Your itinerary
Day 1
Day 1: Santorini
Arrive in Santorini. Meet the group at 11:00 for a welcome meeting, then take a short water-taxi to Thirassia to begin the Cyclades sailing. Free time to explore before or after.
Meals: Breakfast,Lunch
Day 2
Day 2: Cyclades - Ios/Small Cyclades/Naxos
Flexible sailing among Ios, the Small Cyclades and Naxos (weather-dependent). On Ios: relax at Magganari beach, visit Homer’s tomb, walk up to Hora. On Naxos: optional island day trip (Temple of Demeter, microbrewery, Church of Panagia Drosiani, views of Mount Zeus, taverna meal) and a visit to the Naxos Wildlife Protection Association (sea turtle conservation).
Meals: Breakfast,Lunch
Day 3
Day 3: Cyclades - Ios/Small Cyclades/Naxos
Flexible sailing among Ios, the Small Cyclades and Naxos (weather-dependent). On Ios: relax at Magganari beach, visit Homer’s tomb, walk up to Hora. On Naxos: optional island day trip (Temple of Demeter, microbrewery, Church of Panagia Drosiani, views of Mount Zeus, taverna meal) and a visit to the Naxos Wildlife Protection Association (sea turtle conservation).
Meals: Breakfast,Lunch
Day 4
Day 4: Cyclades - Ios/Small Cyclades/Naxos
Flexible sailing among Ios, the Small Cyclades and Naxos (weather-dependent). On Ios: relax at Magganari beach, visit Homer’s tomb, walk up to Hora. On Naxos: optional island day trip (Temple of Demeter, microbrewery, Church of Panagia Drosiani, views of Mount Zeus, taverna meal) and a visit to the Naxos Wildlife Protection Association (sea turtle conservation).
Meals: Breakfast,Lunch
Day 5
Day 5: Mykonos
Arrive in Mykonos. Optional visits to the windmills and Little Venice; enjoy beaches and the island’s nightlife.
Meals: Breakfast,Lunch
Day 6
Day 6: Cyclades - Syros/Paros/Sifnos/Folegandros
Weather-dependent sailing among Syros, Paros, Sifnos and Folegandros. Syros: markets, short hikes, beaches or scuba. Paros: hidden beaches, villages, Naousa port and Venetian ruins. Sifnos: walking trails, views over olive groves and wild juniper, local ceramic workshops. Folegandros: hike, snorkel, and explore the cliffside city of Hora; sunset cocktails.
Meals: Breakfast,Lunch
Day 7
Day 7: Cyclades - Syros/Paros/Sifnos/Folegandros
Weather-dependent sailing among Syros, Paros, Sifnos and Folegandros. Syros: markets, short hikes, beaches or scuba. Paros: hidden beaches, villages, Naousa port and Venetian ruins. Sifnos: walking trails, views over olive groves and wild juniper, local ceramic workshops. Folegandros: hike, snorkel, and explore the cliffside city of Hora; sunset cocktails.
Meals: Breakfast,Lunch
Day 8
Day 8: Cyclades - Syros/Paros/Sifnos/Folegandros
Weather-dependent sailing among Syros, Paros, Sifnos and Folegandros. Syros: markets, short hikes, beaches or scuba. Paros: hidden beaches, villages, Naousa port and Venetian ruins. Sifnos: walking trails, views over olive groves and wild juniper, local ceramic workshops. Folegandros: hike, snorkel, and explore the cliffside city of Hora; sunset cocktails.
Meals: Breakfast,Lunch
Day 9
Day 9: Cyclades - Syros/Paros/Sifnos/Folegandros
Weather-dependent sailing among Syros, Paros, Sifnos and Folegandros. Syros: markets, short hikes, beaches or scuba. Paros: hidden beaches, villages, Naousa port and Venetian ruins. Sifnos: walking trails, views over olive groves and wild juniper, local ceramic workshops. Folegandros: hike, snorkel, and explore the cliffside city of Hora; sunset cocktails.
Meals: Breakfast,Lunch
Day 10
Day 10: Santorini
Depart after breakfast. Shuttle from Thirassia to Santorini (drop-off location may vary). Free time on Santorini before onward travel; your CEO can assist with trip extensions.
