Time on Oahu vs. Maui

Question

Sorry to create a separate thread, but had a different question. We have a full 7 days in Hawaii plus travel days. We fly in on Wed night, have TH through Sunday morning at the Four Seasons on a company trip. On Thursday, I'm going to rent a car and we're going to do the Haleakala Crater. We also have a Molokini and Turtle Bay 1/2 day snorkel on Friday. Saturday I thought we could hang as the resort and maybe take a trip into the nearby towns.

My new plan would be to get a hotel closer to the airport on Sunday morning when my peers leave and do a day on Hana and a day at the North Shore. Then Tuesday morning, fly to Oahu, do Pearl Harbor (my wife wants to see it) and whatever else we decide on Wed. We'd fly out of Oahu on Thursday early afternoon.

I should be able to switch my other accommodations easy enough, I'm diamond status with Hilton.

Sound reasonable? Any suggestions for the two days in Oahu besides Pearl Harbor?

Answer

Your overall plan is very doable and actually quite efficient for a 7-day Hawaii trip where you’re already anchored to the company portion on Maui. You’re covering each island with purpose, not rushing too much, and focusing on experiences that make each island unique. Splitting time between Maui and Oahu can work extremely well when you keep the logistics tight—your plan does that.

Below is a breakdown of how the itinerary flows, what makes it reasonable, and suggestions to maximize your two Oahu days beyond Pearl Harbor.

Wed–Sun Morning: Maui (Wailea & Upcountry/Coastal Activities)

Your Maui portion makes perfect sense:

Four Seasons Wailea is a great home base—beautiful, relaxing, and perfect for the resort day you’re planning.
Haleakalā Crater on Thursday is ideal with a rental car. Go early to avoid clouds and crowds.
Molokini + Turtle Town on Friday is exactly the right pairing and won’t exhaust you.
Saturday exploring Wailea, Kihei, or Lahaina is relaxed and fits the company-trip vibe.

No issues here—this is balanced and enjoyable.

Sun–Tue: Switch to Maui Airport Area → Hana Day + North Shore Day

This adjustment is smart. Having a hotel near the airport or in Kahului makes both Hana and the North Shore more accessible:

Road to Hana Day: Starting from Kahului cuts one full hour off your drive time. You can do an out-and-back or a loop (if conditions allow). This is a full-day experience but very rewarding.
Maui North Shore Day: Easy and relaxed. Visit Baldwin Beach, Paia Town, Ho‘okipa (sea turtles), Makawao town for paniolo culture, and enjoy local food stops.

This portion is completely reasonable and avoids the “two very long drives from Wailea” problem. You’ve structured it well.

Tue–Thu: Oahu (2 Nights)

Flying to Oahu on Tuesday morning and giving yourselves a partial day + a full day before leaving Thursday afternoon is efficient. Pearl Harbor is the key activity, and the rest can be flexible based on energy.

Suggestions for What to Do on Oahu Besides Pearl Harbor

With 1.5 days, choose activities that don’t require long drives and give you a strong sample of Oahu’s highlights.

Downtown Honolulu & Iolani Palace
A unique Hawaiian historical experience. The only royal palace in the U.S., with beautiful architecture and a short, meaningful visit. Easy to pair with Pearl Harbor since they’re close.
Waikīkī Beach & Sunset
Even just a few hours walking the beach, swimming, or enjoying the shops/restaurants along Kalākaua Avenue gives you the classic Oahu experience.
Diamond Head Crater
A very doable 1.5–2 hour hike with great views. Advance reservations required. Great for the morning after Pearl Harbor.
Punchbowl Crater (National Memorial Cemetery of the Pacific)
Beautiful lookout with deep historical significance. Very close to downtown and Pearl Harbor. Quick stop but memorable.
Makapuʻu Point Lighthouse Trail
If you want a scenic coastal hike without going too far from Honolulu, this is a stunning option.
Drive the East Coast (Short Loop)
From Hawaii Kai to Makapuʻu to Waimānalo to Kailua. Gorgeous coastline with easy pull-offs.
Lanikai or Kailua Beach
If you want a soft-sand, turquoise-water beach experience, this is the place. It’s only ~35 minutes from Waikiki.

What Not to Try with Only 1.5 Days

Don’t attempt the full Oahu North Shore drive (Halewia + beaches)—it’s too tight unless you skip Pearl Harbor.
Don’t plan long waterfall hikes or major full-day tours.

Is Your Overall Plan Reasonable?
Yes, it’s absolutely workable. Maui gets the majority of your time, but you’re building in two activity days (Hana + North Shore) that allow you to see more than just Wailea. Your Oahu stop is efficient: fly in, see Pearl Harbor, enjoy Honolulu, and leave without spending a full day in airports.

If you're Hilton Diamond, you’ll also have flexibility with Oahu hotels (Hilton Hawaiian Village, DoubleTree Alana, Embassy Suites Waikiki, etc.), which makes logistics even easier.

Final Thoughts
Your plan is balanced, your timing works, and you’re not overpacking anything. For two days on Oahu, pair Pearl Harbor with either Waikiki + Diamond Head or an East Oahu scenic loop, and you’ll get a great taste of the island without feeling rushed.

Time on Oahu vs. Maui

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