Hawaii had always been on our dream list.
But between the flights, hotels, and rental cars, it always felt just out of reach—until we realized we could book almost the entire trip with points and miles. And we did just that.

From sipping cocktails on a balcony in Maui to hiking through lava fields on the Big Island, this trip had a little bit of everything—adventure, relaxation, and best of all, minimal out-of-pocket costs.

Thanks to points and miles, we turned 114,000 Capital One miles—and one Marriott free night certificate—into a once-in-a-lifetime Hawaii adventure.

Here’s exactly how we made it happen.

Our Hawaii Itinerary at a Glance

Maui — 1 week (Vacasa condo stays booked with points!)
Big Island (Hilo & Volcano area) — 2 nights
(including a scenic 12-seater Cessna flight from Maui to Kona!)
Oahu (Honolulu & Waikiki) — 1 night at the iconic Royal Hawaiian (using a Marriott free night certificate)

Booking Flights with Points

We booked our flights from Tampa to Hawaii using Turkish Airlines Miles&Smiles—one of the best hidden gems in the points world.

Turkish Airlines is a Star Alliance partner of United, and they have an incredible sweet spot redemption:
➔ Flights between the U.S. mainland and Hawaii for just 7,500 miles each way per person (now 10,000 miles each way).

We booked round-trip flights for two people for just 30,000 miles total—an incredible value.

The process takes a little work:

First, you search for United Airlines award availability online through United’s website.
Then you call Turkish Airlines to book the award flights using your Miles&Smiles account.

It’s a bit tricky and requires some patience, but the savings were so worth it for an unforgettable trip to Hawaii.

We transferred Capital One Venture miles to Turkish Airlines during a transfer bonus promotion, which stretched our points even further.

On the way home, we booked United again with points and splurged on a small cash upgrade to sit in Premium Plusfor a little extra comfort on the long leg back to Florida.

Maui on Points: Vacasa Vacation Rentals

On Maui, we booked two different Vacasa vacation rentals using Wyndham Rewards points (by transferring Capital One Venture miles during a 20% transfer bonus promo):

A beachfront condo in Kihei
A resort-style suite in Kaanapali with a balcony and full kitchen

Each stay cost 15,000 Wyndham points per night, and we booked a total of 7 nights across the two properties.

Without the transfer bonus, it would have cost 105,000 Capital One miles—but thanks to the 20% bonus, we only needed 84,000 Capital One miles to cover all 7 nights.

It was an incredible value for ocean views, full kitchens, spacious rooms, and resort-style amenities—all while staying just steps from some of Maui’s best beaches.

Just look at that view from the patio of our Vacasa home in Kihei!

Favorite Maui Experiences

Road to Hana (black sand beach, rainbow trees, Garden of Eden, Kipahulu area)
Olivine Pools (breathtaking and a little wild—be cautious!)
Snorkeling cruise with Trilogy (highly recommend!)
Old Lahaina Luau (genuinely fun, with fantastic food and dancing)
Paia town and Iao Valley State Monument

We also rented a Jeep (paid out of pocket), which made adventuring—especially the Road to Hana—even more fun and flexible.

One of our favorite stops on the Road to Hana was Wai’anapanapa State Park

Big Island: Volcano Adventures

We took a tiny 12-seater Cessna flight from Maui to Kona—a quick, scenic inter-island hop that definitely made the adventure feel even more memorable!

From there, we drove to our Airbnb near Volcanoes National Park: a cozy little gem called Gigi’s Volcano Cottage.

Gigi’s was perfect—a charming cottage tucked into a lush tropical rainforest, just one mile from the park entrance. It felt peaceful, private, and was the ideal base for exploring the Big Island.

Here’s what we loved during our Big Island stay:

Hiking down into a volcanic crater inside Volcanoes National Park
Watching active lava glow at night (a literal bucket list moment)
Visiting Volcano Winery — the southernmost winery in the U.S.! (Fun, low-key wine tasting in a unique volcanic landscape.)
Day trip to Hilo (with scenic stops, waterfalls, and cute local shops)
Celebrating our anniversary with a hike and picnic in Volcanoes National Park

It was wild, beautiful, and unforgettable—the kind of raw natural beauty you only find somewhere like the Big Island.

Volcano Winery was such a fun little stop on the way to Volcanoes National Park

The lava glow at night from the active volcano in Volcanoes National Park

Oahu Finale: Waikiki + The Royal Hawaiian

We wrapped up the trip with one night in Honolulu, booking a stay at the iconic Royal Hawaiian—the famous pink hotel right on Waikiki Beach.

We used an annual free night certificate from my Marriott Bonvoy Brilliant® American Express® Card to cover this stay, making it an extra special (and free!) finale to the trip.

Even with just a short stay, we packed in some amazing experiences:

Visited Pearl Harbor
Explored the North Shore
Watched sunset over Waikiki Beach

It was the perfect grand finale to a trip filled with natural beauty, history, and peaceful adventure.

Waikiki Beach on our last night before heading back to reality

Final Thoughts: How Points (and a Free Night Certificate) Made It Happen

With a little strategy—and a little patience finding award flights—we were able to unlock some serious savings and book a dream trip to Hawaii without the dream-sized price tag.

We used points and certificates for:

Round-trip flights (thanks to Turkish Airlines Miles&Smiles sweet spot redemption, booked with Capital One miles)
7 nights of hotel stays through Vacasa (using Wyndham Rewards points)
Our splurge night at The Royal Hawaiian (covered by an annual Marriott free night certificate)

Total Capital One Venture miles used:
114,000 miles for two round-trip flights and 7 nights of beachfront accommodations in Maui.

We paid out-of-pocket for:

Inter-island flights
2-night Airbnb stay near Volcanoes National Park
Rental Jeeps
Food, excursions, and gas

Between the incredible points deals and unforgettable experiences—like snorkeling in Maui, hiking through lava fields, and watching the sun set over Waikiki—this trip was worth every bit of the planning it took to make it happen.

Rooted Takeaway

You don’t need a luxury budget to take a luxury trip—just the right strategy.
With a little points magic (and a few bonus phone calls to airlines), we turned a dream Hawaii getaway into an unforgettable (and budget-friendly) anniversary trip.

And the best part?
It wasn’t just about saving money.
It was about unlocking experiences—the kind that leave you breathless, connected, and rooted in the moment.

📌 *Pin this for when you're ready to plan your own dream trip to Hawaii—without the dream-sized price tag.*

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