Getting Between Stops
There are four transfers. Only one is a long day. Athens to Hydra is a fast ferry of about one and a half to two hours from Piraeus. Book summer sailings ahead, especially on Friday afternoons and Sunday evenings.
Hydra to Dubrovnik is the big travel day: ferry to Piraeus, taxi to the airport and a short flight. Start early and allow buffer between the boat and the plane. Seasonal nonstops between Athens and Dubrovnik run in summer. In spring and fall you may need to connect, which can make it a full day.
Dubrovnik to Korčula is a catamaran of about two hours from the port at Gruž. Returning, you can take the catamaran or a private car via Pelješac.
You will not need a car anywhere on this route. Hydra has none. Dubrovnik's Old Town is pedestrian.
Where to Stay
In Athens, the Hotel Grande Bretagne on Syntagma Square is the grand old address, with a rooftop restaurant facing the Acropolis. Boutique hotels in Makrygianni and Koukaki cost less and many have view terraces.
Hydra has no big resorts. Places to stay are small hotels in restored mansions. Cotommatae 1810, in a restored captain's house, is a polished choice near the harbor. Rooms higher in town are quieter but come with a stair climb every time you head home.
In Dubrovnik, Ploče, just east of the Old Town, is the classic honeymoon area. The Hotel Excelsior and the Villa Dubrovnik look back at the walls across the water. The Hotel Bellevue sits on a cliff above its own cove to the west.
On Korčula, Lešić Dimitri Palace offers suites in a restored palace inside the old town walls.
When to Go
Late May through June and September are the best months. The sea is warm enough for long swims, ferries and catamarans run full timetables and the heat is bearable on stepped lanes.
July and August are hot and busy. Dubrovnik fills with cruise passengers in the middle of the day, ferries sell out and prices peak on both islands.
Early October is often still warm enough to swim, though boat schedules thin out and some flights stop. From November to April, many hotels on Hydra and most on Korčula close, so this is a summer-season honeymoon.
In any month, plan your Dubrovnik walls walk for opening time and your boat days for the morning, when the sea is usually calmest.
What It Costs
This route costs less than a Santorini and Mykonos trip. As an approximate guide, a good Athens hotel with an Acropolis view costs about $250 to $600 a night for two. Hydra's boutique hotels run roughly $250 to $500 in summer. Dubrovnik is the priciest stop, with Ploče's sea-view hotels from about $450 to $800 or more in peak season. Korčula's old town suites cost around $300 to $500.
Ferries and catamarans are inexpensive. The Athens to Dubrovnik flight varies widely, so book early.
The extras worth paying for are a private boat around Hydra, a sunset sea kayak to Lokrum, a boat day to the Elaphiti Islands and a winery visit on Korčula or the Pelješac peninsula. Dubrovnik restaurants inside the walls charge for the setting, so eat lunch in Gruž or Lapad and save the Old Town for a splurge dinner.
Tips for the Two of You
Pack light. Hydra, Dubrovnik and Korčula are all built on steps. On Hydra the porters are donkeys. A bag each that you can carry up a staircase saves a lot of grief.
Bring water shoes. Most swimming here is off rocks, ladders and pebble coves. Sea urchins live on some rocks, so watch where you put your hands and feet.
The sun is strong from May onward. Reef-safe sunscreen, hats and a refillable water bottle help on wall walks and hikes.
Churches and monasteries ask both of you to cover shoulders and knees. Carry a light scarf or shirt.
You may want different things on your free days. One of you could hike Profitis Ilias while the other reads on the rocks, or one could kayak around Lokrum while the other books a spa hour. Meet for lunch by the water.
Make It Shorter or Longer
With nine or ten days, drop Athens at the start by connecting straight through to Hydra the day you land, or skip Hydra and spend two nights in Athens before flying to Dubrovnik. You lose the Greek island but keep the Adriatic half.
With 14 days, add two nights in Split after Korčula, with a catamaran stop in Hvar on the way. Fly home from Split. Or spend two nights on the Bay of Kotor in Montenegro, about two hours by road from Dubrovnik, for a fjord-like bay and stone villages.
On the Greek side, Nafplio on the mainland is a good addition for history lovers, with the theater at Epidaurus nearby. Couples who would rather finish with more swimming can swap Korčula for Mljet, a quieter green island with a national park and saltwater lakes.