How to Book 7 Nights in Hawaii for FREE!

Alright…I recently posted how we travel hacked Fort Lauderdale WITHOUT credit cards, but if you want to take your travel hacking game to the next level, read on!  See how we booked our entire upcoming hotel stay for Hawaii on points, saving us over $6000 for 7 nights!

As you can see, traveling with a family of five can get pretty pricey so I am always looking for ways to save. I mentioned in a previous post that anytime you’re traveling to a hotel, it’s a good idea to sign up for their free loyalty program.  Not only do you typically earn hotel points when you stay, but you get better rates too! 

I used to travel for work so I’ve been in a variety of loyalty programs for years.  If you don’t stay often, you won’t really rack up the points.  However, it’s nice to get member rates when I do book those hotels!

Fast-Track your Hotel Points with Credit Cards

If you want to fast-track your point earnings for your next hotel stay, consider opening a hotel-branded credit card.  All of the big hotel chains offer credit cards with some form of a “welcome” offer.  These welcome offers typically give you enough points to stay several nights for free with the brand.  Plus, regular spending on the card can even earn you some added perks!

If you do plan to get one of these cards, it’s best to decide either where you want to go or which hotel brand you like best.  For me, I always liked Hilton hotels because they’re affordable, they have a large footprint with hotels pretty much everywhere, they are clean, and many offer a free breakfast.  When it comes to traveling on a budget, this brand checks all my boxes! 

Earning Hotel Status

As you stay more often with a particular brand, you’ll earn “status.”  Each hotel chain has different requirements, but Hilton is my go-to and where I have status.  There are four levels: Member, Silver, Gold and Diamond.

Hilton Honors: MEMBER

You are considered a Member when you’ve signed up for the free Hilton Honors loyalty program.  Even though the program is free, even at this entry level, you get some perks.  Benefits include things like discounted rates, digital check in/check out and the ability to select your room, free wi-fi and no resort fees on reward stays.  When you’re a member, you earn points on your hotel stays that add up and can be used for future stays.

Hilton Honors: SILVER

Once you stay at least 10 nights (in the year), you move to Silver status.  In this status, you get all the same member benefits, plus a 20% point bonus on stays, free bottled water and the 5^th night free on reward stays. 

Our favorite SILVER Perk

One really awesome perk at the Silver level (and above) is the 5^th Night Free on Reward Stays.  Once you have enough points and are staying in a hotel on points, you’ll get one night free when staying five nights.  This means that if a hotel costs 30k points/night, a five-night stay will only cost you 120k in points because that 5^th night is free!  We used this perk last summer when we stayed in Orlando and visited Universal Studios.  And we used it again for our trip to Hawaii!

FAST-TRACK TO SILVER

If you have the Hilton Honors (no annual fee) credit card, you automatically get bumped to Siver status—even if you don’t spend a dime on the card.  Although, if you do get any of the Hilton branded cards (or any other hotel loyalty cards), I highly recommend charging your stay to that card.  Typically, you earn even more points, getting you free hotel nights even faster!  Plus, those welcome offers will usually get you at least a few free nights!

Benefits of the Hilton Honors Credit Card (No Annual Fee)

My first Hilton Honors credit card was the no annual fee card.  I’ve had this card for 15 years and it’s always been a favorite of mine.  This card gave me my first initial boost in points.  I used this card almost exclusively up until last year when I upgraded to the Surpass.

We use a credit card for EVERYTHING that we can.  I rarely spend cash and I never use a debit card.  Why?  Because I don’t earn points with those forms of payment.  I treat my credit card like a debit card though—I charge all of my expenses and pay it off at the end of the month.  This allows me to earn lots of Hilton Points and not pay any interest fees.

Credit Card Disclaimer

If you’re NOT in a place where you can pay your credit cards off MONTHLY, I wouldn’t suggest spending on these cards (or any travel card, really).  Interest rates on travel cards are HIGH (20%+) so if you’re not paying your balance off monthly, you’re not going to save anything—they’ll likely cost you money with those hefty fees.

Hilton Honors: GOLD

Once you stay 40+ nights, you become a Gold Member.  With Gold status, you start getting some even better benefits!  These include room upgrades, an 80% point bonus on stays and a daily food and beverage credit. 

