The most important thing to determine when planning a trip to Hawaii is which islands to visit and thereafter how many days to spend on them. My picks were Centered around meeting my college friend who lives in Oahu so that was definitely going to Be my base. She recommended adding on Maui to my trip so that was it - decision made. However, once there I was regaled with tales from other tourists on how amazing Kuai is and how doing a lava tour on the Big Island is the "best thing we've ever done!". So as you can tell, there is no easy answer to this.
From my experience, Oahu (home to the famous Waikiki beach) is great if you have friends there or if you want a fill blown tourist experience with shopping, best in class restaurants and a little bit of city/island. If you want to get away from the crowds, do NOT go to Oahu - it's tourist paradise and you will get crowds at every tourist spot you visit.
Another important thing to note is that you have to fly inter-island and once you land renting a car is a necessity. Hence, with all the logistics the entire process will still take up half you day so it visiting for a less than 8 days, at most you can see 2 islands!
Also, suggest renting cars, booking tours etc all in advance online. I didn't see any price difference by booking on location (as i usually do) and given the number of activities there are, it's best to have a clear idea of what you want to do in advance specially if you are in a group.
Further, Hawaii is expensive. It's part of the USA and is frequented by tourists from the mainland and Japan so if you are thinking of Asian beach fun at cheap rates, think again!
Finally, and very important- you can book flights into one island and fly back to the USA from another island - this saves you a lot of flying time so check connections to and from the islands you wish to visit.
So here's a snapshot of how I spent my time on the islands - hope this helps you get into the island mood!
Day 1 - Landed in Oahu around 9:30 pm, smooth car pick up and the GPS (most of the time I used both google docs and GPS to navigate - i strongly suggest relying on both) brought me to my friends house. After a super warm welcome I crashed. Drive directly to Diamond Head Crater the next morning. It's an easy hike up (has one stretch of steps) but was super hot and really crowded- i was told to avoid sunrise and sunset hence picked 10 am to visit but it was still totally packed. The views from atop are great but given the number of options for hiking and scenic views in Oahu I thought this can be skipped.
Next, I had a surfing lesson at Waikiki. My instructor was a local college student and while he made the lesson fun, the waves were not strong at all and he was a bit casual in his training, not really focused on form and technique- so for all the hype of learning surfing in Hawaii I was disappointed and did not upgrade to 3 days of lessons as I had originally planned (surf lessons are easily available everywhere, so don't lock yourself into these). I then hung around Waikiki and then drove over to Ala Moana beach for my stand up paddle board yoga class. This beach is away from the crowds of Waikiki and is used more by locals. Learning how to balance on a surf Board (company is called yoga floats and you can pay for a single class - in advance online) while doing yoga poses with the sun setting in the background was a truly awesome experience. Locals and expats who are based in Hawaii are super warm and welcoming (for the most part!). Everyone wants you to enjoy their "home" so they are willing to share ideas/tips etc. Post this, I met my friend at a Japanese Hot pot place that luckily had a yummy mushroom dish that was pure vegetarian. Hawaii is known for meat and sea food so you can't really eat the local food. There are several Thai, Italian, Korean, Mexican places but you need to find them online and ideally book a table.
Day 2 - The next morning, I decided to get out of the Waikiki area and drive East to Lanai beach (some rate this the best beach on Hawaii). You can drive east by going on the longer but super scenic drive along the coast or use the highway that cuts through mountains.
My GPS obviously guided me to the shortest path but along the drive I came across some scenic view points. The East coast of Hawaii is gorgeous and the beaches are not teeming with crowds. The waves here are very mild and beaches are all white sand making the swimming and lounging experience superlative and relaxing. All beaches in Hawaii by law are open to the public and most have secure Parking lots right next to them making it super easy to enjoy a day at the beach. Most beaches in residential areas however do not permit any selling of foods or commercial activities so you should pack your food / drink and book your surfing / kayaking etc lesson prior to going to the beach.
I drove around and explored the beaches around the area and followed the food tips my friend Shireen had shared with me (copied below) making the afternoon ideal to recover from the soreness of the hike, surf and yoga from the previous day.
I had a 3:30 booking at the Kualoa Ranch which is about 40 minutes further north of Lanai beach. The drive up was gorgeous and I discovered many many beaches where one can stop, some with barely any people.
My tour was a 2 hour ATV ride along someone's private ranch cutting through mountains and valleys and in parts overlooking the Pacific Ocean. The ATV ride itself was thrilling since the roads were slightly hilly and curvy and the views were outstanding. The ranch has been used for shooting several Hollywood films so the guides take you to the spots and show you around. For families where everyone can't ride they had an option to rent a small cart that fits 6 where just one person needs to drive. Great tour - strongly recommend carving out enough time for the drive and stopping by a coffee / nut plantation enroute as well.
