Amazing Tips! How to Enter and Win a Vacation

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You know, scoring an amazing vacation prize is totally doable – it’s easier to enter and win a vacation than most people think.

Want the secret on how to win free trips?

Just follow the rules to a T, enter as many relevant travel contests as you can find, and stick with it.

Persistence is key!

My Experience

I’ve been really lucky and managed to win all kinds of incredible stuff through contests and giveaways over the years.

We’re talking cold hard cash, luxurious cruise getaways, brand new computers and electronics, even a sweet new ride!

If you just keep throwing your name in the hat over and over, those vacation prizes will eventually come your way.

Believe me, I’ve lived it!

Contests vs Sweepstakes: What is the Difference

When entering promotions to win a vacation, you will find them in one of two categories – a contest or a sweepstake. But what is the difference?

A contest is a promotion that requires participants to use specific skills and complete the specified objective. By completing the actions, they are qualified to win.  

When entering a travel contest, the skills shown in the entry are normally judged by an independent organization or the contest organizers.

In general, here are some guidelines for contests:

  • Questions cannot be too hard or too easy to answer.
  • Rules for breaking ties are defined in advance and are broken based on the skill. 
  • It is imperative that the judging criteria are objective and clearly explained (for instance, an essay might be judged based on “originality,” “grammar,” or “humor,” however “best” is too subjective).
  • Judges must be qualified to apply the judging criteria.
  • All entrants must be competing on the same playing field and all entries must be judged.

Some examples of contests that require skill are an essay contest where you describe your dream vacation, a photography contest, or a cooking contest. 

A sweepstakes is a promotion in which prizes are given to eligible participants and the winner(s) is randomly selected.

This type of entry is easy and not judged. It is strictly a game of chance. 

Benefits of Winning a Vacation

There are several benefits of winning a vacation that you will greatly appreciate.

When you win a vacation, it offers a range of benefits, from free travel to personal growth.  

Free travel

Firstly, the vacation is at no cost to you!

For vacation sweepstakes, the prizes can include flight, accommodations, experiences, food and drink, transportation services, shopping experiences, or any combination of things.

And it’s free! 

Less Stress

Planning and organizing a getaway can sometimes be a hassle.

But when you win a vacation, the stress is greatly reduced because the vacation experiences are organized and booked for you.

However, there will be opportunities for you to select the dates of flight departure and return.  

New Experiences

There are places that I would have never thought to visit had I not won a vacation.

Winning a vacation can allow you to try new things and have new experiences.

Whether it’s exploring a new city, trying a new activity, or sampling local cuisine, winning a vacation can broaden your horizons and introduce you to new things.

Quality Time with Loved Ones

Vacation prizes are usually provided for an even number of travelers — like a couple, or a group of 4 family members.

If you are looking to spend more time as a family, be sure to review the prize that will be awarded to learn how many people will be accommodated.

Winning a vacation can also allow you to spend time with family and can also allow you to spend quality time with your spouse, create lasting memories and strengthen your relationship.

Common Misconceptions About Sweepstakes

It’s a scam.  I won’t win anything.

This is the prevailing thought of most people. 

And unfortunately, there are scam websites that masquerade as legitimate contests, which can make people wary of entering any contest.

I have even entered a few of them unknowingly.

But as I grew experience with entering contests and sweepstakes, I learned to recognize the fake ones immediately.

There are legitimate travel sweepstakes that you can enter for a chance to win free vacations and vacation giveaways.

Some of them include:

  • Better Homes and Gardens Sweepstakes
  • Travel Channel Sweepstakes
  • Disney Sweepstakes

Because these are reputable and well-known brands, you can register to win a vacation with more confidence instead of using a URL that looks suspicious.   

How to Win Vacations

Entering a contest to win is not difficult, but it does require a bit of skill.

Entering a sweepstakes is less difficult and the advantage is that you have just as good a chance of winning as everyone else, if you know the rules.

Here are the steps that you should always follow when entering a vacation giveaway.


