Check out the week in travel contests and sweepstakes for your chance to win an American Express getaway, ski trips to Chile and Vail, a seven night cruise, and trips to Rome and Ireland.Win A Getaway for Two From American Express TravelWin a getaway for two from Amex TravelTake a travel quiz and win a trip to your choice of the following destinations: Scottsdale, AZ; Paris, France; Sydney, Australia; Mexico City, Mexico; or Costa Rica at Peninsula Papagayo. The winning trip package includes:A three-night stay at a hotel determined by Sponsor (one standard room, double occupancy) in the selected cityA $2,500 American Express Gift Card that winner may use for airfare and all other costs and expenses related to the tripWinner will be required to designate city and preferred travel dates on the Affidavit/Release. Winner must use the hotel stay between January 5, 2015-June 30, 2015 or the prize will be forfeited.The contest is open only to legal residents of the 50 United States and the District of Columbia who are at least 18 years old at the time of entry. Enter by 11:59 p.m. ET on November 15, 2014.Win a Trip to Rome for Two from Fontana Candida WineWin a trip to Rome. Photo courtesy of Shutterstock.“Like” Fontana Candida on Facebook and fill out your information in order to win a three night trip to Rome for two including:Roundtrip economy class airfare for two to Rome from a major airport nearest winner’s residenceThree nights hotel accommodations (one room, double occupancy)One $250 gift card for spending moneyA tour of the Fontana Candida winery in the suburbs of RomeThe Grand Prize winner may opt to have a cash payout of $5,000 in lieu of trip to Rome. 12 Second Prize winners will each receive a $100 gift card.The contest is open only to legal residents of the United States and the District of Columbia (except the states of Illinois and Utah) who are 21 years of age or older at the time of entry. Enter by 11:59 p.m. ET December 31, 2014.Sign up for our daily newsletterEmail addressSign upI would like to subscribe to The Points Guy newsletters and special email promotions. The Points Guy will not share or sell your email. See privacy policy.Win a Trip to “Haunted” Ireland from The Travel ChannelWin a trip to IrelandFill out your information to win a trip to Dublin, Ireland, including:Round trip coach class airfare for winner and one guest to Dublin, Ireland from major U.S. airport nearest winner’s residence within the 48 contiguous United StatesSeven days/six nights hotel accommodationsA visit to the Powerscourt House and Gardens including transfers to and from Powerscourt HouseOne dinner at Coppinger RowA visit to the Science Gallery Exhibition at Trinity College Dublin A visit to the Guinness Storehouse$1,000 spending moneyThe contest is open only to legal residents of the 48 contiguous United States and the District of Columbia who are at least 21 years old at the time of entry. Enter by 11:59 p.m. ET on October 31, 2014.Win Ski Trips to Chile and Vail, Plus Ski Gear from LAN AirlinesWin two ski trips and ski gear for two peopleEnter to win a massive grand prize of TWO skiing trips and ski gear. The prize includes:A six night, seven day ski trip at Vail Resorts (Colorado) during Winter 2014 for twoA six night, seven day trip at Ski Portillo Resort (Chile) in Summer 2015 for twoAirfare from anywhere in the U.S. to Vail and to ChileMeal VouchersAirport transportLift ticketsTwo sets of Wagner Custom skisHelly Hansenski and travel gear for twoThe contest is open only to legal residents of the 48 contiguous United Sates and the District of Columbia who are 18 years of age and older as of date of entry. Enter by 11:59 p.m. Eastern Standard Time on October 31, 2014.Win a Cruise for Two from Cruises Inc.Win a seven night cruiseEnter your information to win a cruise around the Caribbean and Mexico, including one double occupancy stateroom onboard the Norwegian Breakaway or Getaway based on availability. Each cruise is seven nights long and is valid for two people.The contest is open to residents of the United States only that are of valid age. and void in any jurisdiction(s) in the United States where participation is prohibited. Enter by 11:59 p.m. ET November 2, 2014.[card card-name=‘Chase Sapphire Preferred® Card’ card-id=‘22125056’ type=‘javascript’ bullet-id=‘1’]