Finished the tour around 5:45 and drove back to Ala Moana to the Modern Hotel rooftop to meet my friend. Every Friday, the city organizes a free fireworks show and the rooftop bars have the best views!
Post this, we walked to a Mexican place in Waikiki. Every restaurant in Waikiki we went to had great food, superb vibe and lots of energy. But the places are busy and loudish so if you are looking for the peace and quiet of an island then Waikiki is not for you.
Day 3 - since it was Saturday, my friend had the day off. She was driving us to the North shore (famous for high waves and whales during winter season). We started off along the scenic east coast drive Butit began to rain so we drove the other way around first and visited the Dole plantation to eat pineapple ice cream at the farm. They also have the "worlds largest maze" and a train ride - very child friendly. After this out stop we drove up North to Halweia town. We walked around the shops (lots of cute boutique stores) and ate a delicious lunch at Sprouts Sandwich store.
The vibe in the north shore is much more laid back. There are way fewer tourists here making it much more relaxing.
We continued driving and making short stops. Stopped on the famous beach to see turtles crawl up on the beach - incredible! We then decided to drive to Turtle Bay resort and stop for a quick drink. The poolside of the Hotel overlooks the ocean where surfers take lessons. The Hotel also had a small shop where we found some cool souvenirs.
Then we continued our drive back to Honolulu along the coast. For dinner that night we went to Throm Thai (again in Waikiki). Amazing food! Then we walked over to Sky Waikiki (super snobbish place / didn't allow us up cos someone was wearing slippers!).
Day 4 - I decided to hike up an old railroad trail that has essentially become an outdoor stair master for serious gym goers. It takes about 25/30 mins to dive to from Waikiki and there is plenty of free parking available. The climb up took me over an hour and was no mean feat. I recommend doing this if you are in good shape or looking for a challenge. The views all the way up are rewarding an you can turn around and climb down whenever you like. Along the way, I encountered a 70 year old man who was using crutches, few guys who were climbing with heavy weights in their hands, a 4 year old child and even a pregnant woman - they formed my inspiration for the KOKO head trail.
I returned to my car with wobbly feet and knew that a swim in the Pacific was my only remedy. I drove directly to Waiamonala beach (my local friends favorite beach) and swam in the blue green waters till I felt the soreness wearing away.
For lunch I drove another 25 minutes to the Kaihulu Hotel (a luxury resort) where i ate a veggie burger at their poolside overlooking the ocean. This resort also has a dolphin pool with 5-6 captive dolphins and organize "swim with dolphin" trips in the safety of their pool.
Thereafter I headed to the Ala Moana shopping centre (meeting point to see my friend and her mom). The malls in Oahu have pretty much every brand from the mainland spanning high end luxury stores, to Macy's and Bloomingdales to smaller local designers. It's a newly built mall, is gigantic and can take care of pretty much all your shopping needs.
For dinner we headed back to Waikiki and after some restaurant hopping finally ate a veggie Bi Bim Bap at a small Korean restaurant - delicious :)
Day 5 - The next morning, I first drove to Pearl Harbour - they issue out free tickets to one part but I had been checking before I left India and they were sold out (all the tour agents must be booking them). Since I was riding solo, I decided to take a chance and managed to get a ticket for an hour later. There are 2 small exhibits there too that you can see for free, helpful to provide some context on Pearl Harbour. The tour itself was very disappointing. They basically take you on a small boat to see the USS Arizona (ship that was bombed and completely sank). All you can see is some totally rusted bottoms and oil leaking from the fuel container. For those going to pay resort to the martyrs it is a good stop but as a complete tourist I felt I could have easily skipped the tour (preceded by a 15-20 min film that was compulsory).
I continued driving West (less touristy part of Oahu) to reach a man made lagoon area. 4-5 large hotel chains have monopolized these lagoons and built hotels right near them. I drove to the four seasons and through the hotel made my way to the lagoons. I walked along the lagoons and swam in them (extremely child friendly, safe and no waves). For lunch I grabbed a sandwich and coffee at the quick coffee shop at the four seasons and ate it while enjoying the gorgeous views.
Next, I made my way back to the unavoidable Waikiki area one last time to try my hand at rifle shooting. I found around 5 gun ranges in Oahu but the waiki gun club was the most affordable and convenient one. I parked in the near by parking lot and walked over (3 minute walk). The range is small but very clean and well run. It's also open till about 10:30 pm. The instruction was decently helpful too and showed me how to take aim. I was done in about 45 minutes and then drove to the airport to return my car.
Getting back to the car rental place was tricky since I couldn't find a gas station near the airport resulting in lots of loops and some stress. So suggest, checking with your concierge and mapping to the gas station closest to the airport first and keeping enough buffer time in case you get lost like me!
Reached Maui around 8:20 pm and waited for the shuttle to the rental area. Then picked up my car and drove to the hotel to arrive around 9:45 pm. Stayed at the Maui Coast hotel in Kihei. This is a stretch that has hotels on either end and the entire coast line along one end as well.
