A note from Owen
After a lot of research and planning, we're heading to Milos, Greece in May 2027 — and I'm proposing on the first night. I've been planning this for a while and wanted to share it with the people closest to us before it happens. Everything on this site is the full plan — where we're going, where we're staying, and what the big moment looks like. Jay has no idea. Shh. 🤫
The Proposal
May 18 — Arrival Night
Plaka hilltop at sunset on the evening we arrive. The views from there are extraordinary — it's the perfect moment.
The Big Moment
Where We're Staying
Loulou House
A traditional Cycladic home built into the hillside with panoramic views over the port and villages. Already booked.
✓ Booked
Trip Highlight
Private Boat Day · May 20
A full day on a private boat visiting Kleftiko sea caves — only reachable by water. One of the most spectacular things you can do in Greece.
Coming up
Getting There
Boston → Athens → Milos
Connecting through Athens, then ferry or short domestic flight to the island. Flying out May 18, returning May 23.
Planning
5
Nights
1
Proposal
4
Beaches
1
Boat Day
∞
Sunsets
The Proposal
May 18, 2027 · Plaka, Milos · Golden Hour
Kleftiko sea caves — where we'll spend May 20
The plan is to propose on the very first evening we arrive — before the trip even really begins. After landing and settling into Loulou House, we'll drive up to Plaka, the hilltop capital of Milos, in time for golden hour.
Plaka sits at the top of a hill with 360-degree views over the island — the whitewashed buildings, the volcanic coastline, the Aegean stretching out to the horizon. At sunset the whole place turns gold. It's one of the most beautiful spots in Greece.
The moment happens there, at the top, as the sun goes down. Then dinner somewhere in the village after to celebrate — just the two of us on the first night of the trip.
The rest of the week is ours to enjoy as an engaged couple. Which makes every beach, every boat day, and every sunset after that its own kind of celebration.
Location
Plaka, Milos
The hilltop capital of the island. Castle ruins at the summit, panoramic views of the Aegean.
Timing
Golden Hour, May 18
Sunset in Milos in late May is around 8:30pm. The light at that hour is extraordinary.
After
Dinner in Plaka
A celebratory dinner in the village — small tavernas with terraces and views. The first meal as an engaged couple.
5 Days in Milos
May 18 – 23, 2027
18
May
💍
Arrive in Milos · Proposal at Sunset
Long travel day — Boston to Athens, then ferry or domestic flight to Milos. Settle into Loulou House. Then up to Plaka for golden hour. The proposal happens here, on the hilltop, as the sun sets over the Aegean. Dinner in the village after to celebrate.
The Big Night 🥂
19May
Beach Exploration Day
Pick up the rental car and explore the island. First stop: Sarakiniko — the famous lunar landscape of smooth white volcanic rock carved by the sea. Then Firiplaka for long sandy swimming, and Tsigrado if we're feeling adventurous (hidden cove, rope ladder down the cliffs). Dinner back in the village as newly engaged people.
20May
⬥ Private Boat Day
The highlight of the trip. A full day on a private boat heading to Kleftiko — dramatic sea caves and rock arches on the southwest coast, only reachable by water. Swimming inside the caves, floating in impossibly clear water, lunch on board. Late afternoon light on the way back. One of the best things you can do anywhere in Greece.
21May
Villages + Sunset
A slower day. Morning at leisure — maybe a quiet beach or a walk through Adamas. Afternoon in Plaka: the Catacombs of Milos (one of the most important early Christian sites in Greece), then wandering the whitewashed alleys up to the castle ruins for another sunset. Dinner on a terrace somewhere looking out over the island.
22May
Slow Day
No agenda. One more beach. A long lunch somewhere with a view. A final walk through Plaka. The kind of day where you just sit somewhere beautiful and don't really want to leave.
23May
Departure
Early ferry or short flight back to Athens. Connect home to Boston. Back to reality — but engaged.
Loulou House
Milos, Greece · May 18–23, 2027
Loulou House
Hosted by Sofia · Superhost · 4.96★ from 77 reviews
A traditional Cycladic home built into the hillside with views over Adamas port and the villages of Plaka, Tripiti, and Triovasalos. Whitewashed walls, stone floors, and the kind of view you could stare at all day. We have the whole place to ourselves for 5 nights.
