How to Spend a Perfect Long Weekend on Maui Full of Adventure and Relaxation
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Welcome to VERANDA's Perfect Weekend, where we show you how to make the most of a long weekend in one of our favorite destinations. If you want to spend time in Maui, Hawai‘i, connecting with nature, embracing the rich local culture, and coming home with a deeper sense of Aloha, or “the breath of life,” you've come to the right place. World-renowned for its vast rainforest and awe-inspiring tropical landscape, Maui is the ultimate warm-weather destination for summer vacations and beyond, no matter how you like to spend your days away. If you’re an ocean lover, you’ll be thrilled by the island’s white and black sand beaches, vibrant marine life, and towering waves.
If you prefer to keep things on land, you’ll be wowed by the twists and turns of the Road to Hāna, a 64-mile stretch of road that winds through the rainforest and connects the towns of Kahului and Hāna, as well as the scenic drive up to Haleakalā National Park, which is said to be one of the most remarkable places in the world to catch sunrise and sunset. (And we can attest: It’s unlike anything you’ve ever seen.) Meanwhile, if you enjoy perusing the finer things in life while on vacation, rest assured, on Maui there are myriad art galleries, boutique shops, and dining options to suit any taste.
Some things to know upfront: Maui is many things, but walkable is not necessarily one of them. The second largest of the Hawaiian islands, Maui spans 727 square miles and is primarily divided into resort communities along the West and South coasts, with more local dwellings situated in central, Northern, and East Maui. While each of the resort communities is equipped with an array of shopping, dining, and entertainment, if you hope to venture beyond the resort you’re staying in, you’ll definitely want to get a rental car while visiting the island.
Getting around aside, it’s time to discover all that Maui has to offer. Knowing just how abundant the experiences on Maui are, ahead we outline how to spend a long, four-day weekend on the island, plus recommendations for what to do if you have a bit more time to spare. Here's what to do in Maui to make the most of your trip.
Friday Afternoon
If your flight schedule allows, arrive in Maui by Friday morning or afternoon. Once you’ve touched down, pick up your rental car at the Kahului Airport and drive 30 minutes south to Hotel Wailea, Hawaiʻi's only Relais & Châteaux property and Maui’s sole adults-only luxe hotel.
To make the most of your stay, we suggest checking into a Celebration Ocean View Suite. The 750-square-foot escapes feature a bedroom with a king-size bed, deep soaking tub, and large rainfall shower; an open living area and kitchenette, and a private lanai to take in the stunning tropical surroundings. Another perk of booking a Celebration Suite? Breakfast at The Restaurant is included with your stay and the menu is so mouthwatering, you’ll be inspired to start each and every day at one of the ocean-view tables lining its balcony.
After you’ve checked in and gotten settled—and depending on how much time you have to kill before dinner—unwind with an in-room massage, lounge by the pool, or head up to the stunning open-air gym. With picturesque 180-degree views of the landscape and ocean below, the gym at Hotel Wailea makes working out feel like anything but a chore.
Friday Evening
Allow yourself to adjust to the time change with a sunset dinner and early evening on your first night in Maui. If you’re celebrating something particularly special, consider booking The Treehouse ahead of time. By doing so, you’ll get the pleasure of eating a private 7-course dinner in a treehouse among a canopy of mango and avocado trees overlooking the ocean.
Whether the Treehouse is already booked or you simply prefer a different dining set-up, The Birdcage is worth visiting (and staying for a while). The open-air restaurant used to be the hotel’s lobby thanks to its breathtaking 180-degree views of the property and the Pacific beyond. Now, the beautifully decorated, cosmopolitan-inspired space, which was designed by Philpotts Interiors, is a restaurant serving freshly prepared sushi and other Japanese grill specialties, as well as a variety of tantalizing craft cocktails and mocktails.
Beyond the cuisine, The Birdcage has a beloved clientele: lovebirds. The small, vibrant parrots, which mate for life, flock to the rafters of the restaurant—typically in pairs—filling the space with whimsical birdsong that feels straight out of a tropical fairytale. It’s a sight (and sound) you won’t want to miss. Speaking of sound, The Birdcage also offers live music on Thursdays, Fridays, and Saturdays from 6:30-8:30 p.m. By the time the tunes wind down on night one, chances are, you’ll be dreaming of snuggling into your hotel room's plush bed with premium linens.
