Say Aloha to

The Weekly Win: Attempting to go around the world by winning Travel Sweepstakes!

Aloha Makamaka!

At the risk of sounding cliché, I love Hawai’i. I love visiting the Polynesian empire, and I enjoy bringing Hawai’ian cuisine and culture home. It’s one way to bring a little Aloha into every day. Another way is to subscribe to’s email newsletters, which has the added bonus of possibly winning something!

Photo: Giveaways

Once you sign up, you’ll get as many as four or five emails each week. That sounds like a lot, but each one has different content. For example, this week I received:

  • “What’s New This Week” – a recap of new restaurants and activities around the islands
  • Hawai’i Travel Specials – offers from hotels, condos and activities on Oahu, Maui, Kauai and Hawaii
  • Hawai’i Moments – photographs submitted by visitors, with one chosen as a winner each week
  • Two reminders of ongoing sweepstakes
  • An invitation to “Find the Pineapple” – more on that in a moment

Recently, I’ve also received emails about special Hawaiian events like King Kamehameha Day and Lei Day. I’ve come to look forward to those email the most, as they help me learn more about the culture and history of the islands.

Did you say Win a Trip?

You’re probably already thinking, “That’s cool, but what about winning stuff?”

Each newsletter has “power links” which take you back to and award you points. Sometimes there are additional activities, like finding the pineapple for 5,000 points, but most often you get points (up to 1,000) just for following the link. If you submit a photograph and get featured that week, a whopping 10,000 points are coming your way.

Image: "Find the Pineapple" banner

And now you’re probably wondering “what are the points for, brah?”

Fair question. You collect the points to “buy” entries into monthly giveaways. Prizes often include Hawaiian products such as coffee, chocolates, tote bags, and other island mementos. Sometimes, however, the prizes include hotel stays (at some fantastic resorts) or entire trips! (I like to save up points to enter the trip giveaways.) Entries are typically 1,000 to 3,000 points per entry.

See also - because winning vacations is fun!

Image: Panel

Unlike traditional sweepstakes, this is an ongoing chance to win. Your chances of winning are tied not only to how many others enter, but how many points you are willing to spend. Rest assured, though, the competition is pretty stiff. Five or ten entries in most of the giveaways is but a drop in the bucket.


  • Sign up for email newsletters at
  • Earn points by following links in the emails and completing activities on-line
  • Use points to enter giveaways at
  • Rules for each giveaway can be found on the Prizes page

Wishing lots of pomaika’i to you!

Note: Travel Sweepstakes featured in The Weekly Win are not affiliated with, nor administered or endorsed by, TravelLatte. The Weekly Win is neither solicited nor compensated. In the belief that it’s better to win a trip than to scrimp and save for one, we just thought you’d appreciate hearing about some of the travel sweepstakes we find.

2 comments on “Say Aloha to

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