Hawaii Getaway: Exploring Maui on a 4-Day Weekend

The Road to Hana, Maui, Hawaii | TheWeekendJetsetter.com

After 1.5 years of living on the west coast, I finally made it to Maui for a long weekend in early November – and not going sooner may be one of my biggest regrets! Maui blew away my expectations and was one of the best island destinations I’ve visited with the perfect mix of amazing weather, gorgeous beaches, scenic road trips and outdoor adventure. Plus, it wasn’t as expensive as everyone says (if you do it right…).

Where to Stay in Maui

Big Beach, Maui | TheWeekendJetsetter.com

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There are a few different options of where to stay on Maui, and what you’re looking for in a vacation will have a big impact on which town will be best for you.


Touristy Wailea is home to luxury resorts and golf courses like the Four Seasons and Grand Wailea. It offers easy access to beautiful beaches (like Big Beach, pictured above) and snorkeling sites as well as the Shops at Wailea, an open-air mall offering a wide range of stores. Wailea doesn’t have much of a nightlife scene, although there are a couple restaurants worth visiting. The upscale neighborhood has a much older crowd with several condo communities that seemed to be populated mostly be retired people, and everything tends to wind down around 9pm (which isn’t a big deal – keep reading!).


Kihei is close to Wailea and is more of a “normal” neighborhood where you’ll run into a mix of Hawaii natives, tourists and transplants from the mainland. It’s a little more affordable than Wailea in terms of eating out and offers a wider variety of restaurants and stores within strip malls – ideal for travelers on a budget. Kihei is one of the few places in Maui that has a nightlife scene, although it’s still small and condensed in one area. Its location is probably one of the most convenient if you’re looking to explore the whole island given how central it is.


In West Maui, Lahaina and Ka’anapali make another very touristy area, although more affordable and family-oriented than Wailea. Many popular tours depart from Lahaina, and the beaches here tend to be more crowded than others. They also have more amenities, like restaurants and stores right on the beach. There are also multiple snorkeling and diving options – we actually went diving here!


Kahului is probably one of the most heavily populated parts of Maui, and it’s where the airport is located. There’s not much to see and do here as a visitor, but it’s a short drive to touristy areas.


Paia is a small town located at the beginning of the Road to Hana, about a 10-minute drive from the airport. The bohemian area is one of the few places in Maui that’s completely walkable, with plenty of colorful storefronts and restaurants. It also gets very crowded around lunchtime, so if you’re planning to go here, be aware that you may need to hunt for a parking spot! I thought Paia was super cute, but wouldn’t recommend staying here unless you’re an advanced surfer. The beaches aren’t very swimmable, and I was turned off by the public drug use by its sizeable homeless population (apparently, there have also been several incidents of tourists’ cars getting broken into, too). I’m on vacation from San Francisco, thankyouverymuch.


Hana is located, obviously, at the end of the Road to Hana. It’s a pretty quiet and small town that definitely doesn’t require an overnight. Although, if you’re on an extended trip to Maui and want to be more leisurely on your Hana roadtrip, it could be worth a stay. There are a couple restaurants and places to stay here if so.

Where did I stay? We stayed in an Airbnb studio condo in Wailea and found that it was conveniently located to all the stuff we wanted to do. The area was definitely a little ritzy, but since we were driving around most of the day, it met our needs and was more affordable than a hotel. The one night we did want to go out, it was easy and not too expensive to grab a Lyft to Kihei!

Things to Do on a Weekend Getaway to Maui

Remember when I mentioned that it’s not a big deal that almost everything in Maui closes at 9pm? That’s because everything gets started around 6:30am. If you’re taking a tour, expect that it will depart around then, especially if it’s on a boat as the water gets choppier in the afternoon. I kid you not, we were heading out the door at some extremely early hours for a vacation every day!

But really, it didn’t matter because of a beautiful thing called jet lag. Maui is three hours behind San Francisco. So 9pm Maui time is already past my bedtime! This made waking up obscenely early a breeze – in fact, I woke up before my alarm went off every single day.

Weekend Getaway to Maui, Hawaii | TheWeekendJetsetter.com

Diving & Snorkeling in Maui

I love snorkeling and exploring the underwater world and can say that hands down, Maui is one of the best destinations I’ve visited in terms of marine life and coral. When I was planning the trip, I was eager to visit Molokini, a crater that boasts some of the world’s best snorkeling. However, boat trips were costing upwards of $100 per person!

