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, approximate budget and any ideas you already have. Don't worry if you're still undecided—we'll help you shape the right journey.
2) We design your personalised proposal
Within one working day, you'll receive a tailored recommendation, including suggested yachts, route ideas, accommodation options and transparent pricing.
3) Refine it together
We'll answer your questions, adjust the itinerary if needed and help you choose the yacht and journey that fit you best.
3) Confirm when you’re ready
Once you're happy with the plan, we'll secure your yacht and accommodation and start preparing every detail for your trip.
FAQ
Clarity for the calmest possible planning
Do we sleep on the yacht or on land?
You enjoy both. During your stay ashore, you'll relax in your selected villa or boutique accommodation. During the sailing part of your journey, you'll stay on your private yacht, waking up to a different bay almost every morning.
What if the weather does not allow us to sail?
Your safety and comfort always come first. If conditions aren't suitable for the planned route, your skipper will adapt the itinerary and we'll recommend the best alternatives. The result is usually a different journey, not a lesser one.
Can we start or end on different islands?
Yes. One-way journeys are possible throughout the Cyclades, depending on the yacht, availability and weather conditions. We'll recommend the most practical route for your itinerary and help minimise unnecessary transfers or relocation costs.
How far in advance should we book?
For the widest choice of yachts and accommodation, we recommend booking 6–12 months in advance, particularly for July and August. Last-minute journeys are sometimes possible, depending on availability.
What’s included?
Every Sail & Stay Privé journey includes your private yacht with professional crew, carefully selected accommodation ashore, and personalised journey planning from start to finish.
Depending on your chosen yacht and experience level, your trip may also include a hostess or private cook, concierge support, transfers, curated activities and other tailored services. We'll always explain exactly what's included before you book.
What isn’t included?
Flights, airport transfers (we're happy to arrange them), optional activities ashore, crew gratuities, and the yacht's operational expenses covered through the APA, such as fuel, port fees, and provisions on board.
Any unused APA balance is refunded at the end of your journey.
What is APA?
The APA (Advance Provisioning Allowance) is a transparent fund used to cover the variable running costs of your yacht, including fuel, marina fees, and food and drinks on board.
Your crew manages everything during the trip, keeps a record of all expenses, and provides a full reconciliation at the end. Any unused balance is returned to you.
How do you choose the right yacht for us?
We don't expect you to compare dozens of yachts. Based on your group, travel style, and budget, we'll recommend one or two carefully selected options. As we learn more about your preferences, we'll guide you towards the yacht that feels like the perfect fit.
Do we need sailing experience?
Not at all. Your professional skipper takes care of the yacht and navigation throughout the journey.
If you're curious, you're welcome to take the helm or learn a few sailing basics. If not, simply relax and enjoy the experience at your own pace.
Is this suitable for families with young children?
Absolutely. We regularly design journeys for families with young children and will recommend the yacht, route, and pace best suited to your group.
Expect shorter sailing legs, sheltered anchorages, plenty of swimming stops, and an itinerary shaped around comfort rather than distance.
How many people can we be?
We work with yachts suitable for couples, families, and larger groups.
Our signature collection accommodates anywhere from 2 to 12 guests, depending on the yacht.
We'll recommend the most suitable option based on your group size, travel style, and budget.
What’s a typical sailing day like?
Each day follows a relaxed rhythm rather than a fixed schedule.
After breakfast, you'll usually sail for a couple of hours to a beautiful bay for swimming, snorkelling, lunch, or simply unwinding. Later in the day, you may continue to another island or harbour, or remain at anchor if you've found the perfect spot.
Every itinerary is adapted to the weather, your preferences, and the character of each destination.
What about seasickness?
We plan routes that prioritise comfort, using sheltered waters and avoiding unnecessarily long passages whenever possible.
If you're prone to seasickness, we recommend speaking to your doctor before travelling. We can also suggest practical measures that help many guests feel comfortable on board.
Can we customise the length (more than 7 days total)?
Absolutely.
Whether you're looking for a long weekend, a week, or a two-week journey, we'll tailor the itinerary around your available time and preferred pace.
What luggage should we bring?
Soft travel bags are strongly recommended instead of hard-shell suitcases, as they're much easier to store on board.
Is there Wi-Fi and power on board?
Yes. Every Sail & Stay Privé yacht includes onboard Wi-Fi. All yachts also provide 220V power for charging your everyday devices.
Dietary preferences or allergies?
We'll ask about dietary preferences and allergies before your journey so your onboard meals can be tailored accordingly.
If anyone in your group has severe allergies, please let us know as early as possible so we can prepare with the appropriate level of care.
What are the payment terms?
Payment is typically made in instalments, as outlined in your personalised proposal.
Depending on how far in advance you book, this is usually either 20% / 20% / 60% or 40% / 60%, with the final balance due before departure.
What happens if we need to cancel?
Our full cancellation policy is included in your proposal and Terms & Conditions.
Whenever possible, we'll work with you to explore alternative dates or practical solutions before applying cancellation charges.
Are tips for the crew expected?
While gratuities remain at your discretion, they are a well-established part of the crewed yachting industry and are generally expected when you're happy with the service. As a guideline, 10–20% of the charter fee, shared among the crew at the end of your journey, is customary.
Can we bring alcohol on board?
Of course.
We'll provision your yacht based on your preferences, and you're welcome to bring any favourite wines or spirits you'd like to enjoy during the trip.
Are pets allowed?
This depends on the yacht.
Some owners may welcome a small, well-trained dog, while others don't permit pets. Let us know early and we'll advise what's genuinely possible.
Is the experience accessible for guests with limited mobility?
Please let us know about any mobility requirements when you enquire.
Some yachts are significantly easier to move around than others, and we'll recommend the most appropriate option while adapting boarding arrangements, itinerary, and accommodation wherever possible.