How We Booked a $15,000 Spring Break Trip to Kauai for $1,271 Using Points
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I used to believe a dream trip to Kauai with our family of six would stay just that—a dream. Between flights, hotels, and food, we were staring at a price tag at around $15,000. Not exactly in the budget for a family of six. But once I discovered how to stack travel rewards, everything changed.
In this post, I’m not necessarily showing you the absolute best points deals out there—but I am giving you realistic examples of what it can look like to fly during a peak time, like spring break, with a family of six. I’ll walk through what it might cost in points for roundtrip flights and two-bedroom stays at beautiful resorts. These are solid ballpark estimates, and in many cases, you could do even better—especially if you’re flexible—but I want this to feel doable, not overwhelming. We booked our trip fairly, last minute, so this was the reality of the pricing we were looking at.
Sometimes the pressure to find the “perfect” deal can be paralyzing, and my goal is to show you how great it can still be even without chasing unicorn redemptions. For the trip my family took for example- with points, the Southwest Companion Pass, and some creative travel strategies, we brought the out-of-pocket cost down to just $1,271 for a trip valued at nearly $15,000.
If you’re new to this world, here’s a list of cards that can get you on a trip just like this.
Flights to Kauai
We booked our flights on Southwest Airlines, because you really can’t beat the value of the Companion Pass. The loudest only need the points for four tickets- the other two of our family members flew completely free (plus taxes and fees), which dramatically lowered the number of points needed.
Breakdown of Southwest Redemptions:
SLC-LIH: 28,435 points/person for 4 tickets = 113,736 points + 2 Companion Passes
LIH-SLC: 34,120 points/person for 4 tickets = 136,480 points + 2 Companion Passes
Taxes & Fees: $28 total
Additional Points Purchased: $45
About three days before our flight, I checked again and saw that both the outbound and return flights had dropped to 21k and 30k points per ticket. So, in reality, we used fewer points than what I’ve listed here. But for the sake of this example, I’m sticking with the higher numbers to give you a realistic ballpark. If you catch a price drop like we did—especially during a peak time—you could end up using fewer points and have some left over!
Per Account Breakdown:
P1: 85,305 points for 3 tickets SLC-LIH + 1 Companion Pass
P2: 28,435 points for 1 ticket SLC-LIH + 1 Companion Pass
P2: 102,360 points for 3 tickets LIH-SLC + 1 Companion Pass
P1: 34,120 points for 1 ticket LIH-SLC + 1 Companion Pass
Total Points:
P1: 119,425 Southwest points + Companion Pass
P2: 130,795 Southwest points + Companion Pass
Total Cash Value of Flights: $5,119.20
Out-of-Pocket Cost: $73 (Taxes + Points Purchase)
Hotel #1: Westin Princeville Ocean Resort Villas
For our first five nights, we stayed at the Westin Princeville — a stunning Marriott Vacation Club property nestled on a cliff overlooking the ocean. Instead of paying the standard peak rate, we snagged a huge discount by attending a timeshare presentation.
How We Booked:
Special Offer Rate: $1,198 total (5 nights)
Standard Peak Rate: $924/night → $4,620 total
💡 Pro Tip: If you’re open to attending a timeshare presentation, you can score major savings on luxury resorts. Here’s a sample script if you want to call Marriott Vacation Club ask:
You: Hi, I was wondering if you have any special offers for a stay at a Marriott Vacation Club property in Kauai in exchange for attending a timeshare presentation?
If they say no, follow up with: “Do you ever offer these, or is there another way to be considered for a discounted stay?”
Always confirm the minimum stay requirements and any fees before you commit.
Total Cash Value: $4,620
Out-of-Pocket Cost: $1,198
Hotel #2: Grand Hyatt Kauai
For our final two nights, we wanted to splurge- and by splurge I mean stay at a fancier hotel because this was literally $0 for us. The Grand Hyatt Kauai was the perfect ending—think lagoon-style pools, lush gardens, and true luxury. We were absolutely blown away by this property. Ive seen so many videos and pictures of it but some things you really just cant do justice. This property sits on over 50 acres. The swimming pools are really hard to capture in a picuture because everything is surrounded by greenery and winds throughout the property. It makes for a really serene environment even when the hotel is at 100 percent capacity. We also love the saltwater lagoon because we have blonds in our family whose hair does not like extended exposure to chlorine- so it was really nice to be able to give it that natural break. If you want to see videos of both properties and more recommendations on food and things to do- make sure you check out my highlight on instagram.
