Culture, Second-Time Travel
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Second-Time Travel: Santorini, Greece

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The stunning cliffs of Santorini. (Photo: Jennifer Hill)

I love the Mediterranean Sea. Ever since I visited for the first time as a high school foreign exchange student, summer has never felt the same without a trip to this part of the world. The brilliant sunshine, chill attitude of the locals, delicious food and long summer nights are my idea of paradise.

A visit to Greece is a magnificent way to experience the Mediterranean. The amazing cliffside architecture is a marvel — the dizzying, white washed buildings glitter brilliantly at different times of day. (Given the rocky terrain, it’s not for young children.) Find a favored travel partner who is comfortable just relaxing and appreciating the scenery, or visit on your own. The breathtaking views, delicious food and warm Greek hospitality make it hard to leave. Since a flight transfer from Athens is essential, spend a couple of extra days in one of civilization’s capitals to see history for yourself.

Where to Stay

This is the most important decision of your trip. Every part of the island is beautiful, and it is possible to explore it all, depending on the length of your visit. We chose the town of Imerovigli because it’s walking distance from the more populated towns of Thira and Firostefani, which are also magnificent and not overrun by tourists.

The Gold Suites in Imerovigli are incredibly luxurious. Built into the Cliffside, like many Santorini hotels, each room either has pool access or its own private deck with a pool. The hotel only has few rooms, so guests are sparse and the feel is quite exclusive. Although it overlooks the Mediterranean Sea, there is no beach nearby, so the pool serves as a delightful tanning option. (No sandy feet, and poolside food service, too!) The hotel can be pricey during peak times, so check Jetsetter and other travel sites for the best deals.

The Grace Hotel, also in Imerovigli, is outstanding as well. It has luxe, large suites and is focused on creating a customized experience for each guest. There is a beautiful pool bar that overlooks the sparkling Aegean Sea, a spa with a host of fantastic services, an intimate dining area and amazing views all around.

The Best Eats

The food on the island is generally excellent. Avoid heavily touristy places or locations near the shipyard if you want to eat like a local. I could live on Greek food, so every meal there is a major treat for me.

Classic Breakfasts. Many Grecian hotels provide breakfast — and it is amazing! The Gold Suites set the standard exceptionally high for future hotel stays anywhere else in the world. The gracious and effusively friendly staff comes to your room to take your order and will even serve you poolside if requested. I still dream about the fresh squeezed orange juice, Greek yogurt and breakfast rolls.

Old-Style Greek Fare. Anogi is a lovely homestyle restaurant in Imerovigli that serves traditional Greek cuisine. (I think we ate there three times during one visit.) The menu has lots of variety and includes everything from fresh salads with baked feta cheese, tomatoes and peppers to tasty meat and pork dishes. The restaurant books up fast for lunch or dinner — especially the outdoor tables — so make sure to make a reservations well in advance. The service is excellent and the staff goes out of their way to ensure that you have a wonderful culinary experience. The placemats even have recipes, so be sure to photograph it before you start eating!

Meet Mama. Mama’s House also has excellent Greek staples, which are served indoors or in the restaurant’s beautiful courtyard. If you are in the mood for outstanding renditions of Greek staples such as gyros, salads, chicken and baklava, this is the place to dine. It’s a charming, friendly and reasonably priced spot, and the food will fill you up for a day of adventures. Plus, Mama herself is often on site, and she’s quite the character.

Wine Time. If you’ve never tried Greek dessert wine, be sure to do so. It’s excellent and Greeks swear that it is good for your health!

Don’t Forget Dessert! From the most delicious gelato to classic baklava, your sweet tooth won’t be disappointed.

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(Photo: Jennifer Hill)

What to Do

Chill Out: There’s no shame in spending time sitting and doing nothing but looking out over the sea. The beauty of the surroundings is captivating. Be sure not to schedule too many activities, as the scenery alone is one of the things that make this island so special.

Explore the Sea: Ask the hotel about arranging a boat tour around the island, a stop at the volcano, or a snorkeling or diving trip.

Take a Walk: If you love to walk or hike, you can cover a lot of the island during your stay. Ask the hotel staff for guidance on day hikes and how to pack for them. We hiked from Fira to Oia and were awed by the amazing views. You’ll see the island’s unique terrain, beautiful churches, tiny towns and absolutely stunning views of the sea.

Be sure to spend some time each day exploring the Cliffside as you walk to and from your hotel. (Tip: Wear comfortable walking shoes and be mindful of where you step.) You’ll see artists, merchants, locals, photographers and more as they each enjoy the local architecture in unique ways. Sometimes painters will be perched on a step for hours capturing the view on canvas. Other times, you’ll see poets composing and professional photographers taking those amazing photos that entice us to visit in the first place.

Where to Visit

Oia. You’ll want to spend at least half of a day in the small, sweet town of Oia. It’s famous for it’s magnificent sunsets — people flock from all around the island to see them. Find a seaside restaurant with a glorious view and enjoy a cocktail while the sun goes down. Oia also has adorable shops and cobblestone streets to wind your way through. Just be sure to avoid the times of day when the cruise ships are welcomed!

The Akrotiri Archaeological Site. This ancient city was discovered in a heap of volcanic ash in the late 1800s. The excavation is now covered indoors and the history of Akrotiri is fascinating. Nearby are the red sands of Akrotiri Beach, which is sparsely populated, yet known for being one of the most beautiful beaches in Santorini.

Perissa Beach. The black sands of Perissa Beach is must-see, as well as a fun spot to stroll on. The black sand feels heavier under your toes compared to traditional beach sand, and if your feet are sensitive, it might even tickle a bit. Because getting there requires a taxi or bus ride from the major touristy areas, the beach is rarely crowded. Street vendors sell food and other goods along the way, but eat ahead of time and pack snacks just in case.

Santorini is one of the most beautiful places I’ve ever visited. Couple the outstanding views of the Mediterranean Sea with a luxurious hotel, amazing food and the genuinely warm hospitality of the Greeks, and you’ve got an amazing vacation waiting for you.

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