C.K.
We recently took our 23 month old to Hawaii. We were really excited to share that experience with her and have been to Hawaii 2 times before she was born. With that in mind, as pretty as it was, if we had to do it again, i don't know if we would go. When you go to a beautiful destination you want to relax, sit on the beach, have some nice dinners out (not expensive but just outside of the house) etc... Because we live in Wa. state the time difference is 3 hours. She was up every day at 4:30 and after 5 days, it was closer to 5:00am. She was EXHAUSTED by 6:00pm so we only went to dinner once. We had to hang out in the condo for a couple hours while she napped (not such a big deal but just plan for it in your day) Actually your daughter may be still going on 2 naps a day at 16 months which is more inside time. My daughter went to 1 nap a day around 18 months. Whenever you go anywhere your child is your main focus. I found it hard to just relax because I wanted to make sure she was playing, having fun with the sand, and safe. My husband was there too but we just didnt' get much down time on the beach. The weather was also not the greatest. Maybe my expectations were too high since we had been there before she was born. I would highly suggest you do a "trial" trip somewhere. We took our daughter to Cannon Beach when she was 16 month and we quickly realized we weren't on a vacation but a trip. We couldn't do much with her 2 naps a day and had to watch her in the sand so we didn't get much down time together (we should have brought someone but we wanted a family trip, it was our 1st family trip).
I don't mean to boohoo your idea, but it is a lot of work to get ready for a trip and money and when you are there, wherever you go, you might find it hard to relax because you are constantly thinking of her needs. So when you come back, you might not feel refreshed and think "wow, what a great time." It might be "wow, that was a lot of work."
If you do go here are some tips:
--get a condo. It was great to be able to make bfast and lunch there. We did take out for dinner most of the time.
--Find a place that you can rent baby gear from and have it delivered to your rental.
--If you can BUY her a seat! I know you want to save money, but if you go to Hawaii, for example, flying from the Northwest it is easy a 5 hour flight. (We actually didn't buy our daughter a seat but Hawaiian Airlines was WONDERFUL and gave us the extra seat they had that day. (We asked as soon as we got there for an extra seat if one was available). They also had us really close to the front. They were able to do the same thing on the way home! We love Hawaiian airlines! Oh and there are more open seats and it is cheaper to fly during the week. We left on a Tues and came home on a Wed). If she didn't have a seat, we would have gone bonkers! Oh and bring the car seat ON THE PLANE.
-- TAKE SOMEONE with you. A friend, grandma, aunt or uncle. You can really have a little bit of fun as a couple on this beautiful, expensive trip and probably relax a lot more. While your daughter is taking her 2 naps and grandma is there, you two can take a walk, get a drink, lay around the pool/beach for an hour or two.
--I bought an IPOD touch and downloaded her favorite music and movies for the plane, airport and car. I don't use it unless we are traveling so it doesn't lose it's appeal. I know your child is 16 mo. but it might not hurt. If she doesn't sleep for the flight, you will both be going a little batty!
--Bring a new toy or something new for her for the plane and lots of snacks. I brought some crayons and a little coloring book that worked. I also bought some new paperback Elmo books (she loves Elmo) that we looked at. We also did stickers and the Color Wonder markers might be a good idea for the plane, airport or hotel/condo. Bring bubbles too. Those were easy to pack and great to have at the Condo.
good luck!
C.