Our favorite GOLD Perk

We LOVE the Daily Food and Beverage Credit that comes with Gold (and Diamond).  This credit varies by brand and location and is typically only included for hotels that DO NOT include breakfast. 

Some of our favorite hotels in the Hilton brand are Embassy Suites and Hampton Inn.  Both of these have free breakfast so when we stay here, we don’t get the food and beverage credit.  However, on our trip to Fort Lauderdale, we stayed at a Double Tree so we received a $30 credit each day. 

This credit can be used on food or beverages that you charge to your room.  You’ll have to check the hotel for specifics, but we were able to use it at one of their two restaurants, the coffee shop, the hotel’s market and on room service.  The charge goes on your bill, but is immediately credited.  Just know that you need to use it daily, otherwise it’s forfeited.  The credits do not rollover from day to day.

FAST-TRACK TO GOLD

If Gold seems like a good place to be, but you know you’ll never stay 40+ nights, you can fast track to this level by opening the Hilton Surpass Credit Card.  This card gives you automatic Gold status, but has a $150 annual fee.  For years, I stayed away from cards with annual fees, but I’ve realized that in many cases, the benefits of the card outweigh the fee.

Benefits of the Hilton SURPASS Credit Card ($150 Annual Fee)

This card just recently changed some benefits and the annual fee increased; however, it’s still valuable enough to keep both mine and my husband’s cards.  In 2023, we stayed at 8 hotels where we received the food and beverage credit, which gave us $220 back.  We also had access to Priority Lounges at the airport, which was another awesome perk; however, that has ended. 

Hilton did add some perks to replace the Priority Pass.  Now, we get a $50 hotel credit each quarter–$200/year.  This credit more than makes up for that annual fee + the food and beverage credit is now an added bonus.   

In addition, we get an additional 12x points on Hilton stays, 6x points on restaurants, supermarkets and gas stations and 3x points on all other purchases.  We also received 130k points once we spent $2000 in our first three months of using this card.  That means, we ended up with 260,000 points just for our sign-up bonuses.

Free Night Certificates

We also have an opportunity to earn a Free Night Certificate if we spend $15k over the course of the calendar year.  Sometimes Hilton will offer an opportunity to earn one of these certificates for smaller spend amounts too.  We earned one a couple of years ago on the no annual fee Hilton and used it on a fancy hotel in Moab when we visited the Mighty 5 National Parks.

Free Night Certificates are one of my favorite perks to earn because you can use them for almost any hotel in the Hilton Portfolio, regardless of the price!

Hilton Honors: DIAMOND

Once you stay 60+ nights, you can earn Diamond status.  This is Hilton’s top tier status and comes with a few added benefits, most notably a 100% points bonus on all stays.  You’ll also receive room upgrades (up to a 1-bedroom suite), premium wi-fi and a 48-hour room guarantee.  You can also take advantage of the Diamond parking spots at the hotel.

After COVID, they made this a little easier to achieve, with credit card spending.  That has unfortunately ended so now the only real way to get Diamond Status is by staying at Hilton hotels. 

FAST-TRACK TO DIAMOND

If you know you’ll never stay enough to get to Diamond level, then you can sign up for the Hilton Honors Aspire Credit Card.  This card comes with a pretty hefty annual fee of $550, but offers some perks that help offset that cost.  It’s a card that I’m seriously considering upgrading to!

So what do you get with that card? You can earn a 180k sign up bonus after making 4k in purchases in the first three months.  You’ll also get 14x bonus points on Hilton stays, 7x points for flights, car rentals and restaurants and 3x points on all other spending.

In addition, you’ll get a $250 Hilton Resort Statement credit, $250 Airline Fee Credit, $100 property credit for Hilton’s luxury brands, Diamond Status, and a Free Night Reward.  The benefits of this card are really amazing!  If you’re like us, wanting to stay in Maui at a hotel that costs $1200+/night—the $450 annual fee covers that night and more with the Free Night Reward!

Earning Hilton Points

When you log into your Hilton account, you’ll see your point total.  When your credit card statement closes, each month, points for that month are added into your account.  You can either use these points as you get them or let them accumulate.

As an added benefit, you even earn points on your nights booked on points!  Even though you’re already staying for free, you’re still earning even more points!

