Maui
The island has two sides - A lusher/greener side with all the resorts and then a dryer side
Lush Side - Wailea vs. Lahaina area – I believe these are the two resort areas in Maui. We stated in Wailea. This area has the Grand Wailea, a 4 Seasons among others. Nothing on this document really is about the other tourist area (Lahaina, Kaanapali, Kapalua etc.). I’m sure both are great. If we were to ever go back, I’d like to check out the other area
Hana - Hana is on the opposite side of the island and is the last town before the dry side of the island that is more desolate
Hotel
We stayed at the Andaz (Hyatt) and really liked it. It seemed brand new (we stayed in 2017). They rented snorkel stuff and had solid snorkeling right off the property and even some sea turtles. Also they rent kayaks and stand up paddles which was fun and Morimoto restaurant is right on the property. Lots of pools and beach seating.
Restaurants
Morimoto’s was great and on the Andaz property.
Monkeypod was pretty good although if not staying really close by then you can skip in our opinion.
Mama’s Fish House is the most famous spot on Maui. We don’t eat fish and still went and it was good. Super Expensive though. It is kind of out of the way from everything so either go for dinner or on a day you are near the airport since It is close by. Also it has a beach so if you want to swim then bring swimming stuff.
Halekala
This is the big volcano on the island. Lots of people do the 2 AM or 3 AM early morning tours to see the sunrise and then there are tours where you can bike down which seem cool. We opted to do it ourselves and see the sunset. Left the hotel around 1ish (from Wailea) and drove and did a few short hikes as we drove up. The two hikes to stop at along the way. The first is the Halemauu Trail (10 miles), but you can just hike out like 30 minutes to see the look out which is what we did. The second is close to the summit and called the Sliding Sands Trail (also a longer trail) which travels downwards. If you only do one just do this one. You can just walk 10 minutes which is what we did and get the jist of it. It would be cool to go further though. Try to time it so you can get to the summit by Sunset. It’s amazing. BRING WARM CLOTHES and find parking at least 30 minutes before the sunset.
Surfing - I think there is one surf beach where they allow lessons in Maui so everyone will take you to the same spot I think in Kihei (10 mins from Wailea). We used Maui Wave Riders and had a really good experience.
Road to Hana
The Road to Hana is just a 30 mile windy narrow road that leads to the other side of the island from where most of the resorts are. Great for seeing waterfalls on the island and just getting a feel for the landscape on the green side of the island...The reason it takes a long time is because there are tons of pretty stops along the way. If you google "top stops on road to hana" you will get tons of options. You can also ask your hotel what they recommend. All the stops are not really marked by signs. Instead, you have to know what mile marker ("MM") you are looking for and then just pull over and park at the mile marker.
Most people do the Road to Hana in one long day driving to Hana and back. However, if you have time, spending the night in Hana is a great option. Here is what the Road to Hana would look like as 1, 2 or 3 days
1 Day – Do it as a day trip and wake up early and hit as many spots as you can and then drive back. This is what most people do. It’s a long day. Consider driving the back road to Hana and taking the traditional way home to go against the crowds.
2 Days – Take a slower pace and get in more stops and stay the night in Hana. Then do some of the spots and hikes past Hana and take the back road back.
3 Days - Do the Road to Hana. Spend the next day chilling in Hana with some of the stuff around there and then take the back road back.
I’d highly recommend option 2 or 3 but if you don’t have time, then the 1-day is fine and is what most people do. Everyone tells you to wake up EARLY to do it. I’d go along with this recommendation if you are going to Hana and back in the same day…if you plan to stay in Hana (suggested)…then you can leave a little later. We left around 10 am…the later you leave, probably the less traffic and people you have but avoiding the people on this endeavor is kind of a lost cause as it is probably the top thing to do on the island.
There are probably 50 possible stops you can make on this 30ish mile road. Don’t try to do them all. Plan a little ahead and pick some spots you really want to hit and then just see what else looks cool. Here are the ones we made and our thoughts…I bolded our favorite. There are tons of stops along the way and a lot of the best ones are probably the ones not in the guidebooks and the ones we probably didn’t even know about.
