I don’t even know where to begin. This trip had been planned and canceled so many times over the pandemic that I could hardly believe it was here. Covid took me out 5 days before we were supposed to leave so we re-planned it for September for our 10 year anniversary. 

There is truly no where else I have been quite like Hawaii. The diversity in the climate and the variety in the landscape is an out of this world experience. I remember saying multiple times on the trip that I felt like I was in a movie. I have been to a lot of gorgeous places and while they all have their own beauty, this was by far the most surreal. 

Arriving in Maui was like a dream; the airport is quaint and reminded me of the 70’s. The luggage pickup is an open air outdoor area and from there the cutest trolley picks you up to take you to the car rentals.  

Due to the pandemic, I had plenty of time to plan this trip out so check out my favorite spots to eat/drink, stay, how to save some $$, and things to see/do!

Short and sweet tip: Shoulder season in Hawaii is in fall and spring meaning cheap prices and less crowds. 

The early spring allows opportunities to see the whales migrate and bigger surf while September allows for calmer surf and better snorkeling.  Late October in Maui can lead to bigger crowds so consider this if you want a quieter vacation. In September/early October, I didn’t find anywhere overly crowded—post pandemic travel has been full of crowds so it was a breath of fresh air. 

Maui has so much natural beauty to offer that doesn’t cost a dime to see. Consider staying at an airbnb to cook some a few meals; we chose breakfast-it’s easy and allows for quick mornings on the go. Buy a 6 pack and watch the sunset vs. fancy dinner/drinks on the water, jump in your car and drive the coast, etc. Find happy hours, utilize food trucks, etc.

We splurged in certain areas like the flight home for extra leg room and a few fancy dinners but choose what works for your budget- some planning goes a long way! 

How Long to Stay:

At least 12 days if you live on the East coast! We like to stay busy and most days were packed from 7 am until dinner. If you don’t like life in the fast lane, you may want to stay longer. My suggestion is to plan your must-sees and go from there to figure out how long you’ll need-my list was long 🙂 

Traveling between islands does take up some time due especially if you happen to run into a delay like we did– Luckily, they alerted us before we left for the airport so we hung out in Maui a little longer-there are worse places to get stuck. 

Short and sweet tip- most breakfast spots don’t open until 7 or 8 on Front Street so if you are an early riser, you may want to hit up Foodland for some grub to hold you over.  

Where To Stay:

Depends greatly on the vibe you want and your price range. We stayed in downtown Lahaina- the beach, shops, restaurants, bars, tours, Luaus etc are all within walking distance or a VERY short uber drive if you stay near Front Street. It is a small, local town vibe.If you are looking for a fancy resort like you see in the movies, then you will want to stay in Kannapali. Hotel chains line the beach, high end shopping,  fancy restaurants, golf courses, etc. We visited the Sheraton to see Black Rock (a popular spot to cliff jump) and it was a work of art. You cannot go wrong with either option but if you want more of a local feel, I would opt for Lahaina and save the resort stay for a place where you don’t want to leave the resort- like Mexico. 

Do I need a car? 

We rented a car that we ended up using far more than I anticipated. While there is a lot to do in town, it was nice to have a car when we wanted to snorkel in Kaanapali, cruise the road to Hana, and climb to the summit of Haleakala. There are buses but a car saves time and allows you to follow your own schedule. The airport is about a 40 minute drive and while there are shuttles/ubers, roundtrip ends up being around the same amount for a 2 days worth of a car rental. If you want to stay at the resort, no car necessary but if you want to explore, rent a vehicle. 

The Eats:

Down the Hatch- as seen on diners drive ins and dives but it was none of those things. The atmosphere was a tropical paradise situated in the middle of a shopping arena. We went for breakfast and had the loco poco- (it fed both of us for less than $12!) and we ordered the Lahaina sunrise pitcher for a nice morning buzz. Great for late night bites too- it was one of the few places that’s open late on a weeknight in town. I got the shrimp appetizer and it was big enough for me to save for a shrimp omelet the next morning. 

The Plantation House- I booked a reservation for this place about 3 weeks before my trip (books up quickly!) The restaurant is lined with opened windows allowing a cool breeze that works its way through the restaurant. Most of the tables lead to a gorgeous view of mountains and the Pacific in the distance; if you are lucky, you will get a spot right next to the window- I suggest putting this request in your notes when you reserve it. This place was on the pricier side but it was worth the splurge between the views and catch of the day- I had the halibut. Also worth noting that of the many mai tais I had throughout the trip, this one was the best. 

Captain Jacks- a casual, open rooftop spot for dinner. We ordered our first mai tais and seafood here- nothing fancy but big portions and the food was fresh. 

Drift Coffee– We started our day with coffee and chai lattes here after our first morning in Maui when we arose at about 4:45 AM (thanks jetlag) but it was the perfect way to begin our vacation. We sipped our coffees while walking around the quiet, peaceful town with nothing much more than a few roosters roaming the streets ringing in the morning with their cock-a-doodle-doos. We strolled over to the waterfront to watch the early surfers catch a few waves while we sipped our iced beverages, and listened to the waves crash along the rock wall. It was a great way to start our mornings until the rest of the town awoke and breakfast spots began to open. 

Bad ass coffee:  Right on Front Street– they make a great chai latte and sell bags of coffee/chai if you prefer to brew your own in your room 🙂 

Fleetwoods on Front Street- I had to book about 3 weeks in advance but it was well worth it! We opted for happy hour that included food & drinks on the rooftop from 3-5 with views of the ocean on one side and mountains on the other. We were lucky enough to get a corner table with a view of the ocean to our left and the mountains to our right. The BEST poke bowl I had in Hawaii was here! It was so fresh, not fishy, and the handcrafted cocktails paired great with the meal. 

