Travel Contests: May 25th, 2022 – Italy, Antigua, cruises, & more

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castel beseno italy 700x525 - Travel Contests: May 25th, 2022 - Italy, Antigua, cruises, & more

Here are this week’s travel contests. You can win a cruise, plus trips to Italy; Utah; Oregon; California; Antigua; Portugal; Bora Bora; St. Lucia; Cancun, Mexico; Las Vegas, Nevada; San Diego, California; and more.

Good luck & be sure to subscribe to the 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 cruise

  • One Prize (“Prize”) is available to be awarded in the Sweepstakes. Prize includes:
    Two (2) tickets to sail on a Holland America Line MS Rotterdam Europe or Caribbean cruise, which
    cruise much be completed by August 31, 2023 for the Winner and one (1) guest in a Vista or
    Signature Suite stateroom (the “Prize”). The approximate retail value (“ARV”) of the Prize is $2,600
    USD/$2,585 CAD.
  • open only to legal residents of the fifty United States and the District of Columbia, and Canada (excluding Quebec) who are 21 years of age or older
  • Enter by May 30, 2022

Win a trip to Italy

  • $1,000 voucher to travel booking site to book a 7 day getaway in Italy for 2 people, or whatever adventure calls to you
  • $820 virtual cash for airfare
  • 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 lives within the continental United States
  • Enter by May 28, 2022

Win a trip to Utah

  • – 7-night stay at Yonder Escalante, a new Kind Traveler partnered hotel, in a luxury cabin or vintage Airstream, to include (2) dinners, complimentary artisanal morning coffee/tea, breakfast treats and fresh fruit.
    – Canyoneering experience for (2) led by an expert hiker in the majestic Grand Staircase Escalante National Monument
    – $200 donation in the name of the winner to local charity -Grand Staircase Escalante Partners.
  • – Kind Traveler gift box to include eco-conscious products from partners ($250 value)
  • – Get In The Wild Adventures, a Goblin’s Lair Canyoneering Adventure for Two
  • – Solis Lite WiFi Hotspot with global WiFi in 130+ countries, No SIM cards needed ($150 value)
  • – Gift box from Hari Mari, everyday exploring essentials
  • – $300 cash Visa card towards travel
  • 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)
  • Enter by May 28, 2022

Win a trip to Italy

  • Spend 6 nights exploring Italy’s most loved regions by rail. You and a friend will get to stay 2 nights in Rome, 2 nights in Florence, and 2 nights in Venice in standard hotels
  • PLUS
  • $1,650 in electronic cash toward airfare to help get you there
  • WHAT’S INCLUDED
  • Daily breakfast
    Arrival airport transfer
    All transportation, sightseeing, and entrances fees as per itinerary
    Tasting of local products in Florence
    24h Hop On -Hop Off ticket in Rome, including an audio guide with commentary in English/Spanish/Portuguese/Russian
    2nd Class train tickets from Rome to Florence and from Florence to Venice,  (high-speed train with seat reservation)
    30 minutes gondola ride – max 6 pax each gondola
    All currently applicable taxes
  • 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 May 31, 2022

Win a trip to the Willamette Valley, Oregon

  • One (1) trip for two to Oregon’s Willamette Valley. The Grand Prize package includes: two (2) nonrefundable, nontransferable roundtrip tickets on Alaska Airlines from the nearest airport to you that is served by Alaska Airlines to any airport in Oregon served by Alaska Airlines*; one (1) gift certificate for three night’s lodging; two (2) days of wine tasting and culinary experiences for two, ground transportation for two to wine tasting destinations within the Willamette Valley
  • open to people 21 years of age or older who are legal residents of the 50 United States and District of Columbia
  • Enter by May 31, 2022

Win a trip to Rogue Valley, Oregon

  • One (1) trip for two to Oregon’s Rogue Valley. The Grand Prize package includes: two (2) nonrefundable, nontransferable roundtrip tickets on Alaska Airlines from the nearest airport to you that is served by Alaska Airlines to any airport in Oregon served by Alaska Airlines*; one (1) gift certificate for three night’s lodging; one (1) gift certificate for two for guided day of wine tasting; one (1) gift certificate for two to a local restaurant; one (1) gift certificate for two for wine tasting and vineyard tour experience
  • open to people 21 years of age or older who are legal residents of the 50 United States and District of Columbia
  • Enter by May 31, 2022

Win a trip to Portland, Oregon

  • One (1) trip for two to Portland, Oregon. The Grand Prize package includes: two (2) nonrefundable, nontransferable roundtrip tickets on Alaska Airlines from the nearest airport to you that is served by Alaska Airlines to any airport in Oregon served by Alaska Airlines*; one (1) gift certificate for two night’s lodging; one (1) gift certificate for two for guided day of wine tasting; one (1) gift certificate for two to a local restaurant; one (1) gift certificate for two for wine tasting and winery tour experience
  • open to people 21 years of age or older who are legal residents of the 50 United States and District of Columbia
  • Enter by May 31, 2022

