Travel & Holiday Competitions 2019 – Updated Weekly!

Looking to travel more without spending more? I am a big advocate for entering holiday competitions to try to win a holiday. Over the past 18 months, I have won a trip to Barcelona, flights to Iceland and various other day trips. Winning holiday competitions are a great way to travel more without spending any money, and while you may not win them all (or any to start with!), it goes without saying, the more travel competitions you enter, the more chance you have.

On this page, I will round-up all the best holiday competitions I find on the internet, from city break competitions, UK holiday competitions to once in a lifetime holidays. They will all be opportunities to win a holiday, all you need to do is follow the instructions to enter and think positive thoughts.

Win a holiday competition tip: I find I have better chances with ‘effort competitions’ or ‘creative competitions’, this means competitions where you have to do more than just sign up for something for entry. The reason behind this is because fewer people enter as a lot of people cannot be bothered. The more effort you put in, the better your chance of winning.

Holiday competitions 2019:

The newest travel competitions will be at the top of the page and will be updated with new holiday competitions every other day, so be sure to bookmark this page and keep checking back. 

Please note, due to my location, most competitions will be for UK applicants, however, check the competition terms and conditions to be sure.

May the odds be ever in your favour!

Christmas Advent Travel Competitions 2019

Jet2 Advent Calender

Travel Zoo Advent Giveaway 

Bright Sun 24 days of Christmas

Virgin Christmas Winning

Lifestyle Hotels Advent Calender 2019

Switzerland Tourism Advent

Blue Bay Travel – 12 days of Christmas competition

Win a Family Festive Stay In London

Answer the question in this Time Out contest and you can win an overnight stay for a family of four at The LEGO Santa Room at The Savoy Hotel including breakfast, dinner and £400 towards travel expenses. Competition closes on December 16th 2019.

Win a family holiday to Universal Resort Orlando, Florida

Thanks to British Airways Holidays it could be you and your family, experiencing all the action, thrills and excitement of three amazing theme parks at Universal Orlando. The trip includes return flights, admission to all three theme parks, and accommodation at the all-new Universal’s Endless Summer Resort – Surfside Inn and Suites. Competition closes December 26th 2019.

Win flights to New York City 

Win 2 flights to New York City with Virgin Atlantic by playing the addictive game Suitcase Stack. Competition closes on January 31st 2020.

Win a luxury holiday to Sri Lanka

Worth over £4,000 including flights this prize for 2 is from Delicious magazine. Log in or sign up to enter to win two nights’ bed and breakfast accommodation at the Shangri-La Hotel, Colombo in a Premier Ocean Room, three nights’ bed and breakfast accommodation at Shangri-La’s Hambantota Golf Resort & Spa in a Premier Ocean Room plus a ton of extras. Competition closes on December 31st 2019.

Win a trip to Hawaii 

Hawaii Tourism Europe has teamed up with United Airlines and Hawaiian Airlines to give one winner and guest, a chance to create and share their own aloha story.

Your prize includes:

  • Return economy tickets to Honolulu, Hawaii from London
  • Inter-island flights
  • 2 nights at the Alohilani Hotel on Oahu
  • a 2-hour UTV Jurassic Valley Tour at Kualoa Ranch Private Nature Reserve
  • 2 nights at the Kauai Marriott Resort in a Pool View room on Kauai
  • Seats on the Deluxe Tour with Safari Helicopters across Kauai
  • 2 nights in a partial Ocean View Room at Fairmont Orchid with daily breakfast for two at Orchid Court on the Island of Hawaii
  • 4 nights at the Royal Lahaina Resort in an Ocean View Room, with a Luau for two on Maui.

Competition closes on December 16th 2019.

Win A Pair Of Return Economy Flights To Miami

You and a friend could be jetting off to Miami thanks to Bright Sun and Virgin Atlantic. The prize is for 2 return flights to Miami, Florida, please note no accommodation is included. Competition closes December 15th 2019.

Win any Trek America Trip 

Enter Trek America’s competition and you could be in with the chance of winning ANY TrekAmerica trip of your choice! Yep, that’s any trip up to the ultimate Great 48 departure – an EPIC 75-day trip around the entire 48 lower states! Competition closes December 15th 2019.

Holiday competition tip:  For email entries, draft and save a template email with your name, email, address and telephone number, so you can fire it off quickly. Remember to leave a space for the answer.

Win a six-night holiday in the Maasai Mara

Courtesy of National Geographic and Asilia Africa the winner and a guest will travel to the Maasai Mara for a six-day, five-night walking safari. Covering between 10-12 miles per day, you will stay in a mix of fly camps and permanent camps, with all the logistics and transfers taken care of. The prize includes return flights from London to Nairobi. Competition closes Friday 31 January 2020.

Win a trip to Boston

For the ultimate Yankee Candle experience, enter the prize draw to win a trip to Boston, including a day trip to Yankee Candle factory and flagship store. Competition closes on December 11th 2019.


Maximise your chances of winning holiday competitions by reading the Super Lucky Secrets book by Di Coke (currently available in paperback and E-book). Di has bagged over £300,000 of prizes by entering prize promotions – and now you can read a hundred of her tried and tested tips on being a successful winner.


Win a trip to Venice

Win a trip to Italy by simply guessing the number of water bottles which will be refilled by the Excels water stations in 2019. The prize includes return flights to Venice for two people and £1,000 for accommodation and spending money. Competition closes January 5th 2020.

Comping tip: Comping, if done right, can be a really lucrative as well as fun hobby. While a big part of it is done to luck, you can also increase your chances of winning big if you know what to do.

If you are planning on making comping a hobby then I recommend investing in the Super Lucky Secrets book by Di Coke (currently available in paperback and E-book). Di has bagged over £300,000 of prizes by entering prize promotions – and now you can read a hundred of her tried and tested tips on being a successful winner.

Win a couples holiday to Majorca

One lucky winner will win a holiday to Majorca for two people, which will consist of the following; return economy flights from a UK airport to Palma, 7 nights accommodation staying in a 4-star hotel and return overseas transfers. Competition closes on 31st December 2019.

Travel competition tip: A lot of competitions will ask you to sign up for their newsletter in order to be in with a chance of winning. To combat your inbox being filled with emails, create a new email just for comping, this way all emails will be in there and not your main email.

Win a 7 night holiday to Tobago 

Enter the prize draw for the chance to win an incredible trip to Tobago with return flights from London Gatwick with British Airways. Competition closes December 31st 2019.

Win a 10 night trip of a lifetime to Japan 

Win a 10 night trip to Tokyo by waxing your nose! Yep you heard me correctly, Kenashii would like you to film yourself waxing your nose then upload it to social media for everyone to see – only the bravest will win the trip of a lifetime to Japan. Competition closes 31st December 2019.

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Remember to check back weekly for new travel competitions! If you do win a holiday which you have found through a travel competition on this page then I would love to know. Please be sure to send me a tweet at @yokomeshiuk so I can find out all about your win and next adventure.

Travel competitions I have won:

Return flights for two to Iceland with Wow Air – won via a tweet saying where I would like to go.

An all-inclusive city break to Barcelona with spending money – Creative competition with a photo.

An eco-friendly travel accessories gift bag worth over £50 – Guessing a destination on Instagram.

Tickets to a beer festival in Germany plus exclusive camping – Answering a question via Instagram.