Win A Free Trip To Hawaii Sweepstakes

Free Trip to Hawaii Travel Sweepstakes For May 2022

Five contests, one of which ends this week. Hawaii travel sweepstakes return with new chances to win!

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721 thoughts on “Free Trip to Hawaii Travel Sweepstakes For May 2022”

  1. Hello, Do you have any recommendations or articles visiting Hawaii with teens who need to break from electronics? We have never been and appreciate all suggestions. Thank you 😊

    1. Hi Rebecca.

      Very interesting idea. We don’t have any resources but perhaps someone else will comment.

      Aloha.

  2. Thank You for the chance to win a trip to Hawaii!! Please consider me for a chance to go to Hawaii..I’ve never won anything and I’d be so grateful…..how could you not? It’s looks absolutely beautiful.

  3. I would say please please please to any of these fine vacations. I want to take my grandson for his high school graduation to your beautiful islands to experience the history, the beauty and the fun things Hawaii has to offer. It would be a dream come true! Thank you for the opportunity to possibly Win a great vacation!

  4. My wife and I really need this trip. I am a paralyzed Veteran. Have a chronic traumatic brain injury. This trip would make our dreams come true.

  5. This has been a dream of mine to see Pearl Habor adventure we were gonna do it last year, but my husband passed away, so I’m trying to plan a trip with my best friend. Just a trip to see history would be amazing. Good luck to whom ever wins 🙂

  6. My wife and I love Maui Kai condos. Have spent several vacations there. No longer can afford the cost of travel. The only chance to visit again would be to be lucky enough to win this contest.

  7. Hi my name is Dorrie, I would love a free trip to Hawaii. I would be flying out of Mccarren airport in Las Vegas. I would be honored to receive all information regarding the possible free trip. I love the Mahalo lifestyle, and would love to retire in Kauai in the next 5 years. Thank you so very much for this invitation to enter.

    Aloha,

    Dorrie

  8. It would be nice if the sweepstakes where open for all and not just US and Canada.

    Us in europe would love to go to Hawaii too. 🙁

  9. Thank you for the opportunity to apply to so many sweepstakes! Keeping my fingers crossed. x 🙂

  10. Never had a real honeymoon In our 10+ years marriage, this is a ultimate vacation to win. Thanks for the generosity and the chance to win.

  11. Please grant my husband and I our never had honey moon not. To mention never had a vacation

  12. Aloha to all of you out there. I have lived in Hawaii for 10 years I loved it so much I haven’t seen yet Kauai, maui, and big island, I lived on Oahu I would love to win a trip to revisit Hawaii and make the most of it on other islands I haven’t seen, that would be an awesome thing to do is write about it or tell others about Hawaii. and let me say Hawaii is my number one top favorite place to be, or do lots of things, Hawaii has a lot to offer too. I like to go back and visit and stay a week or two weeks at least. to soak up the sun and enjoy the tradewinds from the ocean any time

  13. My lover and I want to move to Hawaii and start our lives there once we get married. It would be a dream come true to win.

  14. Thank you for this serendipitous list. My oldest friend is getting married in Hawaii. We have known each other since we were 6 and we are now 32. I am on a tight budget and am having to scrape and hustle and work (took on a second job just to help pay for the trip) to be able to be there and show my lovr and support for this big moment in my dear friend’s life. How perfect would it be if I won a trip and by some miracle her wedding date was an option?! I had to try! 😉

  15. Just letting you know we entered. My sister in Colorado for 2 of them and my husband and I who recently retired to the BI to several Maui and cash ones. Thanks for gathering the info and getting it to us. You never know!

  16. My daughter and I need desperately a free vacation. She and I are lost my husband her daddy in 2012 and my mother her grandmother in 2016. My daughter graduated with honors this year. She and I have been so depleted that it has not been the happy joyous party that she deserves. I would love to give her this reward and much needed as well as deserved vacation before she starts college. So she and I may just relax for a change. Thank you for your time and for giving someone a nice getaway. I am sure whoever is chosen will be greatly appreciative. Tanya

  17. We haven’t had the chance to take a family vacation with our kids since our budget has been very tight. We would love to take a family vacation since our son has been begging us to take him since all his friends are going away and it breaks my heart that we can’t. Thanks for having this giveaway. I am sure whoever wins it will be extremely lucky and happy! 🙂

  18. Hi! I would love to be the lucky winner to visit Hawaii. It would be a dream come true.
    thanks!

  19. Hawaii is my top place to go out of all the places in the world to visit. it’s been my goal since I was 15 , I truly hope this goal can come to light! I’m from Boston, Massachusetts.

  20. This would be a great opportunity for my family and me to finally be able to go to Hawaii on vacation. Winning this sweepstake would really be amazing since we have been so preoccupied with work and paying for college that a vacation would really come in handy. I really do hope that I am considered. If not then thanks anyway.

  21. Aloha, my name is Kayla. I am nineteen and I’ve never really had the chance to travel anywhere. I have since been struggling to live on my own, as I work and go to school. A vacation sounds wonderful. I sure hope you pick me (and my plus one) to take a vacation. Please consider me and thank you for your time.

  22. Hey!

    My Name is Kristen Masullo and I am entering for a chance to take my mom on vacation! This pst year my parents got divorced and I would love to be bale to take my mom on a vacation this summer! She is always taking care of everyone else and I feel like this would be an awesome way to repay her. Thank you for having this giveaway and for your consideration!!

  23. Newly weds from Philadelphia here and we have yet to go to any trip due to building a new home. Need a stress relief and getaway asap lol. Ive always wanted to go to beautiful Hawaii. Im sure we would love it there so much in peaceful nature. Whoever wins or if we do, I wish us all the best and a wonderful, loving and memorable experience in Hawaii. 😍

  24. My husband and I have never been to Hawaii, so this is #1 on our bucket list to do! We’d love t to win and share our experience. Thank you for offering this awesome adventure!

  25. Thanks for the sweepstakes each month. Some are repeats and for 1 per person so have to take care not to enter 2x. So sorry to hear of the horrible floods in Hanalei. Stayed in a darling little 1 story oceanfront home in December at Haena which I understand was quite hard hit. Hope it is still standing as some of the multimillion $ homes across the street have damage. A friend in Waimea relayed this info to me today. Have visited Kauai every year for over 40 years so the island is quite dear to me. Of course the hospitality industry will play this down. I wouldn’t be surprised if you delete this post but the people of Hanalei area have my deepest sympathy. If there is a relief fund maybe you could post that as there are probably many people who hold Kauai dear to their hearts.

    1. Just got back Kauai. It was absolutely lush and gorgeous. Stayed in Princeville at Sealodge I absolutely encourage all that have vacations planned to still go to Kauai and visit Hanalei. Kauai relies on tourism as a major source of income and everyone was spreading that ALOHA.

  26. Just be aware of who you are giving your info to in exchange for a chance to win. I’ve gotten many more spam emails, texts, and phone calls since entering these. Now I don’t enter unless it’s a company I am familiar with.

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