Little did I know that Maui offers tons of incredible snorkeling and diving right off the beach. We swam with sea turtles multiple times in Makena and Lahaina, explored the pristine reef of the Ahihi-Kinaui Natural Reserve and even tried diving for the first time in Ka’anapali with Maui Diving Scuba Center.

Photo by Jeremy Bishop on Unsplash

Because my underwater iPhone photography is awful… here’s a photo by Jeremy Bishop on Unsplash

If you’re visiting Maui, there’s no need to blow your travel budget on a pricey boat trip just to snorkel. Especially when you consider that for pretty much the same price, you can go scuba diving. Instead, rent snorkels on day one (we got ours from Snorkel Bob’s).

The Road to Hana

The Road to Hana, Maui, Hawaii | TheWeekendJetsetter.com

I was a little bit on the fence about doing the road to Hana, because I’d heard mixed reviews. Generally I’ve found that whatever the “number one” tourist attraction is in a destination is overhyped and crowded. So when I read horror stories about the road to Hana drive taking 10 hours and hitting over 59 one-way bridges, I wasn’t exactly raring to hit the road!

In the end, we decided to go for it and I’m so happy that we did! Yes, we did spend 10 hours doing it – but the beauty along the way was well worth it. We saw – by my rough estimates – a bajillion gorgeous waterfalls. We also saw some pretty epic beach, ocean and mountain views. The reason it takes so long is that you want to stop constantly!

Everyone writes that the road to Hana is about the journey, not the destination, and it couldn’t be more true. That’s why I wouldn’t recommend doing it without downloading the Gypsy Guide app. This app is like having a tour guide right in the car with you for only $6. It’s triggered by GPS to tell you what you’re driving by, when to stop and even offers suggestions for lunch! Honestly, this app made our trip. The “guide” is super informative and his advice about where to stop was spot-on. On the way back, he told us the history of Maui and it was fascinating.

The Gypsy Guide’s commentary is brief throughout so it’s not like you have a tour guide droning on and on. Plus, it can play over bluetooth so you can listen to music too! (We brought a bluetooth speaker, since the older car we rented didn’t have one).

Our biggest regret of the trip is that we did the road to Hana on our second-to-last day, before realizing that we should have been using Gypsy Guides all over Maui! If you want to download the Maui app (vs. just the road to Hana) you can find it here for $10.

Here is just a sampling of the photos we took along the way.

Paia, Maui | TheWeekendJetsetter.com

Road to Hana, Maui | TheWeekendJetsetter.com

Road to Hana, Maui | TheWeekendJetsetter.com

Road to Hana, Maui | TheWeekendJetsetter.com

Road to Hana, Maui | TheWeekendJetsetter.com

Road to Hana, Maui | TheWeekendJetsetter.com

Road to Hana, Maui | TheWeekendJetsetter.com

Road to Hana, Maui | TheWeekendJetsetter.com

Road to Hana, Maui | TheWeekendJetsetter.com

The Road… Not to Hana (Exploring West Maui on Highway 330)

Before we did the road to Hana, we did a road trip around West Maui on Highway 340. We pretty much did this by accident! We’d stopped at the beach in Ka’anapali for a bit but it was honestly way too crowded. Snorkeling is no fun when you’re constantly bumping into people. So we got in the car and kept driving in the hopes of finding a more secluded beach destination.

Well, we didn’t find a good beach but we did end up taking the road all the way around West Maui, back toward the airport and it was well worth it. We seriously couldn’t stop pulling over to take photos of the epic views and oceanside cliffs along the way.

West Maui Road Trip | TheWeekendJetsetter.com

West Maui Road Trip | TheWeekendJetsetter.com

West Maui Road Trip | TheWeekendJetsetter.com

Now, this drive is definitely not for the faint of heart. While it didn’t take us as long, it was definitely hairier than the road to Hana. Hana Highway has one-lane bridges, whereas Highway 340 is one lane for, well, a very long time – including on quite a few sketchy hairpin turns. The good news is that it’s not as busy as the road to Hana, so there were only a couple occasions where we had to figure out how to pass someone.

Now, we only wish we’d downloaded the Maui Gypsy Guide Driving Tour before we went!

Shore Fishing in Maui

Since our trip to Maui happened right around Nick’s birthday, I decided to buy a fishing tour on the island. We’ve taken fishing charters during our travels everywhere from Lake Berryessa in California to San Juan del Sur Nicaragua, Puerto Rico, and the Bahamas to Palawan in the Philippines – it’s safe to say, it’s one of his favorite hobbies! But when I looked up fishing charter prices in Maui, let’s just say it was out of my price range. $1,000 for a boat trip? No thanks.

