Win A Free Trip To Hawaii Sweepstakes

Free Trip to Hawaii Travel Sweepstakes For May 2022

Hawaii Travel Tips / / 721 Comments

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. Brooke M

    This is great, I actually just dreamt that I had won an all expense paid trip to somewhere. Hope it comes true!

  2. Vanessa

    Aloha! I’m 45 and got married for my first time in August, and all my husband and I could afford to do was to drive 5 hours to Ft. Bragg, CA with our dogs. It was foggy and cold and we couldn’t leave the dogs at the hotel. I’m still dreaming of a tropical honeymoon in Maui just the two of us, and so hope to win the contest. Thank you for having it.

  3. Audrey

    Hello everyone best of luck to you all! I’m about 5 and a half months pregnant I just want to get away before our little girl comes just Me and him. We’ve never been on a vacation together this would bring us so much closer and relieve a lot of stress for a while! So fingers crossed!!

  4. LaMara

    Aloha, Hawaii is my family ultimate dream. Please select my family to attend & explore. This will be our first family trip “ever” as times has been very challenging over the years. This would mean the world to us all. We wish all contestants well. Thank You Sincerly.

  5. Christian

    Hello all OR shall I say aloha! I wish everyone luck and would really like to win one of these awesome packages myself. My husband and I have recently married and cannot afford a honeymoon. This would be indescribable. I teach special education in Missouri and have met some really great people from the Hawaiian islands. We would love this cultural experience! Good luck to all 🙂

  6. Val

    Please pick us! I’m a single mom with 2 teenage girls in freezing cold Montana and we would love to go on a trip to Hawaii to enjoy the sun and beautiful landscapes!

  7. Patricia S

    Hi my name is Patricia but my friends and family call me Tricia I would like to win a trip to Hawaii I never been there I would like to take my mom with me if I win

  8. Shannon S

    I am the only one in my family who has been to Hawaii! During the whole two weeks I was on Maui, I could not help but wish that my family ( especially my two younger sisters ) were there with me to share in the adventures and beauty of Hawaii! They would love it! Ever since that trip i have tried to find ways in witch my two sisters and I could go! Hope we get lucky this time!

  9. Todd A

    WE WOULD LOVE TO GO TO HAWAII!

    I believe in fate, and Hawaii has always called my soul! The Aloha spirit sings to me a calm yet energetic tone of welcome! And as of lately everything around me has had Hawaiian influence, commercials! In store products! Hawaiian words people randomly bring up in convo..I feel the universe winking at me 😀

  10. Lorrena R

    Please pick my family
    We would love to go see Hawaii
    We have been married for 44 years what a vacation it would be for us
    Thank you for considering us

  12. Dena

    I would love to win this trip. I was in Oahu Hawaii in September. Hawaii is the most beautiful place I have ever seen! I am ready to move there! Mahalo!

  15. Crystal

    Thank you so much for these opportunities to win a trip to a beautiful island! What a dream come true! Merry Christmas from myself and family!

  19. Tammy D

    What a wonderful gift! Thank you for helping others visit the islands that otherwise may not be able to. Merry Christmas.

  22. Rosie

    Looking forward to next year and our first visit to Hawaii, this site is fabulous for helping us decide which island and when to go. Let me know when you have a contest open to Canadian residents 🙂

  30. Nanette

    Mahalo, Mahalo, Mahalo…LOVE LOVE LOVE… You’re site! It’s so informative, fun, and it keeps me up to date for my favorite vacation destination! Thank you

  31. Ashley

    Hey thank you so much for posting this free sweepstakes to play.But can you please post new ones.It seemed all of them have expired apart from the first two.Thank you so much

      1. Ashley

        Thanks for the reply am already subscribed cant wait for the new upcoming sweepstakes.Am very grateful for this site and all that you guyzs do very helpful

  32. Carol

    Am very grateful for this site i always plays sweepstakes and win.We just got off our frirst trip to hawaii and we absolutely loved it.Thank you you for the links to the sweepstakes.Am a winner for life

  33. Colleen

    We’ve already got our condos books for 2017 – but I went ahead and tried a few these contests. One can never visit Hawaii too often, right? I used to think I could never win a contest until the day I guessed the correct weight of a hog and won it!! Can you believe it? :0) He tasted pretty good, too.

  34. Shelley

    It would be nice if more of the contests that you have listed were also for Canadian residents.

    Thank you

    1. Beat of Hawaii

      Hi Shelley.

      Yes, concur. Being based in Hawaii, we find that many contests exclude our participation as well, so we know how that feels.

      Aloha.

    1. Beat of Hawaii

      Hi Tom,

      Just over $500 with one stop and about $575 on Alaska nonstop. Not very competitive and may not improve.

      Aloha.

      1. Robert

        Hi. What’s a good price for the same route (PDX to KOA), but for summer travel (late July/early August)? Thanks!

        1. Beat of Hawaii

          Hi Robert.

          Right now there are high $500’s for mid-summer on that route, which is really great. Would buy that ASAP if it works for you.

          Aloha.

  36. Stephanie

    I just want to say thank you so very much for posting these links! I am very grateful for your website! We are looking forward to our first Hawaii trip from Arizona in a few months. It will be our 5 year wedding anniversary in February, so we are trying to plan now. 🙂
    Thanks again for the great tips!

    Best regards,
    Stephanie

  38. Derick crosdale

    I am 18 and my parents have done so much for me. I just want to give back to them. I have a job but do not get paid nearly enough to cover the prices followed. Please consider.

  40. Cesar

    Hi,

    I booked to travel to Hawaii September 3rd and heard that hotel prices are cheaper during September but as of today hotel prices are still high. Can you tell me how to find out when prices have been reduced for that month.

    Thank you

    1. Beat of Hawaii

      Hi Cesar.

      You’ll just need to keep checking. Perhaps make a reservation that can be changed if you find something better.

      Hawaii hotel prices are high, but they should be relatively less than in July for example. Perhaps 15-20% difference might be average change.

      Aloha.

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