates & Surcharges: See checkout for live dates and availability.
AUD $2,880
(Tour only)
Per Person Twin Share

Duration: 10 days

Trip Type: Group Tour

Activity Level: Average

Sail through the gorgeous Greek Islands on a ten-day seafaring adventure around the Cyclades. Setting off from Santorini, you’ll cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos.

Price based on per person in Double Room for departure 02 May 2026

Customer Reviews

Overall Rating
Excellent
4.5
Guide
Excellent
4.5
Itinerary
Excellent
4.5
Accommodations
Excellent
4.5
Transportation
Excellent
4.5
Tour Operator
Excellent
4.5
Food
Excellent
4.5
4.5
Mallory
Traveled, September 2023

10/01/2023

Our skipper, George was great! He was highly experienced and knowledgeable. He gave us briefings at every port so we would have local insight and history of the area. We had lots of opportunities to swim in crystal clear water and explore the islands. Great trip!

3.5
Katie
Traveled, September 2023

09/26/2023

This was a great experience sailing around the Cyclades Islands. It's good to get a taste of each island (you don't get to stay at each one for long) and get a taste for boat life. Our itinerary had to change due to poor weather but we got to spend a night on anchor instead which was fun. The swim spots we went to were fantastic. The accommodation on the boat is basic and tight when at full capacity. Definitely pack light if you can. Best for the group when everyone pitches in to help with cleaning, shopping or food prep so be prepared to help out and don't be lazy as your group will notice!

Tour Operator

Intrepid Travel is a global adventure travel company, dedicated to providing sustainable, experience-rich travel opportunities. They’ve been the leader in ethical, small-group travel since 1989 - taking people around the world for more than 30 years. They’re the world’s largest travel B Corporation - dedicated to being the best travel company for the world. In 2002, they established The Intrepid Foundation so their travellers could make a lasting impact on the communities they had visited. Although Intrepid Travel absorbs all administrative costs of The Intrepid Foundation, they are separate legal entities, allowing The Intrepid Foundation to grow independently. Intrepid Travel is made up of a collection of tour operator brands and 28 destination management companies all united by one vision: To change the way we all see the world.

In Business Since 1989