Free Cruises with Just a Little Leg Work… Living Like Rock Stars!

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Back in May, I wrote a post called The Next Mission… Free Cruises Through Casino Status Matches! It was all about how we stumbled upon a way to get free cruises and what we planned to do to make it happen.

Well, here we are several months later and I realized it’s time to update you on how it’s going and what’s next.

It’s actually been a cool little adventure figuring out what we need to do and then taking a quick trip to Atlantic City. We’re now at a point where we’ve got some of the cruises already booked and scheduled. It’s already getting to the point where we’re taking a step back and not doing all of them. We’re going to have one busy year coming up with all these cruises plus some trips we had already booked!

As I mentioned in my earlier post, free cruises don’t necessarily equate to free cruises. As Nick from the Frequent Miler mentions in his post, How to get free cruises by gaming casino status matches, it’s better to think of these as highly discounted cruises rather than free cruises.

That said, this has been a ton of fun so far making this happen and we’ve already lined up a few cruises with more to book soon. So let’s get on with the show!

Making our way to Caesars Diamond status

Just to make this clear, this isn’t something I came up with on my own. For the most part, we’ve been following this article by Nick at the Frequent Miler:

How to get free cruises by gaming casino status matches

We have strayed off the path a bit to experiment and try to gain some additional perks or free cruises.

When I talked about our plan to make these free cruises a reality in my post, The Next Mission… Free Cruises Through Casino Status Matches!, I left off with us planning to sign up for the Wyndham Earner Business credit card. Well, that’s what we did.

We each did our own application because we wanted Diamond status for each of us rather than just one person. That means we’d each be getting free cruises for two rather than just one of us. The idea was that we could each book a room for a free cruise and then we could stay in one cabin and our daughter, Faith, with a friend could stay in in the other.

Anyway, you know we love our credit card rewards, especially the sign-up bonuses to earn free travel. I’ve written about that in several posts over the years:

• A Month-Long Panama Trip for 3 for an Unbeatable Price of Less than $1,500!
• We Got the Chase United Explorer Card… Again. Boom! Easy Free Travel!
• Is It Worth It to Open a Credit Card With a Huge Annual Fee?
• The #1 Best Way To Track Credit Card Rewards
• The #1 Easy Way We’re Getting the Southwest Companion Pass
• Our Travel Perks Are Drying Up and That’s Big $$$!
• Free Nights – We’ve Had 5 at Hilton Hotels Recently
• We Got Turned Down for a Credit Card… Ok, Four!
• Travel Rewards – 12 Free Flights Earned in 9 Months!

I’ll be writing another soon to tell you about how we’re paying for most of our flights and hotels with our upcoming trips… but I’m sure you can guess the answer!

If you decide to take advantage of credit card travel rewards, I’d highly recommend using the free service Travel Freely to help. It can easily track your cards (no card numbers being entered) and keep you informed of bonus deadlines, annual fees, renewal dates, etc. It also tracks important things like Chase’s 5/24 rule and provides you with personalized recommendations on which card to apply for next to keep the rewards coming. Such a great service and well-executed – plus, it’s hard to beat free!

So this shouldn’t have been a big deal – we’ve signed up for a lot of credit cards over the years. Except it turned out to be the biggest pain in the @#$ we’ve ever had with getting approved. Apparently, Barclays is a little more stringent about things and each of us had to follow up with them to fax (yeah, I said fax) them information multiple times. They needed documents to verify my identity, docs to verify my business, and then later they wanted a copy of my Schedule C from my last tax return for my business since it’s an LLC. Lisa doesn’t have an LLC so they just needed docs to verify her identity.

This was fun since we were on our 8-month road trip, but we got what we needed and made stops at libraries to print the docs and fax them as needed. After several back-and-forth phone calls to go with it, we were both eventually approved. But my Lord, that was a lot more hassle than expected.

Shortly after being approved, we could see that we were upgraded to Wyndham Diamond members on our accounts on the Wyndham website… nice!

