In 1492, Columbus sailed the ocean blue and what better way to celebrate his arrival in the New World than getting the hell out of it? Pay homage to the man responsible for giving you an extra vacation day by discovering some far away new place on your own.

Start in Chris’s birthplace of Genoa, Italy. Knowing the Italians, they are still whooping it up from their World Cup victory. Bury your face in a plate of Genoa’s famous pesto then burn off those carbs walking Genoa’s revitalized port and picturesque medieval quarter. Then explore the terraced fishing villages of Cinque Terre. Its sweeping cliffs have beautiful views of the sea.

• Flights to Genoa
• Hotels in Genoa
• Talk to other Kayakers about Genoa

When Genoa stiffed Columbus voyage funding, he tried his luck with Queen Isabella in Spain. With her blessing (and ducets) he eventually set sail from Barcelona, and his statue now overlooks that city’s harbor. Chow down on Barcelona’s best tapas in the rustic bars off the city’s main drag, Las Ramblas or explore the labyrinthine alleys and shaded squares of the Barri Gòtic. If art is your thing, the airy Picasso Museum holds an extensive collection of the artist’s early work, and you can see Gaudi’s handiwork throughout the city, including his masterpiece, Sagrada Familia.

• Flights to Barcelona
• Hotels in Barcelona
• Talk to other Kayakers about Barcelona

From Spain Columbus sailed to Cuba and Hispaniola, now the Dominican Republic. As long as old Fidel still has a pulse, Cuba’s still illegal to travel to from the US, but you can get perfect white sand in your bathing suit at one of the Dominican Republic’s many beach resorts. Or, if you’re into a vacation with a little less relaxation the D.R. offers great golf, horseback riding, surfing, diving, and more. And fall’s the best time to snag a great Dominican deal.

• Flights to the Dominican Republic
• Hotels in the Dominican Republic
• Talk to other Kayakers about the Dominican Republic

After four transatlantic voyages Columbus’ wanderlust continued, even after he died. From his first final resting place in Valladolid, Mexico, his body was shipped to Seville, Spain then back to Santo Domingo in the Dominican Republic then to Havana a few centuries later, and then back to Mexico where his body rests today. A quick flight can get your body to Mexico, where you can live la vida loca at some of Valladolid’s beautiful resorts.

• Flights to Cancun
• Hotels in Valladolid
• Talk to other Kayakers about Cancun or Valladolid

Americo Vespucci may have two continents named after him for discovering America second, but Columbus has no fewer than 32 US cities named in his honor. Why not visit one close to you? The most famous Columbus, Columbus, Ohio is where you’ll find The Ohio State University. There is not better time to visit Columbus than during football season. Ohio State is currently ranked #1 and there’s plenty of room on the bandwagon. The Buckeyes just happen to be in town Columbus Day weekend hosting Bowling Green.

• Flights to Columbus, Ohio
• Hotels in Columbus, Ohio
• Talk to other Kayakers about Columbus, Ohio

Get the Fare Buzz for these Columbus Day destinations from your home airport.

Helping to make the world a little flatter,
Steve and Paul, Kayak.com co-founders

Thanks to “Sideways”, even your hillbilly Uncle Jeb is going on about earthy tones and oaky finishes. Wine consumption is on the rise in the US and now almost every state in the US can turn out a decent wine. What better time to start channeling your inner Sommelier than harvest season? So, bag the California pretensions, warm up with a few sets of pinky extensions, and take a tour in these off-the-beaten-path wine countries.

