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Travel Guru's (Update in Comments)
Re: Travel Guru's (Update in Comments)
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
That is a bummer he won't give the cruise a try. He could have laid by the pool and drank all week the same as at an AI.
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
Hmm. I guess there are a couple hotels named Aston; do you have the full name? I looked at one on Trip Advisor that's just across from Waikiki Beach. If you are anywhere near Waikiki Beach, you are definitely where all the action is. That's arguably the most popular area on Oahu! And, there should be TONS of restaurants within walking distance.
If you want a quieter, slow-paced vacation, you might want to stay away from Waikiki Beach area. However, that is the area we stayed and loved it. We walked everywhere--shopping, beach, activities, restaurants--most of the time we were there. We did rent a car one day and drive up to the North Shore. That area has a cool, funky kind of vibe that's worth the drive. Also drove to Pearl Harbor because I swore I'd never visit Hawaii without paying respects. It's an amazing memorial and definitely worth a visit!
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
Caveat: It has been a long time since I vacationed in HI, but I have a lot of family there. I've never vacationed in the Caribbean islands.
I don't know if this is true in the Caribbean islands, but in the Hawaiian islands almost everything is more expensive because it has to be shipped long distances. That includes items you buy in the grocery store. I remember restaurant meals being a bit more than on the mainland, but most grocery items were a lot more. Probably still cheaper to cook breakfast/lunch for yourself, but not at the same difference it is on the mainland.
Fun, random fact about short+sassy...some of you were talking about the Azores earlier. The family on my mom's side immigrated from there in the mid and late 1800s to go work in the sugar cane fields of HI. Decades before there were tourists.
It's a beautiful place now, I'm sure it was really breathtaking back then. Though extremely isolated. Most of my extended family has never left.
So it looks like it is at the other end of Waikiki Beach from where we stayed but definitely still right there in the middle of the main part of the Waikiki area. Easily walkable to hundreds of restaurants and the beach. I wouldn't be concerned about location as far as accessibility goes.
If you're looking at different hotel options, we stayed at a place called Vive Hotel; the room was really small and it didn't have all the high-end amenities such as a spa, etc, but it was a really nice boutique hotel, easily walking distance to everything, and the staff was super friendly and helpful.
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
We did a helicopter tour in Kauai as well--absolutely magical! My MO for any vacation is to save where I can so I can spend where it matters. Experiences matter.
@brij--In Maui, we visited Ka'anaapali Beach (sp?) and it was a super gorgeous beach. It's right in front of some super fancy resort properties, but that doesn't matter because ALL beaches in Hawaii are public access. I'd recommend it for sure if you are in Maui!
Alos, drive up to the top of Haleakala at either sunrise or sunset. We did sunset. It was absolutely worth it and totally lives up to all the hype you can read about online!
We're between Hawaii and Costa Rica (all-inclusive). But we know for sure that we will do Hawaii at some point, and what's a better time than now?
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
The only things we have on our agenda are to maybe do a snorkeling excursion (with whale watching), and probably a helicopter tour. Just debating which one to do, since there are so many.
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
Wonderful! Your plans sound great and, with everything else you all have had going on, this seems like the perfect time to go on your dream vacation.
My everyday car is a convertible...and it is still a special feeling to put the top down on a nice day...so I definitely give a big thumbs up to toodling around HI in one.