As a side note, we made sure to hit the numbers for the sign-up bonus on each card as well. So now we have plenty of points to book some hotels for the night before each of our free cruises!

Pro Tip: Always arrive at least one day before a cruise because you never know what kind of problems you could run into with a flight or other hurdles… you don’t want to take the chance of missing your cruise!

As soon as we saw that we were Wyndham Diamond, we went to this link on the Caesars website to submit our status match to become Diamond with Caesars Rewards. That was quick and easy to do. It took a couple of days for Lisa to show up as Caesars Diamond and about a week for me. We have friends of ours on this mission as well and it took her about a week to get matched and him a handful of weeks, so you need to be a little patient.

But look at that, with just one credit card, we’re now all Diamond members at both Wyndham and Caesars… pretty cool! Among other perks, being at Caesars Diamond level also gives us each a 2 to 4-night stay at Atlantis in the Bahamas and $100-150 in slot play based on when we’d go. You still pay the resort fee of around $65/day. That might still be worthwhile except that my understanding is that the food prices at the resort are ridiculous. I’m guessing we’re not going to take advantage of this one.

Anyway, onto the next step…

Living like rock stars in Atlantic City

The next step to making this work is a trip to Atlantic City. This is where we get status-matched to some of the other casinos. Remember, the whole idea is that the cruise lines are willing to offer free cruises (or discounted cruises) to folks who they are hoping are going to gamble on their ships. The odds are in their favor if they know that you have high status at land-based casinos because the assumption is that you’re a high roller.

We had hoped to make this trip sooner, but as I mentioned, it took a while for the Caesars match to go through for our one friend. And that’s a critical part of this being a successful mission.

It worked out well though because they were each able to get a free room at Caesars in Atlantic City because of some gambling they had done earlier in the year in Las Vegas. So they booked one for themselves and were nice enough to book one for us in mid-October.

Now, I gotta admit – I had always imagined Atlantic City as a small run-down area. I’m not sure why, but that was just in the back of my mind. But when we got there, I was impressed. The area’s a lot bigger than I envisioned, the casinos seemed well-kept and somewhat fancy, and the boardwalk and beach areas are really nice.

Now, there were some homeless people along the boardwalk and my understanding is that you still need to be careful elsewhere in the area. But overall, it was a nice surprise. And we had good weather so that made it easy to walk everywhere we went.

We knocked out all our missions on day one:

• Went to a kiosk in Caesars and printed off our fancy diamond cards. That worked for two of us but Lisa and our one friend needed to go to the rewards desk to make it happen… no big deal.
• We headed over to Bally’s first, went to their rewards desk, and asked if they would match our Caesars status. They signed us up, matched us to Superstar status, gave us each a hat or t-shirt, and provided us with access to their fancy-pants lounge.
• Then we went over to the Hard Rock and presented our Caesars status. They matched us to Icon status there and gave each of us $50 in free play.
• Finally, we went to Ocean Casino. That was an important visit. They matched our Icon status from Hard Rock to Ocean Prime status and gave us a few goodies:
  • A free 2-night stay at Wynn in Las Vegas. This also comes with a $50 dining credit.
  • A pass for 2 to their fancy Avila Lounge for free food and drinks.
  • A free 10-day MSC ocean-view cruise for 2 that might actually turn out to be two free cruises per person (more on that shortly).

Remember, we each got one of these because we are all rocking our fancy Diamond or equivalent status. They gave us other things at the casinos as well like free stays and meals, but these couldn’t be used until a few days after getting them so they weren’t useful to us on this trip.

And that was it for the missions. We knocked that out in just a few hours even after walking everywhere. With that out of the way, we spent the rest of our time enjoying AC like rock stars.

We had free dinner and drinks at the Avila Lounge in Ocean Casino. And because each pass was good for two people, we only needed one per couple on the visit. That worked out well because we went there for lunch the next day to use the other passes for more food and drinks.

