What Kind of Expenses Can You Expect When You Win a Trip?

Expenses from a Trip WinWinning trips is at the top of my list right now. Our kids are grown and our business is portable so we have a little more freedom to travel. The problem is – no money to travel 🙂 Isn’t that always the way? Freedom, no money – money, no freedom – or no money, no freedom. Sometimes you just can’t win.

Since I recently traveled to Miami on a trip win from ShopRite it got me to thinking – maybe people don’t really realize what to expect if they win a trip. So, I came up with some of the basics you should know if you enter to win a trip.

Is Airfare Included?

Sometimes a trip sweepstakes will only give you hotel accommodations as part of the prize and airfare or any other type of travel may not included. Reading the official rules will tell you whether airfare is included in the trip you are trying to win. Think about this first before entering. Airfare can be quite expensive depending on where you are going.

Trips are Non-Transferable

Trips prizes are almost 99% of the time non-transferable. That means if you win a trip and can’t go, or don’t want to go, you can’t give it to a friend or family member. In that case you would have to turn it down. It’s not fun winning a grand prize and then turning it down. So, make sure you really want to take the trip before you enter.

This happened to me once. I guess I wasn’t paying attention to the rules too much. I know that I was new to the Internet so it must have been about 13 years ago. We won a $7,000 Star Wars trip – Seven Cities in Seven Days – I still remember the name. The prize consisted of airfare and hotel accommodations but guess what this trip was all about? We had to see the current Star Wars movie in 7 cities in 7 days. Each day we would have been flown to a different city, spent the night and watched the movie. No food was included or anything else. And, while the idea of traveling sounded fun I couldn’t see myself sitting through a Star Wars movie 7 times. I feel asleep during just one showing of it. And, we would have had to pay taxes on this trip. So, we turned it down. I wasn’t disappointed this time and I learned my lesson to read the rules more carefully next time.

Is There A Cash Alternative?

Some sponsors may actually give you cash instead of the trip. It is something you will have to discuss with the agency who contacts you about the win. Maybe you can’t go for some reason or don’t want to take the trip. Cash may not be an option but it never hurts to ask. There have been several occasions that we received cash instead of the trip. As long as you are nice to the agency they will often work with you to come up with a solution that benefits both you and their client.

Are There Other Expenses for the Trip You Won?

While many trip sweepstakes will give you airfare and hotel they do not always give you cash or provide for your meals. They may not provide ground transportation while you are on the trip so that may mean you will either have to rent a car or take a cab at your own expense. Most of the time they do not offer extra money for souvenirs or necessities like cash for new clothes, luggage or sightseeing.

When we traveled to Florida last week I can safely say we spent from $300 to $500 out of our own pocket. This trip did come with a $250 AMEX card but the rental car was almost $100. The Internet access at the hotel wasn’t included and I take my computer with me everywhere I go so that was another $9.95 each day. We did get free breakfast everyday but lunch and dinner was not covered. On at least 4 occasions we had to pay for parking (beach and parking garages) and we had to pay for tolls twice when we went to and from South Beach.

Then there is the tipping. You have to tip when you eat unless you always eat fast food and you sometimes tip the Concierge if they really good care of you. We left some money for housekeeping on the last day for taking care of our room.

Then there are the shopping trips. We don’t shop unless we need something. I have learned to control my “impulse shopping” over the years but when you go on a trip some of that tends to go out of the window. Some people like to buy souvenirs or gifts for family.

If you go to any attractions, like when we went to the Fairchild Gardens, all of that is going to cost you. That little 2 hour trip cost us $40.00.

If you are not prepared to take a trip and haven’t set money aside then these added expenses can add up quick and your free trip isn’t so free anymore.

Trip Timeline

Sometimes a trip can only be taken on certain dates. Maybe you won a trip to the Super Bowl and they want you to just go during that game. Many times you can’t plan ahead to know if you will have those dates free, if you can get time off work, or if you will be able to find someone to watch the kids if you aren’t taking them. And, maybe you won’t have extra money planned ahead for expenses.

