Maui, Hawaii. Yes!!

The Vacay Seeker
6 min readJul 13, 2021

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Maui is an amazing destination that you can visit over and over again.

When planning your first trip to paradise, you can get slightly overwhelmed by all the information out there. It can be the trip of a lifetime, and it will definitely cost a pretty penny or two (or a million). So take a look at the following curated itinerary for making the most of every moment!

Day 1: The Long Day of Transit

Aloha and welcome to Hawaii! You finally made it after spending forever and a day in the air. You are probably tired and hungry. So after picking up your rental car, go and grab your first taste of Maui at Poi By the Pound, which is located just a few minutes from Kahului Airport. (The Hawaiian Plate is a great sampler of various Hawaiian dishes.)

There are two major hotel areas on the island, Wailea and Lahaina. Hotels on Maui are generally more expensive than elsewhere. So try to book as early in advance as possible. I prefer staying in Wailea for its central location, and if you’re willing to spend the cash, the Fairmont Kea Lani is an awesome choice. Their smallest room is an 860SF one-bedroom suite, so you will have plenty of space for everyone and everything.

Fairmont Kea Lani Hotel

Days 2–3: Southern Maui (Wailea, Kihei)

If you came to Maui, you probably came for the beaches, and southern Maui has plenty of options. Spend a day or two enjoying the sun and water at Makena Beach State Park’s Big Beach or Little Beach (FYI be ready for nudity at the second one), Keawakapu Beach, or one of the three Kamaole Beach Parks.

Makena Beach

You will find lots of great food options in Kihei and Wailea. Favorite breakfast spots include Kihei Caffe and Piko Cafe. For your daily shave ice fix, check out the Surfing Monkey and their Tiger’s Blood flavor. Dinner can be as fancy or as low-key as you want. The Fairmont’s Ko features a refined dining experience with authentic cuisines from locally-sourced produce. Or, you can pick up some award-winning poke from the local Foodland to enjoy in your own room with a cold beverage of your choice.

FoodLand

Day 4: Above the Clouds in Haleakala (Plus a Little Paia)

Did you wake up super early? Of course, you did. More importantly, did you expect it to happen (after reading this post) and booked a Sunrise Reservation at Haleakala 60 days in advance? Well then, carefully make the one-hour drive from Wailea (two hours from Lahaina) to the top of Haleakala National Park and greet the morning sun. FYI, it gets cold up there! So wear a good pair of sneakers, pack an extra sweatshirt, and spend the morning hiking in the grand volcano landscape.

Haleakala National Park

For lunch, take your time savoring the food and ambience at Mama’s Fish House in Paia. Then, spend the rest of the afternoon at Baldwin Beach Park before calling it a day.

* You can also do this day in reverse by starting a little later at Baldwin Beach Park, driving up Haleakala National Park in the afternoon, and staying for sunset, which is just as magnificent and does not require a reservation.

Days 5–6: Western Maui (Kapalua, Kaanapali, Lahaina)

Don’t forget about western Maui. It also has its share of amazing beaches, like Kapalua Beach, Napili Beach, DT Fleming Beach Park, and Slaughterhouse Beach. (My personal favorite is Slaughterhouse. After walking down a flight of stairs through lush foliage, you are rewarded with an amazing and possibly private cove.)

Slaughterhouse Beach

For a non-beach option, check out the coastal hike at the Nakalele Blowhole. Park at mile marker 38.5 and enter the trailhead leading down to the blowhole. Be sure to wear sturdy shoes. On the way out, check out the banana bread and other mouthwatering delights at Mamalei’s Homemade Goodness.

Restaurant options are plentiful in Lahaina. Check out the Lahaina Grill for an upscale experience or the Paia Fish Market for something more low-key. Both offer some great seafood options.

Day 7: Hana, Maybe…

The Road to Hana is an amazing experience. But, keep in mind that this is mostly a scenic drive. So families with young children (or people who are just not into long drives) may want to skip this activity. If you are inclined to go, consider picking up some drinks and lunch bentos at Takamiya Market before starting out (super early). There are numerous stops along the way, but instead of trying to see small glimpses of them all, take your time at just a few of them.

Road to Hana
  • Mile Marker 10: Garden of Eden Aboretum
  • Mile Marker 29: Nahiku Marketplace
  • Mile Marker 32: Waianapanapa State Park with its black sand and caves at Honokalani Beach
  • Mile Marker 45: Wailua Falls
  • Mile Marker 42: Ohe’o Gulch (“Seven Sacred Pools”)

If a long day of driving is just not for you, it’s OK because you are not alone. ^^

Day 8: Land, Sea, Fire?

If you’re a golfer, you should definitely get in a round or two while you are here. The Plantation Course at Kapalua Bay is a fan favorite, so if you can only play once on the trip, make sure to do it here! And if you can play more than once, check out the rest of these courses:

Plantation Course at Kapalua Bay

If you would rather play in the water, consider a snorkeling trip. You can find tours leaving from both southern and western Maui. Popular destinations for these tours include the Molokini Crater, Turtle Town, and Honolua Bay.

Finally, no trip to Maui would be complete without a luau. If you anticipate jetlag on this trip, it would be best to save the luau for your last night in Maui so that you have time to adjust to the time change. These tend to sell out months in advance, so book early. The Old Lahaina Luau is still the most authentic experience, while the Luau at Andaz Maui is the most luxurious.

Old Lahaina Luau

You can definitely mix and adjust the days of this itinerary to fit your trip. Be sure to check out the fruit or banana bread vendors that you may see along the road. Your week in Maui will go by really fast. So when is the best time to start planning for your return visit? It might be at the airport as you are waiting to board your flight back home. XD

Maui Hawaii Vacation Planning

Vacay Seeker

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The Vacay Seeker

The perfect resource for travel tips, ideas, itineraries, and vacation planning for busy travelers.