The hotel room was large and very comfortable but there was no one to help with luggage, the restaurant was closed, no one answered for room service and in general the place was very quiet. I learned soon that unlike Oahu, Maui and the other smaller islands wind down by 10'pm. Since no restaurants were open, I made my way to the ABC general store and stocked up on fruits and bought a wrap from their cold deli area.
Day 6 - I had to be at the Kihei Harbour (just a 4 min drive thankfully!) at 6:45 am for my 7 am snorkeling tour to Molokini crater. There are many versions of this tour available but I booked the roughest / most adventurous one where they take you on an old military raft into the ocean and do 4 snorkeling stops while showing you the tip of the Maui coastline. The tour was superb, the guides a bit odd (unfriendly at start but got really helpful toward the end when they wanted their trip advisor ratings). The company is called Blue Water Rafting and i booked it on Adventure Maui ( after doing multiple price checks). The highlights were snorkeling with 120 feet depth visibility in 1 location and swimming with giant turtles in another spot. They served us a sandwich lunch on the boat and we were back on shore around 12:45 pm.
I decided drive to the eastern coast of Maui to Lahaina next to explore Kaanpali beach and the shops in Lahaina.
The drive was along the coast line again and very pretty - took about 45 minutes. I wandered the tiny shopping street in Lahaina but after Oahu the shopping here seemed more pricey and not as good. There is a cute gelato place with a backdoor patio / seating area where I hung around for sometime.
I then drove to Kaanpali which again has mild waves and soft sand - I swam there for a while and then drove to fridas beach house (Mexican restaurant) in Lahaina. Delicious food and great service!
It started to pour around 6 pm, so I rushed to my car to drive back to the hotel to retire early for my 2 am alarm setting!
Day 7 - I had booked a sunrise cycling tour on the Haelakala volcanic crater. The company picked me up at 2:30 am, then after more pick ups we reached the start point of the tour. Here they have us wind proof jackets and pants and gloves to go along. We drove up to the top of the crater to arrive at 4:00 am or so. Sunrise was at 4:52 am. We hung around in the freezing cold to see this "glorious" sunrise but honestly I thought this was way too hyped. I literally froze in the cold and the vistas were nothing to write home about. The fun was about to begin.
They company then drove down for about 5-7 minutes to a starting point for our 26 mile cycling ride. The entire ride is downhill so there is no effort / energy needed per Se. However, I'm not an expert cyclist so going downhill at 15-25 miles/hour on steep super winding roads with traffic coming up on the other side of the road was quite a thrill. I went with a group called the Maui Mountain Riders (excellent guides, very helpful, very safe and fully guided tour unlike many of the others). The ride was amazing as were the views down. We made some stops in smaller towns of Maui and drove past some millionaire homes. Not to be missed excursion! I returned to the hotel around 11:30, took a nap and then headed to the Andaz Maui (also in Kihei so just 7 minute drive) for lunch. This hotel has a Japanese restaurant by Morimoto but lunch was closed when I reached. I ate an avocado roll and then hung around their pool side for 2-3 hours since it began to pour.
Around 5:30 I decided to explore the area and kept driving straight on Kihei road till I hit Makena State park - yet another large beach with great views. It was slightly wavy so I decided not to swim but walk along the wave break area. As I walked, I saw a rainbow emerge. First, in part. Then, in full. And literally for the time I saw a full 180 degree rainbow form before me - magnificent!
Next, I drove to the four seasons hotel (2 minutes away) to enjoy the sun set from there. I ate at their Italian restaurant - over over priced, small portion and too much snob value and then returned to my hotel to pack my bags and check out by 7 am the next morning - for my self driven road to Hana tour!
Day 8- I checked out of the hotel with all my luggage and began the 3 hour drive to Hana. Touted as one of the best drives in the world it truly lived up to its reputation. A winding road mostly 1 lane each way (sometimes merging into 1 land roads and bridges) with multiple stops along the way makes you feel like you are headed to a mystical land of fun and fortune. Stop to eat local fruits, banana bread, ice cream, soak in waterfalls, black beaches or simply admire the views and look our points - there is something for everyone one! Get a list of the stops from the internet/ hotel concierge before you leave the hotel. Self drive this and don't take a tour - you should do the drive at your own pace and make the stops you want to. The stops are all marked but you can miss them if you haven't printed out a map / stops to follow. Carry lots of sun block, wear yr swim suit and bring beach sliders (for pebble beaches and rocky climbs) to make the most of the day. There are plenty of food stops so you don't really need to carry any food with you.
Factor plenty of time for the car return at the airport again (my GPS and google map were both pulling me in different directions and I would have missed my flight despite amply buffering since one of the roads was closed down. The rental is right near the airport terminal so follow the signs carefully.
I left from Maui to San Francisco with various shades of emotions for Hawaii. I will return to explore the other islands someday!
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