Things To Do:

Old Lahaina Luau-– Book at least 2 months in advance-it’s one of the best! The Luau sat along the shimmering Pacific and took place around sunset for beautiful shades of pink and purple skies.  The beginning of the evening allows for you to walk around to explore the property, get some pictures, and have a pre-dinner cocktail. Next up is a ceremony around the underground oven that houses the main course. The luau serves a 5 course meal with drinks in between each, and entertainment that immerses you in Hawaiian culture. You will put your dancing skills to the test with a short hula lesson and later on a slow dance under the stars. It’s truly a night to remember in Maui. To close the evening, they send you home with a gift which I enjoyed the next morning. Oh and the fresh leis had to be one of my favorite parts! 

Short and sweet tip- If you want to go to Mama’s Fish House-I  think they are currently booking 4+months out. Bar seats are first come first serve but we didn’t luck out-parking lot was packed at 3 PM! 

Haleakala – I was nervous about the windy roads as I do tend to get motion sickness but there was no way I was missing this spot! I wore motion sickness patches and took some Dramamine and no issues! I suggest driving it yourself vs a tour bus if you tend to get motion sickness. The drive itself, while windy, isn’t as scary as I anticipated as there aren’t big cliffs like the road to Hana, it’s just a bunch of volcanic rock lining the road. The views on the way up are breathtaking and there are a couple of places you can stop to really take in the views. 

Short and sweet tip- bring WARM clothes if you are planning to take the journey to the top of the summit. Bring snacks too-there is nothing to eat once you begin your journey upward. Get up there early if you want a spot in the lot closest to the top or else you will be taking about a 15 minute hike to/from the lot. We ended up getting to the lot around 3:30 PM.   

Sunset or Sunrise? We did the sunset so we didn’t have to get up at 2:00 AM and you also don’t need to book in advance like you do with the sunrise. It was about a 45 minute drive from our hotel and another 45 minutes to the top. The sunset was truly magical and like nothing I had ever seen.  Being atop the clouds while you watch the sun sink behind them is breathtaking from atop the volcano.  Once it gets completely dark, the night sky lights up with the most stars I have ever seen. The Milky Way was as clear as day along with a ton of other constellations. Even though I couldn’t identify many (shoulda paid more attention in astrology class),  it was a beautiful, unique experience and only cost the park entry fee of $30.  

If you plan to do the sunrise vs. sunset, you will need to purchase your tickets 60 days in advance 7 am HST. They do tend to sell out quickly but if you miss the 60 day mark, there is another chance as they release additional tickets 48 hours in advance.

Road to Hana- We headed out early for the Road to Hana–again, there are guided tours but with my motion sickness, we opted to drive ourselves. You can also purchase the Shaka Guide App for a self-guided tour. We opted to do it on our own and still saw a ton! 

Our stops: 

Short & sweet tip: Bring water shoes for the rocky water falls! 

The Garden of Eden Arboretum ($20 entry fee per person)- a botanical garden where you’ll find  a 100 year old mango tree, wildlife, waterfalls, the Pacific, and views of the rock seen in the opening scene of Jurassic Park- a must for movie buffs! 

Short & sweet- wear good shoes here and not flip flops like me(I wiped out twice on the gravel path in my $1 old navy flops) 

Kaumahina State Wayside Park-black sand beach. we did not make it here as I didn’t realize you needed reservations and there were none available for this day but plan a little ahead and add this to your list because where else can you see a black sand beach?! 

We spent about a half day on Road to Hana and didn’t complete the whole thing but got pretty close-definitely save a whole day and leave early in the AM if you want to complete the entire trip. 

Short and sweet tip- don’t leave any valuables in your car, you’ll see warning signs most places but even if it doesn’t seem like a dangerous area. 

Snorkeling–There wasn’t a ton of snorkeling on the Lahaina beaches due to the rougher surf but there were tours that took you to spots where you could snorkel.

Kannapali– Kaalua bay beach/Napili. I rented snorkel gear and fins for 12.50 for 2 hrs and that was plenty of time. A pretty easy place to snorkel on your own and there were lifeguards. The coral reef was visible as soon as you got in-be careful not to step on it to prevent damage to the coral. We saw a sea turtle, an eel, and beautiful multi-colored fish. It literally looked like Ariel’s grotto in The Little Mermaid. 

Honolua Bay- a remote snorkeling spot. We got up early to make the drive up to the bay to avoid the crowds and find a spot  in the limited parking areas plus there is the chance to see dolphins early on. While we didn’t see dolphins, we weren’t disappointed. The path to the bay is  through a beautiful, tropical forest. Once you arrive, the locals are there monitoring the bay making sure you don’t bring any spray sunscreen and that it is reef safe. It’s a rock beach so bring water shoes as it’s a slippery entrance into the water-think slow and steady. I crab walked my way in—I’m not the most graceful creature. Oh yeah and there is a food truck across the street from the Bay– stop here and get the banana bread- we were lucky enough to get it right out of the oven! 

Short & sweet tip- rent snorkel gear at Boss Frogs for 24 hrs for $12.50. Snorkel conditions are listed in the shop for the day as a bonus if you don’t know where to go 🙂

Well there you have it, 5 days spent in Maui. Please feel free to leave me a comment below- would love to hear from you with any questions/comments or to hear about your experience in Maui!