We took advantage of the $50 play we each had at Hard Rock. I can’t remember if anyone walked away with money on that one, but we played for hours on the money regardless and had a lot of fun so it was well worth it.

We also had free dinner and drinks one evening at Bally’s with our lounge access… I like this elite status stuff!

And then we spent time gambling at Caesars. Our thinking was that we’d play there since there are Caesars and their partner casinos all over (including Vegas) so that could mean free rooms later in places other than AC.

When all was said and done, we had a blast. Our friends didn’t do so well on the gambling front but Lisa and I ended up coming out ahead, so much so that even after paying our share of tolls ($55 each way!!! Greedy Pennsylvania!!) and gas, we still came out about $150 ahead on the trip. That’s a big win in my book!

Regardless, we only paid for one meal during our 2-night stay in AC. We walked to Perry’s Cafe & Deli for breakfast one morning. That turned out to be a winning pick – great food and prices. Everything else was covered – all the food and drinks were free. And since we were gambling, the drinks were free, too, though I’ve been sober now for over 2 years so I was drinking non-alcoholic stuff.

Another exception to free was when my buddy bought himself and his wife each a Miller Lite bottle at Caesars without gambling that turned out to be a whopping $20!!! Live and learn, right? 😉

So, Atlantic City was a lot of fun and we’ve talked about maybe doing another visit sometime during warmer weather to take advantage of the beaches as well.

The free cruises that are the closest to actually being free

Ok, here’s what really matters – the free cruises! As I said, they’re not truly free because you’ll end up paying something for them even if it’s a lot less than you’d get otherwise.

The closest to free that you’ll probably get though is the free cruise from Ocean Casino on MSC Cruises. Funny enough, this has been the cruise line that we’ve been doing most of our cruising on already anyway, so we were excited about this.

The deal is that you need to wait to book your cruise until the 15th of the month after you are granted Ocean Prime status. So for us, that won’t be until November 15… even though I’m going to try calling earlier – can’t hurt, right?

The reason the MSC cruise is so valuable is that you don’t pay any port charges or fees. It seems that’s not the case with the other “free” cruises you get. You do still need to pay gratuities of maybe around $15/pp/day with the specific amount varying based on the cruise and class you choose. And you put down a $400 deposit that you get back as an onboard credit on the ship.

All in all, if cruising is something up your alley, this is a no-brainer. My understanding is that they’re pretty flexible and will upgrade you (maybe for a price to a balcony) if desired and available or sometimes even for a slightly longer cruise.

The brochure shows that it’s a 10-day MSC ocean-view cabin for two people anywhere that MSC sails. However, according to Nick’s post, they might have changed some of the small print recently. Apparently, since September, you can only use this for the Caribbean or they tack on a $1,400 fee. We were hoping to use ours for something a little different (like a European cruise) but we’ll save that for a different time… Caribbean it is!

An interesting twist is that the small print also says that you get one cruise per calendar year. My friend Justin from Root of Good has been doing this as well and said that if we fit in one before the end of the year, we’ll actually get another to use before the end of June (when our Ocean Prime status will downgrade).

MSC CRUISES: Offer valid no more than once per calendar year. Sailings must occur prior to June 30, 2025.

And, don’t forget that we each did this, so that means each of us could get two free cruises on MSC.

We already have one 7-night MSC cruise to the Caribbean scheduled for December. This was one we paid for (at a steal!) before this whole idea of free cruises was even something we were aware of.

So, the plan is that around November 15, we’ll call and try to book one of our free cruises to be right before that one and turn it into a 2-week cruise instead. We’ll leave this free one as an ocean-view cabin instead of upgrading. The one we currently have booked is a balcony so we’ll feel like we get upgraded after the first week! 🙂

UPDATE: I called MSC on November 1 – two weeks early but why not give it a shot? And, they were good to book our cruise. The problem we ran into though is that we’re just a few weeks out from when we wanted to take it so the pickings were slim. We ended up slotting an 11-night Bahamas/Mexico cruise that bumped right up to before the 7-night cruise we had already booked and paid for.

