Drake Supper Club presents
Saturday 3 — Saturday 10 October 2026 · Palermo
Stunning natural beauty, exquisite food and wine, watersports and activities, and best of all — great company.
…aboard a Sun Odyssey 440, or similar.
We're thrilled to present the Drake Supper Club Sicily 2026 Trip — a week's sailing through the Aeolian Islands, the volcanic archipelago off Sicily's north coast.
Departing from Palermo on Saturday 3 October 2026, you'll spend a week aboard a Sun Odyssey 440 exploring some of the most dramatic islands in the Mediterranean. Stromboli erupting at sunset. Hot mud baths on Vulcano. Granita and brioche on Salina. Panarea's prehistoric ruins to snorkel. The kind of week that ruins normal holidays for years afterwards. Disembark back in Palermo on Saturday 10 October, with optional Palermo Night Out on Sunday 11 October.
Arrival rule: please plan to arrive in Palermo by Friday 2 October at the latest — you'll need a hotel that night for the muster. No Saturday arrivals — we want the boat warmed up and the safety briefing done in time for an unhurried embark at 16:00 on Saturday.
As a Drake Supper Club member, you'll be joining this subsidised trip in exchange for your feedback, a few on-board lifestyle shots, and a short review. In return, you'll enjoy an incredible sailing holiday at a fraction of the typical cost — without compromising on the experience.
“ where’s the wine…? everywhere. — Jai, somewhere off Greece
Muster: Friday 2 October (hotel night in Palermo) · Embark: Palermo, Saturday 3 October 16:00 · Disembark: Palermo, Saturday 10 October 12:00 · Palermo Night Out: Sunday 11 October
Embark mid-afternoon. Easy first sail east along Sicily's north coast. Drop anchor or moor at Cefalù — dinner ashore under the Norman cathedral, golden hour on the medieval rooftops.
The big push east into the Aeolians. Stromboli on the horizon as we approach. Anchor at Porto di Levante on Vulcano — dinner ashore, and a sulphurous mud-bath under the stars for the brave.
Lazy morning swim, then a short hop to Lipari — the archipelago's lively capital. Mooring in the port, exploring the citadel, and a long dinner ashore.
Sail to Salina — the greenest of the Aeolians. Anchor in Pollara (where Il Postino was filmed), swim, overnight in Santa Marina or Rinella. Granita and brioche for breakfast.
The headline sail of the week. Approach Stromboli mid-afternoon. Anchor off the Sciara del Fuoco for the sunset show — eruptions rolling down the volcano flank into the sea.
Morning swim, then sail to Panarea — the chic Aeolian. Anchor off Cala Junco, snorkel the prehistoric village ruins beneath the water, evening ashore at San Pietro.
Long downwind return toward Sicily. Capo d'Orlando if the wind is light, Cefalù if we're flying. Last night onboard with a farewell dinner ashore.
Easy morning sail back to Palermo. Disembark by midday. Most guests stay on for the optional Palermo Night Out on Sunday 11 October — markets, street food, baroque churches, and one last drink together.
Route is flexible for weather. The east-bound legs (Days 1–2) can flip if the Maestrale's blowing hard from the NW — we'd push directly to the Aeolians and unwind via the north coast on the way back.
Jeanneau's Sun Odyssey 440 is a 44ft modern cruising yacht with twin helms and the distinctive walk-around side decks — low coachroof, easy movement bow to stern. Full-batten mainsail, self-tacking jib, and full navigation electronics. When docked: air conditioning, a well-appointed galley, and stylish indoor and outdoor spaces ideal for shared meals and sundowners.
4 double cabins, 8 berths. Two doubles forward, two aft — each with its own door for proper privacy. Heads (showers/loos) shared between cabins as is standard for the layout. Skipper bunks in the saloon when underway.
Embarkation: Palermo, Sicily · Saturday 3 October 2026, 16:00. Arrive Palermo by Friday 2 October (you'll need a hotel that night). No Saturday arrivals.
Early October on Sicily's west coast — mild, dry, and far less crowded than peak summer. Genuinely lovely sailing conditions.
Prevailing wind is Maestrale (NW). Sirocco occasionally brings warm African air. Strong enough to push 7+ knots downwind, mild enough for a swim every day.
We run subsidised events off the invites SailChecker receives to visit and familiarise with partner bases. Guests are a little more flexible than on regular charters — offset by a great price (typically 3–4× less than a normal week).
In exchange, we ask for your feedback, some modelling for our filming crew, and a short review.
Early bird (before 1 June): £750 paid in full at booking — non-refundable.
