Hawaii on Points: The WanderWise Guide to Paradise
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There's a moment — somewhere around the third hour of a direct flight from the West Coast — when you look out the window and the Pacific turns from gray-blue to turquoise. Then the coastline appears. Green mountains wrapped in clouds, white sand curving along water so clear it looks digital.
That's Hawaii. And it hits different when you know the flights were free.
We're not going to tell you Hawaii is a hidden gem — it isn't. Sixty-five million people visit Hawaii's six main islands every year, and roughly half of them are over 50. What is hidden is how little it needs to cost when you play the points game correctly. We've seen couples spend $8,000 on a week in Maui. We've also seen couples spend $800 out of pocket for nearly the same trip — same hotels, same flights, same sunset cocktails.
The difference? About 200,000 points and this guide.
Here's your complete, plain-English blueprint for visiting Hawaii on points — including inter-island hopping, the best hotel redemptions across four islands, and a 7-day Maui-plus-Oahu itinerary that will make your friends wonder how you pulled it off.
Let's go to paradise.
Getting There: Flights to Hawaii on Points
Hawaii is served by three airports you'll care about: Honolulu (HNL) on Oahu, Kahului (OGG) on Maui, and Kona (KOA) on the Big Island. Kauai's Lihue (LIH) gets fewer direct flights but is absolutely worth the extra connection.
The good news: competition on Hawaii routes is fierce, which means award availability is generally excellent — especially if you book 3–6 months out.
Economy Class Options
| Route | Program | Points (Round Trip) | Cash Equivalent | Notes |
|---|---|---|---|---|
| West Coast → Hawaii | Southwest Rapid Rewards | 20,000–40,000 | $400–$700 | No blackout dates; 2 free checked bags |
| West Coast → Hawaii | United MileagePlus | 25,000–45,000 | $400–$700 | Nonstop from LAX, SFO, Denver |
| Any US City → Hawaii | Hawaiian Airlines (HawaiianMiles) | 40,000–80,000 | $600–$1,200 | Best for East Coast gateways via SEA/LAX |
| Any US City → Hawaii | American AAdvantage | 40,000–50,000 | $600–$1,000 | Web specials drop to 30,000 periodically |
| Any US City → Hawaii | Capital One Miles | Varies | Varies | Book through portal at 1¢/mile; simplest option |
The WanderWise move: If you're on the West Coast, Southwest is the undisputed champion for Hawaii on points. Their points never expire, there are no blackout dates, and every fare earns and burns at the same rate. A round trip from Oakland to Maui can run as low as 20,000 Rapid Rewards points during off-peak windows. Plus, two free checked bags — which matters when you're packing snorkel gear and an extra suitcase of sunscreen.
For East Coast travelers, United offers the best nonstop connections from Houston, Denver, Chicago, and Newark to all major Hawaiian airports. Transfer Chase Ultimate Rewards to United MileagePlus 1:1 and book Saver awards at 22,500 points each way.
Taxes and fees: Domestic award flights on US carriers carry minimal fees — usually $5.60 each way. That's it. Your round trip to paradise costs $11.20 in cash.
First Class / Premium Cabin Options
Hawaiian Airlines operates a lie-flat first class cabin on their A330 aircraft for routes from the East Coast and select West Coast cities. It's not transatlantic business class, but it's comfortable, quiet, and arrives you rested.
| Route | Program | Points (Round Trip, First) | Cash Value | Notes |
|---|---|---|---|---|
| NYC → HNL | Hawaiian Airlines | 80,000–160,000 | $2,500–$4,500 | Lie-flat on A330; 10+ hours |
| West Coast → Hawaii | United (Polaris not available) | Economy recommended | — | First/business not offered on most Hawaii routes |
The WanderWise move: Hawaiian's first class is worth considering for the long haul from the East Coast (JFK–HNL is about 11 hours). From the West Coast, the 5-hour flight makes economy perfectly reasonable — save those premium points for your Europe trip. Transfer Amex Membership Rewards to Hawaiian Airlines 1:1 for the best first class redemptions.
Island-Hopping: The Inter-Island Strategy
Here's where Hawaii gets fun — and where a smart points strategy really shines. Most visitors stick to one island. But Hawaii reveals its depth when you see at least two: the cosmopolitan energy of Oahu next to the lush serenity of Maui, or the volcanic drama of the Big Island alongside the garden-isle beauty of Kauai.
