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best city 2019

The annual Best City To Visit Travel Tournament is back! To enter, all you have to do is nominate a city you love as the best to visit in 2019 in the comments below. The first 64 cities will be matched up and eliminated by weekly reader votes and the person who nominated the final remaining city will win $300 on either the Apple or Amazon online stores.

To enter, write your favorite city in the comments section of this post before Sunday, February 24th 12:00pm US EST.

The cities will then be placed in tournament brackets sorted by geographical region, with the first round of voting beginning on Tuesday, February 26th, 2019. Each week the number of cities will be halved by reader votes, until there is one left. Hopefully, the winning city is the one you picked.

Tournament Rules

Cities are first come first serve and several cities have already been chosen by my newsletter subscribers (who got the first picks). The Best City To Visit Travel Tournament is a round robin style competition, with voting every week during the month of March.

  • Cities Already Taken: Lisbon, Istanbul, Helsinki, Medellin, Rio de Janeiro, Melbourne, New York City, and Anchorage
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Important Dates


Once you enter a city, there’s nothing you have to do… but remember, voting for yourself isn’t a bad idea. These are the (Tues)days in the coming weeks to make note of:

  • February 26, 2019: Round of 64
  • March 5, 2019: Round of 32
  • March 12, 2019: Sweet 16
  • March 19, 2019: Elite 8
  • March 26, 2019: Final 4
  • April 2, 2019: Championship

Check back on this page every Tuesday for each new round. I’ll also post updates on Facebook and Twitter. The winner will be announced on Tuesday, April 9th and the prize will be delivered electronically by June 28th, 2019.

Prizes And Tips

In previous years, the winners have all generally used these tactics to their success which I recommend you read to advance far in the contest. Also, since there are quite a few dates to keep up with – the best way not to miss anything is to get my posts sent directly to your inbox or subscribe to my newsletter.

  • The $300 gift card prize will be sent as a gift card that can be used on the Apple or Amazon online stores.
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More retailers may also be added; or those above modified at any time before the end of the tournament – gift cards must be for the full $300 prize amount and cannot be split among stores, transferred into cash, and will be sent to the email you use in the comments section to choose your city. Best of luck to everyone and please let me know if you have any questions!

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