Standard rate (after 1 June): £800, 50% non-refundable deposit on booking, balance due 56 days before the event.
Payments are non-refundable. If the operator can't deliver, the trip is rescheduled. We make every effort to find replacements for those who can't attend the rescheduled date.
We recommend travel cancellation insurance. EIS is comprehensive and covers most risks.
Shared double cabin · £750 per person
Standard rate £800 after 1 June · Subsidised weekly rate · Sicily 2026
Pre-pair with your chosen cabin-mate. Easiest if it's a partner, but it doesn't have to be — old crew-mates, sailing buddies, anyone you'd happily share a small space with for a week. Your "cabin mate" doesn't have to be your "Mate". Skipper has their own berth and isn't part of the cabin draw.
Cabin pairing is guaranteed only when both of you book and pay together. If you say you're sharing with someone but they're going to pay later, we can't hold a paired cabin — by the time they sort it, you may already be in a single spot, or paired with someone else entirely.
It's a slight change from past years — a deliberate reset. Stiles and I want the trip to run cleanly, with no half-paired cabin tetris in the final weeks. Smaller, more intimate, predictable. You'll thank us come October.
Paying for two? Both send £750 with the same reference — e.g. "Sicily 2026 — Smith & Jones". Two transfers, one reference, you're locked in together.
Once we've confirmed your cabin, transfer the £750 to secure your spot. UK bank transfer via Faster Payments — clears in minutes from any UK bank app.
Paying for two? Both send £750 using the same reference — e.g. "Sicily 2026 — Smith & Jones". Two transfers, one shared reference, you're locked in together. See Cabins & Cabin-Mates.
UK GBP bank transfer
Please use the reference exactly as shown so we can match your payment to your cabin booking. Once received, we'll confirm your booking by email within 24 hours.
Payments are non-refundable. If the operator can't deliver, the trip is rescheduled and we make every effort to find replacements for those who can't attend the new date.
Pre-pair with your chosen cabin-mate (doesn't have to be your "Mate"). Pairing's only locked when both of you book + pay together. See Cabins & Cabin-Mates for the full story.
Breakfast aboard — pastries, fruit, fresh coffee. Lunch a mix of onboard and taverna stops ashore. Sundowners on deck. Some suppers onboard, others ashore.
Mild October sailing — see the Weather & Sea section above for the full breakdown.
Light layers, swimwear, long sleeves for sun protection. Windproof jacket. Non-marking deck shoes. Sunglasses, sunscreen, hat. Soft-sided luggage. Bedding and one towel provided.
A few hours of relaxed sailing, a swim stop or two, time ashore. Paddleboarding, snorkelling, lounging. Fancy dress night returns — bring something playful.
Airport — Palermo Falcone Borsellino (PMO). ~45 min taxi or transfer to Palermo harbour. Direct flights from London (Gatwick, Stansted, Luton) and most major European hubs.
Arrival rule — please plan to arrive by the Friday before we sail at the latest. No Saturday arrivals. Whatever the exact day works out to, we want the boat warmed up and the safety briefing done in time for an unhurried embark.
Muster — Friday 2 October. Arrive Palermo on Friday and book a hotel for that night — we'll run safety briefings and provisioning together on the muster evening. Many guests come a day or two earlier to settle in.
Embark — Saturday 3 October, ~16:00. Arrive at the marina by lunchtime for cabin allocation. No Saturday arrivals from abroad — be in town the night before.
Disembark — Saturday 10 October by midday. Optional Palermo Night Out on Sunday 11 October — keep the room for Sat + Sun nights to stay for it.
Likely room nights in Palermo: Fri 2 Oct (muster, required) · Sat 10 Oct (post-disembark) · Sun 11 Oct (Night Out, optional). Two nights minimum, three if you stay for the Sunday.
Interesting routing option: Wizz Air via Milan. Fly into Milan on Wednesday 30 September, 24-hour layover to see the city morning and afternoon, then onward to Palermo on Thursday 1 October (gives you a buffer day before muster). Adds a day on either end without ruining the budget — and Milan in late September is at its best.
All specific dates & the embark marina will be confirmed once the yacht is locked. Currently planning around the first or second week of October 2026.
If you can tie a bowline you can do about 80% of what the skipper will ever ask of you. Three minutes of practice now and you’re ahead of most of the boat.
A taste of how these weeks tend to go. Photos used with permission of the people in them — it's part of the trip agreement.
Reserve your cabin if you’re ready to commit — a step-by-step form that takes ~5 minutes and gives the skipper everything needed to run a safe, pleasant week. Or just Register your interest with a quick email if you want to be told first when the next berths open.
Prefer to email directly? [email protected]