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Vacation Once A Month (Sometimes For FREE!)

June 5, 2020

You, YES YOU, can take a vacation at least once a month, maybe even more!

I do it all the time and still get my bills paid on time. What’s my secret?

I work the system *insert wink*…

Yes, I said sometimes for FREE (I will put these with a pointer finger in the picture like below), but keep in mind nothing in business is truly free so be prepared to do some work.

OK ladies, get ready to take notes… It’s a lot of info but I’ll try to keep it as short and sweet as I can. As usual, I saved my favorite (Casinos) for last…

FYI : This page includes affiliate links, which means I might get a commission from your purchase at no extra cost to you. This is what helps me work on the free content and freebies I produce for you guys, so thank you for that! Know that, I ONLY include what I use myself and stand behind 100% (learn more)

Click Here For My FREE Stocks & Cryptocurrency Links!

Instead of keeping all of my money in a savings or checking account, I invest it! Your money grows while you sleep!

I’m in no way a financial advisor… But, if you’ve been thinking about it, this is your sign to start investing!

Cryptocurrency is really on the move right now and a lot of my gains have been coming from trading Crypto. So far, I’ve taken at least 5 trips just from my investments alone… and that’s only since November 2020!

Take a day off or switch shifts

This one is pretty self explanatory. Instead of lumping all your vacation time into weeks, break up the days.

Take a Friday off here and a Monday off there. Maybe switch shifts with your coworker. Whatever you can manage, Lengthen your weekends and give yourself more days off.

You can just take a day off when you need it and take a beach day or even just have a day to yourself to Netflix and nap while you collect your paycheck.

Use a sick day (Use sparingly)

If you have pretty good health and don’t find yourself using your sick days much, use them as vacation days.

Let me first say, you can’t use this technique every time you want to travel! They will know what you were up to, especially after you posted all your pics on social media. (DON’T do that either.)

During slow season at work, see if you can take a half day on a Friday (because you’re not feeling well *cough cough*). Then, use one of your sick days that Monday.

My go-to is to say you had the flu or food poisoning because no one wants to see their coworker throw up.

The only major things to remember are: to not use more than two in a row because then you need a doctor’s note. Also, I reiterate to never post this vacation on social media!

The easiest vacation to do using this technique is a road trip. You are NOT guaranteed the half day on Friday. It’s better to have control of your transportation of your travel plans.

Take off on that drive and enjoy your weekend in a new city while your other coworkers wish they had thought to do that.

Keep a strict budget

The more money you don’t spend on clothes, the more money you have to spend on vacations.

That being said, Disney is great, but, you don’t HAVE to take a $3000 Disney vacation getaway every year either!

Spend that vacation money on smaller vacations instead. Maybe you divide it into 6 smaller getaways instead of just one. (Ex – $500 to an all inclusive 3 day Getaway to Cancun, Mexico, $300 to a weekend getaway at a local winery, $600 visiting Chicago, IL for a few days, $200 road trip to visit family, $400 ski weekend getaway, $1000 for a few days in San Diego, CA trip.)

While you’re on vacation, stick to your budget. Remember that this is just one of many vacations for the year. You don’t have to splurge just because it’s vacation! Remember, you will be constantly relaxing at least once a month for the next 6 months!

Work your Credit Cards!

We all have bills and we all need to pay our bills and expenses.

Why not do this with a credit card that has a points program. Follow people on social media who know the latest trends like The Points Guy. They will help you pick a card that will work best for you.

When you choose a card, keep in mind that when you sign up during an event or during a flight, you usually get more bonus points than you would just signing up for the card online.

If done right, they will all get you vacation points. I see a FREE vacation coming!

When you choose to fly, try and take a flight mid-day, the day before you really want to travel. (As in your vacation gets to be a full day starting the next day! Even if you get to your hotel in the evening after the sun went down, you get to wake up and roll out onto the beach!)

Holiday season is the perfect time to put this technique into play. Flights are always getting delayed and overbooked at this time of year. (Here’s my article on what to do if your flight gets delayed.) Guess how they deal with this problem? They ask people to volunteer their seat.

What? Emily, why would you give your seat away? Because the auction is starting.

When no one offers to give their seat away, the airlines enter a bargain with you. Suddenly you hear, “$100 to anyone willing to volunteer their seat.” But, you don’t want to take that deal.

Just wait.

