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Win Trips To Tuscany, New York, San Francisco & More

July 17, 2014
5 min read
Win Trips To Tuscany, New York, San Francisco & More
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There are a few fun travel contests and sweepstakes going on around the web this week. Here are my top picks to win some great travel prizes!

Win a trip to NYC or LA with IHG Rewards Reel Summer.

Win a Trip to NYC or LA: IHG Rewards (formerly Priority Club) is giving away a free three day, two night trip to New York City or Los Angeles to one lucky winner of the Reel Summer contest. In order to enter, you must first register for the contest. Then, make a 15 second video on Instagram re-enacting your favorite movie moment or something fun in your life that is movie worthy. Tag it with #reelsummercontest and you could win a trip including airfare, hotel, $1,000 in cash. and lunch with actor Josh Lucas. The contest is open to residents of the 50 United States, Canada, Chile and Columbia who are 21 years of age or older. Enter by 11:59 pm ET on September 2, 2014.

Win a trip to a Sandals resort

Win a Trip to the Bahamas: Win a trip from Daily's Cocktails for two to the Sandals Royal Bahamian. The grand prize is an all-inclusive resort package with airfare, or you can select a cash option of $5,000 instead. You can enter daily to win. The contest is open to legal residents of the 50 United States and District of Columbia that are 21 years of age or older as of May 13, 2014. Enter by 1:00 pm EST on July 29, 2014.

Win a wine tasting getaway to Tuscany. (Image courtesy of Samot/

Win a Wine Week for Two in Tuscany: You could win a wine vacation including six nights at Villa Montecastello in Tuscany, tours of several Tuscany wineries, and $2,500 towards airfare. By entering, you agree to receive emails from PureWow, Epicurious, The Daily Sip, Hipmunk & Fathom. The contest is open to all legal residents of the 50 United States who are 21 and over. Enter by 11:59 pm EST on July 27, 2014.

Win a $10,000 vacation for sharing your "Vacay Gone Cray Cray" story. (Image courtesty of

Win a 10,000 Vacation: Sometimes vacations don't always go as planned. You could win a $10,000 vacation for submitting the story of your "Vacay Gone Cray Cray" in 250 words or less, sponsored by Choice Hotels. Got photos of your terrible vacay? Submit the best one with your written story. Each week, a story will be chosen and made into a video, and featured on the show, Good Mythical Morning. If you win, you get a vacation "redo", and hopefully it will go more smoothly than your original trip. Enter by 11:59 EST on August 27, 2014.

Win a Ghirardelli chocolate filled trip to San Francisco.

Win a Trip to San Francisco: You could win a chocolate lover's dream trip to San Francisco including:

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  • Two Chocolate & Wine Pavilion tasting tickets to the 19th Annual Ghirardelli Chocolate Festival
  • Roundtrip airfare to San Francisco
  • Luxury Hotel Accommodations
  • A San Francisco Bay Sunset Cruise for two
  • Basket full of Ghirardelli Chocolate

The contest is open to legal residents of the continental United States and the District of Columbia who are 18 years or older at the time of entry. However, you must be 21 or older to enter the Chocolate & Wine Festival. Enter by 11:59 p.m. PST on July 31, 2014.

Want to hate on Spirit Airlines? Get 8,000 free miles for doing so

Reminder: Complain to Spirit Airlines and Get 8,000 Free Miles: Spirit Airlines will give you 8,000 frequent flyer miles if you complain about them, or any other airline for that matter. Technically, it's not a contest, because you will definitely get the miles if you complain (at least until Spirit has given out one billion miles, or until July 31, 2014, whichever comes first).
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Featured image by Win a wine tasting getaway to Tuscany. Image courtesy of Samot/

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