Paia - Town that starts the road to Hana. Lots of restaurants, stores etc. We got gas here and did a quick walk around. Nothing too special. Thai Spice is good for lunch.
Twin Falls - This is a top spot on everyone’s list. We skipped it because there were so many cars parked and we knew there would be other (less traveled) falls to swim in but still probably really cool. Generally the stops at the beginning of the road have more people since everyone sets out to try to do everything.
MM 9.5 - Waikamoi Nature Walk – Very quick trail (20 minute walk). Stop if you have lots of time but otherwise very skippable
MM 17 - Keanae Peninsula – This is a slight turnoff from the main road. Really cool views of the ocean that a lot of people miss because they don’t do the slight turn off. Also, you have to turn off here to get … the best banana bread I’ve ever had (see next)
Sandy’s Banana Bread - Hit the turnoff and it’s a little down the road. Just put it in your GPS and you’ll find it. Not sure how it compares to the Halfway to Hana banana bread but it was pretty great then drive a little further for some more cool ocean views.
MM 17 1/3 - Halfway to Hana – Ali got shaved ice here. Shack that sells banana bread people like and other goodies
MM 18.8 - Wailua State Wayside – Very quick lookout – worth the quick turnoff to see
MM 19.5 - Upper Waikani Falls (3 Bears Falls) – The deal for this one is that I would say it is a must stop if you are adventurous and want to swim. There are many other falls along the way that allow you to swim, but we found this one to be one of the prettiest with the least amount of people swimming…we kind of had it to ourselves. The reason why though is because getting down to the falls is kind of sketchy. If you want to go down to it, you have to pass the falls and just park a little higher up the road and walk down to it. Then there is a little entrance near the bridge which leads down to the falls. I got down in sandals but having real shoes or keens is much better.
Pua’a Kaa State Wayside Park – Another waterfall to swim in if you missed 3 Bears Falls or want another
MM 32.2 - Waianapanapa Black Sand Beach – One of the top stops on the trip. Walk down to the cool black sand beach. This one takes a little more time
Hana Town - We stayed here so got some of the food in town. Hana Ranch Food Truck has a really good burger. Huli Huli Chicken is also really good. I don’t think either is open for dinner. This is where most people turn back to Hana. We stayed in Hana so the following day we did some of these activities below…they would be harder to get to if just doing a day trip, but if you leave early enough its possible.
Hamoa Beach - I thought this was one of the best beaches of the whole trip. If you decide to stay in Hana or have extra time, this is a nice sand beach worth visiting
MM 45 - Wailua Falls – Cool waterfall but not worth seeing unless you are going this way for other reasons (seeing the seven sacred pools, doing a hike, or driving the backside).
MM 48 - Venus Pools AKA Waioka Pond – MUST STOP and my favorite spot on the whole thing. It is tough to find and not marked. You may see 1-2 cars pulled off the side of the road. It’s not on most Road to Hana websites but our conceriage told us about it. If heading away from Hana…it is at mm 48 (like right at the marker) and the entrance is literally at the bridge. You’ll be walking through the meadow towards the water. To get to the meadow you need to find the slight opening right at the bridge then you walk a few steps and then another slight opening in the barbed wire fence where the fence goes from barbed wire to just a metal cattle guard which you can easily climb through (sounds crazy but its worth it). There are two bars that you slide under, then it is a clear 3-5 minute walk towards the water through meadow. Once you get to the pool, you can either carefully walk down to the water (easier in keens or watershoes) OR what most people do is jump in. The cool part is few people know about it besides locals. Supposedly it goes back and forth between being open to public and not but it seems to be open. Watch others jump in first but there are some lower ledges to jump in from.
If you plan to stay in Hana
Ohe’o Gulch – Seven Sacred Pools – Only about a 0.5 mile walk and part of the National Park. Again this one is easier to see if you stay in Hana since it is past Hana. Very beautiful falls and pools…if you are running low on time though and need to get back to Hana, it probably isn’t worth it since it is well past Hana. Also, I think swimming was once allowed here and when we visited it was not allowed. I’d check this beforehand but if it is allowed then it could be pretty sweet.
