Towns and Villages

• Be sure to wear flat shoes that grip the cliffside cobblestone streets of Fira, the largest town roughly at the island's center, and Oia, the picturesque village at the island's northern tip. There are other villages to the south, but none so interesting as these two. Nearly every town on Santorini is family-friendly, so if you have children, explore at your ease.
  
  In Fira, you'll want to start at the whitewashed town square, one of the rare open places in this warren of streets and the spot where motorized traffic stops. From the center, walk straight toward the cliff, where there are rows of shops just waiting for tourists like you. Be prepared to haggle vigorously for memorabilia and gold jewelry. Then walk along the main cliffside drag for a view of the lagoon where the cone of the dormant volcano lies submerged in caldera. You can even take a small boat over to the closest island for a hike up the part of the volcano that remains aboveground, still emitting sulfur fumes.
  
  Oia is quintessential Santorini, bathed in light and views. The old houses, as in the island's other cliffside settlements, are generally small domed structures scooped from the porous stone. Like other Cycladic architecture, they are mainly brilliant white inside and out, with bright blue domes, many with masses of bougainvillea growing over walls and roofs. These early villages were a refuge from marauding pirates. These days, a walk through the narrow lanes is a feast for the eyes. Catch the sunset at the wide castle promenade, and shop at Oia's artisan boutiques for unusual clothing and jewelry.
  
  

White, Red and Black Beaches

• Relax and swim on Santorini's dramatic beaches. There are few or no amenities at the beaches themselves, so bring drinks, lotions and towels with you.
  
  Beginning at the north, walk east down the beach road from Oia to an unforgettable long black sand beach with few people. On the way back up, stop at the beach taverna for a hearty Greek salad and some calamaria (fried squid) or octopus. On Oia's cliff side, there are steps (plenty of them) leading to a stone platform for sunning and diving.
  
  Along the less-challenging east coast, where crops and beaches merge with the sea, stop at the white sand beaches of Perissa.
  
  Then head straight south for the soaring red volcanic cliffs and red sand beach near the Akrotiri archaeological dig. Because this place is so unusual and not so large, it gets pretty crowded. So try to hit it before 11 a.m., after about 5 p.m. or during the off-season.
  
  

Archaeology and Wine Tasting

• Southernmost Santorini is the site of Akrotiri, an 4,000-year-old Minoan settlement preserved, much like Pompeii, in the lava flow. Trod the dirt streets, see houses up to three stories tall with enormous intact clay storage pots and plumbing, such as the oldest known water closets (toilets).
  
  From here, drive north on the main island road and you'll see arid fields with strange, wreath-shaped plants growing close to the earth. These are Santorini vineyards, configured to protect them against the brutal sea winds and to capture the dew overnight. They produce beautiful wine; stop at the gorgeous Boutari winery for a full explanation and a glass of white assyrtiko varietal. In Fira, you'll want to see Argyris Sigalas's "canavas," or wine house---a large wine making and storage room that was once part of every rich captain's house.
  
  

Bars

• There are a range of raucous bars and clubs catering to the students on break and noisy tourist groups who step off the cruise ships that call every day and night. Then there are these really great places.
  
  "Newsweek" named Franco's Bar one of the world's best in 1985, and it still deserves the honor. At least an hour before sunset, head to the center of Fira's main cliffside street and look for the little Franco's sign. If you are lucky, you'll find a lounge chair at the edge of the balcony cantilevered over the cliff face. Order one cocktail you love (more than one can be pricey), and sit back while classical music fills the air and you gaze at the custard-smooth lagoon covering the caldera as the main show begins---an unhindered display of the sun setting in gorgeous shades of orange, fuschia and red.
  
  Or look for the red stucco walls of Kira, Thira's very cool jazz bar. This intimate, welcoming place dates to 1976, which may make it Santorini's oldest bar. (The island had to resurrect itself after a devastating earthquake in 1956.)
  
  

Restaurants and Tavernas

• There are many restaurants and tavernas on Santorini that face the beautiful caldera. That view and reasonably good taverna and Continental dishes will keep you happy. But if you want a wonderful dining experience on Santorini, try one of the following.
  
  In Oia, the place is 1800, a charming old mansion, where a chef prepares Greek and Mediterranean food. Sit up on the roof to watch the spectacular sunset over open sea.
  
  In Fira, you won't be disappointed if you point yourself toward the southern end of town and walk down the steps to Selini, an outdoor restaurant that serves Santorini haute cuisine on broad, canopied balconies overlooking the caldera. The owner insists on traditional Santorini ingredients like wide, marinated caper leaves; cherry tomatoes; dried yellow split peas called fava; white dwarf eggplant and local goat cheeses.
  
  Down near Akrotiri, spend a languid afternoon at Capetan Markos's remote ramshackle taverna on a small bay off a 3-mile dirt track. Expect fish the good captain caught that morning and his wife cooked just for you. It's well known; if you need directions, ask at Almyra beach.