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Here are this week’s travel contests. You can win trips to Cancun, Mexico; Orlando, Florida; Hawaii; St. Croix; Cabo San Lucas, Mexico; Los Cabos, Mexico; Greece; a cruise, Walt Disney World; New York City; Nashville, Tennessee; Breckenridge, Colorado; a Mississippi River Cruise; Detroit, Michigan; Riviera Maya, Mexico; Universal Studios Orlando or Hollywood; Canada; Hawaii; New Zealand; Cheyenne, Wyoming; Palm Springs; California; 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 Cancun, Mexico

  • One (1) grand prize (“Grand Prize”): There will be (1) Prize awarded. The winner of the Grand Prize (“Grand Prize Winner”) in this section will receive the following: Grand Prize Trip for Two to Cancun, Mexico (“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.
    Five (5) days four (4) nights’ (double occupancy) hotel accommodations. Grand Prize Winner may select hotel and accommodations preference.
    Grand Prize Winner to receive Prize Supplier branded swag (cooler chair, pool floats, beach towel, beach hat, trucker hat, BuzzBallz t-shirt)
  • open only to legal residents of the 50 United States and the District of Columbia (NOT including residents of all U.S. Territories and Possessions and overseas Military Installations), twenty-one (21) years of age or older
  • Read about my trip to Chichen Itza from Cancun
  • Read about my trip to Tulum from Cancun
  • Enter by June 30, 2023

Win a trip to Orlando, Florida

  • $250 Frontier Airlines ticket vouchers for Orlando flights, for the winner and up to three (3) guests
    Room accommodations consisting of one (1) standard room with a maximum of four (4) persons for two (2) nights at a Walt Disney World ® Resort Hotel selected by Disney in its sole discretion; based on availability
    Four (4) 3-Day Walt Disney World ®Resort Theme Park Tickets with Park Hopper ®Option
    One (1) Welcome Treats Basket in your Walt Disney World ®Resort Hotel room
    Roundtrip ground transportation between Orlando International Airport and the Walt Disney World ®Resort to be provided by a vendor to be selected by Disney.
  • 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 June 28, 2023

Win a trip to Hawaii

  • A Trip for Two to the Thirteenth Annual Hawaii Food & Wine Festival on Oahu!
  • 160,000 Hawaiian Airlines HawaiianMiles for travel to Honolulu
    Four (4) night stay at Outrigger Reef Waikiki Beach Resort in an Ocean View Room
    Two (2) Priority Access tickets to Hawaii Food & Wine Festival’s Hawaiian Airlines Presents Crush’d grand tasting event at Hawaii Convention Center on Friday, November 3
    Two (2) tickets to Hawaii Food & Wine Festival’s Burn Baby Burn with Maria Chase from BURN Collective fitness brunch at Outrigger Reef Waikiki Beach Resort on Sunday, November 5
  • open to individuals who are legal residents of the 50 United States (“Territory”) and age 21 or older
  • Enter by June 28, 2023

Win a trip to St. Croix

  • 4-night stay for two at The Buccaneer Beach & Golf Resort
    Breakfast for two daily
    Unlimited water sports such as snorkeling, paddleboarding and kayaking
    $250 Visa gift card compliments of Fifty Grande
    $150 Bookshop gift card compliments of Shelf Savvy
  • 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 June 30, 2023

Win a trip to Cabo San Lucas, Mexico

  • 1 winner(s) will receive a Grand Prize Package: An all-inclusive trip to Pueblo Bonito Sunset Beach Resort in Cabo San Lucas, Mexico for seven (7) days and six (6) nights and a year of unlimited Spanish lessons for two (2). User generated content supplied by contestants to Live Lingua is allowing us to use and share the content for our social. Accommodations for 6-nights and 7-day at the all-inclusive Pueblo Bonito Sunset Beach Resort in Cabo San Lucas, Mexico ($6,317 USD – 14 days lead time is required for bookings), a travel Voucher for Airfare for two (2) (max travel voucher $2000 USD total), Unlimited Spanish lessons for two (2) for one year ($4,994 USD Value) and Unlimited Group Classes for 2 ($1794 USD Value)
  • open to residents of the USA and Canada. The States of Florida, New York and the Province of Quebec, are not eligible to participate in the Sweepstakes
  • Enter by June 30, 2023

