How We Took a 16-Day Hawaii Cruise for $2,000 Each

Winnie and I just finished what might be the trip of the year—a 16-day Hawaiian cruise sailing out of Los Angeles.

But honestly, the way we planned it? That’s the real story.

Turning a Promo Into a Strategy

Back in August 2025, I came across a Princess Cruises deal:

👉 3rd and 4th passengers sail free

Most people would scroll right past that if they don’t have kids.

We are not most people.

So instead, we asked:Who says passengers 3 and 4 have to be kids?

Our plan was simple—find two more people, split the cost, and turn an expensive trip into something ridiculously affordable.

My first call? My parents.

Once they heard it would be about $750 per person for 16 days in Hawaii, they were in immediately.

Travel Hacking Our Way There

From there, we leaned into our favorite game: credit card rewards.

Winnie opened a Capital One Venture X card, which worked out perfectly:

• I already had one → referral bonus ✅

• She earned a signup bonus ✅

• We locked in lounge access before program changes ✅

We used those points to:

• Book flights

• Cover two nights in LA (because… if you’re already there, why not explore?)

The Drink Package Loophole

Around Christmas, we found another sneaky win:

👉 Only guests 1 and 2 are required to buy the drink package👉 Guests 3 and 4 don’t need it

So my dad and I split the cost.

That got us:

• Up to 15 drinks per day (each)

• Including specialty coffee (clutch)

• Gratuities

• Internet

• Some upgraded dining

Safe to say… we got our money’s worth.

Getting to LA (The Budget Way)

We flew out of Minneapolis at 3:30 AM—because cheap flights win.

To save even more:

• Booked parking through SpotHero

• Used a hotel shuttle

• Gave ourselves extra TSA time

Once we landed, we pulled off one of the best travel moves of the trip:

• FlyAway Bus → $15

• Subway → $1.50 each

Total win.

First Impressions of LA

We hit Little Tokyo first—and honestly, it delivered:

• Amazing Japanese and Korean food

• Cool shops and gardens

• Heavy anime culture

…but also one very sketchy corner.

Every day, without fail:

• Day 1: naked guy sleeping

• Day 2: someone peeing in a trash can

• Day 3: someone tipping that same trash can into traffic

LA keeps things interesting.

Hollywood… Not Quite It

We did the classic tourist stops:

• Walk of Fame

• Chinese Theatre

• Hollywood Sign

And… yeah.

The Walk of Fame was underwhelming. Just a crowded street with stars.

We’ve had better walks back in Rochester—minus the chaos.

The “Maybe Not Worth It” Splurge

We tried a Hop-On Hop-Off bus tour (~$106).

Pros:

• Covered a lot quickly

• Good history/context

• Saw Beverly Hills, beaches, markets

Cons:

• Expensive

• Not something I’d rush to recommend

It worked—but barely.

Free Travel = Best Travel

On our last LA day, we found something magical:

👉 A free outlet mall shuttle

That’s our style.

We mostly browsed (elite-level non-spenders), but Winnie scored:

• 2 Lululemon tops

• Shorts

• All for $80

Arguably the best deal of the trip.

Cruise Time

We met my parents in San Pedro (hotel booked on points—#DadfortheWin). My share: $75.

We also found a restaurant called Crazy Fish:

• Affordable

• Amazing food

One of the best meals of the entire trip.

Then… we boarded.

Life at Sea (Spending $0 for 5 Days)

For five straight days, we spent nothing.

Life looked like:

• Plenty of specialty coffee

• Hot tubs

• Movies under the stars

• Endless food

• Zero responsibilities

Honestly, it was one of the most relaxing stretches we’ve ever had.

I almost didn’t want to reach Hawaii.

Almost.

Hawaii: 4 Islands in 4 Days

Day 1: Hilo

• Rainbow Falls (no rainbow)

• Carlsmith Beach Park

👉 Highlight: Swimming with giant sea turtles—for free

Bonus: got caught in the rain and used giant leaves as umbrellas.

Nature provides.

Day 2: Oahu

• Visited Pearl Harbor

One of the most powerful experiences of the trip.

Honolulu?

• Crowded

• Expensive

• Not really our vibe

Day 3: Kauai

• Backcountry river tubing ($187 each)

Expensive—but 100% worth it.

Day 4: Maui (Our Anniversary)

We rented a Mustang from Turo ($160) and drove the Road to Hana.

Top down. Perfect weather. Unreal views.

Stopped at a roadside BBQ:

• Fried fish and chips

• Roasted corn

• Expensive—but excellent

Also tried apple bananas… which taste like apples, not bananas.

Hawaii is weird. But in a good way.

Back to Ship Life

We fell right back into cruise mode:

• Coffee in the morning

• Piña coladas by the pool

• Relax, repeat

Highlight: Winnie got pulled on stage during a circus act…

…and I somehow ended up loudly singing Queen while “rescuing” her in front of the entire theater.

Not my finest performance—but definitely memorable.

Upgraded Dining: Not Worth It

We tried the upgraded dining twice.

Verdict:

• Slower service

• Average food

• Not better than the main dining room

We had 4 meals included… used 2.

Could’ve skipped it.

Ensenada Stop

After 5 more days at sea, we hit Ensenada.

We explored on foot:

• Visited the birthplace of margaritas

• Street shopping

• Saw some interesting nightlife

Winnie got her hair done.I replaced sunglasses I broke by sitting on them.

Productive stop.

The Journey Home

Back in LA:

• Shared a cab with my parents

• Arrived 8 hours early (because of their flight)

We passed time watching movies on Winnie’s phone.

Finally got home to Minnesota at 2:00 AM…

…and I was at work by 8:00 AM.

No extra PTO used.

Total Cost (20 Days)

• Cruise: $1,588

• Drink Package: $1,000

• Hotels: $75

• Parking: $114

• Excursions: $537

• Extras: $613

• Ubers: $165

Total: $4,092 for two people

$2,046 per person

Final Thoughts

A 20-day Hawaii trip for just over $2,000 per person is hard to beat.

Not everything was perfect—but that’s part of the experience.

Between the Road to Hana, sea turtle swims, cruise life, and the chaos of LA—it turned into a trip we’ll never forget.

And honestly?

We’d do it again in a heartbeat.

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