Spending Hilton Points

Hotels within the Hilton portfolio can range from 20k to 120k points+/night, depending on when and where you stay. 

On most of our vacations, I’ve used my Hilton points for at least a few nights of our stay.  These points really help me offset the total cost of the trip.  Our Hilton points saved us $3400 on our trip to California last summer.  We’ve been loyal to Hilton for years and have earned more free nights than I can count.

How to book Hawaii hotels for FREE

Our family has been to several Caribbean islands as well as 38 of the 50 states.  Visiting all 50 states is on our bucket list, but one of the toughest states to hit is Hawaii.  Between the 11+ hour flight from Ohio and the cost, it just hasn’t really been at the top of our list.  However, I was determined to get our family there as cheap as I could.

When that goal really started becoming a reality, I saved my points and started my research. We decided that we were going to make the trek over spring break 2024.  In the past, we’ve gone to my sister’s house in Mississippi, but our spring break didn’t line up with my nieces’ break so we decided to head to Hawaii instead.

Hilton Hawaiian Village – Oahu

We narrowed it down to a few different hotels, but by the time we had enough points (still 7+ months in advance), some of the hotels were already booked.  We decided to book 5 nights at the Hilton Hawaiian Village on Oahu.  The hotel is 70k points/night so we needed 280k points to book (getting our 5^th night free, since we’re booking on points).  In August, we ended up racking up enough points to book so we pulled the trigger!

The cash price for this hotel for our 5 nights was $3200.  One of the perks of using Hilton points is that if the hotel has a resort fee (which almost all Hawaii hotels do), the fee is waived.  So not only are we using points and saving money on the hotel cost, but we also don’t have to pay that added resort fee ($50/day).

Food & Beverage Credit

I usually try to book hotels that offer free breakfast, but this hotel doesn’t offer it.  However, with Diamond (or Gold) status, we received $18/adult/day (2 adults max) to use on food and beverage.  Now that amount still usually isn’t enough to cover breakfast for two at a sit-down restaurant, but it does give us enough to grab specialty coffees or cocktails, snacks or a portion of some of our meals.  It’s a nice added perk to have—and remember, we get that perk just by having the Surpass credit card.

For our five-night stay at Hilton Hawaiian Village, our Hilton Honors Surpass card gave us a $180 credit to use on food and beverages during our stay + a $50 statement credit for anything else charged to the bill (i.e. hotel cost, parking, food, gift shop, etc.).  That means that even with the $150 annual fee we pay to have the card, those added benefits wiped out that charge + saved us an extra $80.  So that annual fee ends up being totally worth it with just this portion of our stay!

Grand Wailea, A Waldorf Astoria Resort – Maui

My husband and I also each earned a Free Night Certificate, in 2023, for hitting our spend on the Hilton Honors Surpass Card.  We decided that if we were heading to Hawaii, we wanted to see at least two islands.  Since we booked the first five nights on Oahu, we decided to use our Free Night Certificates to stay in the Grand Wailea, A Waldorf Astoria Resort in Maui.  The cash cost for this hotel for two nights was over $2700, but we stayed for FREE! These free night certificates can be used on a $100 hotel or a $1000+ hotel—so we figured we’d get the most bang for our buck using it at a luxury resort!

And since this was a luxury brand hotel and we are Gold/Diamond members, we got $25/person per day as a food and beverage credit.  In addition, since our stay fell in a new quarter, we were also each able to take advantage of our $50 hotel credit that we get from our Surpass Card. In our case, we used it for our parking fee.  Valet was $65/night, but with each of our credits, we only paid $15/night.

Ready to plan your trip to Hawaii?

If you want to make Hawaii a reality for your too, I’ll share two scenarios that will allow you to pay $0 for your hotel stay in Hawaii.  For these examples, we’ll assume you have two “players” (i.e. husband and wife, best friends, etc.) who are teaming up to earn this hotel stay.  Please note that bonus points earned may change—there are different offers throughout the year.

How to FAST-TRACK your trip

Scenario 1 – Hilton Aspire (FASTEST)

• Player 1 gets the HILTON ASPIRE Card and spends 6k in 6 months –remember your $6k spend should be on your everyday bills (i.e. groceries, gas, bills, car insurance, HOA fees, taxes, etc.) so it’s not an added expense.

