Sail & Stay the Cyclades
Private sailing + hand-picked island stays, in one seamless, curated week
Discover Greece in two different ways.
Sail freely between 3–5 Cycladic islands, then slow down in a beautiful villa or boutique suite; curated by our trusted partners in Naxos, Paros, Mykonos, Syros, Serifos, Sifnos, Antiparos and more.
We shape the week around you, so you simply arrive and unwind.
Stay + Sail or Sail + Stay
We design the rhythm that suits you best.
In three simple steps
Do you prefer to see a sample plan first?
We’ll send you two route ideas and a matched villa within 24–48 hours.
Your yacht
Lagoon 51
Space & comfort for up to 10
Skipper & cook (full board at sea)
5 double cabins; aft, fore & flybridge lounges
Full A/C, watermaker, 220V throughout
BBQ, ice maker, Wi-Fi, beach towels
Seabob, SUPs, snorkel sets, tender & towables
Ideal for guests who appreciate generous spaces, a relaxed atmosphere and plenty of room for everyone to unwind.
Unsure which yacht is the right for you? We are happy to advise in a short consultation.
Your Stay
3–4 nights in hand-picked villas & suites
Beachfront Villa
Light-filled and steps from the sea.
Ideal for couples or small families who love to wake up by the water.
Hilltop Villa
Private pool, wide views and quiet surroundings.
Perfect for friends who enjoy sunsets, privacy and long dinners outdoors.
Family Villa
Space for everyone, close to beaches and tavernas.
Designed for relaxed family time with easy access to the sea.
These categories serve only as a starting point. Our partners offer a diverse selection of villas and suites, and we’ll recommend the most suitable options for you after a short consultation call
Sample Routes
3–4 nights in hand-picked villas & suites
Every journey is tailored, but these ideas show how a Sail & Stay week in the Cyclades can unfold.
Routes depend on weather, your chosen yacht and where you’d like to start and finish.
Naxos → Koufonisia → Amorgos → Iraklia → Naxos
A Cycladic loop of turquoise coves and whitewashed towns.
Calm legs, maximum swim time and quiet anchorages.
Day 1 - Koufonisia
Blue-green coves and natural pools (Pori, Piscina).
Day 2 - Amorgos
Monastery of Hozoviotissa; crystal-clear “Big Blue” waters.
Day 3 - Iraklia
Quiet anchorages, stargazing, and an unhurried pace.
Finish in Naxos
Ideal for Stay → Sail
Arrive in Naxos, settle into your villa, then set off to discover the Small Cyclades.
Athens → Kythnos → Serifos → Antiparos → Naxos
A one-way island-hopper.
Variety without backtracking, from quite bays to culinary immersion.
Day 1 - Kythnos
Kolona sandbar, hot springs, uncrowded bays.
Day 2 - Serifos
Characterful hilltop town, beautiful bays, excellent food.
Day 3 - Antiparos
Caves, sandy shallows, chic tavernas.
Finish in Naxos
Ideal for Sail → Stay
Finish with a few days in a Naxos or Paros villa.
Tell us your preferred dates and islands, and we’ll design a route that fits your group perfectly.
Why travellers love Sail & Stay
Two holidays in one, without the hassle.
What to expect
1) Share your plans (1–2 minutes)
Tell us your preferred dates, group size, whether you start in Naxos, Athens or another island, and which yacht you have in mind.
2) Decide how you’d like to proceed
– Sample quote: receive a sample itinerary and price indication for your dates.
– 15-minute planning call: a short conversation to align on the right route, villa and flow.
– Plan & Hold – €500 refundable: we synchronise yacht and villa calendars, hold both for 5 days and fine-tune your personalised plan.
3) Receive your personalised plan
Within one working day, we send you a clear proposal with route ideas, villa options and a transparent price breakdown.
3) Confirm when you’re ready
Once you approve the plan, we reserve your yacht and stay, then start preparing the details that make the week feel effortless.
FAQ
Clarity for the calmest possible planning
Do we sleep on the yacht or on land?
You enjoy both. During your Naxos stay, you sleep in your private villa or suite. During the sailing part of your journey, you stay on your own private yacht, waking up directly by the sea.
What if the weather does not allow us to sail?
Your safety and comfort always come first. In the rare case that conditions are not suitable for sailing, your skipper will adjust the route and we will curate alternative experiences for the day that fit the weather, so you still enjoy meaningful time in Greece.
Why should I place a €500 deposit now?
Your €500 deposit allows us to secure your preferred yacht and accommodation for your desired dates while we fine-tune your personalised plan. If you decide not to proceed, we will refund the deposit in full up to the date stated in your offer, no questions asked.
Can we start or end on different islands?
Yes. A popular flow is Naxos ↔ Athens, but one-way journeys to or from other Cycladic islands are also possible, subject to yacht availability and weather. Share your ideal route with us, and we will let you know what is realistically and comfortably possible.
