Fly drive

Question

Hi we are thinking of visiting Hawaii in September

Is this a good time ? If we pre booked our first few nights can we hire a car and just drive around and stop and stay as we go

We had done similar thing in the USA before eg Florida and California but was many years ago so unsure how it works now with people now booking on booking.com and Airbnb etc

We are from the Uk so we would come to see the islands for about 3 to 4 weeks

Any information and advice welcome

Answer

Visiting Hawaii in September is generally a great time. The weather is warm and sunny, with slightly fewer tourists than the peak summer months and holiday periods. You may also find slightly better rates on accommodations and flights compared to July and August. Rain is possible, particularly on the Big Island and Kauai, but showers tend to be brief and localized.

Pre-booking your first few nights is a wise idea, especially as you are arriving from overseas. This ensures you have a guaranteed place to stay upon arrival and allows you to pick up your rental car without stress. After those initial nights, Hawaii is very suitable for a fly-drive or flexible island-hopping style vacation. You can drive between towns and islands and book accommodations as you go, although it helps to have at least a rough plan of where you want to stay each night.

Rental cars in Hawaii are plentiful, but it’s worth noting that demand can still be high, especially on Maui and the Big Island. Booking in advance is recommended, particularly for larger vehicles or SUVs, as these are often preferred for exploring the islands comfortably.

Book your first few nights ahead of time in the arrival city.
Reserve your rental car in advance, especially if you prefer a specific type.
Plan a rough route for each island, even if you want to be flexible day-to-day.

For accommodations after the first nights, you can use Booking.com, Airbnb, Vrbo, or local vacation rentals. Many people now book short stays online, and availability can change daily. On some of the smaller islands or more remote areas, it’s possible to arrive and find a room for the night, but in popular areas like Waikiki, Lahaina, or Kailua-Kona, it’s safer to book ahead.

Use Booking.com or Airbnb for last-minute flexible bookings.
Consider vacation rentals for longer stays to have kitchen access and more space.
Check cancellation policies carefully, especially for short-notice changes.

Overall, a 3-4 week fly-drive in Hawaii in September is very doable and gives you the freedom to explore at your own pace. With some initial bookings and flexible planning, you can enjoy both planned highlights and spontaneous stops along the way.

Be sure to keep an eye on inter-island flights or ferries if you plan to hop between islands, as these can sometimes require early reservations, especially for larger vehicles or popular routes.

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