Meals: Breakfast
What’s included
What’s not included
Additional information
Meals Included
No meals included
Group Size
8
Solo Travellers
Meals
Eating is a big part of traveling. Travelling with G Adventures you experience the vast array of wonderful food that is available out in the world. Generally meals are not included in the trip price when there is a choice of eating options, to give you the maximum flexibility in deciding where, what and with whom to eat. It also gives you more budgeting flexibility, though generally food is cheap. Our groups tend to eat together to enable you to taste a larger variety of dishes and enjoy each other’s company. There is no obligation to do this though. Your CEO will be able to suggest favourite restaurants during your trip. The above information applies to G Adventures group trips. For Independent trips please check the itinerary for details of meals included. For all trips please refer to the meals included and budget information for included meals and meal budgets.
On our Greek sailing trips, the G Adventures Skipper/CEO will help you make a food kitty, where around EUR 90 per person, per trip will be added to the kitty for small food items on board to cover breakfasts, lunches and the odd dinner.
Breakfasts and lunches are prepared by yourself, and most dinners are taken ashore at local restaurants.
Minimum Age
Minimum age of 16 years for this trip.
Local Dress
Important Notes
IMPORTANT NOTES
1. Space is limited on the boat and especially in your cabin. You can only take soft sided luggage on board, such as a mid-sized backpack or soft duffel bag. (Less than is 15kgs). Suitcases are not appropriate for our Sailing adventures as they are not pliable enough to fit into the niches available for luggage.
2. Fresh water is very limited on board, and as such, we ask for your understanding that showers are limited to one quick shower per person a day.
3. It’s important to note that the beds in the cabins are not the usual length of a standard bed. The length is approximately 1.8 meters (6 feet), and the single bunks are 1800mm (6 feet) x 610mm (2 feet).
4. Electrical outlets on board are European style with 2 pins (240V), and are only operational while in port. It is recommended to bring an external battery pack for charging personal electronics.
5. This is a self-catering trip, and everybody will be expected to participate, cleaning up after themselves, and keeping the boat ship shape at all times (including washing the dishes, and emptying the bins when ashore.)
6. Physical Rating:
– You should be able to climb up small steep ladders, or walk over a wooden plank (without a handrail) when boarding/disembarking the vessel, and be physically able to carry your luggage.
– You will often be climbing in and out of the yachts inflatable tenders at beach landing spots, and boarding/disembarking the tender from the yacht in sometimes challenging conditions.
– Moving around the yacht while under sail can be challenging as it moves in the waves or heels over to its side. You should be physically able, and comfortable, to move about in such conditions.
7. Please note that this tour combines with other G Adventures tours. As such, the staff and some travel companions on your tour may have previously been traveling together with G Adventures, prior to Day 1 of your tour. Likewise, some staff and travel companions may be continuing together on another G Adventures tour, after your trip concludes. You may also be changing Skipper CEO and boat.
8. If you don’t have an EU Drivers Licence – make sure to get an International Licence, to be able to rent a car on the islands.
9. Pre-Trip Contact (G App)
For an enhanced sailing experience, we highly recommend downloading the G Adventures App. This essential tool provides your joining instructions and allows you to connect with your Skipper CEO two days prior to your departure date. Your Skipper CEO will also reach out through the G app chat section with any updates and information required. Stay informed and prepared by accessing all necessary trip details through the app. Ensure a seamless and stress-free start to your adventure by downloading the G Adventures App today!
OPTIONAL ACTIVITIES
We recommend allowing up to €175 (approx. $200 USD) for optional activities during your trip. This gives you the flexibility to take part in and enjoy unique local experiences, like G curated guided cultural tours, tastings, or outdoor adventures that can enhance your journey and help you connect more deeply with the culture and destination.
Group Leader
Skipper/CEO (Chief Experience Officer) throughout.
About Accommodation
A NOTE REGARDING SMALL SPACES ON SAILBOATS:
– Please note that the rooming for these boats is assigned upon arrival and neither particular cabins, nor berths can be guaranteed. You will be sharing a bunk or double bed with your travel partner or one of your fellow passengers of the same sex and sharing the bathrooms onboard.
– Please be aware that as this is a real sailboat and not a cruise vessel, the space on board is tight. The sleeping quarters on sailboats are generally kept to a minimum size in order to maximize public space and performance.
– It may be possible to smell engine and/or diesel fumes when in the cabins, due to their proximity to the engine room. Most travel is done during the day, so it is unlikely you will be in the cabin when the engine is running.
– Some people are not comfortable with the type of close quarter arrangements typically found on sailboats, however if a real sailing experience on a real sailboat is what you are after, then this experience should more than make up for cramped quarters.
– Opportunities to sleep in open air on main deck are often available.
– Please note that the Skipper CEO will also be sharing the ship’s quarters and amenities with you.