What’s included?
Our full trip design and coordination.
Your journey includes a private, fully crewed yacht -on the Lagoon 51 this also means a dedicated cook for full board at sea; on the First 53 a hostess preparing breakfast and lunch – together with our concierge support before and throughout your trip. On board you have all standard yacht equipment, bed linen and towels.
Your selected villa or suite on Naxos is included in the offer, with on-the-spot concierge support provided by our trusted local partner.
What isn’t included?
Not included are flights, airport transfers (we are happy to arrange these), any additional villa costs, alcoholic drinks, dinners ashore, crew gratuities, and the operational yacht expenses covered via the APA (fuel, port fees, food and drinks on board).
Any part of the APA that is not used is refunded at the end of your trip.
What is APA?
APA (Advance Provisioning Allowance) is a transparent fund used to cover the variable running costs of the sailing part of your journey – such as fuel, port fees, and food and drinks on board.
Our crew manages this for you, keep track of all expenses, and reconcile everything at the end. Any unused amount is returned to you.
Do we need sailing experience?
No sailing experience is required. Your professional skipper is responsible for the yacht at all times.
If you are curious, you are very welcome to join on deck and learn the basics; if you prefer, you can simply relax and enjoy the views. The pace is laid-back and tailored to your comfort level.
Is this suitable for families with young children?
Yes, especially on the Lagoon 51, which is spacious and stable. We design family-friendly routes with shorter sailing legs, calm anchorages and plenty of time for swimming, so that both adults and children feel safe and at ease.
How many people can we be?
Lagoon 51: up to 10 guests plus crew
First 53: up to 6 guests plus crew
If you are unsure which yacht fits your group best, we are happy to advise.
What’s a typical sailing day like?
A typical day starts with an unhurried breakfast on board, followed by a 2–3 hour sail to a beautiful bay for swimming, snorkelling and lunch. In the afternoon, a short hop often takes you to a new island or harbour.
Evenings are usually spent in a small village with local shops and tavernas, or at a quiet anchorage under the stars – you set the rhythm, and we shape the day around it.
What about seasickness?
We favour routes with shorter legs and leeward bays to keep conditions as comfortable as possible. Before departure we share simple, practical tips that help, and on board we can provide natural options such as ginger or sea bands on request.
If you know you are prone to seasickness, we recommend speaking to your doctor in advance about suitable medication.
Can we customise the length (more than 7 days total)?
Absolutely. The core is usually 3–4 days of private sailing combined with your Naxos stay, but you can extend both the sailing and the villa/suite part to create a longer journey that suits your timing and wishes.
What luggage should we bring?
Soft travel bags are strongly recommended instead of hard suitcases, as they are much easier to stow on board.
Is there Wi-Fi and power on board?
Yes. The yachts are equipped with a 4G/5G router (coverage depends on the area) and 220V power via inverter or shore power in port. Your villa or suite also offers standard high-speed Wi-Fi for working, streaming or staying in touch.
Dietary preferences or allergies?
We ask for your dietary preferences and any allergies in advance. Your onboard cook or hostess will adapt menus accordingly, and we will recommend suitable restaurants ashore.
If someone in your group has severe allergies, please let us know early so we can prepare with the right level of care.
What are the payment terms?
Payment is usually split into a first instalment of 20% or 40% (as specified in your personalised offer), a second instalment if applicable, and the remaining balance 30 days before departure.
If you choose to place a €500 early-access hold, this amount is fully refundable until the stated date and, once you confirm your booking, it is credited towards your first instalment.
What happens if we must cancel?
Our full cancellation terms are detailed in your offer and Terms. In short, payments become increasingly non-refundable as your departure date approaches – typically 50% is due up to 30 days before, and 100% less than 30 days prior.
Wherever feasible, we will always explore options to reschedule or adjust dates in order to help you minimise any loss.
Are tips for the crew expected?
Gratuities are never mandatory, but they are customary in yachting when you are happy with the service. As a guideline, 10–20% of the charter price, handed to the crew at the end of your journey, is a usual range.
Can we bring alcohol on board?
Yes. We provision soft drinks and a selection of basics via the APA, and you are very welcome to bring your favourite wines or spirits. We will happily chill and serve them for you on board.
Are pets allowed?
As a general rule, pets are not allowed on most yachts. In some cases, however, we may be able to welcome a small, well-trained dog. If you would like to travel with your pet, please tell us early so we can check what is genuinely possible.
We also recommend speaking to your vet about seasickness and any medication your dog might need.
Is the experience accessible for guests with limited mobility?
Please share any mobility considerations with us as early as possible. The Lagoon 51, with its wide decks and generous spaces, usually offers easier movement than a performance monohull like the First 53.
We will always be transparent about what is and isn’t comfortable on board, and we will adapt routes, boarding arrangements and villa choices to match your needs as closely as we can.