• Pay $550 annual fee (posts immediately, when approved)

• Refer Player 2 and gets 20k referral points

• Player 1 earns 200k Points, pays $550 annual fee

• Player 2 gets HILTON ASPIRE Card and spends 6k in 6 months

• Pay $550 Annual Fee (posts immediately, when approved)

• Player 2 earns 180k Points, pays $550 annual fee

Hilton ASPIRE Summary

Your out of pocket spend is $1100, which covers your annual fees, but you’ll get 380k points between both of you, which is enough to book Hilton Hawaiian Village for 5 nights (or other cheaper hotels for less).  In addition to your 380k points, you’ll earn additional points for the actual 6k spend you put on the card.

You’ll also earn 2 Free Night Certificates and can book Grand Wailea, A Waldorf Astoria Resort in Maui (or a host of other options)—remember, that hotel alone has a price tag of $2700 for two nights!  Since I am earning this hotel stay for free, you better believe I am going big and booking a fancy, expensive hotel!  Why not, right?!

+ ASPIRE CARD BENEFITS:

With your Hilton Aspire card, you’ll get a $200 statement credit semi-annually (that’s $400/year) on eligible purchases made with participating Hilton Resorts when you use your Aspire Card.  In addition, you’ll receive a $200 flight credit ($50/quarter) on flight purchases made directly with the airline on your aspire card.

+ DIAMOND MEMBER BENEFITS:

Because you’re a Diamond member, you’ll get $15-25/day for up to two people at certain resorts in Food and Beverage credit PLUS potential upgrades!

Scenario 2 – Hilton Surpass (LESS $ OUT OF POCKET)

• Player 1 gets HILTON SURPASS and spends 3k in 6 months

• Pay $150 Annual Fee (posts immediately, when approved)

• Refer Husband/Friend and earns 20k Referral Points

• Player 1 earns 190k Points, pays $150 annual fee

• Player 2 gets HILTON SURPASS and spends 3k in 6 months

• Pay $150 Annual Fee (posts immediately, when approved)

• Player 2 earns 170k Points, pays $150 annual fee

Hilton SURPASS Summary

Your out of pocket spend is $300 in Annual fees, but you’ll get 360k points between the both of you, which is enough to book 5 nights at Hilton Hawaiian Village.

If you each spend 12k more over the course of a calendar year (i.e. Player 1 gets the card in January, the other waits until 12k gets spent, then refers Player 2), you’ll earn 2 Free Night Rewards, which will cover the two nights in Maui at the Grand Wailea, A Waldorf Astoria Resort.

This scenario takes a bit more time since you have to spend 30k to get the two free night certificates.

+ SURPASS CARD BENEFITS:

With your Hilton Surpass card, you’ll receive $200 in statement credits ($50/quarter) for purchases made directly with a property in the Hilton portfolio on your Surpass card.

+ GOLD MEMBER BENEFITS:

Because you’re a Hilton Gold member, you’ll get $15-25/day for two adults at certain resorts in Food and Beverage credit PLUS potential upgrades!

Peace of Mind

We always suggest booking REFUNDABLE hotel rooms, just in case you need to cancel.  When booking on points, these hotels allow you to cancel up to 72 hours before arrival.  So, if we did have to cancel, for any reason, as long as we do it at least 72 hours in advance, our points would just get credited back to our account!  How is that for peace of mind?!

Free Night Certificates typically expire one year from when they were earned so we’d have to rebook another hotel before that date to use those, but as long as we did, we wouldn’t lose out.

I didn’t realize how do-able Hawaii was–especially since our stay was completely FREE!!  We earned this trip with just our day-to-day spending.  Things like groceries, medical bills, house improvements, car insurance, sports fees, utilities, vet bills, etc. can all be spent on a credit card and earn you points!

How to save on FLIGHTS

Now you’re probably thinking, well she’s got her hotels covered, but what about flights?! Those have to be outrageous!  Check out my previous post to see how you can earn BOGO Free flights for nearly TWO years!  Stay tuned to see how our flights from Ohio to Oahu, Oahu to Maui and Maui to Ohio were also all FREE!