The Pipiwai Trail – 4 mile trail (part of the National Park) – pretty moderate trail with just some ups and downs. Goes through a really pretty bamboo forest and leads to a huge waterfall. Can’t swim in the waterfall or get too close (at least when we were there). Great activity for if you stay in Hana for a day. Otherwise you probably need to skip. Takes about 2.5 hours. This trailhead is based out of the same parking lot as the seven sacred pools so you can easily do both in 3 hours.
Back Road- Try to get to this but don’t do it at night or anything. Take the back road back if you stay in Hana or in other word the road that circumnavigates the island from the other coast. People scare you off from this road saying “you don’t have cell service” and it “breaks your rental car agreement”. Honestly though if you go slow and carefully its no big deal. Only 5-10% of people go this way and the scenery is amazing. It also doesn’t even take that much longer at all. Not too many places to get out and stop – like the front road – more just a drive.
Big Island
Areas – Kind of like Maui, there are two sides – the Kona side and the Hilo side. The difference with this island I thought is unlike Kauai and Maui with a clear dry and wet side, The Big Island has volcanic rock all over the island so it is not as lush. It is also huge so don’t underestimate how long it takes to drive around the island.
Kona - This is where we flew in to and where we based ourselves. Lots of beach/water activities, high-end resorts and other activities on this side
Hilo – This is a town on the other side of the Big Island (opposite Kona) where tourists can base themselves to see Volcanoes National Park (45 minutes away as opposed to 3 hrs from the Kona side) and also to see Mauna Kea. The area does not have all the fancy resorts that the other side has and you get more of a sense of what Hawaii towns are like. You definitely do not have to go to Hilo but we had time and wanted to see Volcano National Park so it made that trip much shorter. If stretched for time you can have a long day and just drive there and back from the Kona side in a day which is definitely doable and lots of people do.
Hotel
Kona Hotel – We stayed at the 4 Seasons Hualalai near Kona. It was incredible. Hands down the nicest place we’ve ever stayed and would highly recommend. It is crazy expensive but the travel agent hooked us up with upgrades and free breakfast buffets etc. The hotel has everything you could ask for (3 pools, ocean front w swimming and snorkeling, great restaurants, golf, lap pool, spa, etc.)…LOOK INTO IT
Hilo Hotel – The Inn at Kulaniapia Falls. 10 minutes outside of town. Pretty basic bed and breakfast that we based ourselves in for two nights. Coolest part is the property has a beautiful waterfall that only guests can access to swim in, paddle board or kayak in.
Restaurants
Restaurants in Kona – Almost only ate at the 4 Seasons to use our meal credits but the Kona Brewery Company is nearby and was solid. Also, on the way to Hilo we stopped in Tex Drive-In for their famous Malasadas (donuts which were sooooo good)
Activities
Kayak in Kealakekua Bay – Really nice activity. I really wanted to kayak at least once and read this was a top place to go. We went through Kayak in Paradise. The kayaking was really quick and you go out to a bay with beautiful snorkeling. We had great conditions that day but had an annoying tour guide. Not a must do activity and not so much kayaking but really great snorkeling. Lots of tours see dolphins, but we did not.
Golf the Hualalai Course – Loved it
Swim with dolphins - We missed this but really regret it. This is one of few places probably in the world you can swim with dolphins in the ocean. There are a number of tour companies that probably do it (our hotel offered it) but essentially you get on a speed boat in the morning I think and try to find spinner dolphins that are swimming and then jump in the ocean and see if they play and swim with you. It is probably very dependent on the season but I wish we did this.
Manta Ray Dive – If you like snorkeling, scuba diving, or seeing huge marine life, then this is a MUST DO. You can elect whether to snorkel or scuba dive, then the boat take you out and all the tour companies congregate in one place to watch as the Manta Rays come to the area to feed. They almost always see rays but there is no guarantee. We scuba dove with the Company “Manta Ray Dives of Hawaii” but the boat also took out plenty of snorkelers. Snorkelers get a really similar experience and sometimes even better. We only saw one Ray who swam right by us on about four separate occasions. Only seeing 1 Ray was a “light” night so I can’t even imagine the experience of seeing a bunch which is probably more typical. It’s incredible and also great because the tours go out around 5 pm so doesn’t cut into beach time.
