Are you going to Hawaii in 2020? (+ Hawaii Calendar Giveaway)

Calendar winners announced: Congrats to Sylvia and Ray!

As we prepare to welcome 2020 and wonder what the new year has in store, we hope that visits to Hawaii are in your future! We love hearing your Hawaii plans and dreams. Will you be visiting Hawaii in 2020? When will you go? Will you be celebrating a special milestone or occasion?

We’ve had a little tradition for several years to give away lovely Hawaii desk calendars illustrated by Hawaii artists Mike Carroll.

We have two calendars to give away. To enter to win a calendar, use the comment section of this blog post to tell us your plans for visiting Hawaii this year or in the future. Here’s how the calendar giveaway will work:

By commenting on this blog post on (not on Facebook or via email), you are entered to win.

Here’s how to submit your comment/entry:

1. Scroll to the bottom of this post and past other comments to the comment section that looks like the following example screenshot:

^ Sample Screenshot Only. This is not the actual entry section.

2. Enter your comment in the comment field.

3. Enter your name (first names only are fine) in the name field. Please use a real name, because that’s how I’ll be contacting you.

4. Enter your email address in the email field. (Note that your email will not display on the approved comment. It will only be visible to me and used only to contact the winners.)

5. The Website box is optional.

6. Click the “Post Comment” button.(Note that if you are a first-time commenter, allow us up to 12 hours to receive and approve your comment for display. All first-time comments go into moderation at first.)

We will accept entries through December 31, 2019.

Two winners will be selected at random on January 1, 2020. The winners will be notified by email.

So, let’s hear from you! What are your Hawaii travel plans? Use the comment section to let us know.

Calendar winners announced: Congrats to Sylvia and Ray!

  1. My wife and I will be heading to Maui to celebrate our 25th wedding anniversary the last week of July, 2020.

  2. No official plans yet but I am targeting the Maui Film Festival or Maui Classic. Heard my Tar Heels are comin’!

  3. Not sure I can make it in 2020 but looking forward to Merrie Monarch and then Oahu in 2021. But if I win the lottery I’m moving to Oahu.

  4. Spending 9 days in Honolulu, going to visit my granddaughter, can’t wait. May 2020!

  5. The whole family went to Hawaii in 2017. I am dreaming of my husband and I returning soon. Enjoyed all the islands.

  6. My husband and I are very excited to be able to celebrate our 40th this coming February 13-24 in Kauai.
    We will be able to celebrate it with my brother and his wife that are also celebrating there 40th in Kauai at the same time.

  7. We are visiting Oahu in 2020 to celebrate our 30 wedding anniversary, went for our 25 th and loved it, may not come back this time

  8. Been before and have wanted to go again so bad ever sense. No definitive plans as of yet but the sooner the better.

  9. We are heading to Maui the 1st week of March and bringing our 6 year old son with. This will be our first time to Maui and 3rd time to Hawaii (first for our son). We can’t wait to escape the winter weather in MN. He wants to see a bamboo forest!

  10. My kids and I are going to Hawaii for the first time for two weeks in April, 2020. We will be in Waikiki for three days, followed by a 7 day Hawaiian island cruise with Norwegian; then five days in Kailua-Kona.
    We are so fortunate and have so much to be thankful for; we’re celebrating both my 50th birthday and three years cancer-free on April 6…in Maui! 🌴🌺🥰

  11. Vi skal besøge Hawaii her den 29.12.19 til den 30.01.20 🤩☀️🌈🍍Vi rejser med rygsæk og har planer om at besøge flere skønner øer 🌋🏝 Hilsen 2 forventningsfulde danskere 🇩🇰

    1. Aloha, I have dreamed of going to Hawaii for as long as I can remember, nothing is going to stop me being in Hawaii on my 50th birthday! Corny I know but I’ve said it for years Hawaii 50oooo for my 50th, April 2020! I’ve planned our trip and we’ll be spending 8 nights in Maui and 6 nights in Oahu, planning loads of excursions to make the most of our time! Any tips would be greatly appreciated, that’s why I look out for your email! Winning the calendar would be the icing on the cake, something to treasure for ever, to bring back the memories of our dream holiday… 🏖 🌞 🏝😎😍 🍹 🏴󠁧󠁢󠁥󠁮󠁧󠁿 🏳️‍🌈

  12. Leaving on the 3rd of January for our second trip to Molokai. Helps to get through winter in Missouri by spending some time in the sand and sun! Mahalo!

  13. I’ll be going to O’ahu in 2019 but not coming home until 2020! We’ll be spending our fifteenth New Year’s on the beach at Waikiki and I just can’t wait.
    Hopefully this is also the year I get lucky enough to score Merrie Monarch tickets so I can make another 2020 trip.

  14. My children and I will be going to Oahu and The Big Island in May/June 2020 to celebrate my daughter’s graduation from college. Hope to scope out rental properties, as I’m hoping to live there in the next few years!! Aloha!

