Sample trip planning – Hawaii

This last February I was lucky to take my first trip to Hawaii with my husband and kids.  I spent a lot of time planning for the trip months ahead of it.  I know 2 people who live in Hawaii so I asked both of them for tips.  The most basic question I had was which islands I should visit.  They gave me descriptions of the islands.  She said:

  • Oahu – this island is the most populated.  This island is good for people who like to go out to clubs and shopping.  It also has a lot of historical sites including Pearl Harbor.
  • Maui – this island is a balance of remote activities and urban activities.  There are many high-end resorts.  This is a popular destination for honeymooners.  You can drive the road to Hana, bike down Haleakala, or take in a round of golf at world famous PGA courses.
  • The Big Island - this island is known for it’s volcano, ecological diversity, and history.
  • Kaui – this island is known as the Garden Island.  It is known for it’s remote destinations and hiking.
  • Lanai – this island is remote but has 2 top resorts.

Based on those descriptions and flight availability, we went to Oahu and Maui.

Airfare: Last year, my husband and I both got the British Airways 100k credit card sign-up bonus.  We used those points to get all of our airfare.  Since each ticket cost 35k in miles, we needed 140k for all of us.  BA allows  you to create a household account so you can combine miles for anyone who lives in the same house.  We did this so that we wouldn’t have remnant miles in our single accounts.  After getting our tickets, we still had 60k in our household account.  We flew into Oahu and out of Maui.  We bought puddle-jumper flights between Oahu and Maui on go!Mokulele.

We were worried about the long flights down to Hawaii.  We weren’t sure how our boys would behave being couped up for a long time on flights.  I have to say that I was really surprised at how well they did.  We bought them both a DS before the trip so they would have something to keep them occupied.  They also enjoyed looking out the windows and seeing how high in the air we were.  And jet lag wasn’t too bad of a problem either.  We made sure to tell them before we left that we would expect them to sleep at the hotel when we got in.  We got in around 11 PM, which in east coast time is about the time they get up.  But I think because it was dark outside and the long day of traveling, they didn’t have a problem sleeping.

Rental Car: Since we were going to 2 islands, I had to make 2 rental car reservations.  I booked directly with Budget for our rental car on Oahu.  I found a great discount code by Googling “Budget car discount code”.  I booked our rental car for Maui using Priceline (after checking Better Bidding and Bidding for Travel).

Hotel: After consulting, Better Bidding and Bidding for Travel, I used Priceline to book a hotel on Oahu.  I used the method described in a previous post to bid.  I was able to get a room at the Sheraton Waikiki for $110/night (when the lowest you could find using traditional sites was $260/night).  I used Starwood hotel points for one of our nights on Maui at the Westin Ka’anapali Ocean Resort Villas.  And I used cash and points for 2 of our nights there so it only cost us $90/night.

Activities – Oahu: The first thing I did was figure out what activities we wanted to do while we were in Hawaii.  I knew we wanted to go to Pearl Harbor.  Since we were only on Oahu for about one day, we knew we wouldn’t have time to do much more there.  We figured we’d go to Pearl Harbor and spend the rest of the time at our resort and on Waikiki Beach.  We made sure to get to Pearl Harbor early because tickets to the USS Arizona are handed out in the morning.  If you don’t get there early, you may get a time very late in the day or not at all.

Activities – Maui: On Maui, we wanted to go to a luau, see whales, go snorkeling, and my husband wanted to bike down Haleakala.  One of the people I know who lives in Hawaii lives on Maui.  She told me that we would see whales from the shore.  We shouldn’t waste our time with a whale watching trip.  If we wanted to see them up closer, we should just do anything on the water.  Her husband also works for Maui Sunriders which does bike tours down Haleakala.  My husband booked a trip with them.  We killed 2 birds with 1 stone by booking a snorkeling trip.  We got to snorkel and see whales.  There are tons of companies who do snorkeling trip.  We went with the Pacific Whale Foundation because they had discounts for kids.  Kids 6 and under were free.  And kids 7 – 12 were only $35.  For the luau, I searched on-line and researched in travel books.  Luaus can be quite expensive.  Since it was our first luau and we were going with kids, I didn’t want to book a super expensive luau.  I found Maui Hawaii Luau which offered discounts on luaus (I believe the web site is run by Boss Frog’s because that’s where we picked up our tickets).  We booked the Ka’anapali Beach Luau (which is really the Royal Lahaina Luau) because kids 3 – 11 were free with a paying adult.  Plus they had a kids buffet which included hotdogs, chicken nuggets, and chips.

In another post(s), I’ll give reviews of the places we visited.  It was an incredible vacation.  We are looking forward to going back again next year.


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