Heres the breakdown
How We Booked:
Hyatt Points Used: 158,000
35k, 35k, 44k (club access), 44k (club access) for two rooms over two nights. The rates you can expect at this property:
Off-peak nights: 35,000 points per night
Standard nights: 40,000 points per night
Peak nights: 45,000 points per night
The point rates for this property are always affordable thanks to the award chart from Hyatt that we love so much.
Standard Cash Rate: $2,570.51 per room ($5,141.02 total)
Out-of-Pocket Cost: $0
💡 Pro Tip: If you have Hyatt points, this is hands-down one of the best redemptions in all of Hawaii.
What We Actually Used (and Loved) on This Trip
I’m always testing out new things to make travel smoother, especially when we're bouncing between beaches, pools, flights, and long days out. Some of these were longtime staples, others were happy surprises—but all of them ended up being super helpful (and fun!) on this trip. Sharing in case they help your crew too!
For the Plane:
Carry on luggage
We don’t check these bags, but each of my kids has one as a carry-on—and we actually got them from Target! They’re super affordable and easy to spot, which makes it a lot simpler to tell whose bag is whose. No mix-ups, no stress. Find them here.
Snack trays and cheap tablets
Instead of packing our pricier iPads that the kids use for school, we grabbed a few inexpensive Amazon Fire Tablets just for travel. We paired them with basic headphones and splitters (for movie-sharing moments), and now they live permanently in the kids' travel backpacks. It’s been such a good solution. There are a lot of case options, we grabbed these and were happy with them.
We also brought along our favorite snack trays—originally meant to be pill organizers, but they work perfectly for flights. Flight attendants always ask about them! Their grandma usually fills them up before each trip, so it’s a fun little surprise they look forward to when we take off.
The best travel “pillow”
I put “pillow” in quotes because it’s not really a traditional pillow—it straps to the back of the headrest, and the eye mask actually supports your head to keep it upright. I’ve tried just about every travel pillow out there, and this is the only one that doesn’t leave me with a sore neck or shoulder. Total game-changer.
On the Ground
Packable shade
Before you fall over from sticker shock—just hear me out. This was new to us, and we were so impressed. My husband was totally skeptical—he thought it would be loud, flimsy, and basically useless. But I decided to give it a try anyway (thank you, Amazon return policy!), and I’m so glad I did.
We were coming from a long, sunless winter and had several beach days planned, and I knew a bad sunburn could totally derail the trip. I grabbed some packable beach chairs (which I won’t link—sand got completely wedged in the bottom and I wouldn’t recommend them), but the real MVP was the Shibumi Shade.
You guys, this thing is incredible. It’s unbelievably easy to set up, provides a ton of shade, and fits easily in a checked suitcase. It weighs less than 4 pounds, and even when we had to hike nearly half a mile to the best snorkeling beach, it didn’t feel like a burden at all.
I’m so happy with this purchase—it’s officially coming with us on every beach trip from here on out.
Inflatable Pool Floats
We stumbled on these totally by accident. As we were checking in, someone had just checked out and left them outside our room. The bellman offered them to us—and we ended up using them every day in the pools at the Grand Hyatt.
The pools there are so massive that my husband and I just floated in these as we followed the kids around. Total relaxation mode. They even have cupholders on both sides, which was a fun bonus. When we weren’t using them, the kids took over and had the best time with them.
At least three different people stopped us to ask where we got them—because the hotel only sells the basic round tubes. If you want to level up your pool time, definitely grab these ahead of your trip!
The ultimate adventure bag
I have a Lululemon Festival bag that I love using at resorts, but for this trip, I knew I needed something a bit bigger. Enter the Kava sling bag—it was perfect. I was able to fit a snorkel mask, bug spray, one of these oversized packable beach towels we bring on every trip, an external charger, and honestly everything else I could think of. It’s the ideal size for beach days, excursions, or anytime you want to be hands-free but still carry more than the basics.
That said, I probably wouldn’t choose it for a long hike if you’re packing a ton of water—it's a one-shoulder design, so by the end of our Hanakāpī‘ai Falls hike, it felt pretty heavy. But for everyday travel use? It’s been such a great addition.
4 Things You’ll Want to Book in Advance
One of the best parts about covering flights and hotels with points is that it opens up room in your budget to say yes to some of the really fun stuff—like tours and activities you might otherwise skip. We were able to do a few things on this trip that felt extra special because the big expenses were mostly taken care of.