Read the Rules

The rules will provide important information that can help you determine whether it is a legitimate sweepstake or contest, and how to win free vacations.

The rules should indicate a sponsor. This can be found at the bottom of the contest rules. The sponsor is responsible for providing the prize.

The rules indicate the URL to enter the site and the eligibility requirements. Use only that URL to enter, it will help ensure that you are not entering on a scam website.  

Next, look for any restrictions such as age, residing state, and number of times you can enter. If you do not meet the age or state requirements, don’t enter.

Winners are required to provide proof of meeting eligibility requirements either through a notarized affidavit, or a copy of the driver’s license.

Don’t waste your time entering sweepstakes when you don’t qualify for them. 

Finally, look at the award to determine what is included. As previously mentioned, the prize could be a combination of things including flight and accommodation.

The rules will also state if substitutions are allowed.

For example, you may have the option of selecting the cash value instead of taking the vacation.  


Be Persistent

If the rules say that you can enter daily, then do it! If only one entry is allowed, follow the rules.

Entering multiple times when only one entry is allowed will only get you disqualified.

There are ways around this, and I will cover that later. 

It’s not enough to enter one contest and stop. You should find and enter as many contests and sweepstakes as you can.

I used to spend an hour a day doing this as a hobby. After three months of nothing, I was ready to stop.  

My daughter was sitting with me when I said “Maybe, I should give up.” She replied, “Awww mommy, don’t give up.”

There was something in her voice that encouraged me to keep going, so I did.

Two months later, I won $25,000!

How to Find Free Vacation Giveaways

You can use aggregate sites that list contests. These are the expressions that I use in an online search: win a free trip, win free trips, enter to win vacation, free vacation giveaway, win a beach vacation, win trips, win free vacation, and win vacation packages.

Pitfalls to Avoid

There are some pitfalls that you should learn and avoid when entering vacation contests and giveaways.

I have come across a few and I was able to successfully navigate entering and winning without being scammed.

Here are a few that are the most common.  

Scams and Fraudulent Contests

You should NEVER pay money before or after you get the prize.

The only time you will need to pay anything is to the IRS, or directly to a company for their service.

For example, you may be responsible for hotel tax, resort fees, transportation to and from the airport and other transportation, meals, gratuities, travel upgrades, incidental expenses, income, and other taxes, ground and air transportation to and from the city, and all other costs and expenses not specifically listed herein.  

These expenses are incurred while you are taking the vacation and your financial responsibilities should be stated in the rules. But for the most part, the vacation is free! 

Oversharing Personal Information

Be careful about giving your personal information away on the internet. Some entries only require an email address.  

However, you may also need to register for a promotion, in which case it only needs to be done once.

Registration is like creating a profile and the data collected will consist of your name, address, and phone number.  

As a rule of thumb, if you are not comfortable with giving away information about yourself, then don’t.

Be suspicious because you shouldn’t need to give more than basic information like name, address, email address, and phone number. 

Violating Contest Rules and Guidelines

Violating contest rules and guidelines is one of the quickest ways to get disqualified.  If you think you can trick the system, think again. 

I once entered a contest to win a trip to a Western state. The eligibility requirement stated, “must be a smoker”.  

I don’t smoke.  

Without thinking, I answered a phone call (and I don’t recall what it was about, but it was completely unrelated). The caller asked, “Do you smoke?”.  

Without hesitation or thought I replied, “No.”

It didn’t click right away, but I realized that I had just disqualified myself from a promotion.

Falling for Clickbait and False Promises

If you are on a site and see a lot of pop-ups, promises, and paths to other online places, close the window.  

Be skeptical of exaggeration and clicking your way into a rabbit hole.

If you remember these rules, you will avoid most of the clickbait.

  • Legitimate contests will not ask for personal information, such as your social security number, bank account information, or credit card number.
  • Legitimate contests will not require an entry fee or payment to participate.
  • Legitimate contests should not require payment or purchase of a product to enter.

How to Increase Your Chances to Win Trips

There are many ways to win a free vacation and this post mostly covers promotions on a website. 