Sights
Mauna Kea – We skipped since we heard it is a very similar experience to Halekala (seeing sunset, stargazing) – but we heard it’s amazing. Try to go on a night where there is no moon and it is clear. Also, the U of Hawaii does free stargazing tours on certain nights so check beforehand. Also you need a 4X4 to get to the summit.
http://www.ifa.hawaii.edu/info/vis/visiting-mauna-kea/star-gazing-program.html
Hapuna Beach – Huge public beach. One of the top public beaches in Hawaii. Nice stop if close by but no need to go out of your way if you have a good beach at your hotel. If not, this is a great big sand beach to swim or play in waves.
Waipio Valley – Lookout over a vast valley and beach that some people hike in. Very neat if driving by on the way to Hilo like we did. Worth it if driving by or if you have time to hike.
Akaka Falls – Another quick lookout we did on the way to Hilo. Worth it if driving by, otherwise you’ll likely see other similar falls.
Volcano National Park
Worth a Full Day if you are on the Big Island. Drive the Crater Rim Road and the Chain of Craters Road and just get out in areas that look cool. We loved the Sea Arch. Then after these drives that took about 2-3 hours, we did a 2.5 hour (4 mile) hike called Kilauea Iki Trail. The hike goes down through a crater which is an amazing experience. There also happened to be lava flowing while we were visiting so we spent our whole afternoon 3 PM- 7 PM going outside the park and renting bikes to go bike out to the area where the lava is flowing into the ocean. Not going to write much about this because the lava flow is always changing but seeing the lava at night was sweet and a ton of fun.
NOTE: THIS IS THE VOLCANO THAT ERUPTED IN 2018 so check more recent info
Kauai
Kind of like the other two Islands – there are two sides you need to choose from – Princeville/Hanalei (the wetter probably prettier side) or the dry side, Popui, that has more predictable weather but not nearly as pretty
Hotel
We stayed at the St. Regis in Princeville. I would recommend it, but with a caveat. The hotel is clearly dated. It is hard to look past many of the areas of improvement that the hotel could have (even if this note is not a warning). Having said that….there is a ton to love about this hotel. To start, it’s setting is one of the most spectacular of any hotel I’ve ever stayed at, set atop a cliff overlooking the famous Hanalei bay and the start of the Napali Coast. The lobby and restaurants are also very nice and same with the rooms. It is more of the pool area and outside where you notice (but who knows…it was a Sheraton previously and maybe they just haven’t updated all parts of it). Still would recommend but also would look into VRBO in this area.
Activities
Sailing the Napali Coast: A MUST DO – choosing a tour operator is tough. The first thing to consider is where to leave from. If staying in Princeville, you’ll want to choose an operator that leaves from nearby (Hanalei area). Try not to leave from Port Douglas if staying in Princeville. We chose Captain Sundown and had a great experience. The boat doesn’t hold too many so you have plenty of space on a nice boat (I think they take 17 people tops). It is also a sailboat although we did not sail since there was not enough wind. We had a calm day but supposedly, it can get VERY choppy and rough, so if you are worried about sea sickness then maybe choose a bigger boat.
Hiking the Napali Coast (Hanakapai Falls Hike) - Hiking the famous Napali Coast is on the MUST DO list of most people on Kauai. We loved the hike but also, even as experienced hikers found it really challenging and at times a little sketchy. If you do the hike, just beware that it is tough and to have good shoes (and also not be afraid to get wet since there are river crossings)…I did half the hike with my feet soaked. The hike to the falls is 4 miles IN and 4 BACK (8 total). For an abbreviated version that is also much less difficult, you can experience the coastal part of the hike and just hike 2 miles in to a beach and 2 back (4 TOTAL). I think the decision to go to the waterfall depends on your appetite for some difficult hiking and also how badly you want to see/swim in a pretty sweet waterfall. You definitely won’t miss out though if you just go to the beach and if I went back, that is the version of the hike I would do.
Helicopter Tour - Amazing experience
Popui Beach - Large beach on opposite side as Princeville we checked out. Not a must since there are so many other beaches