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Hawaii Trip | Oahu (Honolulu) & Maui


On September 12th, 2010 my husband and I got married and the civil registration officer said, in front of our +100 guests, that by marrying me my husband had just made the commitment to take me on vacation to Hawaii on our 10 year anniversary. She was joking as Hawaii isn't the most common vacation destination for people living here considering how far away it is. Everyone clapped and laughed at her proposal (because it was a joke!), but apparently my husband took it to heart and in late February / early March of this year that promise was kept.

He had told me we were going on vacation to a more nearby destination and only a few days before leaving did he tell me we would be making the 23 hour trip Hawaii!

So, on early Friday morning, on the 24th of February, off we went to the airport to the first of several flights: Lisbon to London. A short flight, with a lay over of about 2 hours, before catching our next flight from London to San Francisco (10 hour flight). We also had a two hour lay over in San Francisco before getting on our 6 hour flight to Honolulu, where we arrived at 11 pm and finally checked into our hotel: the Hyatt Regency Beach and Spa.

There are 8 main islands in Hawaii, although only 6 islands to pick from and each with its own special characteristics, so it really depends on what you're looking for. Each is distinct, with its own climate and feel. We were only staying for 5 days (!) so we picked two islands to visit: Oahu and Maui. However, if you are going to enjoy a longer stay, take the chance to visit some of the other islands too. Just keep in mind that you may not want to spend all of your vacation in airports / airplanes while island-hopping, but it may be worth the while if you stay in Hawaii for a while and have the time for it.

Features of the Different Islands

Kauai - It's the oldest island in Hawaii and nicknamed the "Garden Island". Good option for a peaceful vacation as you will get the rural feel throughout.

Oahu - The most urban and also most popular island in Hawaii, with the greatest population density in the island chain. This is a great choice if you're looking for good opportunities to shop and enjoy some nightlife (Waikiki Beach resort district, for example), but not so much if what you want is a calm and serene vacation. You can also get great insight into the Hawaiian culture and history here (for example, the Pearl Harbor Memorial).

Maui - The second largest island in Hawaii. It is a very popular tourist destination and can at times be very crowded with tourists, but is in general very calm. The famous "Road to Hana" is a great day trip in order to check out the beautiful waterfalls and beaches along the way. As many say, "the "Road to Hana" is not about the destination, but rather the trip"! If you're craving some nightlife while you're in Maui, visit Lahaina as there is more hustle & bustle there, in comparison to other areas in Maui.

The Big Island - Mainly rural and undeveloped, The Big Island, or Hawaii Island, is the largest of all Hawaiian Islands... and that keeps on growing as the active volcano on the island keeps gushing out lava! The island's newness means that there aren't as many beaches and the ones that there are are most black and grey sand beaches. The wide array of climates all in one island, from tropical rain forests to snow covered mountains, make this island very appealing.

Molokai and Lanai - These are the two smaller islands, off the coast of Maui, and are mainly underdeveloped with only a few local residents and a few resorts and golf courses. Basically, virtually no tourists, no nightlife, deserted beaches and pure country life; hence, the best islands if you're looking for quiet, empty beaches and pure serenity.

Niihau and Kahoolawe - although they are part of the main Hawaiian islands, the first is a privately owned island and the second is uninhabited, and access is prohibited.

We were only staying two days in Honolulu before catching our flight to Maui so we had to make the best of what that beautiful island had to offer in that short stay.


Our Day-by-Day Itinerary

Video available here

Day 1 (Honolulu)

  • 7:30 am - Walk around Waikiki Beach along Kalakaua Avenue. We then caught bus nº 22 (you can then switch to nº 23 or 24) to visit the KCC Farmers Market. We ended up walking all of Monsarrat Avenue to get there.

Fact: Waikiki Beach was once a "playground" for Hawaiian Royalty.

  • 9:30 am - Walked up Diamond Head Trail from the Farmers Market (its nearby) and then up to the Diamond Head crater. Its a pretty tough walk for some so make sure your wearing comfortable shoes and don't forget your bottle of water. After the winding hike up the mountain, you're already out of breath when you suddenly find a few flight of stairs and a tunnel before reaching the top and finally taking in the beautiful scenery from above!

  • 11:00 am - Unfortunate idea to walk from Diamond Head to the Kahala Mall! You get some beautiful views of the luxurious millionaire homes while walking the Kahala Ave but it's a very, very long stretch! We could've just taken the bus but were feeling extremely "adventurous" after hiking up to Diamond Head. Bad move!
  • 2:00 pm: After lunch we got bus #22 to Hanauma Bay, rated the #1 beach in the US. Its a 20 minute bus ride but you get the chance to really see beautiful untouched nature landscapes. It costs $7.50 to enter the park and before entering you have to watch a video about the importance of wildlife preservation. The water was somewhat cold (for me, anyway) but you can tell just by looking at its color, the level of transparency and cleanliness, making it one of the best snorkeling spots in the world.