However, there are also giveaway posts on social media including Instagram, TikTok, Twitter, and Facebook.  S

earch these channels and follow brands that giveaway trips.  Barilla Pasta and Mionetto Prosecco are a couple that has given away trips to Italy.

Change Your Mindset

If you want to win a vacation, you must change the way you think. Most people will not enter because they think they don’t have a chance. Not entering is a sure way of not winning. 

Keep in mind that brands want to bring attention to their products. In addition, tourism bureaus want to promote the cities they represent so that people will visit. Sponsoring sweepstakes to win a vacation is one of the most popular ways to bring more traffic and these giveaways are part of their marketing strategy.

Seriously. They want to you enter to win a free vacation and tell your family and friends. They want you to tweet about it, post about it, and spread the word. And whether you enter or not, somebody is going to be the winner. So why not you?

Research and Enter Multiple Contests

You can increase your chances of winning a vacation by entering multiple sweepstakes. You find promotions through sweepstake sites like,, and  

Some sites ask for payment to gain access to promotions, like a site membership.  This is legal because they put in a lot of work to find those promotions and make it easy for you to find them.  They may also offer richer functionality like filtering on prize category, and type of entry (e.g., daily, monthly, one-time).

Also, check local TV and radio stations for travel giveaways.  You will have the best odds of winning because the entire US population will not be competing against you.

Follow Contest Rules and Guidelines

I can’t emphasize reading and following the rules enough. You may find that entries are accepted multiple times across multiple platforms, thereby increasing your chances of winning.

If there can only be one entry per household, then your spouse or eligible children should not enter. Follow the rules to the letter for the best chance of winning a vacation. 

Don’t Ignore the Little Prizes

While it’s nice to win a grand prize, the little prizes are nice to win too. I have won lots of travel accessories including cell phones, luggage, power banks, Bose noise-cancellation headphones, USB wall chargers, and travel gift cards. 

All of these items are travel essentials and will help save money for vacations. We have won gift cards from Exxon Mobil,, Expedia, and many other travel and tourism brands. 

Even if you only win a luggage tag. Just think of it as the start of winning your next vacation!

Engage with Contest Hosts and Sponsors

To be honest, I don’t engage with contest sponsors for every promotion.

I would also question if this were a valid way of winning, especially if the selection of the winner is supposed to be random. However, it doesn’t hurt to get noticed!

Keurig ran a sweepstakes for the new Keurig 2.0 coffee maker on their Facebook page and I wanted one.

There were hundreds of comments on the post, and it was mostly about how terrible the coffee maker was designed. Especially since they rigged the machine to only accept Keurig K-cups.

I commented on the post and said “Wow, after reading these comments I don’t think I want the Keurig 2.0 either”.  

Then boom. It was as if the coffee gods heard me and said, “You are getting a Keurig 2.0 and you are going to love it!”.

Two days later, I received a winner notification with a code to get the coffee maker, for free.  

I have engaged with brands and sponsors for other travel sweepstakes and while it is good to let the brand know how much you love their products, it doesn’t guarantee a win. 

What to Expect When You Win a Free Vacation

Congratulations! Big News! You’ve Won!

This is where a lot of people can get into trouble, especially senior citizens who are scammed out of their retirement funds or life savings.  

Now that you’ve won the grand prize, you must claim it.

But there are a few things you need to know beforehand.

  • The value of the prize will be reported to the IRS as income. Thus, the promotion will request your social security number and driver’s license when you claim the prize. 
  • You may have to pay taxes on the value of the prize.
  • You may need to complete a notarized affidavit.
  • The sponsor has the right to change the prize if it is stated in the rules.

My Success Stories

Since first entering travel contests in 2016, we’ve enjoyed telling family stories from our vacation wins. 

I’ve been fortunate enough to win several travel prizes, such as travel certificates with JetBlue and Virgin Airlines, the Ultimate Disco Cruise, hotel stays with Embassy Suites, a getaway prize bundle in New Braunfels, TX, and a getaway prize bundle in Bloomington, MN, a Vail townhome getaway, a Ventura beach retreat, and many more.