Make sure you understand the dates when you enter the trip. A trip that must be taken on certain dates will usually be indicated in the official rules.

Turning Down a Trip

A reader reminded about something when they asked if it is in bad taste to turn down a trip. You can always turn down a trip. The agencies understand that it doesn’t always work out for people. Sometimes the trips have to be taken on certain dates and that is often hard to plan around. Another thing you can do is to see if you can get a lower prize. Explain that you entered for a lower prize. I have never been able to “trade down” but for the most part we have always taken what we won so I haven’t tried much either.

Taxes on Trip Wins

Uggg – taxes. Yes, you will have to pay taxes on this fabulous trip you won. But, the good thing is you don’t pay taxes until the next year after you take the trip. We were trying to take this trip in February because then we wouldn’t have to claim it until the next year but that was not an option.

When you are traveling save every receipt you get and put it in one envelope. I carried an envelope with me and every receipt went into it and when we arrived at home there was no work or confusion to figure out where those receipts were.

Ask the desk clerk for a printout of the hotel expenses and see if you can get an estimate of the airfare. If your receipts add up to less than the actual 1099 you receive you can claim less on your taxes. But, you will need all of those receipts and documents to keep with your tax paperwork in case you ever have to prove it.

How Many People Can Go on the Trip?

Most trip prizes are either for 2 or 4 people. This seems to be the standard amount of people for trip prizes. Some sponsors may allow you to take another person with no extra charge but most likely you will have to pay extra to take more people than the trip allows.

Is it worth it?

Absolutely! As long as you are prepared and know what you are getting into, winning a trip can be wonderful. We have gotten to go places we could have never gone or could afford and I hope we continue to win more trips.

There are always exceptions to any of these rules and you may find a sweepstakes that is giving away a fabulous trip that will allow you to take everyone in your family, give you cash for the extras, pay for meals and ground transportation, includes hotel and airfare and more. However, you will need to read the official rules concerning the particular sweepstakes you are enter to find out all of the details. Reading the rules is the best way to know exactly what you are getting if you happen to win a trip prize from a sweepstakes.

Disclosure: this sweepstakes listing may contain an affiliate or tracking link but we do not use referral links. Read about our policies for more details.

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  1. Thanks for the trip info. Hopefully one day I will win one 😉

  2. Thanks Sweetie for posting this! Sometimes you get caught up in the excitement of entering for a "nice trip" you don't pay attention to the logistics and specifics of it. Something to now think about …


  3. Thank you for the info and congrats on your trip!
    I was wondering what to do when I enter ones that have a trip as the grand prize but I am only playing because I am interested in the 2nd or 3rd prize. Is it poor taste to turn down a trip?

  4. Wendy (Sweetie) says

    You can always turn down a trip. The agencies understand that it doesn't always work out for people. Sometimes the trips have to be taken on certain dates and that is often to plan around. Another thing you can do is to see if you can get a lower prize. Explain that you entered for a lower prize. I have never been able to "trade down" but for the most part we have always taken what we won so I haven't tried much either.

  5. Thanks you so much Sweetie for the wonderful information. Sometimes winners get so excited about a trip that they dont look over the fine print as well as they should. Thanks for explaining the costs of a "free" trip.

  6. Thanks for this article. I often wonder when entering a trip for 2 if I can pay for my daughter to come along with us? I definitely would want her to come along with us and I see that is an option, even if we have to pay extra for it, just wondering though how that would work. Do trip wins usually involve booking through their agency and then they will deduct the cost of the two who won but you have to pay extra to bring a third person along?

    Also, I wonder about those trips where you also win tickets to attend a specific event or meet a specific person – what if you just want the trip but don’t want a meet and greet with a celebrity or to go to a concert, sporting event, etc. that’s part of the trip? Are you obligated to go or can you just go on the trip and not show up?

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