They let us pay for the extra night (since they only cover 10 nights) and we were sticking with the ocean view for this. We also had to pay for Faith since it only covers two people. In the end, the total cost was slated to be $1,523 with pre-paid gratuities, but $400 of that we would get back as onboard credit. So really, we’re looking at $1,123 for 3 people on an 11-night cruise.

That’s actually pretty good. However, we’d be on the same ship that we plan on going on in early December and hitting all the same stops (except for one). After a lot of discussion between the three of us, we decided to take a pass on this one. It was just too much for right now.

So, we’re ready to book an MSC cruise for March sometime. With this one, we’ll each use our free cruise and book one cabin each. That way, Lisa and I can stay in one and Faith can have her own room and bring a friend. We’ll likely upgrade our cabin to a balcony room and leave hers as an ocean-view cabin.

That’s it on MSC. Assuming nothing changes (it will), we could repeat this whole process with Ocean Casino in 18 months for more free cruises on MSC.

Note that Ocean Prime will match your status a second time, but not until 18 months have passed with no activity on your Ocean account. You’ll need to wait 18 months from your previous match or 18 months from your most recent time playing at Ocean Casino Resort to try matching again.

How to get free cruises by gaming casino status matches — Nick Reyes

That would be sometime in mid to late April 2026 for us. Fingers crossed!

A couple of other free cruises and one exciting heavily discounted Alaskan cruise

Lisa and I are trying to do our match requests with the cruise lines methodically like we know what we’re doing (we don’t). But for us, the gold standard is a Princess Cruise. We’ve been on a couple of these years ago and they were top-notch.

Since Carnival owns Princess and Holland America, we’re treading lightly. If we “waste” a free cruise on Carnival or Holland and don’t gamble enough in their eyes, Princess can see that and take a pass at offering us up a freebie. So while we’re fine getting and lining up cruises with the other lines, our goal is to get and book an offer from Princess before actually taking a cruise on Carnival or Holland.

But, something interesting happened. I submitted a PDF with photos of my Caesars, Hard Rock, Ocean Prime, and Bally’s cards to Holland America’s match program. One of the people there reached out to me via email and asked me if I had any casino offers. I sent him a screenshot of the Caesars website showing free rooms on the calendar. He then emailed me the following offer:

Complimentary Interior Cabin & Drinks for two (2) while playing in the casino *Excludes government taxes & fees, and required cruise fees and expenses in the amount of approximately $175 USD per guest for a 7-Day sailing. Redemption of offer is subject to the payment of a non-refundable deposit of $200 on sailings starting January 1, 2025.

Now, according to Nick, some folks were getting offers up to 12 or 14 nights. What can I say though – beggars can’t be choosers.

Lisa and I talked about this for a while and then decided that this might be a good opportunity for the three of us to do an Alaskan cruise, which we’ve always wanted to do. We also know that we’d want an upgrade to a balcony for an Alaskan cruise. I didn’t know if any of this would be something they’d do, but we gave it a shot when I called.

Long story short, we spent a lot more on a “free” cruise than we would have hoped, but we couldn’t pass it up. They were able to incorporate an early booking of their “Have It All” Promo to give us some good stuff. So in June of 2025 (which is supposed to be prime time for these cruises), we have the following booked for a 7-night Alaskan cruise:

• A balcony (or verandah as they call it there) cabin for the three of us that’s portside (on the left) because supposedly we’ll get much better views on that side
• $100 each in on-board credit for me and Lisa ($200 total)
• $100 off a shore excursion for each of the three of us
• One night of specialty dining for the three of us
• Pre-paid gratuities
• The elite beverage package for the three of us
• Premium WiFi for 2 devices

The grand total out the door was $3,954.00. That’s a helluva lot more than we’ve ever paid for a cruise. However, the money we saved with this offer made it almost half what it would normally cost (it would have cost $7,567 without the discount). This has been something on our bucket lists for a while so we decided why not do it now while we have this nice offer?

