Island Time in Oahu – A Spring Escape

A Quick Escape to Paradise

What better way to celebrate spring than by hopping on a plane to paradise in Hawaii.

With Southwest running surprising deals to Hawaii, we jumped on a late-March escape to Oahu. Four nights, one compact rental car, and a simple goal: good food, warm sun, and a frictionless time on the beach.

While the hotel experience was slightly below our expectations, we still made the most of our time and came home with sandy toes, sore calves, and zero regrets. This also marked a rare occurrence where we spent all cash and zero points on a trip, a nice reset from our usual redemption-heavy approach.

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Planning

The idea of this trip came from a Southwest promotion last November, offering cheap flights from the West Coast to Hawaii for spring travel. Once we locked in the airfare, the rest of the planning process was smooth. Being a popular vacation destination, Oahu is well-documented, and we had no trouble piecing together an itinerary using a mix of blogs, Reddit threads, and local tips.

Flights

We jumped on the deal and snagged roundtrip tickets from Oakland to Honolulu during the spring shoulder season for $225 per person.

It’s worth noting that neither the Oakland airport nor the Honolulu airport has a strong Priority Pass lounge. Honolulu’s IASS Lounge offers limited seating and just a few drink options. Still, getting a good deal on flights always outweighs any lounge perks in our book.

Accommodations

Oahu has no shortage of lodging options, ranging from luxury resorts to affordable Airbnbs. We prioritized Hyatt properties due to our Globalist status, which typically helps us save on resort fees and access upgrades.

Out of the three Hyatt properties on the island, we chose the Hyatt Centric Waikiki Beach for its modern furnishings and central location. The cash rate was reasonable at the time, so we paid out of pocket and applied a Suite Upgrade Award to secure a city view king suite.

Unfortunately, the hotel fell short of expectations. Globalist recognition was minimal, and while the room was clean and spacious, the overall experience didn’t feel elevated. You can read our full thoughts in our Hyatt Centric Waikiki Beach Review.

Transportation

We briefly considered using public transit, but quickly realized a rental car would better suit our itinerary. A car is especially useful if you plan to explore the North Shore, East Side beaches, or hiking trails.

With a corporate discount code, we booked a Mazda 3 for around $200 total for 4 days. It was the perfect size for navigating the island’s roads and Waikiki’s tight parking garages. Street parking in Waikiki is inconsistent, so having a hotel with a dedicated parking structure made a big difference.

Tip: Parking garages in Waikiki can be narrow. Choosing a compact car makes it easier to get around.

Expense Breakdown

Here’s the breakdown of the major trip expenses, this is a rare occurrence where we didn’t spend any points because the cash rate was reasonable enough.

Itinerary Highlights

Waikiki & Kailua

• Morning walks along Waikiki Beach, best before the crowds
• Beach lounging and people-watching in the soft sand
• Day trip to Kailua Beach: fewer tourists and powdery soft sand

North Shore

• Stopped by Dole Plantation (touristy, but the pineapple whip was worth it!)
• Surfed at Waialua Bay with calm waves and sea turtles
• Lunch at Kua Aina Sandwich Shop
• Capped the day with a peaceful sunset at Sunset Beach

Adventure Day

• Started the day at Kona Coffee Purveyors
• Hiked the Koko Crater Trail – a steep climb with a rewarding summit view
• Post-hike meal at Tonkatsu Tamafuji

Takeaways

We thoroughly enjoyed our first Hawaii trip – from the warm weather to the amazing food and stunning nature. A few takeaways:

• Flight deals are everything: Hawaii airfare swings fast. Jumping on a sub-$250 deal saved us serious money.

• Car rental is worth it: Parking isn’t always cheap, but having a car allowed us to discover lesser visited beaches and local eats.

• Hyatt Globalist travelers, choose wisely: Hyatt Centric didn’t deliver the experience we hoped for. Consider Hyatt Regency Waikiki for beachfront access or Hyatt Place Waikiki Beach for a no-frills, budget-friendly stay.

Would we go back? Absolutely. We’re already tracking flight deals for our next island escape.

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