“$300 to anyone willing to volunteer their seat.” Now this is where it gets tricky. Be patient and look around. Do you have any competition? Only two people got up to volunteer their seats. You’re not the only seasoned traveler about the board the flight. “$500” (They won’t offer much more than that. The most I’ve heard has been $800 but I didn’t get it because they ended up squeezing me onto the flight.) Now jump, take the deal because now people stopped hearing “give up their seat” and they take out their headphones when they started hearing “free money.” Get the deal before the others realize what’s happening.

Even though they offer to put you on a later flight, it is not guaranteed so wait at the gate. They will load the plane and you won’t get your new ticket or your gift card till after. The airlines are cheap. If they can fit you on the flight, they will.

Giving away money is a last resort. This is why it’s best to try to cash in on this technique during the holiday season. The airlines are more desperate then. And remember, DON’T just get up and go offer to volunteer your seat the minute they ask, because they won’t offer you anything in return! They will just put you on the next flight and thank you for volunteering.

Let me break it down for you…

Airfare – included

Stay – included

Food – included

Drinks – included

Airport Pickup – can be included

Everything is “free” on this vacation!

The only thing you need to bring is money for souvenirs and tips. It’s so relaxing to know you do not have to budget or worry about anything. Are you hungry? Go eat. Still hungry? Make yourself another plate! You don’t like that crazy mixed drink you would never try unless you were in Jamaica? Don’t drink it. Try a different one. It’s no extra cost.

The resorts themselves are also amazing. Most of them always have pools, beaches, and awesome common areas. (My favorite common areas are often the sports bar and the lobby bar, that’s where everyone hangs out.)

Most all inclusive resorts have entertainment every night. It’s a nice night cap or a good motivator to start the night off right with dancing! If you are looking to be more social, go to a smaller resort that only has one choice for a bar and club. It will guarantee a good time because no one has anywhere else to go. Even if there are only 100 people there, there’s a good chance 30 of them will be at the same bar! The bigger resorts do have more people, but they are also more spread out so you may only end up at 10 people at each bar. It just depends on the resort.

Either way, if you go to the nightly entertainment, they will lead you in the right direction. When I stayed at Grand Palladium Montego Bay, Jamaica the entertainment lead everyone who was up for keeping the party going on to the location of the night. They also stayed with us and helped to get the party up and running. If you look at the customer reviews, they will lead you towards the right resort for you. There are all inclusive resorts for all types of people so find your tribe.

Now when I say do your research, I mean don’t just look at the stars, look at the reviews! All inclusive resorts are not created equal! Some are more spa-like, some are catered towards children, some are more for spring break, etc. Depending on the kind of vacation you want to have, you can click on these factors when searching for your vacation.

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As you can see from Cheapcaribbean.com, there are so many different kinds of all-inclusive resorts. If you don’t really care about the aesthetic (as long as you are in an exotic place), maybe concentrate on the food. Every all inclusive always has a buffet. But, if you are looking for more of a culinary experience, if they only have a fondue place and a Mexican place as their “Restaurants that are reservation only” then that one may not be for you. Find one that has a SteakHouse and an Italian Restaurant, or whatever you like to eat, etc. Again, all this research can be done before you go there.

The only thing I will say is remember that some places you travel are smaller countries. For example, steaks and hamburgers cooked to the temperature “Well Done” in Jamaica is the norm (because they do not get the same quality of meat as we do in the USA and also that’s just how they grew up cooking it.) Same with other kinds of foods, they are served differently and usually cooked all the way through. There are 5 Star Branded resorts like Sandals that will give you “Medium Rare” etc but they will more likely cost more. A larger country like Mexico will be more likely to have “Medium Rare” available at most resorts. So make sure you do your food research before you go somewhere.

To give you some basics to go by, here are some general assessments I’ve made from my travels. If you are looking for baller food at an all inclusive then maybe Jamaica or Mexico is more for you. If you just want breathtaking beaches then maybe Dominican Republic is for you. If you want adventure then they all are for you, each has numerous kinds of excursions. It really depends what you are looking for but again, it can be all found online.

I get so annoyed when people write a bad review about something that they clearly could have found out before they went on vacation there. They will say an experience ruined their whole vacation. Sometimes this is true, don’t get me wrong, but if you picked a 2 star spot and expected filet mignon, what did you think was going to happen? Yes it was cheap and has a beautiful beach etc, but clearly the food and service is not going to be the same as a 5 star that has the 5 star price attached to it.

