How It Feels Winning Travel Contests

How It Feels Winning Travel Contests

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It feels fucking great. Thanks for coming to my Ted Talk.

Okay, I’ll write more. This post is approximately 3 years late. The last big travel contest I won was a trip to Montreal in 2019. I’ve won smaller non-travel prizes since then (including a $200 Amazon gift card). I recommend reading my series series about tips for winning travel contests first. This is an unofficial part four to that series.

I’m gonna get woo for a second, but stick with me. Maybe you’ve heard of phrases such as law of attraction and manifestation. I’m not an expert with these, but I know a little bit about them. Apparently, you shouldn’t just think about what you want (that’s a start). Instead of just thinking about what you want you should feel the feeling of having what you want and know it’s coming to you. When I entered the big travel contests I won (the trip to New Orleans in 2012 and the trip to Montreal in 2019) that feeling of being there was something I focused on when entering. I’d been to New Orleans earlier that year and I focused on the feeling of being in New Orleans, walking around and hearing the music in the streets, eating all the delicious food, etc. Similarly, I’d been to Montreal a few years prior (in 2013) and focused on how I felt when I was in Montreal.

Remembering the fun I had in New Orleans in June 2012. A few months later I was back in that city with the trip I won.

I can’t guarantee that feeling like you’re at the winning destination of a contest will help you win that contest. I might be good at winning contests, but I’m not a psychic. In my opinion focusing on the positive feelings of winning a contest, and feeling like you’re at the destination isn’t a bad thing. Before you start entering contests all willy nilly read my series about winning contests, particularly the part about not being scammed. Even in part 1 of that series I talk about getting into a winner’s mindset. My hope is this post gets you in a winning mind frame. Elite athletes will often visualize themselves winning the big game, the race, the tournament of champions, etc. This is the same idea, but with free travel so it’s better.

The Email

First, let’s talk about the email you’ll get, because chances are whatever contests you’re entering requires your email. Hopefully, you’ve been keeping track of your contest entries on a spreadsheet, so you can be sure any emails you get saying you’ve won a contest is for a contest you actually entered. I recommend a free email service specifically for entering contests (don’t use your personal or business email) and check that email daily. If I get an email saying I’ve won something at my personal email I know it’s a scam because I don’t use that email when entering contests.

You’ll receive an email from someone either working for directly or hired by the main company sponsoring the contest. We’ll refer to the sponsoring company as the sponsor and this person sending the email on the company’s behalf as the contact person. This contact person could also be an employee of a marketing or pr firm the sponsor has hired. In any case the contact person is representing the sponsor, and perhaps other companies/organization who’ve contributed to this prize. Basically what I’m trying to say is that the email you get should be somewhat professional. It doesn’t needs to be boring in tone; there’ll probably be some enthusiasm in it because you did win a contest. But an email stating you won a contest that seems unprofessional, and/or has misspellings and/or weird punctuations, spacing or capitalizations (whether in the subject line of in the email itself) is a red flag. No professional representing a legit company will send an email with subject of CoNgRaTuLaTiOnS you.WON ★★★NEW iPHONE★★★.

Additionally, if the email was automatically filtered to your junk/spam folder it’s likely a scam. I always check my contest spreadsheet. Chances are if the sponsor and draw date for when I get the email doesn’t match up with the contest spreadsheet I have then it’s not legit. Another tip if you’re not quite sure if the email is for a legit contest would be to print the email (you can choose to save it as a pdf instead). Look at the email subject line and who it’s from. Amazon won’t be sending a free gift card from an email address like i(that’s not even the right spelling for the company; another dead giveaway). Finally, if feel like something is off listen to that and trust your gut instinct. Remember you’ll never have to give your credit card, bank information or social insurance/social security, or any other form of ID* to confirm a winning or claim a prize (*with an exception; keep reading the post for more information on that).

In 2014 I won a $500 travel voucher, which I used for flights and hotel in Las Vegas (I stayed here at The Excalibur). While this winning was from a charity raffle (meaning I bought a raffle ticket for entry) I didn’t need to pay any additional money to claim my prize.

One day you see an email in your contest email account saying you won a 5 day trip to London with airfare, hotel plus some meals and activities covered too. You look at the email closely and it seems legit. It’s for a contest you actually entered. The email is contacting you around the contest draw date as stated in the rules. They’re not asking for anything suspicious like your credit card or bank details (which is a scam). The contact person asks you to respond back with some information within 48 hours to claim your prize. They need your first and last name, email, phone number, and address. If you’re Canadian you may have to answer a math question as part of our weird contests laws (seriously, that’s a thing). Sometimes the initial email you get will ask you to first respond to verify you’re the winner. Then they’ll ask for your contact information and/or the answer to the math problem on the next email. Once you respond back with the information the contact person will send further instructions.

Once you know the contest and email is legit don’t wait until the last minute to respond back. The contact person/sponsor could be in a time zone ahead of you. If the email says respond back by 2pm on the 3rd if the contact person/sponsor is in a time zone several hours ahead of you you’ll want factor that in, and respond quickly. For all contest there a time limit for your response (usually within 48 hours, sometimes les). If you don’t respond back within that limit you’ll be forfeiting the prize to another person. Do you want to miss out on free travel because you were too lazy to send an email? I thought not.

