A solo week in Hawaii for 200,000 points and $1,816, with exactly zero points left over

I'm gonna be honest with you: I don't really chase business class tickets, which definitely puts me in the minority amongst the Daily Drop team. 🫣

I'm just not an aviation nerd and I'm not bothered about trying the latest business or first class "products." 🤷‍♀️ I treat flights as the means to an end. They get me to where I want to go. I'm way more excited about the destination than the metal tube that will get me there.

So obviously the first thing I did on this challenge was book business class to Honolulu.

(We'll get there.)

My other confession, and this one matters more for the itinerary: I'm not really a beach girlie. Give me a forest ANY DAY and my heart is happy.

Which is how a Hawaii trip ended up with three nights in a volcano.

Here's what I decided before I searched anything:

• Nonstop out of New York if I could get it

• Two islands, because as an East Coaster, if I’m flying all the way to Hawaii, I’m gonna visit at least two of them

• Sleep IN the forest for the middle of the trip, not next to it

The ground rules

Refresher on the challenge: one traveler, departing the East Coast, seven nights inside a fixed window over Thanksgiving week. 200,000 points or miles, $2,000 cash, flights and hotels only, and a maximum of three credit cards.

I used two: the Chase Sapphire Reserve® and the Bilt Obsidian Card.

The Bilt card was there for the transferable points, and the Chase Sapphire Reserve® and the did all the paying, both for the earn rate and to trigger the travel insurance benefits.

Two cards, four bookings, and a points balance that hit zero on the way home. Sorted. 

The flight out: 95,000 points and $12

The first flight I came across was 30,000 points to Hawaii, which seemed fantastic. Until you looked closer at the details. 👇

I personally think an 18-hour layover is some BS that should not be allowed in the flight world, but here we are. (Apparently one is supposed to sleep in the airport or book an overnight hotel?!?)

This is basically like a built-in positioning flight, so you have the protection of booking on the same itinerary. Which, if you wanted to stay in Seattle for a night, sure. (Honestly, I would. I've been wanting to visit.)

But if you flew out from New York (JFK) on the Sunday, you would have a direct flight that gets to Hawaii before the Saturday flight does, and for fewer points.

Which obviously makes way more sense, so that's what I'm going with here. 👇

Compared to the cash price: 👇

For business, that's 2.56 cents per point, which is an epic value by our scale. 👇

For economy, that's 2.78 cents per point!!

The splurge I said I'd never make

Back to the thing I opened with.

My MO with points and miles has always been spending the least amount of money out of pocket possible. And even when you're getting great deals on biz class flights, they're almost always going to be more points than economy flights.

I just don't want to spend my points that way, because that means fewer hotel nights I can book on points, and therefore more money that I have to spend out of pocket.

However, most of my travels up to this point have taken me to Europe (I used to live in Spain and have family in Hungary) or Latin America, and the longest flight I've taken to date is probably around 7-8 hours.

So for this 11-hour journey, and since this is an imaginary pamper myself vacation that I definitely actually need, I'll splurge for the biz class flight. 💅

Was it the optimized play? Absolutely not, and I'll show you exactly what it cost me at the end.

Would I do it again on an 11-hour flight? Maybe. Depends on the trip and what I’m workin’ with.

Home base #1: two nights in Waikiki

My research showed me that Hyatt has A LOT of excellent hotels and resorts in Hawaii.

Sadly, my 200k points balance was mostly depleted by flights. 😭

Luckily, I was still able to book two nights at the Hyatt Place Waikiki Beach on points. 👇

Two nights, 30,000 points, $0 cash. That's 15,000 a night for a bed a short walk from the water during the busiest week of the year, and I'll take it.

If you had 10k more points, you could book at the nearby Hyatt Centric or Hyatt Regency, which are category 5 resorts and a bit more upscale and modern.

A couple of days hanging by the pool in Honolulu, and then it's time for the part of the trip I actually planned this whole thing around. 

Getting to the Big Island

Honolulu (HNL) to Kona (KOA) is a short hop over to the Big Island to visit Hawai'i Volcanoes National Park and hike in the lush forests. 👇

$105, and if you have them available, these short puddle jumper flights are usually available for 5-8,000 points too.

When you get to the airport, pick up a rental car to navigate the island and get to all the awesome hiking. 👇

$226 for the three days. I'd book this through a travel portal for increased earnings, so I put it through Chase Travel℠. 

Home base #2: three nights in the forest

My goal for the Big Island was ALL THE FOREST BATHING in the national park and all the other natural areas around the island.

That includes accommodation. Put me somewhere IN the forest please.

