How to Plan a (Basically) Free Honeymoon
I’m not gonna lie to you, planning a wedding during COVID has been tough, but at this point I am living for our honeymoon. LIVING, HONEY! It’s not that I’m not excited for the actual wedding day, it’s more that my idea of our special day is so up in the air and ever-changing that I feel more confident in us having a true honeymoon together than I am for a “normal” wedding. With that said, I really think we’ve set the standard for how to approach our honeymoon in the most budget-friendly way without compromising anything. Because we’re all in this together, Ben and I brainstormed the best way to really work the system and created a simple step-by-step approach that can easily be reproduced by any other couple that wants to have a (basically) free honeymoon!
Decide Your Hotel & Destination
While you may get more excited about dress shopping, picking a caterer or choosing the best photographer for your big day, I cannot stress enough that, in order for this to work, you will need to plan your honeymoon before all else. For Ben and I, we have had extensive experience working the points/credit card systems due to how often we travel(ed) for work. With that said, back in May 2020, before we truly started planning or making deposits for our big day, we decided to research honeymoon destinations and which hotel(s) we wanted to stay at. Since we realized that COVID could very well still be an issue in July 2021, we decided that staying domestic might be the safest option. We therefore chose Hawaii for our honeymoon spot and quickly began researching the best resorts for our stay.
The beauty of this system is that almost no resort was off limits! It saved us so much money that we were able to truly consider the most expensive and bougie resorts, which normally wouldn’t be in our budget. We ultimately decided to stay on two islands and therefore selected two resorts - The Grand Hyatt on the island of Kauai and the Grand Wailea on Maui.
Decide Which Credit Card is Best
This step is not truly secondary to selecting the destination, but more-so a step 1b type of situation as it can help sway your decision towards a hotel choice. While we were considering all the best hotels on Maui & Kauai, we researched their respective rewards/credit card programs as well. This is an important piece, because you can see which program offers the best rewards per dollar, upgrade options, etc. You also want to pay close attention to whether any of the hotel chains have “blackout dates,” where they won’t accept points for room purchases. Long story short, once you decide which program will give you the best bang for your buck - go for it! Ben found a great site to help compare cards and points systems - check out The Points Guy - it helped us a ton!
Ben and I ended up getting the Hilton Aspire American Express card, since it offered the most in terms of new user points, free room upgrades and was associated with one of my favorite Waldorf Astoria resorts, The Grand Wailea.
Pro Tip: Don’t get scared of cards with high annual fees as they often provide much better rewards. My Hilton AMEX, for example, has an annual fee of $450, however, it gave me the best bonus points and even reimburses me when I shop. For example, I spent over $100 on Anthropologie Christmas gifts last year and they reimbursed me $25 just for shopping there. The card pays for itself very quickly and can be cancelled at any time (after your honeymoon, of course)!
Decide What Room You Want
Woohoo! You’ve decided what hotel you’ll stay at and what credit card is going to get you there for free. Get pumped! From here, there is a crucial step that will help you calculate how many points you need to acquire for a free stay. If we take the Grand Wailea for example, what we did is went to the site and started the process of a room reservation. Once you select the dates of your desired trip, it gives you the option to view rates by dollar amount or by point amount. When you select the “Use Points” radio button, it will switch from showing $700 per night to 80,000 points per night. Using this as an example, we then decided that we wanted to stay in Hawaii for at least a week and calculated (80,000 pts x 7 nights), which told us we would need to accumulate at least 560,000 points before we could book. BOOM! Now we have our goal.
Pro Tip: Many of the resorts/hotels give free perks to their card members, often in the form of a free room upgrade upon arrival. If this is the case for you, you may want to consider booking a room that is cheaper than the one you actually want since it is very possible you will get a room upgrade for your card status when you arrive. Room upgrades are usually based on availability, but if you go to your destination in the off-season, you should be good to go!
SPEND!
So I know what you’re thinking - that you couldn’t possibly spend enough money to get the thousand of points you will need for a week long vacation in paradise. But that’s where you’re wrong! For starters, a lot of the credit card programs run promotions that give you a head start. It usually reads something like: “Spend $3,000 in the first three months and get 100,000 bonus points!” But additionally, think about it - this is going to be a big spend year for you and your families. Even if you are fortunate enough to have your parents or in-laws take care of some of the wedding bills, why not ask them to let you put the points on your new credit card and they can just reimburse you? Hello?? Venmo?!?
While Ben and I are paying for a good chunk of the wedding ourselves, we have also asked our parents to let us use our card for their portion of the big day and just pay us back in cash. This way, we get the points for what we are spending but what they are spending as well.
All in all, its fairly simple to decide how many points you will need for your stay. What it really comes down to is timing. Since the first thing we did was discuss the honeymoon and get proper rewards credit card, we were then able to use that for all of our subsequent wedding deposits: photographer, DJ, wedding dress, save-the-dates and so on. We also decided to use the card for all of our general spending like groceries, gas and any other miscellaneous expenses. If you want to accumulate points faster, some property managers will allow you to pay your rent on a credit card as well, which as many of you Chicagoans know, will add up FAST! If all else fails, pay more than just the deposit. Your DJ is never going to complain if you want to pay the total upfront; just make sure their refund policies are flexible, especially during the pandemic!
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So there you have it, kids. A basically free honeymoon. To give you an idea of how far this point system can go, we will be staying in Hawaii…. for 12 days…. for free.
Yes. Completely free.
Now this doesn’t include food and drinks that we will of course spend on our trip. (I mean…Momma needs her ceviche and mai tais)… But we will not pay a dime to stay at not one but TWO of the nicest hotels in Hawaii. To take things a step further, we also worked the Southwest system (Ben has their credit card and companion pass), so if you wanna get real crazy you can work the airfare system, too. Regardless, this trip would easily have a retail price tag of around $20,000 - a laughable amount considering how much we were willing to spend. SO with that said, start doing that research, and feel at least the teensiest bit better about making those wedding deposits this year.
Best of luck and happy travels, friends!