Win a trip to California

  • GRAND PRIZE (1): One (1) winner will receive an exclusive winery Grand Prize trip that includes three (3) nights, four (4) days hotel accommodations for themself and one (1) guest to the Central Coast within the 2022 – May 2023 calendar year, with the exception of limited blackout dates (hotel chosen by Sponsor). Guest must be twenty-one (21) years of age or older at the time of travel. Trip also includes roundtrip, coach class air transportation for winner and guest from a major U.S. airport (up to $750 per person) near winner’s residence to Central Coast airport, exclusive winery visit for two,Into the Wild gift basket (includes picnic basket, cooler, blanket, cheeseboard, electronic wine opener, and wine glasses) outdoor excursions, and a $100 dining credit that excludes alcohol
  • open to individuals (“Entrants”) who are at least twenty-one (21) years of age and are legal residents of the United States or the District of Columbia (the “Sweepstakes Area”), except those residents of MS, SD, WV and WY
  • Read about 49 fun things to do in San Francisco
  • Read about great day trips from San Francisco
  • Read about craft beer in Paso Robles, California
  • Read about craft beer in Atascadero, California
  • Enter by May 31, 2022

Win a trip to Antigua

  • One (1) Grand Prize Winner will receive: One (1) 5-night stay for two at the Verandah Resort & Spa in Antigua.
  • Deluxe Accommodations
  • All meals and drinks included
  • Resort activities included
  • $500 Credit to the resort spa
  • $2,000 Delta Gift Card
  • $250 Spa & Wellness Gift Card
  • You must be a resident of the fifty (50) United States or the District of Columbia (Washington D.C.) or Canada. You must also be twenty-one (21) years of age or older
  • Enter by May 31, 2022

Win a trip to Portugal

Win a trip to Bora Bora

  • Win a 6-day getaway at the 5-Star Conrad Bora Bora Nui (flights included)
  • Relish in a breathtaking overwater villa with a private infinity pool and floor-to-ceiling windows.
  • Score $5,000 to treat yourself to rejuvenating massages, open-air dining, exciting excursions and more.
  • Open worldwide
  • Enter by June 3, 2022

Win a trip to St. Lucia

  • 4-night all-inclusive stay for two adults in Ti Kaye cottage with daily maid service at Ti Kaye Resort & Spa in Saint Lucia
    Complimentary welcome drink, coffee and tea
    All-inclusive meal plan (full breakfast, two-course lunch and three-course dinner) at on-site restaurants, select cocktails and specialty wines
    Complimentary snorkel gear and use of kayaks and paddleboards
    Complimentary Wi-Fi
    $250 Visa gift card compliments of Matt’s Flights
    $250 gift card compliments of Daniella Shevel
    $250 Visa gift card compliments of Woman’s World
    One month supply of dog supplements compliments of Bestfriend ($68 value)
  • 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 3, 2022

Win a trip to Antigua

  • A 5-night all-inclusive stay for two adults to Pineapple Beach Club Antigua
    All meals including breakfast, lunch and dinner and beverages including non-alcoholic and alcoholic, round-trip airport transfers and included resort activities
  • Other prizes include a $250 Sivana gift card, $200 Visa gift card compliments of 1440, $250 Visa gift card compliments of Your Tango and a $200 Laya gift card.
  • 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 3, 2022

Win a trip to Cancun, Mexico

  • You could win a 4-night stay for two at Grand Fiesta Americana Coral Beach Cancun All Inclusive Spa Resort including all meals and beverages (room service not included)
  • – $250 Visa gift card compliments of The Gist
  • – $200 gift card compliments of Banda Bags
  • – $200 in product compliments of ICU Eyewear
  • – $200 gift card compliments of Tiny Rituals
  • – $200 Visa gift card compliments of Dunhill Travel Deals
  • 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)
  • Read about my trip to Chichen Itza from Cancun
  • Read about my trip to Tulum from Cancun
  • Enter by June 3, 2022

Win a trip to Las Vegas, Nevada

  • Grand Prize:
    VIP Experience at International Fight Week: 2 Tickets to UFC 276, UFC Hall of Fame Ceremony, VIP access to 2-day fan experience, UFC HQ and Performance Institute tour, Airfare, Hotel Accommodations
  • open only to legal permanent residents of the United States (excluding Puerto Rico, and the U.S. Territories and Possessions) and of Canada (excluding Quebec), United Kingdom and Brazil, who are at least 18 years of age or the age of majority in their jurisdiction
  • Enter by June 5, 2022

Win a trip to San Diego, California

  • One (1) Grand Prize – A 3-day/2-night trip for the Winner and three (3) travel companions to San Diego, CA (“Trip”), including round trip economy air transportation from major airport nearest Winner’s home, hotel accommodations (1 room, quad occupancy), four (4) 1-Day Passes to the San Diego Zoo and one (1) Inside Look Tour for four (4) people as determined by SDZWA. (ARV: $4,026; actual value will vary depending upon point of departure and date of travel booking (see additional Trip Prize Details below); One (1) First Prize- Four (4) one-day passes to the San Diego Zoo (transportation and accommodations are not included) (ARV: $240); One (1) Second Prize – A Swag Bag comprised of San Diego Zoo merchandise and Lenny & Larry’s goodies (ARV: $100). The ARV of all Prizes (defined below) is $4,366
  • open only to persons ages 18 and older during the Sweepstakes Entry Period, and, who, as of the time of Entry, are legal residents of, and physically located within, the 48 contiguous United States or D.C.
  • Enter by June 6, 2022

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!

Note: I realize that right now may not be a good time to be traveling. However, as long as there are still contests available, I will continue to share them.  Hopefully, once this all passes, we’ll be able to freely enjoy traveling again, but for now, we can dream, & most of these contests have redemption deadlines long in the future. In the meantime, please practice social distancing & keep safe. Thanks!

Last updated on May 24, 2022

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