An island in the Aegean: cerulean water, sunset castles, long taverna dinners — and exactly the right people. Seven nights, all of it handled by three of your favorite people: Kyle, Francesca & Sergio.
Last summer a few of us spent a week at Francesca's family home on Leros and called it one of the best of our lives. This year, we want to take care of our friends and plan the whole thing.
You book your flights, you show up, and you don't think about a single logistic or detail for seven days. That's the idea.
Leros sits in the Dodecanese — an island chain closer to mainland Turkey than to mainland Greece. No cruise crowds, very few tourists; some weeks you might be the only Americans on the island. It's untouched, remote and hard to reach — and it offers all the beauty you expect from the Mediterranean, at a fraction of the cost.
Hover a card to explore.
Climb to the Castle of the Virgin Mary for sunset, then a cocktail in a 17th-century windmill bar.
Alinda outside the door, calm shallows at Krifos, coves you can only reach by boat.
Lazy afternoons at the beach club, long dinners of fresh fish under the stars.
WWII tunnels carved into the rock, a battle museum, neoclassical mansions in Lakki.
A day boat to Patmos and its clifftop monastery, or tiny islands almost no one visits.
Paddleboards, windsurfing, jet skis, or a private boat to chase the coves.
A rhythm, not a schedule. Every activity, meal and transfer on the island is included — dip in, or laze on the beach. (We'll fine-tune the days as the group comes together.)
Land, settle into Alinda, gather at Villa Betty, then a welcome dinner in Pandeli and a nightcap at the windmill bar.
A slow morning on Alinda beach, then up to the Castle of the Virgin Mary for the sunset.
The heart of the week: a long, candlelit family dinner at the villa — a private chef, everyone's feet under one table, the energy we live for.
Around the island to coves you can't reach by road — swim stops, cliff jumps, and the serene Krifos beach.
Across the water to the hilltop Monastery of St. John, whitewashed lanes, and lunch by the sea.
Watersports at Vromolithos, a Greek cooking or dancing class, the WWII bunkers — or nothing at all.
Shopping in Agia Marina and Pandeli, a wine tasting, last swims — then a farewell feast and Greek dancing.
Coffee by the water and goodbyes — or extend your stay and linger a few more days.
Nothing here is mandatory. The best days on Leros are often the ones you spend doing very little.
Everything is in Alinda — a green, pine-shaded bay on the north of the island — and nothing is more than a 15-minute stroll away. Villa Betty is our heart; you'll sleep in comfortable rooms just across the street and along the lane.
Villa Betty · the terraceFrancesca's family home and the soul of the trip — where we gather for family dinners, morning coffees, and the meet-up before every boat day.
Hotel Alinda · garden & beachA relaxed beachfront hotel directly across the street, with a garden, its own restaurant and bar, and the sand a few steps away.
Pleiades · traditional farmhouseA charming traditional farmhouse with a garden and terrace, a short walk away — for those who'd rather have a house feel.
As the group grows we'll add more hand-picked hotels and houses in the same pocket of Alinda — all walkable, all near the water, all near Villa Betty. Tell us your preference on the form below and we'll match you to the right spot.
A taste of what's on offer through the week — all included, all optional. Do all of it, or find a sun lounger and do none of it.
The island's crown, best at golden hour over Alinda Bay.
Coves and swim spots only reachable by water.
The clifftop monastery and a long harbor lunch.
A walk to a serene beach — with a boat to carry us home.
Lessons and gear for first-timers and pros alike.
Out on the bay at your own pace.
Learn the dishes you'll be eating all week.
For the farewell night — no skill required.
A relaxed afternoon tour of local pours.
Tunnels carved into the rock at Lakki.
Mint-green Vespas and open roads (for confident riders).
Lime Bar, Vromolithos, and long dinners by the water.
Fish pulled in that morning, watermelon in the afternoon heat, and family dinners at Villa Betty that run until the candles burn down. Half the reason we keep coming back.
Off the harbor grill.
The afternoon table.
Whatever came in.
Sun-warm, daily.
At the windmill bar.
One long table.
From Pandeli's fish tavernas to the windmill kitchens above the bay — we know exactly where to take you.
This isn't a tour group. It's our favorite people, gathered on purpose.
Back home, Kyle & Francesca host family dinners — and that's the exact spirit we're bringing to Leros. Everyone here is someone we wanted at the table, and that's what turns a nice week away into the kind you talk about for years.
You'll arrive knowing a few of us and leave with twenty new friends.
A small group, chosen one invitation at a time.
Warm, easy, a little chaotic — in the best way.
By day two it feels like you've known each other for years.
A photo of the three of us — Kyle, Francesca & Sergio, your hostsThe only thing not included is getting to Leros. You book your own flights and ferries — and we'll walk you through exactly how. More on that below.
For couples or friends sharing a double — the best value, and honestly the most fun way to do it.
Your own room, your own space.
A deposit will be requested once the final group is locked in, before we book accommodation. Spots are limited.
Everything routes through Athens. Tell us your home airport and we'll personally map out the exact flights and ferries for you — and make it as easy as possible. Here are the main ways in:
Into Athens, then a short domestic hop to Leros (LRS) with Olympic Air or Sky Express. Book early — the small planes fill up.
Athens → Leros · ~50 minFly to Kos, then a quick catamaran across. Easy to add a few extra Dodecanese days to either end of the trip.
Kos → Leros · ~1.5–2.5 hrsFrom Piraeus straight to Leros — book a cabin and sleep through most of it. A few sailings a week.
Piraeus → Leros · ~9–10 hrsNo payment yet — just leave your details so we can hold your place and send the next steps. We're keeping the group small (think 15–20), so the sooner we hear from you, the better.
We've got your details and we'll follow up shortly with next steps. If your email client opened, hit send to reach us directly.
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