With whitewashed villages that cling to steep hillsides, which drop precipitously toward the deep blue sea, few people think of the Aegean Islands as a wine destination. But if you look carefully, you will see that the island of Santorini is essentially one large farm, Samos has terraced vineyards on Mount Ambelos, and Crete is home to a variety of white and red grapes. All three islands have excellent choices for lodging and fine dining, and the network of ferries and short-hop flights make visiting one or more of these convenient and simple. —Mike DeSimone & Jeff Jenssen

Where to Dine

In Fira on Santorini, Restaurant Assyrtiko has an excellent Greek and international wine list, delicious cuisine and stunning views from its balcony over the caldera. Restaurant Selene has two levels, one casual and one more formal. Don’t miss the opportunity to take one of its signature cooking classes. When you’re in the town of Heraklion on Crete, treat yourself to a seafood adventure and creative Cretan cuisine at 7 Thalasses.

Where to Stay

Part of the Small Luxury Hotels of the World group, Aressana Spa Hotel and Suites in Santorini is steps from the main pedestrian thoroughfare in Fira. It offers five-star accommodations, great dining and a trendy lobby lounge. On Samos, Proteas Blu Resort has a beautiful pool and two private beaches. Intimate white-canopied sun beds are the perfect place to relax and catch up on summer reading or to enjoy a chilled glass of wine.

Other Activities

There are many choices for sunset cruising, but if you’re feeling adventurous on Santorini, climb aboard the Schooner Thalassa and sail across the caldera to hike to the top of the volcano. Afterward, swim where the volcanic hot spring meets the sea. When you climb back on board, you’ll catch the most romantic sunset of your life.

Budget Tip

The best way to see the rim of Santorini’s volcanic caldera is to hike from Fira to the town of Oia. The three-hour journey ventures through several small villages, passing picturesque churches and chapels.

Left photo by Georgios Drakopoulos / Top right photo by Antonis Eleftherakis / Bottom right photo by Antonis Eleftherakis

When to Go

April to October are the busiest months with the best weather, but true wine geeks aim for the August grape harvest.

Local in the Know

Stela Kasiola, of Santo Wines on Santorini, says, “One of my favorite places to spend a day with friends is Vlychada Beach—it has a spectacular landscape, and the drive there takes you through vineyards and fields of huge volcanic rocks. Besides relaxing on the beach and swimming, you can walk to the medieval castle in the village of Pyrgos. It is a magical place with little winding paths and small churches. It has a great aura and gives you a wonderful feeling of what Santorini must have been like in the past.”

Where to Taste

There’s no better place on Santorini to taste wine while watching the sun descend over the caldera than Santo Wines. Order a flight of six wines and pair them with specialties including cheese, olives, bread and spreads made from tomato and fava beans. Before leaving, visit the newly renovated boutique to purchase wine and locally grown products. In Crete, sit back in a comfortable reclining chair, sample a variety of wines and learn about the history of Greek winemaking at Boutari’s state-of-the-art theater. On Samos, visit the Malagari Winery, part of the Union of Vinicultural Cooperatives of Samos, to sample the local sweet wines and to visit the Samos Wine Museum. The union has controlled virtually all of the viticulture and production on the island since 1934, ensuring that standards and quality are high.

Prominent Wines

Visitors to Santorini quickly learn that Assyrtiko is the most important variety on the island. Crisp, clean and delightfully acidic, it’s the perfect wine to pair with grilled octopus-and-tomato keftedes (meatballs)—sheer perfection in every mouthful. Other varieties include Aidani, a lightly floral white wine, and Voudomato and Mavrotragano, earthy, medium-bodied reds that go beautifully with local cuisine. Samos is known for delicious sweet wine made from Muscat grapes, and Crete offers a variety of wines, including zesty Vilana and apricot-scented Vidiano. Mantilari is considered one of the best Cretan reds—it’s aromatic and pairs perfectly with lamb.