Tom Petty Was Right

The waiting is the hardest part. You’ll be excited and anxious to hear something back from the contact person, but it could take a few days, maybe even a week to get a response back. With both the big trips I won (New Orleans and Montreal) I wasn’t the only prize winner. The same could be true for the contest you win. The contact person you’re communicating with may also be emailing several other prize winners and getting their information as well. If you haven’t been asked for your guest’s contact information (assuming you can bring a guest) make sure to get all that information ready to go. Remember this trip involves international travel (unless you live in the UK) so be sure to bring a travel buddy with a passport.

You won a trip to London. Do you know who you’ll be bringing with you to see Lizzie’s place? Don’t take too long picking a guest for any trip you win.

Soon enough you’ll get a response email letting you know all the information provided is good. This email response may have a release form that you and your guest will have to read and sign. Most of it will be a liability form protecting the sponsor and any other company/person involved with the contest from lawsuits. Other things the form will likely include are; information about how the prize cannot be transferred/sold, safety regulations you’ll need to follow, what is and isn’t covered by the prize, and anything else you’ll need to have with you on the trip. With the trips I won I needed to bring a credit card for any incidentals at the hotel like if I wanted to order room service, which wasn’t covered by the prize (and for any spending money for activities/meals not covered by the prize as well). They will probably need you to give an emergency contact for you and your guest.

*Now for that exception from earlier. If your prize involves international travel then they’ll need a photocopy of your passport and you’re guest’s to book the trip (also probably for some assurance you will be able to board the flight). I had to do this for the New Orleans trip I won since I’m from Canada, but obviously not for the Montreal trip I won. The passport information (if required ) should be sent right away. If you or your guest doesn’t have a passport you’ll need to get a rush passport (happened to the friend I brought with me to New Orleans). This passport information (if needed) won’t be required in the first email. They’ll ask for your other details (as well as your guests) and confirm you are eligible ad still want prize (duh doy you do). Then maybe on the 2nd or 3rd email ask for the passport information (again, only if required). If the trip doesn’t involve international travel but does involve a flight (like my Montreal prize) they may need you to send a photocopy of a photo ID to book the travel. If you have any hesitations reach out to the contact person for more information.

More Emails

There may be another email (or several) once the contact person verifies your and your guest’s information (including passport or ID if need be). During the correspondence you may be asked about allergies and health concerns for you and your guest. The sponsor wants everyone to be safe and have a good time on the trip, and someone getting sick or going into anaphylaxis because of an allergy (which could have been prevented) is not want they want. If the contact person hasn’t asked about allergies, food intolerances and health concerns that could affect the trip for you and your guest be sure to send out an email giving them a heads up. Keep it friendly, polite, and sure. A simple “Hi, I just want to let you know my friend who’ll be joining me on this trip has an allergy to seafood. Hope this won’t be a problem. If you need more information please let me know.”

Eventually, you’ll get an email with an itinerary of the trip. This may include information about your flights, ground transport to your hotel (likely you’ll need to find your own transportation to/from your home airport), the hotel reservation, and any meals and activities covered by the prize. There may activities you’ll be doing involving the sponsor. Both the New Orleans and Montreal prizes I won were sponsored by different alcohol companies. There were some meals/events where we got to try different alcohols from the company and learn a bit about them. As mentioned earlier you might not be the only prize winner on the trip. Both my New Orleans and Montreal prize had several winners, and we did several activities together as a group.

If you win an a trip from a sponsoring company there might not be a ton of free time in the schedule. But we’re talking free travel, where most of your expense will be covered. That’s a small price to pay. And really drinking free booze like I had to for a couple days is hardly what I’d call a sacrifice. Once you get the final dates for the trip (if you don’t know them already) be sure to book the time off work if haven’t done so.

I won a 2 night apartment stay in London back in 2017. With this prize it didn’t include other expenses (like the flight). Luckily I was living in Dublin at the time so flights to London were pretty inexpensive). If you win a prize like this (that just covers accommodation) you’ll have a bit more flexibility with your trip, but of course there’s a lot more costs you’ll have to cover.

Before The Trip

I recommend printing or taking a screenshot of the email with all your itinerary information. Contact your bank and/or credit card company to inform the of your trip so you don’t have any holds put on your accounts. If you’re Canadian and looking for a credit card with no foreign transaction fees I recommend Home Trust visa. You’ll still have to pay whatever the exchange rate is, but there’s no extra foreign fees like most credit cards have.