But remember how I mentioned that you don’t need to take a boat trip to snorkel or dive in Maui? Well, turns out, you don’t need to do that to go fishing either.

I booked us a trip with Maui Shore Fishing instead, and it ended up being really fun. Our guide Brian picked us up at 6am from our Airbnb and took us to a rocky point overlooking Big Beach. From there, we fished from shore for about four hours. Brian was awesome and really helpful — I actually caught around 10 fish by myself! While normally I easily get bored on a fishing charter, it was hard to get tired of the beautiful beach we were fishing by and I loved learning about the different colorful fish we caught.

Shore Fishing Maui | TheWeekendJetsetter.com

I saw quite a few of them hanging out in the reefs while we were snorkeling and diving later that weekend, and it was fun to know what they were.

We threw back all the fish we caught, but weirdly, Maui doesn’t have any regulations surrounding how many fish you can catch and keep – in fact, you don’t even have to buy a fishing license. We learned that this is understandably having a negative impact on some fish populations. If you do go fishing there, make sure you’re going with a guide who is environmentally conscious. And unless you’ve done some research in advance, don’t keep the fish!

What to Eat in Maui

Eating in Maui is expensive – even if you only shop at the grocery store, you’ll find that food costs significantly more than it does on the mainland. We ended up spending quite a bit on food – but fortunately, a lot of it’s really good!

Since we were only in town a few days, I’ll point to the eateries we loved in case you want to check them out, too.

Restaurants & Fast Food in Maui

The Pint & Cork (Wailea) – This modern, upscale sports bar is located inside the Shops at Wailea, and is also one of the few places open late at night for drinks in Wailea. The cocktail and food menus were surprisingly gourmet for a sports bar — and have no fear, there were plenty of Hawaiian specialties (think poke bowls and ahi sandwiches) available alongside comfort food staples like burgers, fries and wings.

Monkeypod Kitchen (Wailea and Ka’anapali) – Another rare, hopping destination in Wailea is the Monkeypod Kitchen, a modern farm-to-table eatery with a lively bar scene, nightly live music and a mixture of indoor and outdoor seating. This place had a great atmosphere for a fun night out, and the food was awesome as well (try the poke tacos)!

Teddy’s Bigger Burgers (Lahaina) – This Hawaii-based chain is reminiscent of an old-school diner, but serves up tasty burgers complete with all the modern toppings you could desire – including bacon, avocado and pineapple. Perfect for a quick bite in between adventures!

Maui Brewing Co (Lahaina and Kihei) – Make sure you visit the Maui Brewing Co for a flight or bite while on the island! My favorite beers were the Mana, which was light and refreshing, and the Imperial Coconut Porter. I usually hate porters as they’re heavy and dark, but this one is super smooth and really does taste like coconut. We ended up bringing a couple bottles home, since you can only buy them in Maui!

Maui Brewing Co | TheWeekendJetsetter.com

Roadside/Street Food in Maui

Nahiku Marketplace – Stop here for lunch on the road to Hana, and you won’t be disappointed. Our Gypsy Guide recommended Island Style Tacos, but unfortunately, we were there on the one day it’s closed. Fortunately, the other vendors looked just as welcoming! We ended up getting some coconut shrimp at a place called Island Chef that was delicious. 

Coconut Shrimp on the Road to Hana | TheWeekendJetsetter.com

Coconut Shrimp on the Road to Hana | TheWeekendJetsetter.com

Maui Pineapples – Between Kihei and Lahaina on Honoapiilani Highway, you’ll spot a colorful juice stand next to the Olowalu General Store. Stop in for a smoothie, or just pick up a Maui pineapple from the fruit stand. Seriously, these pineapples are the best you’ll ever taste!

Maui Gold Pineapples, Lahaina | TheWeekendJetsetter.com

Banana Bread – Maui claims it’s home to the world’s best banana bread and you’ll notice it’s for sale alongside the road everywhere on the island. We picked up a loaf on our first day at a farm stand, and it made for a delicious and quick breakfast in our Airbnb each morning.

Banana Bread, Maui | TheWeekendJetsetter.com

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1 Comment on "Hawaii Getaway: Exploring Maui on a 4-Day Weekend"

  1. Hi Anna,

    You have some wonderful images in this post. We too found that if you search for the out of the way main spots, their are many fabulous snorkeling waters not too far away, with some fantastic adventure waiting for you.

    Cheers Sharon…
    Sharon McKenzie recently posted…The Best Hawaii Snorkeling Tours – Bring your Full Face Snorkel Mask!My Profile

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