Matzos by Sail
A crewed sail through Matzos — empty anchorages and sunsets on your schedule. A private, tailored journey of 8 Days · 7 Nights in Naxos, Greece, designed end to end by a Forest Travel advisor — with Virtuoso privileges at the finest luxury hotels, from US$9,800 per traveler.
- Ideal length: 8 Days · 7 Nights
- Best time: Late May through September, when the Aegean is warm, the meltemi winds are kind and the islands settle into long golden evenings.
- Private guiding, access and transfers throughout
- From US$9,800 per traveler — a starting point, tailored to you
- Designed one-to-one by a Forest Travel advisor
- Virtuoso privileges at the finest luxury hotels
A crewed sail through Matzos — empty anchorages and sunsets on your schedule. A private, tailored journey of 8 Days · 7 Nights in Naxos, Greece, designed end to end by a Forest Travel advisor — with Virtuoso privileges at the finest luxury hotels, from US$9,800 per traveler.
Greece pairs the world's oldest antiquities with an easy, sun-drenched glamour few destinations can match.
When to go
Late May through September, when the Aegean is warm, the meltemi winds are kind and the islands settle into long golden evenings. Your advisor times it to the light, the crowds and your own calendar.
The experiences
A sense of what this journey can hold — each one arranged privately and shaped to you:
- A private anchorage off Koufonisia at dusk, where your crew sets the table on deck before a single other boat appears.
- A negotiated berth at the Naxos Town quay so you can walk to Grotta beach and the Portara at your own hour, not a ferry schedule.
- A day under sail through the Iraklia passage — Cycladic light, a Force 3 breeze from the north, and a captain who has worked these channels for twenty years.
- A chef's-table lunch built from whatever the morning fish market in Apollonas offers, served at anchor in a bay you will have entirely to yourselves.
A sense of the rhythm
Mornings begin when the meltemi allows — sometimes early, sometimes not until ten — because the wind sets the agenda and the crew reads it for you. Afternoons resolve into an anchorage chosen that same day, so every sunset is earned rather than scheduled. The pace is genuinely unhurried: the only fixed point is departure day.
Bareboat charter versus a fully crewed yacht for this route
A bareboat gives you autonomy but costs you the local knowledge that makes the difference between finding Alimia cove and missing it entirely. On the lesser-known anchorages between Naxos and the Small Cyclades — Schinoussa, Iraklia, Donoussa — a captain who has been returning for two decades knows which bay holds a swell on a north wind and which taverna in Aegiali will open early if asked the night before. Our crewed arrangements also include a chef, which changes the economics and the experience: provisioning, cooking and washing up disappear from your itinerary. For a circuit of this length, the crewed option consistently produces a more relaxed journey.
How to do it well
The counsel our advisors give travelers planning this journey:
- Reserve the yacht by February for July and August departures — quality crewed gulets and sailing yachts working the Cyclades are contracted by March and rarely return to market.
- The meltemi blows reliably from mid-July through August; if you prefer calmer water and more flexible itinerary adjustments, plan for late June or September when the wind is lighter and anchorages less crowded.
- Build your Naxos Town stopover for a Saturday morning, when the market near the Old Town runs longest and your chef can provision for two full days at anchor in the Small Cyclades.
- Greek coastal passage permits and cruising tax (TEPAI) require documentation prepared before embarkation; we handle this in advance so there are no quayside delays on day one.
What only your advisor can open
The difference between a good trip and an unrepeatable one is access — and access is a relationship, not a booking. Every guide, room and moment is chosen and sequenced for you.
Who it's for
Travelers who value privacy, time and doing it once — beautifully — and who would rather have one trusted advisor orchestrate every detail than assemble it themselves.
Estimated investment
From US$9,800 per traveler, based on double occupancy — scaled to your dates, party size and level of privacy. A starting point, not a final quote; confirmed once your advisor tailors the itinerary.
Designed entirely around you
Nothing here is a package. A Forest Travel advisor shapes the whole journey and stays one message away before and throughout your trip.
Your Virtuoso privileges
As a Virtuoso member, Forest Travel includes benefits reserved for Virtuoso guests at the finest luxury hotels, at no added cost: a room upgrade on arrival when available, daily breakfast for two, a property credit toward dining or spa, and early check-in with late check-out when the hotel allows.
Continue exploring Naxos
Part of our Naxos travel guide. Related private journeys:
Begin the conversation
Tell a Forest Travel advisor how you like to travel and they will design Matzos by Sail around you — privately, every Virtuoso privilege included. Request your private consultation →
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