Island-Hopping in Hawaii

I have been eagerly awaiting the trip report from my clients Dana and Andrew who just returned from a much-anticipated two-week honeymoon in Hawaii. This trip was more than a year in the making, and included three different islands, a to-die-for private villa in Maui, and some really cool sightseeing tours.  Their feedback is below. Ready to pack your bags and follow in their footsteps?

Hi Ann!

Aside from some flight issues, everything else went perfectly!

Outrigger Reef on the Beach– This place was perfect for us. Waikiki was a little busy for our tastes, but we expected that. The pool, restaurants and staff were all great, and we really didn’t feel we needed to wander too far. Since we were there for such a short time, it was really nice to be right on the beach. We were also really happy with the KOS “Lost” tour. The 5 hour was perfect; 2 hours would have been too short, and we wouldn’t have had the attention span for any more. We also both really liked that we go to see a bit of Oahu, so the tour perfectly doubled. The guide was great, and he had a binder full of photos and a portable DVD player, which helped the locations “click” in your head.

Kauai – My favorite… Looking back, we are so happy we split the trip between 4 nights here and the rest in Maui. After the wedding and all, we needed a place that was “all inclusive”-esque. We wanted to simply charge it all to the room, know another cocktail waitress would be coming around again, and a breakfast buffet every morning. Typically, that isn’t the type of trip we are drawn to, but for our honeymoon, it was nice. The resort (the Kauai Marriott) was gorgeous! The staff seems genuinely to like their jobs. While there was no need to leave, we are happy we did. Ziplining was amazing, and I am really glad we had a reason to go to the north side of the island. Andrew, who is normally afraid of heights and prone to motion sickness, proved to be an amazing zipliner! The Napali coast was my favorite part of the trip. I think my only regret was not doing a helicopter tour here. While I lobbied for it, we decided we would rather see lava flowing. Unfortunately, however, we learned you can’t take helicopter tours from Maui to see the Big Island, you have to leave from the Big Island. So, sadly, we missed out on both. But, now we have a reason to go back.

Maui – Andrew’s favorite… As soon as you are sick of $12 cocktails all the time, it was nice to be on our own and fending for ourselves. The villa was everything we hoped! We didn’t realize how close we would be to Wendell’s (the owner’s) house (it was just across the driveway), but he was a really laid back guy and gave us all the privacy we needed. I was also really happy to be in Lahaina, it was such a cute town. The Haleakala bike trip was so worth getting up early for – and yes, very cold. It was 36 degrees and blowing 70 mph before sunrise. We also really liked the Road to Hana, which we did the “wrong way”. Someone suggested we go around the backside of Haleakala first, so we would be on the water side of the road and not behind a row of cars. I liked that. We swam in the Seven Sacred Pools and were to Hana for lunchtime. We also went snorkeling one day (just on our own), but we tried to just give ourselves plenty of time to just hang out. We spent 2 days at the villa doing nothing, and loved it. Also, I would 100% recommend the grocery delivery service. All groceries were expensive, so the delivery fee was barely noticeable. We picked up fresh food and the alcohol we wanted, but we didn’t waste time pickup up coffee filters… Also, we found out the hard way that Luaus need to be booked well in advance. When we called the one you recommended (I am blanking on the name), they were booked until June 20th. We went out to the Hyatt instead, which we really enjoyed. It is hokey, but you have to do it in Hawaii.

The only restaurant we went to and would recommend, other than resort restaurants, was the 5 Palms in Lahaina. We went there our last night for dinner before heading to the airport. The food was amazing, and we were able to watch the sunset into the Pacific one last time. The other places we found were good, but not the kind of place we would tell someone to go out of their way to go to.

Let me know if you think I missed anything or want more specific details. I could probably write a novel about this trip…

Thanks again,



You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)