This will sound silly to a lot of people. I get it, who wants to stay close to their home? Most of the time, people don’t realize that there are so many things to do that are just an hour away if you look into it! While living in Ohio, running off to a vineyard for a day was so relaxing to me. While living in NYC, I have stayed a night in a hotel in the middle of Times Square with a rooftop pool and felt like I was in a different city just because of the hotel’s theme. I was also in a part of the city I generally stayed away from most of the time because of all the people. It really comes down to what do you want to do and how do you make the most of it.

For me there are only really three rules…

I pretend like I am out of the country and I cannot be reached by phone for 2-3 days.
I go somewhere I would never go one my day to day after work, cocktail or adventure.
I stay on the property or within walking distance. I don’t want any stress of trying to find something. If I get bored that’s a different story. But basically, it’s all about the rest and relaxation.

The key to this method is to have multiple social media accounts.

Make a couple email accounts and social media accounts so that you have them just for the purpose of giveaways.

For example, have a couple of Instagram accounts with their own emails. Whenever you come across a free trip giveaway you are interested in, use them to apply for the trip. Keep them for only vacation information like giveaways and also sign up for cheap flight notices. (Kayak is my favorite. I also sign up with specific airlines I like.)

The giveaways and contests are usually a call to action. Sometimes it is follows everyone on a list or comments so many times. Either way, it literally takes all of 10 minutes tops. Would you rather save up for weeks or spend 10 minutes giving a giveaway a try? Plus, you’re on social media all day anyways right? Once the giveaway is over and you realize you didn’t win, simply “unsubscribe.”

WARNING- A GIVEAWAY WILL NEVER ASK FOR YOUR PERSONAL INFORMATION!!!!!!

Just be smart about it people! Don’t be ignorant! The only thing you should ever give is your email and never list it in a public viewing area. You should also always do a look through their friend’s list. If they only have like 100 followers it is probably a bot and a scam!

Here is a pretty good example… In this one you didn’t even need an email or anything. Simply tag people, comment, and win…

If you drive, you know just how often they are giving away stuff on the radio. This is a bit old school, but now we have Podcasts to add to the mix too. In a way, I think the competition is less because not as many people call in anymore. So why not take the chance.

They may not be giving away a “free vacation” but they are always giving away money. You can use this money for your next free trip!

Please be careful. Otherwise, enjoy your free vacay and you’re welcome! Send me a pic from wherever you went!

Are 5 star vacations your thing? Do you want to go for free?

Again, you have to put in a little bit of work on this one. You have to spend at least three hours of your time for this free vacation.

Timeshares always offer perks to come and check out their properties. I have been offered anything from free dinner to free vacations. It’s all about how you work, the representative offering you the free stuff.

When you go on vacation, you are more than likely to come across a timeshare representative. They are most likely well dressed and in the front of a busy area talking to almost everyone that walks past. They’ll say something like, “Free show tonight?” or “How long are you guys in town for?”

Once they have your attention, barter with them. But Emily, they are offering us a free show and a free dinner… Wait, they will offer you more, they will just keep tacking it on. The more uninterested you seem, the more they will give you for free.

I’ve only done this one time, but it was so worth it! We were in Las Vegas and the representative was right in the middle of a high traffic area. First, they offered me a free show, I said I wasn’t really interested in shows. Then they offered me a free buffet. I told them I get free buffets because of my loyalty card. I acted interested enough, I even said I’ve always been curious about timeshares. That’s when they offered me $400 in freeplay money, now they had my attention.

My friend was with me and she wasn’t interested at all but they told her, if she did it also, they’d give her freeplay AND a free week vacation to any of their properties. We looked to see where their properties were and one was in the Dominican Republic that caught out eye.

We went for the presentation and learned all about timeshares and how they can be a great investment “for your family’s future.” (In my opinion, they are great if you vacation once or twice a year with the whole family, but that’s a lot of money to spend for just one or two vacations. They do have black out dates and are almost impossible to sell investment-wise. For me, the cons outweigh the pros.)

Here’s what you need to take into consideration.

1- How long is the presentation? – The one I went to was about a half hour of free buffet breakfast, about a half hour overview, an hour of the presentation, then an hour of us one on one with an agent who tried to sell us the timeshare.