I thought I'd have plenty to work with a $2,000 budget, but turns out the lodging on Hawaii is expensive! Especially when you added in my desire for a hot tub. (Okay, I am bougie about some things.) 💅

I found this one at Aloha Crater Lodge. 👇

Three nights, $605, private bath, king bed, and a fish pond. Independent, in the forest, and a fraction of what a resort would have cost me on the same dates.

I couldn't resist sharing the one that would've been my first choice. 👇

But at $1,788.10 for the stay, that didn't give me much to work with for other expenses (inter-island flights, rental car, and last night hotel).

If you were traveling with a group or partner, though, this looks like an awesome option as it's an entire cottage. Just look at how many points you'd rack up with this stay when booking on Rove. 18,171!!!!

There is also an outdoor hot tub. 'Nuff said. 

Home base #3: the last night, and the dolphins

After three days of hiking and relaxing, I'd fly back to Honolulu the day before my final departure, treating myself to one more luxurious night before flying out.

You could grab an afternoon flight, which would let you relax in your Big Island hotel in the morning, and arrive when you can already check into your next hotel on Oahu. 👇

I did find that you could fly out of KOA to the mainland and skip the trip back to Honolulu, but getting back to the East Coast from KOA meant several extended layovers. So I honestly would fly out of HNL, which is the bigger airport and gives you more options.

Plus, it gave me the option to splurge with my remaining cash on a final night in Hawaii.

I chose the award-winning Kahala Hotel & Resort. 👇

I picked this room because of three words: private dolphin lagoon.

Yes, please. 👇

One night, $727.11, taxes and fees included.

Plus, this is a Leading Hotels of the World property, so with your Leaders Club membership (free to join), you'll get a variety of perks. 

The flight home

Here's where the bill for that business class seat comes due.

On our dates, return flight options weren't great no matter how you sliced it. 👇

75,000 points and $6, in economy.

There's no way around it: this redemption ain't great, and it was the best I found.

It's a perfect example of why being locked into dates is the enemy of good redemptions, and why we always preach being as flexible on dates as possible. If you were able to shift your trip back by just 2 days, you'd save over 50,000 points on the return flight alone.

And I looked. I looked into a ton of positioning options, and while there were a couple of choices that would've saved some points, the connections were terrible or not feasible at all. All other options would've extended the journey home to almost two days.

For example, this one was 40k points, but it had a 9-hour layover during the day in Calgary, getting into Toronto too late to take another flight to our final New York destination, meaning an overnight stay after a red eye flight out of Honolulu the night before. 👇

No thanks. 

The damage

Here's the bill:

Points: 95,000 (business class out) + 30,000 (Hyatt, 2 nights) + 75,000 (economy home) = 200,000

Cash: $12 + $105 + $226 + $605 + $135 + $727.11 + $6 = $1,816

Two cards. Every single point spent. And $184 of the cash budget left sitting there, which in hindsight I probably should have spent. 

What else I looked at

• The 30,000-point flight with the 18-hour layover. Cheapest points price I found and I still said no. If you want a night in Seattle out of the deal, it's a way to get a protected positioning flight.

• Hyatt Centric or Hyatt Regency Waikiki instead of the Hyatt Place. Category 5, more upscale, more modern, 10,000 more points for the two nights. If my flight hadn't eaten my balance, that's where I'd have been.

• Points for the inter-island hops. 5-8,000 each, and I had none left. Cash it was.

• The Mist Cottage in Volcano. $1,788 for the stay and my first choice on vibes alone. Wrong call for one person on a $2,000 budget, right call for a group.

• Flying home out of KOA. Skips the Honolulu backtrack. Multiple extended layovers, so no.

• Positioning home through Canada. 40,000 points instead of 75,000, at the cost of a 9-hour daytime layover, a missed connection, and an overnight after a red eye. Not worth 35,000 points to me. 

The bottom line

Shifting flights by even a couple of days can make A HUGE difference. That's the single biggest lesson from this whole thing, and it's the one that costs nothing to apply.

I also stand by my decision to normally book economy flights. I went for the biz class flight here since I had $2,000 to spend, but those 70K points could've definitely been used on some hotels, and if I were actually booking this for myself, that's probably what I would've done. It would've meant less money out of pocket.

I also learned that I definitely need to earn Atmos points. Alaska and Hawaiian, (unsurprisingly) came in super useful here.

So: was 200,000 points and $1,816 a good deal for one person, six nights, and a business class seat to Hawaii? For the flight out, absolutely. For the flight home, absolutely not, and I'm not going to pretend otherwise.

If you're not locked into these dates, you can do this trip for dramatically less. If you are locked in, this is roughly what it costs, and it's still a week in Hawaii. 🌺