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Here are this week’s travel contests. You can win trips to Puerto Rico; Italy; Denver, Colorado; Orlando, Florida; Japan; Dublin, Ireland; Italy; Dominican Republic; Mexico; California; Las Vegas, Nevada; Miami, Florida; Los Angeles, California; Miami, Florida; and more.

Good luck! Be sure to subscribe to my weekly newsletter so you don’t miss any sweepstakes, and please share this post with friends who might take you along if they win!

Win a trip to Puerto Rico

  • There will be (1) Prize awarded. The winner of the Prize in this section (“Grand Prize Winner”) will receive the following prize package (“Grand Prize”): a Four Night Trip for Two to Puerto Rico (“Trip”). Trip will include:
  • · Roundtrip (coach class) air transportation from the nearest major airport closest to the Grand Prize Winner’s home address to the Trip destination for two (2) people.
  • · Four (4) nights’ (double occupancy) hotel accommodations.
  • · Grand Prize Winner to receive a total of $4,000 in spending money towards food, activities, transportation, etc. (Prize awarded by check in the name of the Winner).
  • open only to legal residents of the 50 United States and the District of Columbia, eighteen (18) years of age or older
  • Enter by March 31, 2024

Win a trip to Italy

  • There will be one (1) Prize awarded. The prize winner (“Winner”) will receive the following prize package (“Prize”): six (6) nights’ trip for the Winner plus one (1) guest to Tuscany, Italy (“Trip”). Trip will include:
  • Six (6) Nights Hotel accommodations;
  • Roundtrip airline transportation for two (2) to Prize destination in Italy; and
  • One elaborate cooking class for the Winner and his/her guest.
  • open only to legal residents of the 50 United States and the District of Columbia, Canada (excluding Quebec), and Puerto Rico, twenty-one (21) years of age or older
  • Enter by June 30, 2024

Win a trip to Denver, Colorado

  • One winner will receive the following for themself and a friend:
  • 2 pairs of Icelantic Skis
    2 VIP tickets to Icelantic’s Return to the Rocks
    Bindings/ Mount from Boone Mountain Sports
    IV Hydration Package from ONUS IV
    Goggles from Pit Viper
    Gear from Spyder
    x Global Travel Bag Roller & 2x Global Briefcase From Topo Designs
    Inflatable Kayak from Smartwater
    2-night stay in Denver + Roundtrip Flights to Denver from Visit Denver (*See Terms and Conditions for Canadian entrants flight requirements)
    3-day Adventure package from Titus Adventure Co in Colorado
    Awesome Prize Packages from Pacifico, Quiznos, Wana Brands, Dasoro and more
    And MUCH MORE!!
  • open to all residents of the United States and Canada (excluding Quebec) who have reached the age of at least eighteen (18) years old
    Enter by March 25, 2024

Win a trip to Orlando, Florida

  • There is one (1) Grand Prize available (one (1) consisting of one (1) 4-day / 3-night trip for the winner (“Winner”) and up to three (3) Guests to Orlando, Florida (the “Trip”). The Trip includes:
  • (a.) Air transportation vouchers, provided by Frontier Airlines, for the Winner and up to three (3) Guests to Orlando, Florida from an airport served by Frontier Airlines (as selected at the sole discretion of Sponsor). Winner will receive one (1) flight voucher per traveler, and each voucher will have a value of $250 to be used against selected flights. Winner and Guests will be responsible for securing any transportation to/from the closest Frontier Airlines served airport to their home, any costs not covered by the provided flight voucher, and will be responsible for securing their own flights using the provided voucher;
  • (b.) Hotel accommodations for three (3) consecutive nights in one (1) standard room (with a maximum of four (4) persons per room) at a hotel at the Walt Disney World ®Resort selected by Disney in its sole discretion; based on availability;
  • (c.) Four (4), 3-Day Theme Park Tickets with Park Hopper ®option;
  • (d.) Four (4), 1-Day Disney Water Parks Tickets; and
  • (e.) Roundtrip ground transportation between Orlando International Airport and the Walt Disney World Resort to be provided by a vendor to be selected by Disney operating in its sole discretion.
  • open only to legal United States residents residing in the forty-eight (48) contiguous United States or Washington, D.C. Entrants must be at least twenty-one (21) years of age
  • Enter by March 27, 2024

Win flights to Japan

Win a trip to Dublin, Ireland

Win a tour of Italy (airfare not included)

  • GRAND PRIZE
  • A thoroughly curated week of food, wine, cooking and culinary immersion in Modena Italy for two people with Italian Culinary Adventures ($12,400 value).
  • Additional Prizes:
  • A luxurious PluMy Thindown duvet from MIIO, Made in Italy Only ($2,200 value).
  • A Parmigiano Reggiano tasting package, complete with a tasting flight of cheeses, branded tools, cutting board and an apron, courtesy of the Parmigiano Reggiano Consortium ($250 value).
  • A 1-year Tavola membership from Dalla Fonte with four deliveries of Italian specialty foods ($480 value).
  • A lifetime membership to Dream of Italy, the award-winning travel website and magazine founded by host Kathy McCabe ($500+ value).
  • Swag from our favorite travel content streaming app, GoTraveler ($50 value).
  • *The weeks valid for this prize are: September 15-21 or September 29 – October 5,2024.
  • Airfare and transportation to Modena is not included.
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Florida, Hawaii, New York, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by March 31, 2024

Win a tour of Italy (airfare not included)

