Well as I come up on my 5th anniversary from when I got to go to Hawaii, my sister recently scored an amazing deal for under $400 per person round-trip. Both my sister and brother-in-law have never been to the Hawaiian Islands before, and are looking forward to going, even though it is over 10 months away (February 2012). So I started reminiscing about my amazing time on the islands, and offered some advice and pointers to the my sister and others.

When I went to Hawaii, all the way back in May 2006, I was just starting to date my wife. I had planned the trip months in advance, and so I went alone to Hawaii. I was used to traveling alone, and staying with friends if possible, but that was the one downside to going to Hawaii alone, when your future wife is sitting at home. It is incredibly romantic and beautiful in Hawaii. Knowing I had a girl sitting at home and not with me when I was experiencing Mother Natures wonders was slightly depressing. So my first recommendation is, do not go alone. I could not afford at the time to pay a premium to have my new girlfriend come along with me, nor do I think it would have been feasible considering my wife’s work schedule.

I was very fortunate to have a college friend that lives on Oahu, so I saved a bundle getting to stay with him a week of my two weeks on the islands. Even though I was seldom in the room, I always had a hot shower, nice bed with the island breeze blowing through the windows, and a kitchen to make some quick meals to take along for the day. While I was in Maui, I stayed at the Wailuku Guesthouse, which is a private residence complete with individually decorated rooms, attached bathrooms, and a pool. It was an amazing place for accommodations, the owners for friendly and helpful throughout my stay, and it was very affordable. My second recommendation is to evaluate your options for where to stay throughout your trip.

Assuming you have airfare and hotels reserved, the next step is how you plan to get around the island. The islands do have transportation services including buses and taxis. However, you are on vacation, so I recommend renting a vehicle. This way you can plan your vacation at your own pace. One of the great things I like about the Hawaiian Islands, which I will discuss more below, is the idea of being able to pull off the road at a certain mile marker, and jumping into the ocean to snorkel or hike. There are so many spots on the islands that most tourists never even realize. I rented a total of three vehicles for my time in the islands; one for my first couple days on Oahu, one for Maui, and then one for my last leg of the trip in Oahu again.

There are a couple keys things to think about when renting a vehicle. 1) You are on an island; rent a convertible! Take full advantage of the ocean breezes and sun (remember to wear your sun screen). I remember riding around in my everyday vehicles and being slightly envious of all the other vehicles because EVERYONE is driving with their tops down. 2) Rent a vehicle suitable for where you plan to go on the islands. All the rental car companies will tell you that you are not allowed to take the vehicle to certain parts of the islands. That is because the terrain is rugged, often times with one-lane, unpaved roads.

I, of course, wanted to explore every part of the islands, and got extremely lucky when it came to my rental car return. While on Maui, I had a Chevy Monte Carlo, and wanted to see all the road to Hilo, including the unpaved side of the island and various other areas. The problem is there are lots of one-lane roads with tight turns. Let’s just say my vehicle had scratches and a damaged bumper due to the tight areas. I was so worried when I returned the vehicle, but I was lucky that they never said anything, possibly because I was having other mechanical issues with the car.

I do not know if I would necessarily rent a jeep because of the security issue discussed below, but definitely pay the extra and get a vehicle you will enjoy driving to take in the whole experience.

You will often hear that crime, particularly vehicle break-ins, is very high in Hawaii. Therefore, it is always recommended to lock up all your valuables, leave them back in your room, or take them all with you. Try not to look like a tourist if at all possible.

The last thing to remember when it come to a vehicle is make sure to have a full tank of gas when going to certain areas of the islands. On the day I went to Hilo, I filled up my tank, and by the time I got back around the island and into civilization, I was on empty. There can be few, if any, service stations in some of the more natural areas. On a map it may not seem like it that far of a distance, but you are typically driving at less then 15 MPH winding through the hills, around blind corners. Therefore, it is appropriate and you need to be considerate by honking your horn before going around a blind corner, because there will be vehicles coming the other direction.

Ok that is enough for one post. I will continue my tips in another thread.