Hawaii: The Ultimate Guide to Your Maui Vacation

Hawaii has always been a dream of mine. What better way is there to get halfway around the world to a tropical paradise without even needing a passport? After stumbling on a pair of cheap plane tickets to Kahului, Maui’s main airport, I jumped at the opportunity for a winter escape and booked my Maui vacation.

I touched down in Maui mid-December, ready for some road-tripping and time in the sun. The weather was perfect – a sunny 75 degrees on most days (although due to the islands volcano and rain shadow effect, the weather varies dramatically as you travel from the windward side in Paia where its cloudy and rainy to leeward side in Wailea where its hot and dry). I had a total of 7 days on the island and am happy to say I think I covered almost all of it! Check out my itinerary below to see the best of Maui during your week in paradise:

Day 2: Road to Hana

Its time to conquer the Road to Hana! If you’ve done any research prior to your Maui vacation then you probably have heard of the Road to Hana. I was a little skeptical as it is over hyped on a lot of the travel blogs. Luckily, it did not disappoint! And the best part is that the Road to Hana starts in Paia on the Hana Highway, allowing you to wake up and hit the road early as to not get caught up in the traffic that start to form throughout the day.

Hana is the small town at the end of your journey where the road gets its name from. Its important to note that the Road to Hana isn’t about the destination, it’s all about the journey (cheesy I know, but everyone says it and its true!). Also, a word of warning, the roads do get winding and narrow. The bridges are all single lane and the turns can be harrowing so make sure you have an experienced driver. As treacherous as they might be, the roads are surrounded in beautiful scenery and half the fun was gazing out the window along the drive.

There a million cool things to do along the way and about a hundred apps and guides you can download. I highly advise you do this. Our app’s narrator not only give us tons of information on the history of Maui, but also pointed out places to stop I had never heard of. Search “Hana Highway” in your phone’s app store and pick an app (most cost some amount of money, we paid a well-used $0.99).

In addition, be sure to research that the stops your app suggests are not private property, illegal, or scared lands to native Hawaiians. Unfortunately, many guidebooks and other bloggers overlook this which leads to travelers trespassing and mistreating local land.  Below are a couple of my favorite spots along the Road that have been listed by the local Hana Highway Regulation’s Code of Conduct as suggested highlights that have been consulted upon by locals.

My Favorite Stops on the Road to Hana

• Ho’okipa Lookout: Want to catch a wave or just watch some lazily from above? This is one of the first spots along the Road to Hana. It has a raised parking lot and viewing area overlooking the incoming swells. You can watch the hordes of surfers fighting for the best and biggest waves
• Keanae Peninsula Point: We stumbled upon this almost by accident. We turned down a road off Hana Highway per and found ourselves driving up to a perfect lookout point. This spot has views of the surrounding coast line, complete with jaw-dropping cliffs and black lava rocks. Keep following the road around to see the waves shoot 20 feet in the air after crashing on the rocks.
• Waianapanapa State Park: This is a must-do! It was my favorite stop along the road to Hana. Although it gets pretty crowded, it’s still worth visiting. Check out the jet-black sand beaches, hidden caves, and ocean blowholes!

Time for a change of scenery. Make your way from rainy Paia to the Wailea-Makena/Kihea area for some dry, hot, and sunny weather. This area is in stark contrast from Paia’s surfer hippy vibes. Commercial and luxury hotels line yellow sand beaches that stretch down the coast. We rented an AirBnB in Kihea, right outside the glitz and glamour of Wailea, but still in close proximity to good food and beach options. Due to my obsession with warm weather and sun, this was one of my favorite parts of my Maui vacation. We spent two days exploring, soaking up some sun, and hitting the surf. I listed some of my favorite activities below.

My Favorite Activities:

• Maui Wine: Travel up into the mountains for glorious weather and unique wines. This is a bit of a ways to get to, but the car ride was half the fun. As you make your way up the mountain, views of the Wailea valley greet you from below. The winery is sitting on a picturesque landscape with plenty of outdoor space to sip while enjoying the weather. Inside is a tasting room where you can sample the unique wines – made from pineapples and raspberries. It’s so good you will want to ship some back state-side to enjoy after your Maui vacation, and you can! The winery has really good deals on shipping. Or if you just want to enjoy the wine the rest of your time on the island, grab a bottle from the winery before leaving or it can be found at most grocery stores in Maui.
• Makena State Park: Check out Big Beach and Little Beach! This is a spot you can’t miss is in Makena State Park. The clear blue water laps perfectly onto a long stretch of yellow sand. As the name suggest, Big Beach is the bigger beach at the end of the state park. It is easy to park and walk right up to the beach. You can access Little Beach via a trail from Big Beach, but be prepared, its supposedly the most well-known nude beach on the island!
• Lava Fields – Kings Trail: If you want to get up and close with the aftermath of a volcano eruption, check out the Lava Fields past Makena State Park. There is a well-marked trail that will wind you through fields of black rock, twisted into grotesque shapes.
• Maui Brewing Company: Taste-test Maui’s local beer selection by heading to its brewery! The brewery is in a beautiful glass building with plenty of space for outdoor seating. There is a variety of beers to choose from and food trucks are parked out front ready to take your order – what more could you ask for!

Day 5 – 6 : get lost in lahaina 

Ready for the third leg of your Tour d’Maui? Just a short drive from Kihea, make your way over to the ever popular Lahaina, known for luau and whaling.  This is Maui’s most popular destination. Here resorts line the famously sunny Ka’anapali Beach and tourists swarm Front Street. We stayed right on the edge of the action at the Hakuna Matata hostel. Lahaina is a good spot for water activities, including fun tours like whale-watching (if you are there during whale season in the winter months) and snorkeling. Below are the top things to do in Lahaina.

My Favorite Activities:

• Molokini Snorkel Tour: Thanks to an under-water ecology class I took in college (I know way too much about species of Caribbean reef fish), snorkeling is one of my favorite activities. Molokini is a crescent moon-shaped crater off the coast of Maui. It’s actually the top of a submerged volcano and is covered in underwater wildlife. We did a half day tour (several companies to choose from if you do some research online) and the experience was amazing! After our excursion into the various reefs filled with colorful fish, we sipped on some Maui brews and Mai Tais on our boat ride back to port.
• Ka’anapali Beach: Previously named one of America’s best beach, it’s no wonder with its miles of sandy beaches that fade into perfect blue water. You can pass a day here by just people watching and playing in the surf.

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