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. Love Kaua’i and Hawai’i and enjor the hustle on Ohau.
    I would just love to experience Maui or Molaki

  2. Me and my boufriendneed this vacation so bad! We both been doing school everyday, work everyday and we really new a vacation! Please help us out. Thank you so much

  3. Aloha from snowy Vermont! Mahalo from the bottom of my heart, for the chance to return to where my soul belongs. .

  4. This hopeful entry isn’t for me, but on behalf of my parents. My parents have been married for 33 years now and have sacrificed and dedicated their life to both my sister and I. My sister and I were both diagnosed with pancreatitis at a very young age and collectively have had 40 sugeries. Financial problems have occurred, which resulted in my parents struggling at times to pay the bills. Words do not describe the unconditional love they have shown us and I just want to say thank you. My parents could not afford a honeymoon when they got married and I truly want to bless them with one, 33 years later. I love you Mom and Dad!

  5. Thank you very much. we have been to Hawaii one time before and considering moving there.

  6. Perfect Days Hawaii Sweepstakes – I noticed in the Official Rules: Enter by January 31, 2018, random drawing to take place December 31, 2018 – travel required by December 31, 2018.
    I’m hoping it is just a typo because if not, it would be pretty tough for the winner if drawn on December 31, 2018 to travel by December 31,2018.

    1. Hi Trisha.

      We inquired and were told this is an annual contest and that they were just updating the rules, so it is likely they will fix this.

      Aloha.

  7. Have always wanted to go on a honeymoon with my sweetheart but could not afford one due to both of us being on meager incomes when we were married in 2001. Since then, kids and life have prevented us from experiencing the trip of our lifetime. Hardship occurred early for us since a number of illnesses hit both me and my sweetheart. Through all this we have learned that the best moments in life are that we still love and cherish each other through the tribulations we have and are currently experiencing.

  8. I’ve been to Hawaii once with my husband and daughter back in 2008 and would really love to go back! I want to go with my sister & our 2 daughters who are the same age with birthdays 6 days apart! I would be very happy and grateful if I was chosen for this trip.🙂🌺🌸🐋☀️

  9. My husband and I took our honeymoon to Maui 20 years ago. Would love to take our two beautiful children there as a family!!! It is our dream to go back there!!!Absolutly paradise!!!💞🌺🌸

  10. I’ve been to Hawaii in 1978 as a teenager had a blast.again in 2008 this time
    Went on a Hawaiian pride of America cruse had a penthouse had the best vacation of my life.
    I have arthritis being in Hawaii eased my pain.the only thing I would change would be to fly first class.
    Hopefully I someday will get the chance to return.

  11. Haven’t been to Hawaii in over 15 years.
    Want to travel with family members after losing my father to bond and start anew.

  12. -Moana Find Your Way Sweepstakes from Hawaiian Airlines wants your first born child (read the legalese)
    -Where Will You Go Sweepstakes not available in NJ

  13. Hello,
    I wonder if anyone could please help with approx airfare cost. I’ve been checking airfare from BDL (Hartford CT) to KOA and then a return from LIH. My travel dates are April 28 to May 26th 2017. Airfares seem to be around $1120 and up. Has anyone found a better price? I’m wondering if I should book or wait a little bit longer to see if I can find a better price. Thank you very much in advance for any advice!
    Eileen

  14. Hello i really hope i win a trip its my dream if i don’t at least please shear or help me reach that dream thank you

  15. Wish there are more affordable flights and hotel vacation packages from Atlanta to Hawaii. Hawaii is on my bucket list of dream vacations in 2017.

  16. We met in Hawaii, married in Hawaii, honeymooned in Hawaii, lived there for six months followed by California, France, Virginia, New Jersey and now-Texas. Love the Islands and want to live there our last years! Have to move back soon as we are already both 81 years old (including 55 years of a fantastic marriage).

  17. I want to see hawaii as we never goes out of Country but it’s amazing to experience such beautiful sites and it’s my dream Country.

  18. Please consider my family for your vacation giveaway. I lived on Oahu in the 90’s as a military spouse. We were unable to afford to do many of the “touristy” things. I would love to go back and be able to see all that we missed before. Thank you for giving away this vacation.

  19. Wanting to plan a trip to Maui from Kansas City with no time in mind yet. What is the cheapest time to fly?

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