  15. My wife and I will be visiting Oahu (Waikiki) in 2021, this will be our 8th visit to Hawaii. We are Aussies.

  16. My wife and will be visiting Kapa’a Kauai for two weeks in April celebrating her birthday and Easter. Love Kauai.

  17. Went to Oahu this past May for the Lantern Floating Ceremony-just awesome.
    Planning to go back again in 2020. May is a wonderful month to be in Hawaii!

  18. It would be a great birthday gift for my husband. I let him choose our Easter 2020 holiday destination and he said Hawaii. But he was actually joking as it is about 20hrs of travelling from The Netherlands. Little did he know I actually booked a trip to Hawaii and he recently found out about this. We are going to celebrate his birthday in Oahu on April 10th.

  19. I hope to visit Kapolei to visit my daughter who moved there nearly 2 years ago and married an American guy, they send me amazing pictures of Hawaii!

  20. Hawaii in July, that’s my first and main goal for 2020. Have to go back to Honolulu!!Can’t wait!

  21. Hi there, we are going to visit in 2020 for husband’s 50th birthday. Hoping to stay on Oahu north shore.

  22. We are a group of 4 Australian seniors travelling to Hawaii in August 2020. We are looking for accommodation and ideas of what we can do for the 2 weeks we are there.

  23. My husband and I will be visiting Hawaii Island in June of 2020, AND I won’t rule out trying to talk him into a November anniversary trip to Kauai as well! We have made it a priority to visit the Islands as often as possible and this will be our 11th Hawaii trip since our first to Maui in 2008.

  24. I’m so excited to be heading to Kauai and Maui in March with my 17 year old daughter, Sydney. This is our ‘girls’ trip before she graduates from high school and moves off to college. We look forward to lots of hiking and beach time!! But especially just sharing the time together and making lifelong memories in a beautiful place!

  25. My husband and I are going to Maui the beginning of March. Maui has a special place in my heart because that is where my brother lived and died. I love it there. Hawaii is one of my favorite spots in the world. It is so unique and beautiful. Maui holds a my heart in its hands.

  26. Our son, Michael, just graduated from college on December 20th with his Masters and we are coming to Maui to celebrate! Instead of stressing out over Christmas shopping, wrapping, baking, cooking, cleaning etc. we will land on New Year’s Eve and will be tossing our bags in the condo and heading out for food, drinks and fireworks in Kihei/Wailea area. We look forward to traveling the Road to Hana, surfing, swimming, hiking and visiting as many of the beautiful beaches as possible.

  27. We are visiting Honolulu, early in January. The last time (and our first time) that we visited Hawaii, we were on Big Island for five days only, which was too short. This time we are going to spend two weeks, hopefully, relax, enjoy, see some new things… We very much look forward to this vacation.

  28. Traveling to Maui & Oahu in January! None of us have visited Hawaii before and we are incredibly excited. We have much to celebrate and be thankful for this season. Looking forward to adventure, relaxation and renewal in the Hawaiian paradise. This site has been greatly helpful in our trip planning thus far — thank you!! 🌄🏖🌺

  29. Our family is just days away from landing in Oahu! Jan 2-10, 2020!!!
    We have rented a home on Ewa Beach and have every day planned. We can’t talk about anything else, we are so excited! This will be our 3rd trip!

  30. We are visiting Hawaii and cruising 3 islands with a group of friends in February. My Husband and I are celebrating our 40th Wedding Anniversary! Cannot wait!!

  31. So excited to visit Hawaii this summer to experience all the scrumptious foods recommended by the foodie YouTubers! Leonard’s Malasadas, shrimp scampi from Giovanni’s, poke from Ahi Assasins, Waiole Shave Ice, Helena’s Hawaiian Food, plate lunch from Rainbow Drive Inn, Pho French Dip Sandwich from Pig and the Lady, spam musubi and many more! 🙂

  32. We will be on Maui for the last two weeks of March. The last few years we have spent a month in the state, but only had this much time this year. Obviously, we love all the islands!

  33. I’m very excited to be going to Oahu and then Maui in February/March of 2020. My father just turned 80 and my mom will be turning 75 in a few months, so this is a combined milestone birthday trip.

    In addition, this will be the 50th state that my mother has visited! So it’s a big deal all around.

    Thank you for this website. I only wish that I had seen it earlier in my planning process.

  34. My family is going to Kauai for a week the first week of July and then for 3 weeks on the Big Island. My wife and I are celebrating our 25th anniversary.

  35. Hoping to visit Hawaii this year to celebrate our 30th anniversary & hubby’s 60th bday.
    Not sure if we will do a cruise or stay on one island. Hubby doesn’t like small planes and we want to see and do everything. Happy New year!

  36. Mahalo for all the entries! We’re excited to hear your plans.

    Congrats to Sylvia and Ray who were both randomly selected as the winners of the calendars.

  37. My husband and I had reservations to visit Maui for the 1st time, in August 2020, and it was going to be celebrating our 5th anniversary. We had to cancel our reservations, and postpone our trip due to COVID-19! We are very sad about it, but we hope to get to take
    the trip later, hopefully in October 2020, if the pre-testing program goes through.

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