Drake Supper Club presents
Friday 3 — Friday 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.
Reserve your cabin →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 Friday 3 October, 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 Friday 10 October in Palermo, then optional Saturday Night Out in the city on 11 October.
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. — overheard, somewhere off Sicily
Muster: Thursday 2 October · Embark: Palermo, Friday 3 October 16:00 · Disembark: Palermo, Friday 10 October 12:00 · Palermo Night Out: Saturday 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 Saturday 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.
Comfortably accommodates up to 8 guests plus skipper across 4 double cabins. Designed for sociable, accessible sailing — generous cockpit, easy deck access, and the kind of relaxed, modern interior that makes a week aboard feel like staying in a boutique hotel.
Embarkation: Palermo, Sicily · Friday 3 October 2026, 16:00.
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.
Muster — Thursday 2 October. Arrive Palermo on or before Thursday so we can run safety briefings and provisioning on the muster evening. Many guests come a day earlier (Wed 1 Oct).
Embark — Friday 3 October, ~16:00. Arrive at the marina no later than midday for cabin allocation and lunch.
Disembark — Friday 10 October by midday. Optional Palermo Night Out Saturday 11 October — keep the room one more night.
Interesting routing option: Wizz Air via Milan. Fly into Milan on Tuesday 30 September, 24-hour layover to see the city morning and afternoon, then onward to Palermo on Wednesday 1 October. Adds a day on either end without ruining the budget — and Milan in late September is at its best.
“ I think the water shortage might be connected to my 30-minute shower… — ditto
One song that kept coming back to the cockpit playlist.
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? charter@sailchecker.com