Here are some highlights of our favorite family vacations. 

Promotion: Photo Contest Cruise Giveaway

Win your next vacation
Win your next vacation

Sponsor: Grandbaby Cakes

Prize: 7-Day Carnival Cruise for four (4) on the Carnival Vista from Port Miami. The cruise includes accommodations and all meals, activities, and entertainment normally included in the cruise fare.

Promotion: Pasta World Championship

Sponsor: Barilla

Prize: A trip for two to Pebble Beach, CA to attend the qualifying event for the Barilla Pasta World Championship.

The trip package included round-trip coach-class air transportation for two from a major airport near the winner’s home to San Francisco, CA, 4 night’s accommodations at a hotel determined by the Sponsor, an allowance for a rental car for the length of the stay, and a $3,900 check for spending money.  

This win happened during the month of lockdown, so they gave me a check for $10,000 instead. 

Promotion: Everyday Moments

Win your next vacation

Sponsor: American Express

Prize: A trip for 4 to Yosemite National Park. The trip package includes roundtrip coach-class air transportation from an airport near the winner’s home to Fresno, CA; three night’s accommodations at Tenaya Lodge, a $500 check that the winner can use for a rental car or transportation, an American the Beautiful Pass, winner’s choice of two activities from a list provided by the sponsor, $500 spending money for the winner. 

Promotion: 12 Days of Ellen

Sponsor: The Ellen Show

Prize: Amazon gift card, Parrot Zik 2.0 headphones, Visa gift card, The Beatles CD Collection, Panasonic Blu-ray player, WestJet Airlines round-trip airfare to Vancouver, British Columbia, 4night/3day stay for two in a deluxe studio suite at the Westin Resort & Spa in Whistler, British Columbia.

Promotion: Priceless Experience in Chicago

win your next vacation
win your next vacation

Sponsor: IHG & MasterCard 

Prize: Each grand prize includes two (2) round trip coat airline tickets for the winner and one guest to Chicago; three (3) nights of hotel accommodations, ground transportation between the airport and hotel, a spa experience, a helicopter tour of Chicago‘s skyline, a private wine tasting event, a $600 Mastercard prepaid card, dinner with chef Graham Elliot, a signed copy of Graham Elliot’s cookbook, and a $5,000 check made payable to the winner. 

Promotion: A Weekend in Milan

win your next vacation
win your next vacation

Sponsor: Conde Nast

Prize: The grand prize winner will receive round trip coach class airfare and hotel accommodations for two (2) people (grand prize winner and travel companion) for a three (3) night/four (4) day stay in Milan.

The trip includes one (1) food shopping experience for two (2) people at Eataly in Milan and one (1) cooking class for two (2) people at La Scuola de La Cucina Italiana (the school of La Cucina Italiana). 

Final Thoughts on How to Win a Vacation

There are legitimate methods on how to win a free trip. Just remember to select a contest that best suits you.

Also, each contest may have different requirements:

  • Sweepstakes
  • Skill-based Contests
  • Social Media Giveaways
  • Travel Writing Contests

So, the next time you see an advertisement for vacation sweepstakes, check the rules, and go for it!

You may be on your way to a dream getaway.

Safe travels.

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  1. Um, this is the coolest thing ever and I’m totally going to try winning some vacations now!! I’ve traveled for free a few times, but from winning fellowships

    1. Tanya Taylor says:

      Congratulations! It’s always nice when everything is planned for you. Let me know if you have any questions. I hope you win, good luck!

  2. Yasma Daniels says:

    Thanks this is great Tanya

    1. Tanya (Admin) says:

      Thank you, Yasma! ❤️

  3. I do not even know how I ended up here but I thought this post was great I dont know who you are but definitely youre going to a famous blogger if you arent already Cheers.

    1. Tanya (Admin) says:

      Thank you so much, Kaylee. You may want to subscribe to the email list for more goodies! Toodle-dee-doo 😎