Inter-island flights are short (30–45 minutes), frequent, and cheap on points.
| Route | Airline | Points (One Way) | Cash Equivalent | Flight Time |
|---|---|---|---|---|
| HNL ↔ OGG | Southwest | 4,000–8,000 | $60–$130 | 35 min |
| HNL ↔ OGG | Hawaiian Airlines | 7,500–15,000 | $60–$130 | 35 min |
| HNL ↔ KOA | Southwest | 4,000–8,000 | $70–$140 | 45 min |
| OGG ↔ LIH | Hawaiian Airlines | 7,500–15,000 | $80–$150 | 40 min |
The WanderWise move: Southwest's inter-island service is the secret weapon. Because their pricing is revenue-based (no award charts), cheap flights mean cheap point costs. A one-way hop from Oahu to Maui during shoulder season can cost just 4,000–5,000 Rapid Rewards points. That's barely a rounding error in your points balance, and it unlocks a completely different island experience.
Book your mainland-to-Hawaii flights on United or Hawaiian, and your inter-island hops on Southwest. This "two-airline strategy" gives you the best of both worlds: strong Saver award pricing for the long haul and rock-bottom inter-island costs.
Where to Stay: Hawaii Hotels on Points
Hawaii hotel prices are famously aggressive — $300–$600 per night is standard for anything beachfront, and luxury properties routinely clear $800. Points transform these from wince-inducing to genuinely exciting.
Hyatt Properties (The Sweet Spots)
Hyatt is the undisputed king of Hawaii hotel redemptions. Transfer Chase Ultimate Rewards to World of Hyatt 1:1 and enjoy some of the best cents-per-point values in the entire loyalty ecosystem.
| Hotel | Island | Category | Points/Night | Cash Rate (Approx.) | Why We Love It |
|---|---|---|---|---|---|
| Andaz Maui at Wailea Resort | Maui | 7 | 25,000–35,000 | $700–$1,200 | Beachfront luxury, adults-oriented pools, sunset views |
| Hyatt Regency Maui Resort & Spa | Maui | 6 | 21,000–29,000 | $450–$700 | Ka'anapali Beach, whale watching from your balcony |
| Hyatt Regency Waikiki Beach | Oahu | 5 | 17,000–25,000 | $350–$550 | Steps from Waikiki Beach, rooftop pool |
| Hyatt Centric Waikiki Beach | Oahu | 4 | 12,000–18,000 | $250–$400 | Boutique feel, excellent location, great value |
| Grand Hyatt Kauai Resort & Spa | Kauai | 7 | 25,000–35,000 | $600–$1,000 | Stunning grounds, saltwater lagoon, championship golf |
The WanderWise move: The Andaz Maui at Wailea is the crown jewel. This is a legitimate five-star resort where rooms routinely sell for $900+ per night. On points? 25,000–35,000 Hyatt points per night, depending on dates. Four nights at the Andaz costs 100,000–140,000 Hyatt points — achievable with two Chase card sign-up bonuses. You'd pay $3,600–$4,800 in cash for the same stay. At these rates, your points are worth 3–4 cents each. That's magic.
World of Hyatt Globalist members (their top-tier status) get suite upgrades, free breakfast, and late checkout. Even without status, Hyatt's award stays include the same room quality as paid stays — no "award room" purgatory.
Marriott Bonvoy Properties
Marriott's Hawaii portfolio is enormous, spanning budget-friendly Courtyards to the iconic Ritz-Carlton:
| Hotel | Island | Points/Night | Cash Rate (Approx.) | Location |
|---|---|---|---|---|
| The Ritz-Carlton, Kapalua | Maui | 70,000–100,000 | $800–$1,500 | Kapalua Bay, world-class golf |
| Sheraton Waikiki | Oahu | 40,000–60,000 | $350–$550 | Beachfront Waikiki, iconic infinity pool |
| Westin Maui Resort & Spa | Maui | 50,000–70,000 | $500–$800 | Ka'anapali Beach, family-friendly |
| Courtyard Oahu North Shore | Oahu | 20,000–30,000 | $200–$300 | Quieter North Shore, near Turtle Bay |
| Wailea Beach Resort (Marriott) | Maui | 50,000–70,000 | $500–$800 | Wailea Beach, quieter than Ka'anapali |
The WanderWise move: Use Marriott's 5th-night-free benefit on award stays to stretch your points. Five nights at the Sheraton Waikiki drops from 250,000 to 200,000 Bonvoy points — a 20% savings that's automatic when you book four or more nights. The Sheraton's infinity pool overlooking the ocean is worth the stay alone.