And whenever we book tours like this, we always try to go through a shopping portal like Rakuten so we’re also earning a bunch of extra points on top of it. It’s such an easy way to stack even more rewards.
If you’re heading to Kauai, here are a few experiences we booked (or meant to!) that I’d definitely recommend locking in ahead of time—especially during busy seasons like spring break. These were total highlights for us and made the trip feel even more memorable, without the scramble of trying to find availability last minute.
1. Luau Kalamaku at Kilohana Plantation
This was the luau we booked, and it ended up being such a fun night. It’s set on a historic plantation, and if you arrive early, you can ride the little train around the grounds before dinner. The food was solid, the atmosphere was really open and welcoming for families, and the fire dancing finale was everyone’s favorite part.
👉 Book Luau Kalamaku & Buffet Dinner
If this is your first time visiting Kauai, this luau is such a fun way to kick off your trip and give the kids a peek into the local culture.
2. Lydgate Farms Chocolate Tour
I’ll be honest—I wasn’t sure this one was going to be worth it. But it ended up being one of the biggest surprises of the whole trip. It’s a working cacao farm, and the tour was kind of like what I imagine a wine tasting would be like… if you could bring your kids and swap wine for chocolate and exotic fruit. (We don’t drink, but you get the idea.)
We learned all about how chocolate is grown and made, tried all kinds of flavors from different regions, and even tasted a bunch of exotic fruits- including the cacao fruit (nothing like you expect it to be like 👆. It felt special and immersive, but also super family-friendly. We left with full bellies and way more appreciation for what goes into that little square of chocolate.
👉 Book Lydgate Farms Chocolate Tour
I’d absolutely do this one again—and I think our kids would too.
3. Hanakāpī‘ai Beach Hike (Without Doing the Whole Trail)
The Kalalau Trail is one of the most famous hikes in Hawaii—but it’s also 22 miles long and requires a permit beyond the first couple miles. With kids (and limited time), we opted to hike just the first two miles to Hanakāpī‘ai Beach… and it was plenty.
The views were unbelievable. We got to see the Na Pali cliffs, the ocean, and lush valleys all without needing to commit an entire day. It’s not an easy hike—it’s muddy, rocky, and includes some elevation—but our family handled it just fine and it was totally worth it.
Important: You must reserve a spot in advance for Hā’ena State Park, even if you're just hiking to the beach. If you’re staying farther away or don’t want to fight for parking, the shuttle is the easiest way to go.
This is a great way to experience the Na Pali Coast on foot—without biting off more than your family wants to chew.
4. Na Pali Coast Snorkel Adventure
We actually booked this one—and then a huge storm blew in and it got canceled the morning of. Total bummer. But I kid you not: the number of messages I got from followers saying this exact tour was the best thing they did in Kauai totally convinced me that we’ll be rebooking it next time.
If you're not doing the hike or just want a different angle, this is the way to see the Na Pali Coast in all its glory. The boat takes you along the cliffs, stops to snorkel, and often sees dolphins along the way.
👉 Check Out the Na Pali Coast Snorkel Adventure
If this is high on your list, book it early and maybe keep a backup day in mind in case the weather doesn’t cooperate.
Final Trip Points Summary
| Expense | Cash Value | Points Used | Out-of-Pocket Cost |
|---|---|---|---|
| Flights | $5,119.20 | 250,220 Southwest points + Companion Pass | $73 |
| Westin Princeville | $4,620 | N/A (Timeshare Rate) | $1,198 |
| Grand Hyatt Kauai | $5,141.02 | 158,000 Hyatt points | $0 |
| Total Trip Value | $14,880.22 | 408,220 points | $1,271 |
If we had used points from one of these Capital One cards, we could have covered all of these expenses with rewards instead of cash. Cards like the Capital One Venture Rewards, Venture X, or Capital One Spark Cash Plus all offer flexible ways to earn and redeem rewards for travel—making trips like this completely free instead of highly discounted.
Upgrade Request to Grand Hyatt Kauai
If you’re staying at a luxury resort like the Grand Hyatt Kauai, it’s always worth reaching out ahead of time to politely ask for an upgrade. Here’s a sample email you can use—feel free to copy, paste, and personalize it.
When we stayed at the Grand Hyatt Kauai, the hotel was at 100% capacity. While our room technically faced the parking lot, I’m convinced the email we sent ahead of time helped us land a spot with a beautiful view just steps from our door. It never hurts to ask—especially when it comes to making a special trip even more memorable. Here is what it looked like:
Want to see how we booked similar trips? Don’t miss these related blog posts:
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