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Here are your travel contests for this week. You can win trips to South Africa; New York City; the Cayman Islands; Rome, Italy; Telluride, Colorado; Paris, France & more. Good luck!

Win a trip to South Africa

  • 5-Night VIP Accommodations at Cape Town’s #1-rated One & Only Resort and the Luxurious Mont Rochelle Nestled in the Vineyards of South Africa.
  • Roundtrip Airfare for Two Provided by South African Airways.
  • Private Winery Tour and Estate Reserve Library Wine Tasting at Fort Simon Winery in Stellenbosch.
  • Winemaker Dinner with Eighth Wonder’s World Acclaimed Winemaker, Therese de Beer.
  • Airport Transportation Provided by UBER.
  • Enter by December 23, 2015

Win a trip to New York City

  • 2 night hotel stay plus $500 toward travel
  • Exclusive portrait session with Izak Zenou, renowned fashion illustrator
  • A one-of-a-kind Henri Bendel handbag hand-painted by Izak Zenou
  • $1,500 shopping spree at Henri Bendel!
  • Enter by December 24, 2015

Win a trip to the Cayman Islands from Sherman’s Travel

Book your hotel in Travel Contests - Win A Free Trip! now!

  • 5-night stay for two at the Westin Grand Cayman Seven Mile Beach Resort & Spa, a AAA 4-Diamond resort
  • Airfare certificate for 2 from a Cayman Airways gateway (see rules for details)
  • Daily breakfast and one dinner for two at Beach House restaurant
  • Soaking up the sun in a complimentary cabana on the Grand Cayman’s Seven Mile Beach, Rated #1 Beach by U.S Travel News
  • Red Sail Sports Activity Package: Choice of Two days of 2-tank diving, or a Discover Diving course and a sunset sail
  • Enter by December 30, 2015

Win a trip to Rome, Italy from Fontana Candida

  • Grand Prize winner will receive a three (3) night trip for two (2) people to Rome, Italy. The trip includes roundtrip economy-class airfare for two (2) to Rome, Italy from major airport nearest winner’s residence, three (3) nights hotel accommodations (1 room, double occupancy), one (1) $250 gift card for spending money and a paid trip to tour Fontana Candida winery in the suburbs of Rome
  • Enter by December 31, 2015

Win a trip to Telluride, Colorado

  • A trip to Telluride, Colorado
  • (a) a one (1)-year subscription to Glossybox (ARV: $250), (b) a $500 American Express gift card (ARV: $500), and (c) a $500 shopping credit to stayful.com
  • Enter by December 31, 2015

Win a culinary trip to Paris, France

  • A total of three (3) prizes will be awarded. Each prize consists of the following: Round-trip, coach class air transportation for winner and one (1) guest from a major airport near the winner’s residence (as determined by Sponsor) to Paris, France (up to $1,500); six (6) nights accommodations for two at a hotel of Sponsor’s choice (one double-occupancy room); and enrollment of winner and guest for three (3) culinary classes in a culinary school of Sponsor’s choice. Trip must be taken and completed (i.e., departure through return) by December 31, 2016
  • Enter by December 31, 2015

Win a trip to Paris, France

  • One (1) Grand Prize Winner will receive a travel package for two (2) winner and one (1) guest to Paris, France. The travel package consists of the following: (i) round trip, coach-class airfare for Grand Prize Winner and one (1) guest between a major U.S. airport located within the 48 contiguous United States nearest Grand Prize Winner’s residence and Paris, France (airports determined by Sponsor in its sole discretion); (ii) five (5) days, four (4) nights deluxe hotel accommodations (one double occupancy room, room rate and tax only); (iii) round trip airport transfers in Paris; and (iv) all taxes related to accommodations and airfare
  • Enter by December 31, 2015

Want to see previous weeks’ travel contests? Go here!

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