Hilton Properties
Hilton has a massive Hawaii footprint, and their points — while individually less valuable — are easy to stockpile with Amex Hilton cards:
| Hotel | Island | Points/Night | Cash Rate (Approx.) | Notes |
|---|---|---|---|---|
| Hilton Hawaiian Village | Oahu | 60,000–95,000 | $300–$500 | Legendary Waikiki resort, lagoon, Friday fireworks |
| Grand Wailea (Waldorf Astoria) | Maui | 95,000–130,000 | $700–$1,200 | Ultra-luxury, stunning pools and grounds |
| Hilton Waikoloa Village | Big Island | 50,000–80,000 | $250–$400 | Resort with tram system and dolphin lagoon |
The Hilton Hawaiian Village is a Waikiki institution — it's a small city unto itself, with multiple towers, a lagoon, restaurants, and a Friday night fireworks show visible from the beach. Not the most intimate experience, but undeniably fun.
The 7-Day Maui + Oahu Itinerary
Here's how we'd spend a week in Hawaii, splitting time between two islands and using points for virtually everything. This itinerary is designed for travelers 55+ who want a mix of relaxation, culture, and gentle adventure — no 12-mile hikes required.
Days 1–4: Maui (The Relaxation)
Stay: Andaz Maui at Wailea Resort — 4 nights on Hyatt points
| Day | Morning | Afternoon | Evening |
|---|---|---|---|
| 1 | Arrive Kahului (OGG), pick up rental car, check in at Andaz | Pool time, settle in, explore Wailea Beach Walk | Sunset dinner at Ferraro's (at the Four Seasons next door) |
| 2 | Road to Hana (partial — drive to Twin Falls and back, ~3 hours) | Return to hotel, spa or pool time | Dinner at Mama's Fish House (book 2 months ahead) |
| 3 | Morning snorkel at Molokini Crater (book a morning boat tour) | Lunch in Paia town, browse galleries | Sunset at the hotel, room service |
| 4 | Sunrise at Haleakalā (optional — it's early but unforgettable) | Ka'anapali Beach stroll, Black Rock snorkeling | Farewell Maui dinner at Monkeypod Kitchen |
Maui tips for 55+ travelers: The Road to Hana is spectacular but the full drive is long and winding — 620 curves, 59 bridges. We recommend the half-day version: drive to Twin Falls (about 2 miles in), enjoy the waterfalls, and turn around. You get the best scenery without the white-knuckle switchbacks. For Haleakalā sunrise, you'll need to wake up around 3 AM — it's genuinely magical but only if you're a morning person. The sunset version is almost as good and far more civilized.
Day 5: Island Hop to Oahu
Flight: Southwest inter-island, OGG → HNL (35 minutes, ~5,000 Rapid Rewards points)
Check in at Hyatt Centric Waikiki Beach. Drop your bags and walk to the beach — you're 30 seconds away. Lunch at Duke's Waikiki, then explore the shops and energy of Kalakaua Avenue. Evening: sunset cocktails at the House Without a Key at Halekulani (a Waikiki institution with live Hawaiian music and hula).
Days 5–7: Oahu (The Culture + Energy)
Stay: Hyatt Centric Waikiki Beach — 3 nights on Hyatt points
| Day | Morning | Afternoon | Evening |
|---|---|---|---|
| 5 | Arrive, check in, beach time | Explore Waikiki, Kalakaua Avenue | House Without a Key for sunset |
| 6 | Pearl Harbor & USS Arizona Memorial (book timed tickets online) | Lunch in Chinatown, explore Iolani Palace | Dinner in Kaimuki neighborhood (try Mud Hen Water) |
| 7 | North Shore drive: Haleiwa town, shrimp trucks, Sunset Beach | Dole Plantation (touristy but fun), drive back | Farewell dinner at Roy's Waikiki, pack up |
Oahu tips for 55+ travelers: Pearl Harbor is a must — give it a full morning. Book your timed-entry tickets through the National Park Service website at least 2–4 weeks in advance; they're free but they sell out. The North Shore drive is gorgeous and easy — about 45 minutes each way from Waikiki. Giovanni's shrimp truck in Haleiwa has been serving garlic shrimp since 1993; the line is long but moves fast.