Win a trip to Los Cabos, Mexico

  • Winner will receive a four (4) night Los Cabos, Mexico vacation package for winner and one (1) guest (“Guest”) (hotel and air only), which includes: roundtrip United Airlines economy airfare for winner and Guest from the 48 contiguous United States or D.C. (excluding, Alaska, Hawaii, Guam, Puerto Rico, and all other U.S. territories) and a four (4) night, all-inclusive (meals and beverages only), Deluxe Ocean View Room (double-occupancy) hotel accommodation with an additional romantic dinner for two at Grand Fiesta Americana Los Cabos, Mexico (subject to availability). Travel not valid between December 21, 2023 – January 7, 2024
  • only open to permanent legal residents of the fifty (50) states of the United States (“U.S.”) and the District of Columbia (“D.C.”) (excluding Guam, Puerto Rico, and all other U.S. territories and possessions) who are currently physically located and residing therein. Entrants must be eighteen (18) years of age or the age of majority in their state of residence
  • Enter by June 30, 2023

Win a trip to Greece

  • Trip for two (2) to Greece and its Islands with Collette Tours (“Tour Operator”). Includes 16 days/15 nights hotel accommodations, roundtrip airfare from the closest major airport to the winner and tour of Greece and its islands provided by Collette Tours
  • open only to persons, who are, as of date of entry, 21 years of age or older, legal residents of, and physically located within, the 50 United States or D.C.
  • Enter by June 30, 2023

Win a cruise

  • One (1) Grand Prize winner will receive up to a 7-night Norwegian cruise and 500,000 AAdvantage® miles
    Five (5) First Prize winners will receive 100,000 AAdvantage® miles each
  • open only to legal residents residing in the 50 United States and D.C., 21 years of age or older
  • Enter by June 30, 2023

Win a trip to Walt Disney World in Orlando, Florida

  • Round-trip coach airfare for four people
  • Ground Transportation
  • Accommodations for four nights
  • Four Five-Day Theme Park Tickets with Park Hopper® Option
  • One Disney Gift Card with a value of $300
  • you must be at least 18 years old and a United States citizen or
    legal resident, except Tennessee
  • Enter by June 30, 2023

Win a trip to New York City

Win a trip to Nashville, Tennessee

  • One (1) Grand Prize: VIP Trip to Nashville for Four: The Grand Prize consists exclusively of: roundtrip (“R/T”) coach air transportation for Grand Prize winner and up to three (3) travel companions between major gateway airport nearest winner’s residence and a destination airport in Nashville, TN; three (3) consecutive night hotel room accommodations (two standard rooms, double occupancy; room and tax only); R/T ground transportation between airport and hotel in Nashville, TN; private tour for four (4) of Ole Smoky Distillery facility including one (1) meal and beverages; four (4) Ole Smoky gift baskets containing branded merchandise and apparel items; tickets for four (4) to the Grand Ole Opry or a Nashville, TN-based sports team to be selected by the Sponsor, and which is dependent upon the travel dates selected; one (1) $500 gift card which the winner may elect to use for meals while in Nashville; two (2) Nashville Music City Attraction Pass, good for four people total to experience over 25+ area attractions
  • open to legal U.S. residents who reside in the fifty (50) United States and the District of Columbia “(DC”) who are 21 years of age or older
  • Enter by June 30, 2023

Win a trip to Breckenridge, Colorado

  • GRAND PRIZE (ARV $12,000):
  • 7 nights in a one-bedroom residence at the Grand Colorado on Peak 8.
    $5,000 cash to spend however you’d like!
    Adventure Prize Package:
    Brown’s Canyon white water rafting excursion for four with Performance Tours Rafting.
    Guided fly-fishing float trip for two, including Colorado fishing license and flies, with Mountain Angler.
    Vail Pass Bike Shuttle for four with Alpine Sports.
  • Must be 21 years of age or older at time of entry to be eligible for this contest and a legal resident of the fifty United States and Washington, D.C
  • Enter by June 30, 2023