I’ve heard of some going for a whole day where you have multiple presentations and then go offsite and tour the property as well. Others take up half the day, usually offering a lunch presentation and then a tour of the on-site property. I suggest the shorter presentations. Taking a full day away from your current vacation, just to get another future vacation isn’t really worth it in my opinion.

2- Do Not Drink Beforehand! – They try their hardest to get you to buy. Believe me they make it sound like this magical deal. For some people with big families it is great to have a condo to yourself! But for me, a solo – one – other – person – with – me traveler, purchasing one doesn’t make sense. I also like staying in a hotel. I don’t want to cook my own food and just stay at the timeshare property.

But, if it’s something you are interested in doing, they can and will work with you. You can get your payments down to as small as (a friend of mine who only pays) $30 a month for one. You just have to work them down.

3-Once you sign, you’re in it for life. If you do not want to buy, simply lie and say you just lost your job before you came on vacation or say your spouse won’t agree to it. Just do not sign anything!

4- Read The Fine Print – Hidden fees. They all have them! The ones that do not have immediately hidden fees are probably getting you somewhere else, probably with the small amount of properties you are able to go to unless you upgrade. Do all of your research and read customer reviews beforehand. The best way to get the deal is with the rep in front of you. No deal you were offered during the presentation is secure unless you sign in person.

When we took our “free” vacation, we ended up spending $800 in fees for the week. Now for us, our free vacation to a 5 star all inclusive resort was well worth it for $400 a piece for 10 days. But again, free is never completely free, always keep that in mind. More often than not you must always pay for the flight. Then, as we found out, there can be a fee on top of your price you have already paid for the timeshare.

Read the fine print!

Stick It Out – You’ve already invested 2 hours. Why would you walk out on the third? If you want your free offers, you must complete the whole thing in order to get them. If you leave early, they will not give you your free gifts and you will have spent two hours of your time for nothing.

On the other hand, if you are just overly annoyed by the whole thing, just get up and walk out. Who cares about the free stuff. At least you got a free meal out of it. Don’t feel like you are stuck in prison. There’s no security guard keeping you in the presentation.

There are all kinds of loyalty cards for hotel chains, resorts, entertainment parks, etc.

I’ll use casinos as an example…

This one is ALWAYS a guaranteed free vacation! Do you know how many casinos there are around the world? It’s crazy! So, think about it, what does a casino want you to do? Gamble right? Well you can’t gamble unless you are at their location. So what do they do? They offer for you to stay for free there thinking you will at least spend as much as the room would have cost anyways.

Now if you are a gambler, it’s a great deal! But, if you aren’t a gambler, it’s still a great deal! Do you know how much stuff there is to do in Vegas? Do you know how pretty it is in the Fall in Connecticut? There is so much more to casinos besides just gambling.

Do your research and see which casinos are close to things you want to see. Then, free stay here you come.

Again, it’s an email list. So get your “junk mail” vacation email ready. Maybe think of a fun one like “imonvacationbitch@email.” Then, go online to the casino’s site. Each casino has a rewards program. Some casinos are individual units and some are companies.

The best comped room I have gotten so far was at Nobu in Ceasars (Las Vegas)

Sign up for EVERY loyalty card and watch the emails start rolling in. At first you may just get a discounted rate, but once you have stayed there once, the free stay deals just keep coming. What I also love about the casinos is that there is no off season, so they are trying to get you to come anytime!

The only catch is that it is not completely free. Either way when you stay at a casino, they will charge you a “resort fee” on top of your rate. So even if you get a room for $30 a night, you will still pay the resort fee of $30-75 a night on top of that. So do your research first. And… just like any other hotel, they always put a hold on your credit card for potential damages. So again, do your research and shop around and make sure the free room offer saves you money.

Example – $30 a night plus $30 resort fee is $60 VS free night with $75 a night resort fee is $75 (Generally the free room offer is cheaper but always double check!)

The other good thing about casinos, is if you do gamble you get rewards points. So, always use your card in the machine even if you are just trying to gamble with $5. Also, use your card when you are purchasing anything in the casino, including your room! After you leave the money spent on resort fees and taxes etc will all have given you points on your card.

Example – Once you have collected points, which you definitely will, you can then redeem them in the casino. I always use mine towards Starbucks and dinner.

One time a friend and I had two free three-course steak dinners all because we had collected points while shopping and they had given us some coupons at check in. We literally only had to pay for the bottle of wine we got!