10 Mistakes When Planning a Trip to Hawaii

Biggest mistake I made was on our second trip to Maui. Do not plan TOO many activities that will take up a bunch of "windshield time". Do enough activities to make it worthwhile but be sure to enjoy the relaxing island vibe. Too much driving is less time for relaxing.

I'm a concierge on the big island and the top two mistakes I see guests make are over scheduling themselves, and not leaving time to travel to the sites they want to visit. When people have three days of tours booked in a row, why are you staying at a luxury resort with a resort fee? When they ask to see a waterfall or the volcano, but are unwilling to drive 1.5 to 2 hours one way from the Leeward side...it's a big island, it takes time to reach the tropical side. The happiest travelers enjoy the resort and nearby beaches for 2/3 of their time, and execute a well planned daytrip, manta tour, our scenic drive for the other 1/3.

Our biggest mistake on our last trip was underestimating the power of the ocean. My husband took my two kids (10 and 7 years old) out with a boogie board. They were quickly swept out and could not get back to shore. Thankfully a kind man with a surfboard jumped into the water and rescued them one by one as I stood helplessly on shore watching. It was terrifying! We’ve been to Hawaii several times before on vacations and haven’t had any problems. I think it gave us a false sense of security. Lesson learned for sure.

The timing of this video is perfect! This is the weekend I'm finally, finally, finally going to book my trip! I've spent quite a bit of time doing the planning (perhaps overthinking a few things), but now it's time to actually make reservations and commit! I can't tell you how much you've helped me in this process!!! (And yes, that includes your itinerary for Hawaii.) I'm still a bit terrified of doing something wrong in terms of planning, but with all your help, I don't think I'll do things too wrong. Thank you!!

I'm a frequent world traveler. My advice on the jet lag is to pre-adjust yourself. You want maximum productivity (or relaxation time) away. If you start 3-5 days beforehand on the destination time you can greatly reduce the acclimation time.

When I went to Oahu recently, I rented a car but didn’t even use it much so it was a waste of money to me. Parking spots are very limited too. So we walked everywhere around Honolulu and it was so fun. The tour buses and guides were great for us first timers to explore the scenic spots and beaches when you don’t know where to start.

We just came back from our first trip to Maui and the family itinerary made our trip! I cannot say thank you enough for all of your content, but I would have missed so much and wasted so much time without that itinerary! Thank you for helping make our first Hawaii trip incredible! We will be back 🏝️

When I was in Maui in 2018, I did parasailing, a helicopter tour & finally a Lula. This was out of my comfort zone; but now I am glad I did it. Try something new on your vacation. You will not regret it. Aloha 🌴😎🤟

Definitely take advantage of the jet lag, we were visiting family on Oahu last year for an event so there wasn’t much time for sightseeing but our Airbnb was on the beach so I was able to get in the water and enjoy the sunset every morning before the kids got up. Especially when traveling with family, make time to take in the quiet moments.

Love you guys!! We went to the Big Island in April last year and it was a great trip. Your recommendations for beaches and local cuisine was spot on. Hapuna is still one of my favorite beaches of all time. I am super thankful for all you do!!