Win a Mississippi River Cruise

  • Win a 9-day American Queen Voyages river cruise from Memphis to New Orleans. Experience the Cajun charms of the Bayou in small towns filled with profound history, complemented by the big city energy of the Big Easy and Baton Rouge. Prize includes a one-night pre-cruise hotel stay, ground transfers between hotel and vessel, personally tailored unlimited guided tours, unlimited beverages at open bars and lounges, acclaimed cuisine in multiple venues, in-room dining, unlimited Wi-Fi, and live entertainment and enrichment onboard.
  • Other prizes include a $250 Visa gift card compliments of Matt’s Flights, a $250 Visa gift card compliments of Your Tango and a $200 Visa gift card compliments of Fifty Grande
  • 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 June 30, 2023

Win a trip to Detroit, Michigan

  • Grand Prize consists of a
    trip for the Grand Prize winner and one (1) guest to attend the
    2023 SummerSlam event scheduled to take place in Detroit, Michigan
    on August 5, 2023. Trip consists of roundtrip, coach class air
    transportation from a major U.S. gateway airport nearest
    winner’s residence to a Detroit, Michigan area airport, two
    (2) nightsstandard hotel accommodations (one room, double
    occupancy, room and tax only) from August 4 – August 6, 2023
    in the Detroit, Michigan area, ground transportation to/from
    destination airport and hotel, ground transportation to/from hotel
    and 2023 SummerSlam event, two (2) tickets to attend the
    SummerSlam event on August 5, 2023, one (1) $500 prepaid gift
    card, one (1) smartphone (Samsung, LG or Apple; to be determined
    by Sponsor in its sole discretion), and twelve (12) months of
    Cricket Wireless service with its Unlimited Extra Plan
  • open to legal
    residents of the fifty (50) United States and the District of
    Columbia, who are at least twenty-one (21) years or older
  • Enter by July 2, 2023

Win a trip to Riviera Maya, Mexico

  • A 4-night all-inclusive stay for two in a Signature Casita King at the luxurious Fairmont Mayakoba Riviera Maya Resort, Mexico with breakfast for two daily, a property boat tour and a snorkeling excursion for two
  • Other prizes include a $250 Visa gift card compliments of Rank & Style and a $250 gift card to Reef.com
  • 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 July 3, 2023

Win a trip to Universal Studios Hollywood or Orlando

  • There will be one (1) Grand Prize (“Grand Prize”) awarded. The Grand Prize Winner (“Grand Prize Winner”) will receive a trip for Grand Prize Winner and up to three (3) Guests (“Guest(s)”) to the Grand Prize Winner’s choice of either (a) Universal Orlando Resort in Orlando, Florida; or (b) Universal Studios Hollywood in Hollywood, California. Grand Prize winner will also receive one (1) Jurassic Park Product Pack and one (1) $100.00 Target Gift Card.
  • a. If the Universal Orlando Resort destination (the “UO Trip”) is chosen, the Grand Prize will include round trip economy class air transportation from a major commercial airport near Grand Prize Winner’s home (as determined by Universal Orlando in their sole discretion) to Orlando, FL*; three (3) nights’ standard hotel accommodation (one room, quadruple occupancy, room and tax only) at Universal’s Cabana Bay Beach Resort or at another Universal Orlando Resort hotel (as determined by Universal Orlando in their sole discretion); non-exclusive ground transportation to and from airport and hotel in Orlando, FL*; 3-Park 3-Day Park-to-Park tickets for admission to Universal Studios Florida, Universal’s Islands of Adventure and Universal’s Volcano Bay Water Theme Park for Grand Prize Winner and up to three (3) Guests. The Fair Market Value (“FMV”) of the Universal Orlando Resort Prize is Four Thousand Six Hundred Forty-Nine and 40/100 Dollars ($4,649.40)
  • b. If the Universal Studios Hollywood destination (the “USH Trip”) is chosen, Grand Prize will include round trip economy class air transportation from a major commercial airport near Grand Prize Winner’s home (as determined by Universal Studios Hollywood in their sole discretion) to Los Angeles, CA**; two (2) nights’ standard hotel accommodation (one room, quadruple occupancy, room and tax only) at Sheraton Universal Hotel (or at another nearby hotel as determined by Universal Studios Hollywood in their sole discretion); non-exclusive ground transportation to and from airport and hotel in Los Angeles, CA**; two (2) days general admission tickets to Universal Studios Hollywood for Grand Prize Winner and up to three (3) Guests. The Fair Market Value (“FMV”) of the Universal Studios Hollywood Prize is Four Thousand Four Hundred Thirty-Two and 00/100 Dollars ($4,432.00)
  • open to U.S. citizens in 48 states (void in Hawaii and Alaska) and DC, 18 or older
  • Enter by July 4, 2023