• Virginians have a long history of partaking in the grape; Thomas Jefferson stuck the White House with a $10,000 bar tab when he left office. Virginia’s major wine region around Charlottesville is named after old TJ’s Monticello estate, but vineyards dot the state. The Virginia Wine Festival, September 30-October 1 in Leesburg, is your opportunity to swirl, sip, swallow and spit your way through the Virginia wine country while satisfying your palette for live music, local arts, and great food.
  • Flights to Charlottesville
  • Hotels in Charlottesville or Leesburg
  • Talk to other Kayakers about Charlottesville
• Doing its best to change wine’s wussy reputation, Texas wineries have reclaimed wine for the beer-swilling cowboy set. And nothing goes better with Texas longhorn than a nice bottle of Pinot Noir. The Texas Hill Country Wineries, centered in Fredericksburg, have channeled know-how of the area’s German and Italian immigrants to make the state the 5th largest wine producer.
  • Flights to San Antonio
  • Hotels in Fredericksburg
  • Talk to other Kayakers about San Antonio or Fredricksburg
• New York’s got your award-winning white wines right here. Its slightly sweet Riesling has been fighting for national recognition for years. Finger Lakes wineries around Keuka, Seneca and Cayuga have organized “wine trails”. The Hamptons’s vineyards are an easy drive from New York (and a stretch Hummer rental ensures that you arrive in style). Kayak’s oenophile chief architect Bill O’Donnell says you must visit Grapes of Roth, Jamesport, and Paumanok on the North Fork (where you should stick to the Merlot) and pick up a bottle of the 2004 Heron Hill Riesling Late Harvest if you make it to the Finger Lakes. Designate a driver to avoid adding a mugshot to your vacation photos.
  • Flights to Corning, NY or New York
  • Hotels in Finger Lakes or The Hamptons
  • Talk to other Kayakers about Finger Lakes or The Hamptons
• Wine is not the first thing you think of when you think of Utah (Skiing, Sundance, polygamy). But after a long day of skiing (or polygamy), there is nothing like uncorking a bottle and soaking in the hot tub. You can enjoy “lily rose” white wine and great mountain-biking in Moab, please just not at the same time. Right outside Moab, Castle Creek Winery overlooks the Colorado River and Utah’s red rocks. Head to the nearby Spanish Valley Vineyards to make it a full-day vinopallooza.
  • Flights to Moab
  • Hotels in Moab
  • Talk to other Kayakers about Moab

Get the Fare Buzz to these US wine regions from your home airport.

Slightly buzzed, but still giving you the Buzz,
Steve and Paul, Kayak.com co-founders

Did you know that Kayak fare alerts let you track prices to your favorite destinations? And setting a max price on the alerts makes sure you have budget to bring home a case of your favorite grape.

Attention wanna-be Mensa members and braniacs. School’s in, and now is a great time to match IQ points with the brightest of the bright. Why not take a trip to some of the world’s intellectual Meccas, institutions that will make even the smartest traveler feel like Homer Simpson.

• Geeks with tans, that’s what you’ll find on the sunny Palo Alto campus of Stanford University. The sprawling, pastoral Stanford campus (a.k.a. “the Farm”) is regarded as the most beautiful on the West Coast (although the tree huggers across the bay at Berkley might disagree). And the surrounding Silicon Valley will give you plenty of opportunities to get your nerd on, talking tech with Apple programmers. Another smart bet is to drive north to explore San Francisco, or to kill some brain cells in Northern California’s wine country.
  • Flights to San Francisco
  • Hotels in Palo Alto
  • Hear what other Kayakers say about Palo Alto
• College rivals Harvard and MIT make Cambridge, Massachusetts a tough place to win at bar trivia. Even the village idiot has a PhD. See if you can still split the atom after a few beers at Miracle of Science bar in Central Square, near MIT. Or head to Pinocchio’s Pizza in Harvard Square and have your own “Good Will Hunting” moment by mentally dressing down some Ivy League jerk (and grab a slice of the best pizza in Boston) Check out the tiny Café Pamplona at any time to do a few shots, of espresso. As we all know caffeine, and beer are what truly fuel academia.
  • Flights to Boston
  • Hotels in Cambridge
  • Hear what other Kayakers say about Cambridge
• If the provincial intellectual snobbery of Cambridge, Mass is below your elitist tastes, you’ll feel right at home in its sister city. Cambridge and Oxford are just a short train ride from London. Established in 1096, Oxford is the oldest English-speaking University in the world, we’re talking real ye olde school here. Bask in the kind of old European ambiance that makes Harvard feel like a Wal Mart. Oxford is the home of such illustrious alum as Roger Bacon, Sir Walter Raleigh, Lewis Carroll and the inventor of Green Eggs and Ham, Dr. Seuss.
  • Flights to London
  • Hotels in Oxford
  • Hear what other Kayakers say about London
• * Beating Oxford by a mere six years (in your face Oxford), the University of Bologna is the oldest still-operating university in the world. At this time of year, the bars, cafes, and squares are teeming with students, and an eclectic mix of concerts, art exhibits, and ballet and theater performances that will broaden the mind so much, your head might not fit through your hotel room door. If you’re feeling intimidated by Bologna’s intelligencia, come back at the end of the school year, when traditional commencement celebrations involve activities like graduates wearing diapers and standing in fountains while reciting Dante. Not the same as the time you streaked through campus singing “Freebird”, but it’s the thought that counts.
  • Flights to Bologna
  • Hotels in Bologna
  • Hear what other Kayakers say about Bologna