  • Experience the romance and beauty of 3 iconic cities: Rome, Florence & Venice
  • Two nights hotel stay in Rome, Florence, & Venice, for a total of 6 nights!
  • Daily breakfast at each hotel
  • High Speed Train Travel between the cities
  • A $250 Kiss Giftcard
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories
  • Enter by March 31, 2024

Win a trip to the Dominican Republic

  • Grand Prize Includes:
  • Flights for 2 people to Dominican Republic
  • 5-night stay in a 1 bedroom suite at Sublime Samana Hotel
  • Welcome drink and amenities upon arrival
  • Daily breakfast a la carte, yoga and pilates classes
  • Non-motorized aquatic activities, 10% off services at Coconut Whispers Spa
  • Nutritional program with mindful eating classes and private nutritional coaching (subject to travel date)
  • A Kind Traveler gift box ($200 value) & Organic Traditions gift box ($200 value)
  • Contest is valid only in Canada (excluding the province of Quebec) and the United States (US). To enter and be eligible to win, a person must (at the time ofentry) be (21) twenty-one years and older, a legal resident of Canada (excluding the province of Quebec) or the US and have a valid Canadian or US mailing address
  • Enter by March 31, 2024

Win a trip to Mexico (no donation required)

  • A 5-night all-inclusive package for two to experience Backstreet’s Back at the Beach with Jason Derulo at Moon Palace Resort in Mexico on April 18, 19, 20, and 21
  • Access to the oceanfront concert area, daily pool parties and late night programming
  • Exclusive MiiR Gift Pack
  • Round-trip flights to Cancún International Airport (CUN) for you and a guest
  • Airport transfers to/from Moon Palace
  • Deluxe hotel accommodations for 5 nights at Moon Palace
  • Open worldwide
  • Enter by March 31, 2024

Win a wine trip to California

  • Grand Prize: One (1) Grand Prize will be awarded in this Sweepstakes. The Approximate Retail Value (“ARV”) of the Grand Prize is $10,000. Grand Prize Winner will receive a two (2) night trip to California for the Grand Prize Winner and up to three (3) guests (each, a “Travel Companion”). Trip will include; (a) round trip coach class air transportation through an Airline of Sponsor’s sole choosing for Grand Prize Winner and Travel Companion(s) from a major commercial airport near Grand Prize Winner’s home (as determined by Sponsor in their sole discretion) to a city to be determined by Sponsor in California, (b) round trip ground transportation from the airport to the hotel in the destination city; (c) two (2) night hotel accommodations at the Hopper House located on a Sponsor Vineyard in California (based on one (1) room, two (2) beds), including resort fees, if any; and (d) daily meals (including breakfast, lunch and dinner).
  • open only to legal residents of the fifty (50) United States and the District of Columbia, who are twenty-one (21) years of age or older
  • Enter by March 31, 2024

Win a trip to Las Vegas, Nevada

  • Grand Prize: There will be one (1) grand prize (the “Grand Prize”) awarded. Grand Prize winner (“Winner”) will receive a three (3) day, two (2) night trip for winner and up to three (3) guests (each a “Guest”) to Las Vegas, Nevada* to experience a Dolby Live VIP Experience (the “Trip”). Trip will include: round trip coach (economy) class air transportation for Winner and up to three (3) Guests from a major commercial airport near Winner’s home (as determined by the Sponsor in its sole discretion) to Las Vegas Nevada*; two (2) nights standard hotel accommodation (one room, quadruple occupancy, room and tax only) at Park MGM® (or at another nearby hotel as determined by Sponsor in its sole discretion); four (4) tickets to Dolby Live; and Dolby swag valued at $120, *If Winner lives within 200 miles of Las Vegas, Nevada air transportation may be substituted with another method of transportation by Sponsor in its sole discretion
  • open only to legal residents of the fifty (50) United States (and the District of Columbia), who are at least twenty-one (21)years old
  • Enter by March 31, 2024

Win a trip to the F1 race in Miami, Florida (does not include airfare despite Matt’s Flights being a “sponsor”)

  • Your prize includes:
  • (2) Two 3-day Autonation Turn 18 Grandstand Tickets (valued $1,500 each)
  • (2) Two-night stay at the luxurious Acqualina Resort & Residences, the closest Five-Star property to the race track
  • Enter by April 5, 2024

Win a trip to Los Angeles, California (no donation required)

  • What You Can Win
  • A special invitation for two to attend a private dinner party in Cher’s Malibu home on April 27, 2024
  • Photo opportunity with Cher
  • Roundtrip airfare to Los Angeles, CA for you and a guest
  • Hotel accommodations for two nights
  • Open worldwide
  • Enter by April 7, 2024

Win a trip to Miami, Florida (no donation required)

  • What You Can Win
  • A special invitation to attend a private dinner party with JUANES at his recording studio in Miami, FL on April 25, 2024
  • Private acoustic performance and reception
  • Round trip flights for you and a guest to Miami, FL
  • Hotel accommodations for 2 nights
  • Open worldwide
  • Enter by April 7, 2024

Go on an adventure at home or when you’re away with a tour or activity via Get Your Guide.

Which travel giveaway are you most excited about winning this week?

Why not share this post with your friends? If they win, maybe they’ll take you!

Want to see the newest travel contests? Go here!

Hi, I'm Jonathan, the traveler, writer, photographer, enthusiast, & terrible dancer of Everybody Hates A Tourist with decades of travel expertise. I've visited over 40 countries so far. Join me as I share my personal experiences finding the best food, craft beer, cocktails & spirits, wine, culture, & history around the world!

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