Pack your bags, but don’t bring too much, after all it’s only a 5 day trip. Be sure to bring your passport, and wallet with a credit card for incidentals/spending money. If you want to bring cash don’t go to the currency exchange booths at the airport as they have the worst exchange rate. I’d recommend not bringing too much cash since the trip is short (particularly if most of your expenses will be covered). Make sure to charge your phone for the plane and bring a spare battery or power bank for your phone as well. If you’re flight is a red-eye you might want to bring some melatonin, and a travel pillow to get some sleep on the flight. Finally, both the big prizes I won involved a couple of dinners out, so you might want to pack a nice outfit to wear. You could always email the person who’s been corresponding with you about the trip to see if there is a dress code for any events. Don’t stress about this too much. If you’ll be attending a black tie gala I’m sure they’ll let you know.

The Trip

The big day is here. You checked into your flight ahead of time and just need to get to the airport a few hours before your departure. The prize doesn’t include transportation to your local airport, so you get a taxi there. You know the flight will land at Heathrow just after 9am local time. Your flight goes well, and after you clear customs at Heathrow you know to look for the driver holding a sign with your name. You and your guest go with driver and are taken by cab to your hotel in central London. At the hotel you check in, and know you’ll be meeting for lunch at the hotel restaurant in a few hours. Despite the jetlag I advise you to power through and stay on local time as much as possible. With the free time before lunch you may want to have a shower and freshen up, go for a walk around the neighborhood (get some oxygen to help with the jetlag)

There’s a good chance the contact person you’ve been emailing will be at the destination to make sure everything goes smoothly. There may also be other representatives on the trip to help out, provide information, and keep the itinerary organized. Be sure to be polite and thank these people for their help. They’re probably not paying for the prize out of their pocket, but they are working and may be organizing several meals, events, and activities for you and the other prize winners. There could also be other people from the company, especially if there are activities planned around the sponsor (like touring the sponsor company’s brewery as an example). Be friendly and polite. Generally, just don’t be a douchecanoe.

Aside from that enjoy the trip you’ve won. Follow the schedule and itinerary that has been presented to you. If something comes up, like if you or your guest isn’t feeling well and you have to forgo one of the events make sure to let the contact person who’s there know right away. Depending on what’s covered in the prize you might not have to pay for meals or tips. If you’re not sure about tipping ask the contact person if you should tip anything for the meals (assuming they’re being covered in the prize) and they’ll let you know. Of course in some countries, like the UK, tipping isn’t a big thing. The overall bill might up to the next pound or two, but a 15% to 20% tip won’t be expected like in Canada or the US.

Other Things to Know

As mentioned earlier depending on the schedule you might not have a lot of free time to do your own thing. Don’t plan on a day trip out to Stonehenge or something like that (unless that’s already included in the prize). I’d recommend not wasting time in souvenir shops either. Instead some take some photos on your phone, and then if you want you can use an app like MyPostcard. This take the photos on your phone and turns them into digital postcards, which are then printed and mailed to your friends and family (or whoever else you want to send a real postcard too). It’s a fun way to create your own postcards (and you can always design and send them when you get home. If you sign up to MyPostcard with this link you’ll get a $3 credit for free. If you do have some spare time on your trip pick an activity nearby to check out. London has lots of free museums, and I always love visiting parks. In Montreal my mom and I had a bit of free time on our last day, so we went on La Grande Roue de Montreal, had some poutine at a restaurant for lunch, and tested our skills at the Canadian Olympic Museum.

View from La Grande Roue de Montreal. The building in the foreground is Marche Bonsecours or Bonsecours Market. The pirates were part of an adventure park. We did not go on the pirate ships.

Finally, a word of advice; winning a free trip is amazing, but you’ll need to be flexible since you won’t be deciding what your doing, where you’ll be staying, etc. If you need to control what you do, where you go and when you go there, then a free trip (as weird as it may sound) could be a bit stressful for you. Now it’s important to remember that important details like your flights, hotels are being taken care of (you don’t have to stress about that). But let’s say you’ve never been to London and it is your dream destination. If there are certain things you’ve always wanted to see or do while your in London you may or may not get to do those things on this trip. If you have a rigid attitude of “this is my dream trip and I have to eat fish and chips from this particular pub and then I have to take a tour of the Tower of London” you may be in for some disappointment if those things aren’t in the itinerary. I don’t want to discourage you from entering contests for all expense paid travel prizes, but as mentioned before you won’t have a lot of free time. You need to have a go with the flow approach for this kind of trip. You could always ask the contact person if there’ll be any free time in the schedule, but don’t be surprised if it’s pretty jam packed.

Now I’d like to stress that my attitude for my trips was more of a go with the flow.. Although with the New Orleans trip my friend and I hoped for a bit more free time, but that trip was literally 36 hours in the city so it was rushed. When it came to the Montreal trip I told my mom we probably wouldn’t have any free time, but we were good with whatever. I was pleasantly surprised when we had a few hours our last morning there to do a few things. Chances are the free time you may have might be when you first arrive and/or on your last day before you leave. Of course a lot of this will have to do with the flights you’ve been booked on. If your flight back home leaves at 6am then there won’t be much free time that day.

Now you know what it’s like to win a travel contest. Your experience may vary, but hopefully this gives you a general idea. Now go out and win some travel prizes, and consider me if you need a travel buddy for any trips you win. I’m pretty chill and I have a passport so I’m ready to go.

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