Travel & Holiday Competitions 2020 – Updated Weekly!

sunset view from plane, flying with cbd oil

Do you want to win your next holiday? Here is my weekly round-up of the best 2020 travel competitions.

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.

family standing at the beach on holiday won on a travel competition

Holiday competitions 2020:

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!

Win a 5-star holiday to Sharm el-Sheikh!

Enter this prize draw and you and a friend could soon be jetting off on a fantastic 5-star holiday to the Red Sea resort of Sharm el-Sheikh. The prize includes 7 nights at The Grand Hotel, Sharm el-Sheikh on an all-inclusive basis, plus return flights from the UK.

Competition closes April 30th 2020

Win an All-Inclusive Holiday to Croatia 

Now’s your chance to win a seven-night All Inclusive holiday for a family of four to Croatia! You’ll stay at the gorgeous four-star Gava Waterman Milna Resort on Brac Island, on the Dalmatian Riviera.

You won’t want to miss out on this great giveaway! Enter our competition to win a seven-night All Inclusive holiday for a family of four to Croatia and you could be in for an incredible trip. The enchanting Gava Waterman Milna Resort boasts three outdoor pools, views of the lush surrounding scenery, an exciting kids’ club and playground. You can also expect buffet dining, two bars for grown-ups and fab entertainment.

Competition closes April 14th 2020

Win A trip to Mexico for Day of the Dead (worth £2,600)

Lonely Planet have teamed up with G Adventures to offer you and a companion the chance to win an incredible six-day tour of Mexico City when the Day of the Dead festival takes place.
The Prize:
– Two return economy flights from London to Mexico City
– Two places on G Adventures’ six-day ‘Day of the Dead in Mexico City’ tour, guided by G Adventures’ Chief Experience Officer, with five nights’ hotel accommodation and a variety of excursions included.

Competition closes April 12th 2020

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.

Win a Trip for 2 to Madeira 

Win a trip for 2 to Madeira and have an exclusive MTB experience with Espresso Monster. Add your details for a chance to win a trip for 2 to Madeira and have an exclusive MTB experience with Monster Energy!

Competition closes on June 30th 2020

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.


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 holiday to the Maldives for two 

Thanks for Monster Energy Drink you could win a 4-night luxury trip to the Maldives for 2 people (incl flights) with surf lessons and yoga activities during Maud Le Car. Two trips up for grabs!

Competition closes on April 30th 2020.

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.


Subscribe to my mailing list to receive a round-up of the best competitions to your inbox each month!

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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.