The Points Budget: What This Trip Actually Costs
Here's the total points-and-cash breakdown for two travelers on our 7-day Maui + Oahu itinerary:
Flights
| Segment | Program | Points (for 2) | Cash Taxes/Fees |
|---|---|---|---|
| West Coast → Maui (economy) | United MileagePlus (via Chase UR) | 50,000 | $11.20 |
| Maui → Oahu (inter-island) | Southwest Rapid Rewards | 10,000 | $11.20 |
| Oahu → West Coast (economy) | United MileagePlus (via Chase UR) | 50,000 | $11.20 |
| Flight Total | 110,000 | $33.60 |
Hotels
| Property | Nights | Program | Points (1 room) | Cash Equivalent |
|---|---|---|---|---|
| Andaz Maui at Wailea | 4 | World of Hyatt (via Chase UR) | 120,000 | $3,200–$4,800 |
| Hyatt Centric Waikiki Beach | 3 | World of Hyatt (via Chase UR) | 45,000 | $750–$1,200 |
| Hotel Total | 7 | 165,000 | $3,950–$6,000 |
Trip Summary
| Category | Points Used | Cash Spent |
|---|---|---|
| Flights | 110,000 (50K United MileagePlus + 10K Southwest RR + 50K United) | $33.60 |
| Hotels | 165,000 (Hyatt, transferred from Chase UR) | $0 |
| Rental car (Maui, 4 days) | — | $280 |
| Dining & activities | — | $800–$1,200 |
| Total | 275,000 points | $1,114–$1,514 |
| Cash equivalent of same trip | $6,500–$9,500 | |
| You saved | $5,400–$8,000 |
How to Earn 275,000 Points
That number looks big. It's not. Here's a realistic path:
- Chase Sapphire Preferred sign-up bonus: 80,000 Chase UR points
- Chase Freedom Unlimited (add to household): 20,000 bonus + ~18,000/year from everyday spending
- Transfer 165,000 Chase UR → World of Hyatt (hotels) and 50,000 → United (mainland flights)
- Southwest Rapid Rewards Plus sign-up bonus: 50,000 points (covers inter-island + part of mainland if Southwest preferred)
- Normal spending on both cards for 6–9 months: fills the remaining gap
A couple starting from zero can realistically accumulate 275,000+ total points within 8–10 months of normal household spending. No manufactured spending, no gaming the system — just putting groceries, gas, dining, and utilities on the right cards.
Best Time to Visit Hawaii on Points
Hawaii is a year-round destination, but timing affects both your experience and your point costs:
- Peak season (December–March): Whale season on Maui, drier weather on south/west shores. Highest hotel point costs and tightest award flight availability. Book 6–9 months ahead.
- Shoulder season (April–May, September–November): Our favorite window. Warm weather, smaller crowds, and the best award availability. Hotel points costs drop to standard rates. September in particular is a sweet spot — summer crowds have departed but the weather is still perfect.
- Summer (June–August): Warm and busy with families. Award availability is moderate. North Shore surf is flat (south shore picks up), making it ideal for swimming everywhere.
The WanderWise move: Book your flights as soon as award availability opens (330 days out for United, rolling for Southwest) and aim for September or October. You'll get standard-rate Hyatt points, wide-open flight availability, warm water, and beaches that feel like they belong to you.
Frequently Asked Questions
Do I need a rental car in Hawaii?
On Maui: yes. The island's best experiences (Road to Hana, Haleakalā, Kapalua) require a car. On Oahu: optional. Waikiki is very walkable, and Uber/Lyft serve the island well. If you're doing the North Shore day trip, rent a car for that day.
Can I use points for inter-island flights?
Absolutely. Southwest and Hawaiian Airlines both accept points for inter-island hops. Southwest is generally the better value — their points price tracks the cash price, so cheap flights mean cheap redemptions.
Is Hawaii good for travelers with mobility concerns?
Very much so. Hawaii's tourism infrastructure is mature and ADA-compliant. Most beaches have accessible paths, major attractions offer accommodations, and resort hotels (especially the Andaz and Grand Hyatt) are built for comfort at every mobility level. Ask the hotel concierge about accessible excursions — they'll have a list ready.
How far in advance should I book?
For award flights: 6–9 months for peak season, 3–4 months for shoulder season. For Hyatt hotels on points: as early as possible — Andaz Maui award nights during peak season are among the most competitive redemptions in the Hyatt portfolio. Off-peak? You'll have plenty of availability even 6–8 weeks out.
Your Next Step
Hawaii isn't just a vacation — it's the trip that proves this whole points thing works. When you're sitting on Ka'anapali Beach with a Mai Tai, watching the sun drop into the Pacific, and you know the entire trip cost you about $1,200 in cash? That's when the light bulb turns on.
That's when you stop wondering if points are worth it and start planning the next trip.
Ready to start?
- 📊 Take our Travel Score Quiz to see how close you are to a free Hawaii trip
- 💳 Read our Best Cards for 55+ guide to start earning
- 🌴 Download our free Hawaii on Points Planner (PDF) — just enter your email
- 💬 Join the WanderWise Facebook Group and tell us which island is calling your name
All point values are approximate and based on current program pricing as of early 2026. Award availability and point costs fluctuate — always check current rates before booking. WanderWise may earn a commission from credit card links; see our affiliate disclosure for details.