Aug 11, 2026 · 16 min · 9 segments
Are you planning your Hawaii trip in the wrong order without even realizing it? 👉 Start planning with the Hawaii Trip Planner Hub Most people start with…
Moving to step two is then choose the island that fits that trip that you're wanting to do.
Oahu gives you plenty of variety, beaches, history, food, Waikiki, and the North Shore, Westside, Ko'olina, plenty of great places around the island of Oahu.
Maui gives you a great mix of both resort time, beaches, scenic exploring, some road trips.
Then you have Big Island, Hawaii Island, which gives you Volcanoes National Park, huge landscapes, a lot of driving.
If you have young kids, it's going to be a drive from Kona over to Hawaii Volcanoes National Park.
The question is, which fits the people, the group? Again, go back to who's going on this trip.
What fits that group that you're traveling with and the kind of trip that you're hoping to do right now in today's stage of life? Step three is then to figure out the shape of the trip.
So meaning like how much do you actually have to spend on this? Maybe it's just going to go on the credit card or whatever.
But what time of year are you going? How many nights are you going to be on island? Or do you want to island hop? Is it one island or two? or three please don't try to do three if you're not staying three weeks and just a quick if you are gonna island hop i'd highly recommend if you can at least do at least 10 days minimum but two islands especially trapping as a family within seven days is is pretty tight and i've done episodes on that i'll link below but this is i think where i'd be careful about trying to do you know too much Because every island change, it costs you, will cost you money.
So you got to pack up, check out, return the car, go to the airport, flight, another rental car, check in again.
But when you're looking at the itinerary from home, that might not sound like much.
Moving to step two is then choose the island that fits that trip that you're wanting to do.
Oahu gives you plenty of variety, beaches, history, food, Waikiki, and the North Shore, Westside, Ko'olina, plenty of great places around the island of Oahu.
Maui gives you a great mix of both resort time, beaches, scenic exploring, some road trips.
Then you have Big Island, Hawaii Island, which gives you Volcanoes National Park, huge landscapes, a lot of driving.
If you have young kids, it's going to be a drive from Kona over to Hawaii Volcanoes National Park.
The question is, which fits the people, the group? Again, go back to who's going on this trip.
What fits that group that you're traveling with and the kind of trip that you're hoping to do right now in today's stage of life? Step three is then to figure out the shape of the trip.
So meaning like how much do you actually have to spend on this? Maybe it's just going to go on the credit card or whatever.
But what time of year are you going? How many nights are you going to be on island? Or do you want to island hop? Is it one island or two? or three please don't try to do three if you're not staying three weeks and just a quick if you are gonna island hop i'd highly recommend if you can at least do at least 10 days minimum but two islands especially trapping as a family within seven days is is pretty tight and i've done episodes on that i'll link below but this is i think where i'd be careful about trying to do you know too much Because every island change, it costs you, will cost you money.
So you got to pack up, check out, return the car, go to the airport, flight, another rental car, check in again.
But when you're looking at the itinerary from home, that might not sound like much.
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