  • 4:50 pm - Bus back to Waikiki. Make sure you get there early, as the bus is typically very full.

Additional note: be sure to take a sweater or light jacket as it seemed that all of the buses we get were always extremely cold!

  • 7:00 pm - Dinner at the Royal Hawaiian Center. It's a large shopping center with many food and restaurant options, from more gourmet dining to your more basic fast food options. We just ate a slice of pizza since we were so beat from all of the walking on that day! It was too bad because the night life at Waikiki is astounding - a bustling city with so many options for dining, shopping, having a drink, etc.

Day 2 (Honolulu)

Completely beat from our over 13 miles (21 km) walk the day before, we decided to take it easy -- especially considering our jet lag was getting the best of us and we had woken up at 4 am!

  • 6:30 am - Had breakfast at Eggs 'n Things. Highly recommend getting there early because a line starts building up at the door after 7:30 am! It has an old, diner-like feel but the food is well worth it!

  • 8:30 am - Caught the Waikiki Trolley (2 person day pass for the purple line cost us $25 per person). Definitely not worth it considering the only thing worth visiting on this line in the Pearl Harbor Memorial and considering the price it wasn't worth it. We would have been better off just taking The Bus (the public bus transportation) - they're always passing by whereas the trolley only goes by every hour or so.
  • 9:15 am -  Visit to the USS Arizona Memorial / Pearl Harbor Memorial - a great visit to get the history behind it. It's far away from pretty much everything, so make sure to keep in mind the time for your next bus (or trolley).

  • 10:15 am - Since we still had a long wait before our next trolley, we walked to the Aloha Stadium to see the Swap Meet market. Its a 10 minute walk (in a not very good path) from the Pearl Habor Memorial but was worth it because it's great for souvenirs and seems to cater to many locals too.

  • 11:15 am - Waikiki Trolley back to Waikiki Beach
  • 12:30 am - Quick lunch at Giovanni Pastrami sports bar. Nothing beats a pastrami sandwich and a beer when you're tired!

  • 14:00 am - Walked around Waikiki for some more shopping and coffee before heading off to the airport.
  • 16:45 pm - Hawaiian Airlines flight from Honolulu to Maui (40 minute flight)

We arrived at Maui airport at around 6 pm and picked up our rental car. Its was a 25 minute drive to the Wailea Resort on the south shore of Maui. It's a luxurious resort community with world class beaches and golf courses. We stayed at the Residence Inn by Marriot. The hotel itself was a good option for us considering it was a very recent hotel (opened about 6 months ago) and, although it's only 3 stars, the fact that it was brand new made you feel as if you were in a 5-star more luxurious hotel. We highly recommend! Also, it's only a 15 minute walk to the beach, so a good option considering the rates at the beachfront hotels.

Everything in Wailea (and Hawaii as a whole, I guess) was pretty expensive and although you have a small supermarket in the resort area (our room was a studio, so we had our own kitchen), we ended up buying some groceries at Safeway in Kihei.

Day 3 (Maui)

  • 8:30 am - The start of our extraordinary "Road to Hana" trip!

  • 10:00 am - Stopped for coffee at the historic town of Pa'ia in Maui's north coast. There are some lovely shops and it's a great stop to feel the town's vibe.

Along the drive to Hana, the amount of stops are endless. We already had an idea of some of the places we wanted to see, but ended up stopping at many more. Basically, wherever we a stop with lots of cars, we figured there was something worth seeing and would stop too!

  • Twin Falls - First accessible waterfalls on the Road to Hana at mile marker #2. Absolutely gorgeous!

  • Wailua Valley State Wayside - Beautiful views into Ke'anae Valley. From the park you can also view waterfalls, the Ko'olau Gap, Wailua Peninsula and the rim of Haleakala Crater. This is also a good stop for a bathroom break.

  • Halfway to Hana - Self-acclaimed best banana bread in the world. I think that's questionable but we were hungry so it did taste like the best banana bread I'd ever eaten. Also a good stop for a bathroom break if you missed the Wailua Valley State Wayside.

Tip: Make sure you go to the bathroom whenever you get a chance as many stop's don't have restrooms. We got stuck on the road for quite a while due to a landslide and were lucky enough to have stopped earlier to go to the bathroom.

  • Upper Waikani Falls - Also known as Three Bears Falls because there are two larger falls and one smaller fall. This is a great stop to get some photos.
  • Upper Hanawi Falls - Also a great stop for photos along a bridge.

