You're going to Greece.
Your family has planned every day of it: two islands, one summer, and nothing left for you to organize.
July 2 – 17, 2027
Your family has been keeping a secret.
They have booked you the Aegean: a hilltop villa on Naxos where breakfast takes an hour and dinner takes four, then a boat south to Crete, where the beach is long, the sea is warm, and no one ever reaches for a wallet.
In between are caves you can swim into, islands you reach by boat, a mountain kitchen, and old harbors that look painted. It is a trip built so that three generations spend their time together instead of organizing it.
Naxos
Marble quarries, citron groves, and the longest lunches in the Cyclades.
Whitewash, dry stone, and a table for nine.
The villa rests on its hillside as if the landscape had grown it: whitewashed cubes, dry-stone terraces, reed and dark timber overhead. Fields roll toward the sea below, and every window is framed by them.
An infinity pool seems to pour into the hills. Loungers wait for the afternoon. At the far end of the terrace are a stone kitchen, a bar, and a table long enough that no one ever sits at the end of it.
Mornings begin here, coffee in hand, with the whole island laid out below.
Then the sun drops, the pergola lights come on, and dinner begins.
Four ways to leave the villa.
You will want to. Naxos rewards the curious, and each of these days is designed to feel like a gift inside the gift.
A day at sea, from cave to island
Nine hours, lunch included.
You leave Agia Anna harbor at 9:15, with the sun already warm. The boat follows Naxos's west coast to Rina's Cave, a hollow in the cliffs that can only be reached from the water. Swim into it. Dive from the rock above if the family dares you. Then rinse off at the pebble beach beside its freshwater spring.
Farther on is Koufonisia, where the water turns a shade of turquoise that looks edited. Lunch is a barbecue on board, with local wine and produce from Naxian farms. Then two free hours on Ano Koufonisi, the smallest inhabited island in the Cyclades, before the boat brings you home by seven.
Two islands, a short boat ride away.
Look west from the terraces of Naxos town and Paros is right there across the water, with its smaller neighbor just beyond.
Paros
Paros is where the Cyclades dress up: a harbor town of white lanes and bougainvillea, cafes that turn into dinner, and boutiques you wander into by accident.
Antiparos
Antiparos is Paros exhaling. A village of a few streets, water clear enough to read a book through, and the kind of afternoon that leaves nothing on the calendar.
An afternoon of kitron and wine.
Four to five hours.
Kitron is Naxos's best-kept secret: a fragrant liqueur made from the citron, a fruit like an oversized lemon, and a family craft on the island for more than a century.
Walk through a citron tree garden heavy with fruit. Taste secret family recipes in a working distillery, then visit a second in Halki where five generations have perfected the same recipe. The afternoon ends at a hidden vineyard where the young producer pours his own wines and homemade spirits.
Lost in the old town.
The story goes that Chora's lanes were laid out to confuse pirates. They work just as well on visitors, in the best possible way. Whitewashed walls turn to blue shutters, and bougainvillea spills over every doorway.
Around every bend is a place to stop for coffee. Wander through the morning, shop and snack through the afternoon, and let the lanes decide where you end up.
Then stay for dinner. After dark the taverna squares glow under rows of lantern shades, and it is the loveliest last night on the island.
The photographs from the old town, the sea day, and the sunset were taken by Rochelle on her own trip to Naxos.
One epic crossing.
Platinum class turns the ferry itself into part of the adventure: the comfortable end of the boat, hours of open Aegean, and island silhouettes sliding past before Crete rises on the horizon.
Crete
Mountains that fall straight into the sea, and a resort that has already thought of everything.
Everything is already included.
Crete is where the family exhales. The resort has its own stretch of beach, restaurants that follow the sun toward the water, and an all-inclusive rhythm that means no one splits a check or does math all week.
Two pools, a long beach of umbrellas, and the sea a few steps beyond. Wake up, choose a pool or a patch of sand, and let the day arrange itself.
Waterslides for the teenagers, and anyone who insists they're too old.
The resort has its own water park, with slides for every level of brave and a splash zone for the youngest.
Wake up to balconies that open onto the mountains or the sea.
Dinner over the water, with the sunset doing the decorating.
Tables are set on a glass-railed terrace above the bay, and the evening light does the rest.
Three days worth leaving the resort for.
Crete is bigger and wilder than it looks from the beach. These three days show you why.
Dia, by private catamaran
Six and a half hours, just the family.
Dia is a wild, uninhabited island a short sail off the coast of Heraklion, which is exactly the kind of place a private catamaran was invented for. The boat is yours: a Fountaine Pajot 41, chartered for the nine of you.
More anchorages, more time to do nothing at all, and the coastline read slowly rather than passed.
A Cretan table, cooked from scratch
Lassithi Plateau. Six and a half hours.
Lassithi is a high, green plateau ringed by mountains, a world away from the beach.
At 850 metres the cooking is done the way the mountain taught it. A local chef takes the family through a Cretan table from scratch — the part of the trip the teenagers will actually describe when they get home.
Chania, Kournas and Rethymno, with your own guide
Eleven hours.
One guide, one air-conditioned car, and three of Crete's loveliest places. Chania comes first: a Venetian harbor, a lighthouse from the sixteenth century, and lanes of saffron walls and cobalt doors lined with cafes and boutiques.
Then Kournas, the island's only freshwater lake, for a walk, a paddle, or a swim in the shade of old trees.
Lunch is at a family-run taverna, ordered with your guide's help. Rethymno finishes the day with its Venetian harbor and old markets, before the ride back to the resort. It is a full day, with about four hours on the road, and water and wi-fi on board.
More than a booking.
Anyone can reserve a villa. What makes a trip like this feel effortless is everything wrapped around it.
Five planning meetings
From the first consultation to the post-trip recap, five meetings, virtual or in person, with more than six and a half hours set aside between them.
Unlimited changes
Rework the daily agenda as many times as you like. Big changes to bookings can incur fees, but reshaping your days never does.
We book it all
Flights, villa, ferry, resort, boats and guides. We reserve it, pay for it, and time it to work together.
A trip app
Your whole itinerary in your pocket and updated live, with a printed copy for the fridge.
Know before you go
Packing lists, destination notes, and the small details that make arriving feel easy.
Help when it counts
If a ferry runs late or a plan shifts, we are the ones you call.
What's included for nine.
- International flights
- Private port and airport transfers in Crete
- 7 nights at a luxury villa in Naxos
- 7 nights at a 4-star all-inclusive resort in Crete
- Fast ferry from Naxos to Crete
- Round-trip ferry tickets to Paros
- Full-day boat tour in Naxos
- Half-day kitron and wine tour in Naxos
- Full-day private culinary tour in Crete
- Full-day private yacht charter in Crete
- Full-day private guided tour in Crete
Optional
9-person van rental in Naxos
Prices, availability, and agenda can change. Gratuities are not included.
Ways to enhance your trip
This birthday getaway has been thoughtfully designed as a complete experience. If you’d like to make the celebration even more memorable, these optional enhancements offer a few ways to add an extra touch of adventure, indulgence, or relaxation.
Add
- A night or two in Athens on the way in or out
- A private sunset sail off Naxos
- A guided morning at the palace of Knossos
- A Cretan wine tasting
- A private driver to Naoussa and Paros beaches
Change
- Swap the sea day for a beach day
- Switch kitron to olive oil and cheese, if it strikes your fancy
- Trade the Chania tour for a slow day at the resort
- Turn a lazy day into one with ATVs
Optional enhancements are available upon request and subject to availability. Additional package costs and planning fees may apply.