Traveling To Hawaii in 2021

Marcia and Mike planned an amazing bucket-list trip to Hawaii to celebrate their anniversary in 2020. While COVID derailed those original plans, we were able to re-create the itinerary for May of 2021 and they did not let the remaining travel restrictions take away from the overall experience!

At the time they traveled, visitors had to provide a negative COVID test taken within 72 hours of their flight to the islands, and then test again before their interisland flights. That has since changed, and fully vaccinated travelers no longer have to test.

If you’re wondering whether it’s “worth it” to travel to Hawaii right now, here’s their first-hand feedback:

Napali Hawaii mountainous coast

“Thanks for helping us plan our once-in-a-lifetime trip to Hawaii. We had a wonderful time! We both agree that the helicopter experience on Kauai was the highlight! Breathtaking views of the island! And surprisingly I was not nervous at all! It was so much fun and we would highly recommend it!

Some things to note for any one else going in the near future…

On Maui, the sunrise at Haleakala requires reservations between 3 and 7 am to get into the park.  They were booked up so we could not do that but we did go up later that morning (no reservations) and we would recommend it.

Also, the black sand beach on the Road to Hana (Wai’anapanapa State Park)  needed reservations. We took the only available, 3 – 6 pm, which, due to the timing, prevented us from doing the full Hana drive.  Ended up ok because unfortunately, it was rainy/cloudy the whole time.  Also, note that the ticket that you paid for at Haleakala is also good for the Ohe’o Gulch (Seven Sacred Pools) stop on the Road to Hana.

We loved Mama’s Fish House for the food, ambiance, and view.  (We made reservations well in advance while still at home and they were still only able to get lunch at 2:30). The Old Lahaina Luau was great… we enjoyed that.  We also went to Fleetwood on Front (they gave us two complimentary glasses of champagne for our anniversary). Nice sunset there. Paia town was cute( ate at the Flatbread Company which was good.  We had to wait a short while for a table but did not need reservations.  Also stopped at a town called Makawau which had some cute shops. 

Our hotel on Maui {Fairmont Kea Lani} was beautiful.  They had a beach walk that was nice. We got a morning walk on one of the days.  Everything was very expensive… cocktails were between $15 and $22 (on all islands).  And thankfully our breakfast was included.  The breakfast buffet was $50/person/day!!  I’m sure we could have found something cheaper in the neighboring towns (like Kihei maybe). But we loved the hotel and would recommend it for that part of the island.   Another gorgeous area of the island was the west side (Lahaina, Ka’anapali, Kahana, Napili, Kapalua).  We took a ride up there before the Luau.  Would have liked to have explored more there if we had the time. 


Left beautiful sunny Maui, arrived in beautiful sunny Kauai, and after standing in a 45-minute line at the airport, and then picking up our Jeep, we finally made it to our hotel.  Got our bathing suits on, went to the pool and then we felt the raindrops.  Haha Oh well.  Aside from our day on the Road to Hana, that was our only rainy day.  Our room at the Sheraton was very nice. Our room had a patio and a beautiful view of the sunset.  We ate on our patio night one with Mexican takeout from Da Crack on Poipu Rd.  Really good and huge portions.  And reasonably priced.  By chance, we also found a great place for breakfast called Anuenue (means Rainbow) which was just across the main road from our hotel in an outdoor marketplace where Starbucks is located (think it was called Plantation Gardens?) Awesome sweet bread french toast with lemon curd and raspberry sauce…yum!  

At the Sheraton, only the pool restaurant was open. The other 2 restaurants at the Sheraton were closed.

Aside from the helicopter ride where we saw the beautiful island sights, we did not venture out too much on this island. Think we needed some chill time from all the activities on Maui! We liked the pool/ beach at our hotel and were very happy relaxing there. Surprised that the beach chairs and umbrella were not complimentary though. We had to pay for them each day. We had a Sunset dinner at the Beach House which was very good (expensive) and we enjoyed that. We did make that reservation way in advance and were able to get a sunset time slot for dinner – totally worth it!

We’d say Kauai was our favorite island. Very relaxing and laid back. Everyone, on all the islands, was super nice!


Our least favorite island. Loved our Pearl Harbor tour.  Our bus driver and tour guide, KoKo, was great! And of course, the memorial at Pearl Harbor was very moving.  We also drove through the Punchbowl cemetery which was also very moving.  As for Honolulu, though it was city-like, it was very upscale and felt pretty safe.

We found a breakfast place near our hotel called Eggs n Things. One of their specialties is pancakes. We got the strawberry pancakes, which was enough to share, and they were delish!

We were very disappointed in the Outrigger Reef hotel. Though we had a beautiful room with gorgeous views, and the staff was super nice, the hotel was under construction. It was noisy, limited pool seating which was enclosed in blue construction walls with no view of the ocean, a sewage-like smelly walk down a sketchy alley to a tiny beach where there was no room to even sit. Not paradise-y at all. We spent most of our time a few beaches down in front of the Sheraton and other Outrigger, though very crowded, and we had to pay for beach chairs/ umbrella for the day. And the restaurants where we ate were located down there as well (Duke’s and Hula Grill ). We also checked out of the hotel at noon but had to kill time until 5:00 when our airport shuttle picked us up (we did not have a car). Ended up having lunch at the Cheesecake Factory and sitting in one of the sitting areas at the Sheraton until it was time to go. Sort of a wasted day…in hindsight, we would have tried to schedule an earlier flight home. And also should probably have stayed at the Sheraton. Fyi – The Outrigger Reef did ask for our feedback which I gave…they are supposed to be refunding the resort fee. I did mention to them that I didn’t know what that was supposed to cover since everything but the pool and pool bar were closed.

In general Maui and Kauai were just relaxing restrictions so not much opened and the places that were opened were closed by 9pm. Oahu was pretty much open. Travel, though it went pretty smoothly for us, found us spending a lot of time scheduling tests, taking tests, filling out questionnaires, and waiting in lines at the airport for clearance to get into the islands. 

My husband — who is much less patient than me 🙂 — suggests limiting travel to one island until the COVID rules are relaxed. Thankfully you were very clear in what we needed to do and when, so we planned ahead and did not have any issues (except for wait times).

a happy couple on their anniversary trip in Hawaii

“All in all, it was a wonderful trip and we had a great time! Thanks so much for all your hard work to make it a very special vacation for us.”


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)