These are all amazing tips. My wife and I got back from our honeymoon in Maui about three months ago. From the moment she said “yes” to my proposal, I started researching various honeymoon destinations. A month later, after watching a few of your videos, we decided on Maui—the activities and vibes from your videos matched what we wanted our honeymoon to be like—particularly the overnight trip to Hana (we love a good road trip!). I then sorted through all of your videos and watched everything related to Maui in great detail—multiple times! I think 90% of our honeymoon activities and restaurants came from suggestions in your videos. I’m sure you hear it all of the time, but THANK YOU, thank you, thank you! You guys have amazing and wonderful suggestions! I don’t think our honeymoon would have been half as memorable without so many amazing suggestions! Now, for what we learned… a mistake to avoid. Take some time to relax! We were coming from the east coast, so to get the most out of our visit to Maui, we took the earliest flight out of Savannah to Maui and the latest flight back home. In all, we had 7 full days, a half day after arriving, and a half day before leaving. Because we thought this would be a once-in-a-lifetime trip, I crammed many of the amazing things your videos have covered into our visit. I didn’t want to regret missing something amazing. Sunrise on Haleakala, a day and a half roadtrip to Hana (with highlights at Twin Falls, Wai’anapanapa State Park, and the Pipiwai Trail), sunrise snorkeling at Molikini Crater, a sunset dinner cruise, a luau at the Feast at Lele, checking out the shops in historical Lahaina, farm tours (pineapple, coconut, chocolate), a special dinner at Mama’s Fishhouse, a doors off helicopter tour with Air Maui, lunch at Duke’s Beach House, shakes at the Burger Shack, seeing the Nakalele Blowhole up close, jumping off of Black Rock, ziplining at Kapalua Ziplines, visited beautiful Kepaniwai Park, had a Mai Tai at Monkeypod, used the GyPSy Guide app across the entire island (it was a lot of fun and very informative)… oh goodness, there’s even more, but those were the highlights! I even built in a “makeup” day in case weather forced us to reschedule or if we wanted to do something we didn’t account for. I spent the better part of 6 months planning everything—researched AirBnBs/hotels and car rentals (we went through Turo), made reservations for everything (as suggested), and used Google Maps to calculate drive times between activities and meals to ensure we had enough time to commute to everything. And in the end, we did a LOT, and we had an amazing, memorable time. But with everything we did, I think we forgot to relax! Quite frankly, I’m surprised we were able to fit in as much as we did. Luckily, the weather was very cooperative—barely a drop of rain, even on the Road to Hana. We have since vowed to come back to Maui (maybe as a major anniversary trip) and make it a bit more relaxing. We want to visit Kauai too (that was our runner-up honeymoon destination), so I’ll have to take my own advice when we visit that island. So our lesson—a mistake to avoid—is don’t over-do it. Relax. Soak in the Hawaiian vibes. If you want to do as much as possible, plan a longer trip. If you can’t afford a long trip just yet in your life, plan to come back (like an anniversary trip). There’s too much to see and do in a short visit. I’m glad that I was able to convince my wife to stay more than 5 nights, but even 8 nights wasn’t enough. I blame you guys—your videos are far too informative—you make everything look too enticing! LOL Thank you Erica and Jordan for your amazing work!

So my husband and I thought we could just grab a boogie board and hop in the water in Waikiki like we saw all the little kids doing. We both almost drowned and we both had to be rescued. The gentleman that pulled me out said he had been pulled out from the exact same spot 20 years earlier!! Treat the water, the waves, the ocean with the utmost respect!!

Heading over for the first time in April from Australia. Gathering lots of info from your guys videos. Thank you 🥰

Thanks for helping to educate tourist visiting Hawaii - It is so important right now. Locals get upset when tourists don't act properly or with no respect. Mahalo!

We are coming from the east coast in august leaving at 6:30AM landing in Maui at 12:00. We had the same idea you did and we booked our sunrise tour for the next morning since we will be on east coast time. We did Alaska this past August, jet lag is no joke folks. Good video great tips guys…..thanks

You two are awesome! We are arriving the first week of June with the kids, planning on staying in Maui/Kauai,I just purchased two itineraries Thursday thank goodness! So helpful

Continue to love watching your Hawaii video’s!! Learned so much. Also, love reading your newsletters!! Going to order the Maui and Oahu Itineraries soon!! Finally, going in May!! Mahalo for your knowledgeable information!! 🤙🏼

I absolutely LOVE LOVE LOVE your itinerary guide. I planned my whole trip to Maui with it and plan to use it while I'm there. Thanks again.!!!!!!!

This is a great video! You nailed it! I love that you mentioned taking care of the islands. Malama the aina. I think you would be doing the islands a great service if you did a video on aloha, treating the island and its inhabitants with respect and sunscreen. You have a lot of followers and although people mean well sometimes they don’t know so you have a great platform to help out. Your videos are refreshing and full of great information. Mahalo!

I’m surprising my wife with a trip over from Florida for our late honeymoon/anniversary. jet lag will more than likely hit us but we’ve been watching all your videos and just can’t wait to come visit. Mahalo for making these videos.