  • 1:30 pm - We had lunch at food trucks right before reaching Hana. We had the traditional Island Fish Taco and Kalua Pork Taco for only $7 each!

  • 2:00 pm - Wai'anapanapa State Park - Highly recommend this stop right before reaching Hana to visit Pa'iloa Beach (Black Sand Beach). This beach is made of volcanic rock with black pebble lava remnants created by lava flows several hundred years ago. Other things you can visit here a blowhole, freshwater caves, lava tubes, cliff jumping and overall beautiful views.

We reached Hana shortly after and didn't really find much to see there so we just grabbed a cup of coffee and turned back around. There are folks who like to continue, but make sure your rental car allows that, as many have restrictions in that sense because of the overall quality of the roads after that.

  • 2:30 pm - Return back to Hotel through Hana Highway. The trip back was slightly tougher because we got heavy rain on the way back. Also, since we didn't make nearly half as many stops as we did going to Hana, my husband got car sick from all of the twists and turns (620 curves and 59 bridges in total)!

Tip: make sure to check the weather the day before the trip. 

  • 5:30 pm - Back to our hotel where we then got an Emergency Flash Flood Warning on our cell phones and stayed in for the rest of the evening because of the bad weather.

Day 4 (Maui)

  • 8:00 am - Breakfast at the Hotel
  • 9:30 am - Long walk along the Wailea Beach Path. It is approximately 1.5 miles and the scenery is beautiful as you walk along the beach in a path built in front of all of the beachfront resorts.

  • 11:30 am - Back to the hotel for lunch
  • 2:00 pm - Visit to Maluaka Beach, or Turtle Beach. It's a 15 minute drive from Waileia in the Makena southern district. The turtle shells are brown and can sometimes be mistaken for rocks, so keep your eyes peeled. Unfortunately we didn't get to see any turtles but the beach is wonderful.
  • 2:20 pm - Makena State Park - There is a beautiful uncrowded beach here, very popular for sunbathing and bodyboarding by both locals and tourists.
  • 3:00 pm - Visited downtown Kihei, which is a short drive from calm Wailea. There is definitely more hustle and bustle when compared to Wailea as it has several beachfront hotels, condos, and shops.

  • 4:00 pm - Visited The Shops at Wailea shopping center for some last souvenir shopping. It has some of the top brands such as Gucci, Louis Vuitton, Swarovski, and Tiffany & Co. 

Considering all of the walking and hiking we had already done since arriving at Oahu and Maui, and considering the weather was still not that great, we decided to make it more of a "chill out" day at the hotel and bar area, and had some much needed rest.

Day 5 (Maui)

  • 08:00 am - Breakfast at the hotel

  • 09:00 am - We took off to the helipad located near the airport in Kahului. There are several companies offering helicopter rides to choose from but after going through hundreds of reviews we ended up choosing Blue Hawaiian (unless you have some sort of special discount, prices don't really vary all that much between companies).

Tip: If you're far from the airport area and afraid the weather may not allow you to take the helicopter ride, make sure you call in advance.

  • 10:00 am - The weather kept getting worse as time passed so, as we had already expected, our helicopter ride over Hana Haleaka was cancelled due to poor weather conditions (please note, that contrary to some of the reviews we saw, we got a full refund).

  • 10:15 am - We had lots of time to burn before our flight so we decided to explore the western side of the island. We stopped at Lahaina and took a stroll down Front Street.

Fact: Lahaina was once the capital if the Hawaiian Kingdom and you'll find several shops and galleries to visit there.

  • 10:40 am - a little north of Lahaina, we stopped at Kaanapali, the original resort destination of Maui. We took a few moments to absorb the beauty around us and if you have the chance take a walk along the 3 mile long white sand and crystal clear water beach.
  • 11:00 am: Continued along northwest Maui and at the foot of the west Maui mountains we stopped at Kapalua and then turned back around to Lahaina for lunch.

  • 12:30 pm - We had lunch at the Lahaina Fish Co, a waterfront restaurant on Front Street in Lahaina, where we ate some of the the best traditional dishes. They have great choices, such as ahi sashimi, steamed clams, lobster ceviche and a lot of varieties of fresh Hawaiian fish favorites. I had the wonderful Ahi Poke Tacos (yummy!)

We took off after lunch onto the airport and started our 23 hour trip back home from Maui to San Francisco to Boston and, finally, to Lisbon.

A trip to the Hawaiian Islands is truly a unique experience as there is so much to see and do so make sure you plan your itinerary and what you want to visit ahead of time.

We hope to have helped give you some ideas for your Hawaii Trip!

-  LX Crafts Co

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