– Power onboard is 220V on European 2-pin sockets. Please note that this is not suitable for sleeping aid machines(CPAP), as the power source will not always be available. Bringing a battery pack for charging is recommended.
Cabin Types and Bookings:
– Sailboats offer a mix of different cabin types and sizes. Some cabins have bunk beds, others have double beds, and in some cases there are ensuite bathrooms while in others bathrooms are shared.
– Specific cabins cannot be guaranteed unless pre-booked, but you may choose to book a particular cabin type in advance with our sales team, where availability allows. Booking an ensuite option provides the added convenience of a private bathroom, while shared facilities are common in standard cabin arrangements.
What to Take
There is very limited space on the yachts. We recommend the use of a soft duffel bag or backpack. A good size daypack is also essential, as is a waterproof / windproof ‘spray’ jacket, even in warm climates.
PLEASE NOTE: Hard suitcases are not permitted due to limited space. Curling tongs and hairdryers cannot be used onboard.
Spending Money
Every traveller is different and therefore spending money requirements will vary. Some travellers may drink more than others while other travellers like to purchase more souvenirs than most. Please consider your own spending habits when it comes to allowing for drinks, shopping and tipping. Please also remember the following specific recommendations when planning your trip.
Syros Ermoupoli Markets & Ano Syros Lanes
On day 6–9, a call at Syros invites you to stroll Ermoupoli’s waterfront markets, where neoclassical facades and the Vaporia quarter frame the harbour. Hear your skipper’s pointers to landmarks like the Apollo Theater and sample a slice of local culture with famed loukoumi sweets from traditional confectioners.
Climb the steps to Ano Syros, a medieval hill town of tight lanes and stone terraces with sweeping views of shipyards and domes below. As the administrative capital of the Cyclades, Syros blends Catholic and Orthodox traditions, a history of 19th-century shipbuilding and trade, and a relaxed island tempo—perfect for a coffee pause and people-watching before returning to the marina.
Paros Naousa Venetian Ruins & Parikia Old Town
Touching Paros between day 6 and day 9, amble through Naousa’s fishing port, where caiques bob beside the Venetian Castle ruins at the harbour mouth. Follow white-laned alleys laced with bougainvillea to find cafés and boutiques, or pause by the seafront for a snack as waves lap the quay.
In nearby Parikia, visit the revered Panagia Ekatontapiliani (the “Church of 100 Doors”; entry subject to opening hours), and learn how Parian marble once travelled the ancient world. Your skipper will highlight spots for sunset views and taverna dinners so you can enjoy a free evening soaking up Cycladic light and easy-going island life.
Sifnos Trails Walk & Ceramics Stop
On day 6–9, stretch your legs on Sifnos and walk the island’s waymarked trails past olive terraces, thyme-scented hillsides and blue-domed chapels. Views open towards Kastro’s clifftop houses and quiet coves where the water glows a translucent turquoise—ideal for a cooling dip after your hike.
Sifnos is famed for pottery, so your skipper can point you to a small, family-run studio to meet local ceramicists and browse hand-thrown bowls and amphora-inspired forms. Learn how clay and kilns shaped the island’s economy, then enjoy a free afternoon in Apollonia’s lanes or by the shore before returning to the yacht.
Folegandros Hora Evening Stroll & Sunset Views
When we moor at Folegandros (typically day 6–9), ride up to Hora’s traffic-free squares, where white facades, wooden balconies and bougainvillea-draped courtyards create a timeless Cycladic tableau. Wander the Kastro quarter for intimate lanes and glimpses of the sea between houses.
As evening softens, those keen on a short climb can follow the zig-zag path to the Church of Panagia above town. From the terrace, sunset over the Aegean bathes cliffs and rooftops in rose-gold light—an ideal moment to pause for photos and reflection before a relaxed taverna supper back in the square.
Mykonos Town Orientation & Windmills Viewpoint
On day 5, join your skipper for a short orientation that threads through Mykonos Town’s whitewashed alleys to the iconic windmills and the seafront arcades of Little Venice. Get tips on navigating the maze-like lanes, finding quieter cafés, and choosing beaches that suit your mood.
Hear how Mykonos evolved from pastoral outpost to cosmopolitan hub, balancing glamour and Cycladic tradition. With bearings set, you’ll enjoy a free afternoon to swim, shop for local crafts, or photograph the blue-shuttered mansions as the Aegean breeze ripples the harbour.