Get the Fare Buzz for these college towns from your home airport.

Yours in the smartest of smarty pants.
Steve and Paul, Kayak.com co-founders

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The days may be getting shorter but to us that means just one thing: Oktoberfest is only a short fermentation away. Stop and you can almost hear the hops a-malting. So get out your lederhosen and your favorite oversized beer mugs; it’s time to cry “O’zapft is!” (”It’s tapped!”). Officially, the boozing begins (make that celebration of the harvest) September 16. Here are a few of our favorites:

• Visit the land where it all started when Crown Prince Ludwig married Princess Therese von Sachsen - Hildburghausen (imagine that for a Scrabble triple word score) and the town celebrated for five days. To honor the age-old tradition, the world has upped the party to two weeks of nonstop fun from September 16th to October 3rd. Check out the beer tents, food, entertainment, and carnival style games during your stay. Feeling adventurous? Or just anti-social? Try Hankase mit Musik (hand cheese with music), a cheese marinated in oil, vinegar, and onions. The musical element of this dish begins 30-40 minutes after consumption.
  • Munich Flights
  • Munich Hotels
• If you find your self in LA or San Diego this fall, check in on the 36th Annual Big Bear Lake Oktoberfest which runs six weekends in a row starting September 16th. Live bands and entertainment straight from Germany, log sawing contests, stein holding contests, and safe beer slam drinking contests round out the activities in between gorging on obscene amounts of food. Enjoy some hiking, fishing, and mountain biking to work off some of that bratwurst during your stay.
  • Los Angeles Flights
  • Big Bear Hotels
• Boston’s 17th Annual Harpoon Oktoberfest owns the bragging rights for the largest festival celebrating barley and hops in New England. Show up the last weekend of September at Harpoon’s Brewery for keg bowling, authentic German cuisine, drinking, contests, music, and the best Chicken Dancing this side of the Alps. Hanging around after the festival ends? Take a tour of Harpoon’s brewery while you’re there and stock up on their 64 ounce collectable bottle that they fill right from their taps. How long the contents remain collectable is up to you.
  • Boston flights
  • Boston hotels
• Nothing says Oktoberfest like Helen, Georgia. OK, one or two more places may come to mind before this picturesque mountain town but trust us, this place means business. Helen’s Oktoberfest runs two months – from September 14th to November 5th – and boasts the biggest party in the Southeast. The celebration comes complete with beer, Bavarian food, contests, dancing, beer gardens, trout tournaments, and more.
  • Atlanta flights
  • Atlanta hotels

Want to help spread the word about Kayak? Vote for Kayak in this BusinessWeek survey as the best travel site and, in honor of the season, the next time we see you the beers are on us. Polls close on 9/8 and, unlike Kayak, BusinessWeek won’t wait for you.

Prost!
Steve and Paul, Kayak.com co-founders