Location
Between Adamas and Plaka
The perfect central base. Adamas (the port town with restaurants) is 5 minutes away. Plaka (best sunsets on the island) is 10 minutes up the hill.
The Views
Panoramic over the port & villages
Views of Adamas port, Plaka, Tripiti, and Triovasalos from the hillside. The kind of view you'd see on a postcard.
Nearby
Close to Agia Kyriaki & Palioxori
Two excellent beaches within easy reach by car. The rest of the island's beaches are 20–30 minutes away.
Host
Sofia — 11 years hosting
Airbnb Superhost with over a decade of experience and a near-perfect rating. Exactly who you want looking after you on a trip like this.
Places to See
Beaches, villages, and sea caves
Beaches
Sarakiniko
The most photographed beach in Greece — smooth white volcanic rock formations carved by the sea into something that looks like the surface of the moon. Unlike anything else in the world. Best in the morning before it fills up.
Firiplaka
A long sandy beach on the south coast with turquoise water and a calm, clear bay. One of the best swimming beaches on the island. The kind of beach you stay at for four hours without noticing.
Tsigrado
A hidden cove at the bottom of a cliff accessed by a rope ladder. Small, dramatic, completely worth it. One of those places that feels like a secret even when you know about it.
Kleftiko
Sea caves and rock arches on the southwest coast — only reachable by boat. The centrepiece of the boat day. The water inside the caves is an otherworldly shade of turquoise blue. One of the most spectacular places in the entire Mediterranean.
Villages & Sites
Plaka
The hilltop capital of Milos — whitewashed Cycladic architecture, narrow alleys, and castle ruins at the top with 360-degree views. The best sunset on the island, every evening. This is where the proposal happens.
Catacombs of Milos
One of the most important early Christian monuments in Greece, carved into the rock beneath Plaka. Over 2,000 years old, with an extraordinary atmosphere. Worth the short guided tour.
Pollonia
A quiet fishing village on the north coast with good tavernas right on the water. Laid-back and beautiful, a nice contrast to the more dramatic south coast beaches.
Adamas
The main port town — practical base with a pretty waterfront, good restaurants, and the ferry dock. Five minutes from Loulou House and the place we'll end up most evenings for dinner.
Why Milos?
The island, the decision, and what makes it special
Milos, Greece — May 2027
Most people haven't heard of Milos. That's kind of the point.
It's a small volcanic island in the Cyclades — the same island group as Santorini and Mykonos — but it draws a fraction of the tourists. The landscapes are more dramatic, the water is clearer, and it hasn't been turned into a resort. It still feels like a real Greek island.
It's also the island where the Venus de Milo was discovered in 1820. So it has that going for it.
Volcanic Landscape
Milos was formed by volcanic activity — which gives it landscapes unlike anywhere else in Greece. White pumice beaches, sea caves carved into the cliffs, lunar rock formations. It looks like another planet in the best possible way.
The Clearest Water
The water around Milos is consistently ranked among the clearest in the Mediterranean. The colours — turquoise, deep blue, emerald in the caves — are genuinely as good as any photo you've seen.
70+ Beaches
Milos has over 70 beaches — remarkable for an island this size. Each one is different. Sandy, rocky, hidden, dramatic. You could spend a week doing nothing but moving from one to the next.
Not Santorini
Santorini is beautiful but it's also extremely crowded, extremely expensive, and extremely busy in late May. Milos has everything Santorini has — the sunsets, the white buildings, the Aegean views — without any of that. It was the obvious choice.
Late May Timing
Late May is the sweet spot for the Greek islands. The weather is warm and sunny (mid-70s), the sea is swimmable, the tourist season hasn't peaked yet, and the good places aren't full. By July it's a different story entirely.
The Right Place for This
A proposal deserves a backdrop that's genuinely hard to top. Standing on a hilltop above a volcanic Greek island as the sun sets over the Aegean is about as good as it gets. That's the plan.