Win a trip to Canada

  • One 3 day / 4 night adventure to CMH Cariboos in the Canadian Rockies including lodging, meals, and professional guide service for two from CMH Summer Adventures
  • Airfare up to $1000 USD provided by Mountain Gazette
  • Two pairs of Wildfire GTX approach shoes and Via Ferrata lanyards from Salewa
  • Two sets of Hiking Apparel including Shirt and Shorts or Pants from Flylow
  • Four pairs of Sunglasses from Glade Goggles
  • Two pairs of Sneaker Boots from Forsake
  • One $300 USD Gift Card for socks from Darn Tough
  • Utu High Alpine Sunscreen Kits from Utu Skincare
  • Two Recovery Gift Packs from Dad Grass
  • $250 USD in merchandise from Mountain Gazette
  • Open to US Citizens 21+ only
  • Enter by July 7, 2023

Win a trip to Hawaii

  • One (1) Grand Prize Winner will receive a 4-night/5-days vacation for 4 people to AULANI, A Disney Resort & Spa in Ko Olina, Hawai‘i including:
    Roundtrip coach airfare transportation for the Winner and up to three (3) guests
    Four (4) round trip airport ground transfers
    Hotel accommodations consisting of one (1) standard room for four (4) persons
    Up to four (4) preferred seating passes to KA WA‘A, A Lū‘au
    One (1) Five-hundred-dollar ($500) Disney Gift Card
  • Open to legal residents of the 50 U.S. & D.C. and Canada (excluding Quebec) who are 18+
  • Enter by July 7, 2023

Win a trip to New Zealand

Win a trip to Cheyenne, Wyoming

  • Two tickets to Cheyenne Frontier Days Rodeo tickets for July 29-30
    Two tickets to Jon Pardi concert with Carly Pearce on July 28
    Two tickets to Cody Johnson concert with Whiskey Myers on July 29
    $2,000 Mastercard Gift Card for food, travel & lodging
  • open only to those who sign up and who are 13 as of the date of entry. The Contest is only open to legal residents of the United States and Canada (excluding Quebec)
  • Enter by July 10, 2023

Win a trip to Palm Springs, California

  • Kind Traveler Prizing Package Includes:
  • · 3-night stay at Miramonte Resort & Spa (a Kind Traveler partnered hotel), a couples massage and a $125 food & beverage credit
  • · 2- night stay at The Good House in Desert Hot Springs (a Kind Traveler partnered hotel), $150 food and beverage credit, 50 percent discount on any spa service, three all-day soak passes (for two), and unlimited access to amenities
  • · Two tickets to the Palm Springs Aerial Tram, the world’s largest rotating tram car transporting riders to the pristine wilderness of the Mt. San Jacinto State Park in just 10-minutes
  • · Two tickets to The Living Desert Zoo & Botanical Gardens specializing in the deserts of the world with a mission of desert conservation through preservation, education, and appreciation
  • · Two tickets for one of the Red Jeep Desert Tours capturing the true essence of the California desert
  • · $200 donation to local Greater Palm Springs charity, Friends of the Desert Mountains, a local environmental charity working to preserve land and support education, conservation and research in the Coachella Valley
  • · Kind Traveler gift box to include eco-conscious travel products to inspire kind travel
  • · Gogh Jewelry gift box to include a $500 gift card towards conscious jewelry that empowers
  • · Mowellens gift box offering hemp CBD botanical health products and beauty rituals
  • · Elims gift box offering dentist-crafted, sustainable oral care to improve the planet and smiles everywhere
  • · $300 Visa cash card towards travel expense
  • open to anyone who is at least twenty-one (21) years of age 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)
  • Read about craft beer in Palm Springs
  • Enter by July 11, 2023

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!

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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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