Naxos Highlights Road Trip: Temple of Demeter, Panagia Drosiani & Tastes
Between day 2 and day 4, opt for a full-day excursion to explore inland Naxos. With route suggestions from a local expert, you’ll drive to the Temple of Demeter amid fertile fields, continue to the Church of Panagia Drosiani to view rare early-Christian frescoes, and pause at scenic lookouts facing Mount Zeus (Zas). There’s time to visit a microbrewery for a tasting and unwind over a traditional taverna meal.
This experience reveals the island’s agricultural backbone—olive groves, citron orchards, marble hamlets—and its layered history from antiquity to Byzantium. This is an Optional experience at additional cost, bookable on tour with your Skipper/CEO. Note: Non-EU drivers require an International Driving Permit to rent a car.
Syros Scuba Diving Experience
While in Syros (day 6–9), venture below the surface on a guided dive with a local centre. After a safety briefing and gear fitting, descend along rocky reefs where groupers cruise and octopus dens hide between boulders. Expect excellent visibility and the gentle sway of sunlit, blue water as you fin past ledges and swim-throughs.
Instructors share the island’s maritime heritage and point out endemic species, tying your underwater time to the Cyclades’ broader ecology. This is an Optional experience at additional cost, bookable on tour through your Skipper/CEO. Suitable for certified divers; introductory dives may be available depending on conditions.
Mykonos Windmills & Little Venice Aperitivo
As evening falls on day 5, join a relaxed outing to the Mykonos windmills before settling into Little Venice for a seaside drink. Watch waves lick the quay as cafés light up and the sun dips over the harbour, casting a warm glow across white facades and cobalt shutters.
It’s a simple, stylish way to experience the island’s glitzy-meets-traditional spirit—perfect for photos and people-watching. This is an Optional experience at additional cost (drinks not included), bookable on tour with your Skipper/CEO, who can recommend the best spots and secure a sunset table when available.
G for Good: Naxos Wildlife & Conservation Awareness Experience
During our time near Naxos (typically on day 2–4), join a session with the Naxos Wildlife Protection Association, a G Adventures–supported initiative. Learn about sea turtle biology, the challenges facing Caretta caretta in the Aegean, and the rescue protocols for injured or stranded turtles. The team shares practical tips for observing wildlife responsibly and reporting issues.
This is more than a talk; it’s a chance to engage with a community-led effort safeguarding fragile habitats. Gain insight into nesting beaches, light pollution, and fishing-line hazards, then leave prepared to take responsible action on and off the water. The experience connects your voyage to the islands’ living ecology and underscores why these seas deserve careful stewardship.
Ios Chora Hill Walk & Magganari Beach Time
When winds and schedule align between day 2 and day 4, step ashore on Ios for a gentle climb to Chora’s whitewashed lanes, passing blue-domed chapels and the hillside Odysseas Elytis amphitheatre. Your skipper points you towards the viewpoints so you can enjoy a free afternoon exploring cafés and tiny squares at your own pace.
Those seeking the sea can continue to Magganari Beach on the island’s south side for translucent shallows and pale, fine sand. If time allows, some choose to visit the evocative site known as Homer’s Tomb for wide Aegean vistas. The balance of hilltop heritage and relaxed shoreline gives Ios its easy-going Cycladic character.
Aegean Swim & Snorkel Stops
Between day 2 and day 9, your skipper will drop anchor in sheltered bays for refreshing swim breaks and easy snorkelling from the stern ladder. Use the included gear to snorkel over Posidonia seagrass meadows and rocky reefs alive with damselfish and curious wrasse, or simply float in clear, sapphire water warmed by the Mediterranean sun.
These pauses reveal the Cyclades’ coastal textures: pumice shelves, pale-sand coves and white-sculpted cliffs that glow at midday. Your crew will indicate best practices for the sea—respecting marine life and currents—so you can pause for photos and reflection or enjoy a free half-hour of saltwater therapy before hoisting sails again.
Santorini Welcome Meeting, Safety Briefing & Embarkation Sail
On day 1, meet your Skipper/CEO and travelling companions for a concise welcome meeting and safety briefing. Learn the layout of the 17m sailing yacht, how to move safely on deck, and the etiquette of life at sea, including the shared food kitty used for onboard breakfasts and lunches. Your skipper outlines the flexible route and the influence of the Meltemi winds.
Weather permitting, you’ll set sail from Santorini, gliding beneath the volcanic cliffs crowned by Oia and Fira. Hear how this volcanic caldera shaped Cycladic history and admire the inky-black lava shoreline against whitewashed villages. Settle into the rhythm of the boat, stow your gear, and enjoy a free evening on deck as the Aegean breeze signals the start of your voyage.