We’re all very excited about this one!

So what’s next?

Ok, so we know the MSC offerings are about as close to free cruises as you’re going to get with this. We also know that we went the other direction completely and booked a cruise that was just shy of $4k! But what else?

Well, the first cruise I actually heard back from was Margaritaville. I had emailed them photos of my Caesars, Hard Rock, and Ocean Prime cards and they offered us a choice of several free cruises on their two ships. We paid $693 for a 5-night balcony cruise in January for the three of us. That price covers port fees, taxes, and gratuities. Drinks are free for us in the casino.

I don’t know a ton about Margaritaville but we thought, why not? This will get me out of Ohio for another week in the winter. Lisa has an offer as well but we’re just going to sit on that one for now.

Then there’s Carnival. We’ve both submitted to the Carnival Players Club Fun Match Program. I uploaded photos of my Caesars, Hard Rock, and Ocean Prime cards a few weeks ago. I haven’t got anything exciting so far. Lisa received an offer for $500 off so we’ll be patient and see if we get a free cabin eventually.

Now the jackpot for us would be Princess Cruises. We’re getting the ball rolling with all these other cruise lines so we have some ammo to use with them. The goal is to be able to send them copies of the free offers we’re getting from the other casinos (land and sea) to hopefully get an offer from them. As I mentioned, we just need to do this before we take our Holland cruise or a Carnival cruise since they’re all under the same parent company. Once we do one, if our gambling isn’t good enough, those offers could dry up.

Virgin Voyages is one we probably need to reach out to as well but haven’t gotten to yet. Some folks are getting offers for 7-day European cruises. We’ve got way too much lined up over the next year to do that, but maybe we could see if we get an offer just to leverage it with Princess Cruises.

An additional perk from Ocean Casino Rewards Prime status is that they give you a complimentary 2-night stay at the Wynn in Las Vegas plus a $50 dining credit. That’s 2 nights and $50 for each of us. Lisa and I are talking about taking maybe a 3 or 4-night visit there for the heck of it. That could make for a nice little getaway for a few days and would give us a chance to visit my uncle who lives out there, too.

So what else?

First off, as a reminder, you’re not required to gamble on these free cruises. Of course, they want you to and that’s why they’re offering it to you – in hopes that you do. Just be aware that if you don’t gamble much in the casinos, those offers will probably dry up pretty quickly. We’re not going to spend a ton of money gambling but we’ll do a little bit and whatever happens happens.

The other important thing is that we love our travel rewards. Leveraging credit card points and miles has saved us thousands upon thousands of dollars. All these cruises we’re doing, all these other trips we have planned (we’ll probably take an insane 8 or more vacations over the next year!) – we’ll use points and miles mostly earned from credit card sign-up bonuses to cover most (if not all) of our flights and hotel stays.

If you have good credit, pay off your credit card bills every month, and enjoy travel, credit card travel rewards are truly an amazing benefit you should be taking advantage of in your life. Start with Travel Freely (it’s free!), read some of the posts I mentioned earlier on the subject, and get started. It’s not hard, you don’t spend any more than you currently are doing, and it can help make your travel dreams come true.

I had a lot of folks asking how the mission for free cruises has been going, so that’s why I wrote this post now. I’ll probably write another sometime next year to give you another update on the good, the bad, and hopefully no ugly!

We love going on cruises – that’s, by far, my favorite vacation. But, this is going to be a lot of cruises crammed into one year. Maybe this will be too much or maybe we’ll be clamoring for more, but the opportunity is one we don’t want to pass up.

If you enjoyed this post, you should be on the mailing list. I’ll keep you posted when new posts come out, fill you in on some of the things I don’t always talk about in the blog, and I’ll send you some awesome spreadsheet freebies as a welcome gift…

Plan well, take action, and live your best life!

Thanks for reading!!

— Jim