Get warm with a free trip to the Cayman Islands

It’s been a doozy of a winter so far, and there are no signs that the temps are suddenly going to increase. You’ve got a long few months to go before you get warm again….unless you happen to win the Cayman Island’s new contest. The lucky winner will receive a trip for four, including air and hotel, to the tropical Cayman Islands.

The winner and friends will stay at the Grand Cayman Marriott Beach Resort on Seven Mile Beach, and will receive a free boat and snorkel trip to Stingray City, where they’ll swim with massive stingrays.

To enter, you’ll need to upload your best photo that shows one of your coldest winter moments. Upload it by March 1 and encourage all your friends to vote for you. The ten entries with the most votes will move on to the final judging, and a winner will be announced by March 10. You must be 18 or older and a resident of the US to enter and travel must take place by December 31, 2011.

Of course, for many people, the worst of winter will be over by March 10. So maybe the contest won’t help you escape the cold right away, at least not in the most literal sense. But maybe the thought of a Cayman Islands vacation – especially a free one – will warm your heart just a bit.

Blue Ridge Parkway celebrates 75 years by giving away a free trip

This year, Virginia’s scenic Blue Ridge Parkway celebrated its 75th birthday. What better way to celebrate than by giving away a six night, seven day vacation package?

The winner of the prize will receive round-trip airfare for four people to Dulles Airport, a seven-day Enterprise hybrid car rental, six nights of lodging at stops on the Blue Ridge Parkway and several great activities along the way. The winner and family will have the chance to explore the Luray Caverns and the Mill Mountain Zoo, and to go canoeing, kayaking, mountain biking, or rock climbing. They’ll enjoy ice cream at the Split Banana, dinner at Shenandoah Pizza and a picnic at Peaks of Otter plus much more as they explore this beautiful area of Virginia.

To enter, just fill out the online form. The winner must be 21 years old and a resident of US. The winner will be selected on November 10, 2010 and travel must take place between November 15, 2010 and October 31, 2011.

Become a Facebook fan of JetBlue and win free travel

Remember those amazing All-You-Can-Jet passes offered by JetBlue last year? Well here’s your chance to win one.

All you have to do to enter is become a fan of JetBlue on Facebook. That will get you one entry into their grand prize drawing. If you want to increase your odds of winning, you can also do one bonus entry every day and sign up for the team prize drawing. One pair of round-trip tickets will be awarded each week along with one team prize – a 5 day, 4 night vacation package for 4 people – and the grand prize, the mother of all All-You-Can-Jet passes, which will be good for an entire year of unlimited travel on JetBlue.

The contest ends January 31 and you must be 18 years of age or older and a resident of the US to enter.

Win a free trip to Costa Rica from Nomadic Matt and Gap Adventures

Globetrotting blogger Nomadic Matt took his very first international trip to Costa Rica with Gap Adventures back in 2003. Ever since then, he’s been traveling the world, blogging about his adventures and teaching others how to make money from their own blogs. Now he’s paying his success forward, and awarding one of his lucky readers a free two-week trip to Costa Rica with Gap Adventures.

The winner will go on the Gap Adventures Costa Rica Explorer Tour that departs on March 28. The trip includes stops in Tortuguero, at Arenal Volcano, Monteverde and Manual Antonio National Park. Most breakfasts and a few lunches and dinners are included, but the winner will be responsible for other meals and activities not included on the tour. Airfare is covered in the prize, and the winner does not need to be from the United States.

The winner does have a few responsibilities though, other than just going on a pretty sweet (and almost totally free) trip. You will need to blog about your adventures both on the trip and afterwards, reflecting on the experiences had and the lessons learned. But don’t worry, Matt will be there to help you out with a blog set-up and tutorial. You will need a computer, digital camera or video camera though, and for that, you’re on your own.

So how do you win? You can check out the full list of instructions on Nomadic Matt’s website, but the gist is that you’ll need to write a 500-word blog post or create a 90-second video explaining why you want the trip and what you hope to get out of it. The top 50 entries will be voted on by the public, narrowed down to a field of ten, and then chosen by Matt and a panel.

You must enter by February 14th, and you need to be 18 year of age or older to win.

Hawaii’s on sale with cheap flights from United and Hawaiian Airlines

Winter may not have officially started yet, but it certainly feels like it has. With temps in the double, and even single, digits and snowstorms covering the country, there’s no denying that a tropical vacation sounds pretty darn good right about now. Luckily escaping to the warmth of Hawaii this winter will be surprisingly cheap thanks to two great airfare sales.

Book a ticket through the Hawaiian Airlines sale by December 16 for travel January 5 to March 11 and April 6 to June 10 and you could fly for as little as $288 round trip (plus taxes). Seattle or Portland to Honolulu, and Portland to Maui are the cheapest routes at $288 round trip. Los Angeles and San Francisco to Honolulu are $368 and Seattle to Maui is $318.

Rates are even lower through United’s sale, which ends a day earlier on Dec 15. The travel dates are more limited – just January 12 to March 4 – but there is a wider variety of cities to choose from. For example, Chicago to Maui is $302, LA to Honolulu is $261, San Francisco to Kona is $265, and Denver to Maui is $285.
And if you need a reason to go to Hawaii this winter (other than “it’s warm there!”) Hawaiian Airlines offers a few more. January to April is whale watching season, now is the perfect time for surfers to catch huge waves formed by storms, and in February there are several Chinese New Year celebrations and the Big Island’s Waimea Cherry Blossom Festival. Plus, did I mention, it’s warm there?

If you can’t afford the flight, check out Portland International Airport’s website by January 2 and enter to win a pair of tickets from Portland to Maui. Okay, actually you can choose Maui or Chicago, but let’s be real – you’ll choose Maui.