Sept. trip - taxi, rental car, and sightseeing info

Question

Hi! My husband and I are planning 2 weeks in Oahu in Sept.

The first 9 days we plan on renting a car at the airport upon arrival and driving to a condo rental on the east side of the island. From there we are just going to sightsee at our leisure (horseback riding, visit various beaches, etc.)

Then we are going to return the car and spend the last 5 nights at the Outrigger Reef in Honolulu.

The main reasons to stay on Waikiki at the end of the trip is to be nearer to some of the sights (and maybe tours for pickup) that we want to do like Pearl Harbor, Diamond Head, and a snorkel or sunset sail. And we also want to be closer to the airport at the end of the trip to be able to taxi to the airport for departure.

Does this sound doable / decent plan?

Any car rental company recommendations? We would love to be able to return the car downtown Honolulu if possible but I don't see too many rental offices located there.

Are taxis or Ubers the way to go in Waikiki? We figured we would be sightseeing during the day with a couple of tours and mostly walking or Uber at night to restaurants.

Also, any insight on Outrigger Reef? I have exhausted all of my research skills and it was a toss up between this one and the Marriott. I liked the location of this one a bit better for some reason.

Thanks!

Answer

Your plan for a two-week trip to Oahu in September sounds very doable and quite sensible. Splitting your time between a more secluded east-side condo with a rental car and then finishing in Waikiki without a car allows you to experience both the quieter, scenic side of the island and the convenience of central Honolulu for sightseeing and dining.

Regarding the rental car for the first 9 days:

Car rental companies: Major providers like Hertz, Avis, Enterprise, Alamo, and Budget are all located at Honolulu International Airport (Daniel K. Inouye International Airport). They offer competitive rates and good availability, especially if you book in advance. Enterprise is known for excellent customer service, while Alamo is often slightly cheaper and more geared toward tourists.
Returning downtown: Most airport rental car companies do not have convenient drop-off locations in downtown Honolulu, so returning at the airport before heading to Waikiki is the typical approach. It’s only about a 20–25 minute drive from the airport to Waikiki, and you can take an Uber or taxi with luggage to your hotel.

For transportation while staying at Outrigger Reef in Waikiki:

Taxis vs. Uber/Lyft: Uber and Lyft are very popular, usually cheaper, and more convenient than traditional taxis. Short rides around Waikiki or to nearby attractions work well. For evening dinners, trips to Ala Moana Center, or nightlife, rideshare is efficient.
Public transit: TheBus is an inexpensive option if you don’t mind a slower pace. It can take you to some tourist spots, though with multiple stops and transfers, rideshare is often easier for short stays.
Walking: Waikiki is very walkable, so many restaurants, beaches, and shops are accessible on foot from Outrigger Reef.

About Outrigger Reef:

Location: It is right on Waikiki Beach and very close to shopping, dining, and the start of the beach path. This central location is ideal if you want easy access to Pearl Harbor tours, Diamond Head hikes, and snorkeling or sunset sails that depart from nearby harbors.
Atmosphere: It’s more low-key and classic compared to the larger, more modern Marriott, which can feel busier. The property has direct beach access, ocean views, and a historic Hawaiian vibe that many guests enjoy.
Amenities: Pools, beach services, and on-site dining make it convenient if you plan to spend some downtime at the hotel. It’s also friendly for a mix of relaxation and activity-based sightseeing.

Overall, your itinerary balances flexibility, sightseeing, and convenience nicely. Renting a car for the first part of the trip gives you freedom to explore the island’s east and north sides, while finishing in Waikiki without a car simplifies logistics and maximizes access to urban attractions, beaches, and tours.

Sept. trip - taxi, rental car, and sightseeing info

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