Getting Between Stops
Fly from the US to Athens, then connect on a short domestic flight to Santorini. Delta, United and American all fly nonstop to Athens from several US cities, with more seasonal routes in summer.
Santorini to Milos is by ferry. High-speed boats run in summer, usually taking about two to four hours depending on the route and stops. Schedules are seasonal and are published a few months ahead, so book once they appear. The meltemi wind can delay or cancel sailings in July and August, which is one reason this route ends in Athens with a full day to spare.
Milos to Athens is a short flight or a three to four hour fast ferry to Piraeus. Rent a car on Milos, since buses thin out quickly. On Santorini, use hotel transfers and a private driver; taxis are limited and roads are narrow.
Where to Stay
On Santorini, stay on the caldera rim. Katikies Santorini is the classic Oia choice, with white cave suites cascading down the cliff. Canaves Oia Epitome sits just beyond the village above Ammoudi Bay, with suites facing west over their own pools. Grace Hotel Santorini in Imerovigli, the highest point of the rim, is quieter with the widest views. Book your splurge here.
On Milos, Milos Cove near Pollonia has private pools and its own beach. Skinopi Lodge has seven stone villas on a hillside above the bay. Melian Boutique Hotel & Spa has sea-view rooms on the Pollonia waterfront. Klima's converted boathouses, where the sea laps below the door, make memorable rooms.
In Athens, choose a room or rooftop with an Acropolis view. Hotel Grande Bretagne on Syntagma Square is the grand old address, while Makrygianni and Koukaki have boutique hotels near the museum.
When to Go
Late May, June, September and early October are best. The sea is warm enough to swim, ferries run frequently and the islands are lively without the August crush. September often has the warmest water.
July and August are hot and crowded, with the highest prices on Santorini and the strongest meltemi winds, which can make boat trips choppy and cancel ferries. Athens can be very hot in midsummer, so plan the Acropolis for opening time.
April and late October are good for walking and sightseeing, though the water is cool and some island hotels and ferry routes have not started or have already wound down. Many Cyclades hotels close from November to March.
Budget and Booking
Plan on roughly $450–1,200 a night for two in good boutique to luxury hotels. Santorini's caldera suites sit at the top of that range and above it in peak season. Milos and Athens usually cost less for similar quality. These figures are approximate.
Book Santorini first, since the best caldera rooms sell out early. Then book Milos, where the small boutique hotels also fill fast for June and September. Reserve the Kleftiko boat trip and the caldera catamaran when you book the hotels.
Other costs: domestic flights, ferry tickets, the Milos rental car, private transfers on Santorini, the Acropolis and museum tickets and a nightly accommodation tax at each hotel.
Make It Shorter or Longer
For eight days, spend three nights each on Santorini and Milos and one in Athens before your flight.
With two weeks, add three nights on Folegandros between Santorini and Milos. Fast ferries from Santorini take around 45 minutes to an hour and a half and Folegandros also connects to Milos. It is the quietest island on the route, with a cliff-edge village and walking paths to coves.
Couples who want a mainland finale can swap one Athens night for two nights at Nafplio, about two hours by car, or stay at a resort on the Athens Riviera near the airport for a beach day before the flight.
Honeymoon Tips
Pack light. You will carry bags on and off ferries and up steps on Santorini, where many cave suites sit far below the lane.
Book sunset dinners and boat trips early and accept that Oia's castle will be crowded at sunset. A caldera-view terrace in Imerovigli or a boat at sea is far more romantic.
Sun and wind are strong at sea, so bring high-factor sunscreen, a hat and a light layer for boat days. On Milos, watch for loose rock at Sarakiniko and take care jumping into the water. In Athens, wear comfortable shoes on the slippery marble paths of the Acropolis and carry water.