Saturday Morning/Afternoon
Fuel your morning with an early breakfast at The Restaurant at Hotel Wailea. While many hotel breakfasts leave something to be desired, The Restaurant at Hotel Wailea offers a menu that will leave you wishing you had more room. From the flavorful Wailea Benedict and the bountiful Lanai Breakfast to the juicy island fruit plate and unforgettable garlic sticky rice, The Restaurant will inspire you to eat all your breakfasts on property. While you’re there, be sure to treat yourself to a coconut iced matcha to kickstart your day—you won’t regret it.
After breakfast, pack your backpack, apply your SPF, and hop into a luxury sprinter van to explore 618 breathtaking twists and turns through Maui’s world-renowned Road to Hāna. (You’ll have to book this experience ahead of time through Road to Hāna Tours—specifically, we suggest the Small Group Road to Hāna Tour).
From the comfort of your sprinter, you’ll get to take in the island’s verdant rainforest, towering oceanside cliffs, beautiful rainbow eucalyptus trees, and more. Outside of the van—on several scheduled stops—you can look forward to indulging in Aunty Sandy’s famous banana bread, swimming in a waterfall pool, and exploring Waiʻānapanapa State Park.
On the tour, you’ll also get to visit Maui’s North Shore, where Hawaiian Green Sea Turtles sunbathe by the dozen (As intrigued as you may be, be sure to respect their space—the majestic sea creatures are protected by the Federal Endangered Species Act, as well as Hawai‘i State Law, both of which recommend keeping a distance of at least 10 feet).
In total, the tour is 10 hours long and features pick-up and drop-off at Hotel Wailea (or other nearby hotels). Although 10 hours may feel like a major commitment on one of your few days in Maui, the sights and experiences along the Road to Hāna prove to be 100 percent worth it, especially from the comfort of a luxury tour van.
Saturday Evening
After 10 hours of exploration, you’ll likely feel beat. You have two options: Go back to Hotel Wailea to try yet another sure-to-please item off the menu at The Birdcage or explore the local food scene in Wailea by stopping in at Monkeypod Kitchen by Merriman. The popular craft food kitchen is open later than many restaurants in the area, so you won’t have to rush to get there or to complete your meal.
In terms of cuisine, you can anticipate delectable appetizers, salads, hand-tossed pizzas, and farm-to-table and fresh-caught entrees. From poke tacos, taro ravioli, and lobster deviled eggs to prime rib, seared ahi steak, and coconut cream pie, there’s something for everyone. And let us not forget: Their mai tais are as picture-perfect as they are flavor- and booze-forward.
After dinner, head back to Hotel Wailea to unwind for the evening. Another full day of adventure awaits on Sunday!
Sunday Morning
If you’re up for it, set your alarm for the wee hours of the morning to catch sunrise at Haleakalā National Park. The park is nestled 10,023 feet above sea level and is known to be one of the most beautiful places in the world to watch sunrise and sunset, as well as to stargaze. Depending on how early you’re willing to wake up, you can catch stargazing and sunrise in one fell swoop.
Just keep in mind that this is a popular destination with limited parking. To ensure your viewing pleasure, be sure to book a reservation. To do so, create an account, search your date up to 60 days in advance, and book accordingly. (And be sure to bring a coat or blanket—it’s cold up there. Where it can be in the 70s and 80s in Wailea, the summit can hover around the 30s.)
If you choose not to head up to Haleakalā, instead, wake up early to enjoy the complimentary outrigger experience that Hotel Wailea offers on Sunday mornings. An outrigger canoe isn’t your average canoe; it’s a stabilized, wood-carved vessel considered to be one of Hawai’i’s “most treasured cultural activities.” It’s also the state’s team sport. When paddling in unison in an outrigger, you’re able to move and connect with the water without fear or toppling in; you can peer over the side to see coral reefs and sea turtles in their natural habitat; and you can even surf the waves in. It’s a truly special experience that feels downright spiritual.
Sunday Afternoon
Following your early-morning adventures, determine how you want to spend your afternoon to narrow down your breakfast or brunch options.
If you want to go back to Wailea to lounge at the beach or by the pool, or to go shopping at The Shops at Wailea, rely on old faithful (The Restaurant) or grab something like at Brekkie Bowls or Akamai Coffee, both located just down the road from the hotel. Another option? Book a beach picnic through Hotel Wailea and they’ll set you up for a relaxing day at the beach with zero personal prep work.
If you want to spend your afternoon taking in the local art scene, make your way from Haleakalā to Pā'ia Town, a small surf town known for its local shops and galleries, such as Maui Hands (a long-standing gallery that represents 300 local artists) and the Maui Craft Guild (which is a collective of printmakers, jewelers, textile artists, photographers, and more, all of whom display and sell their work under one roof). On the way, stop in at Baked on Maui, a family-owned and operated bakery specializing in pastries and hearty breakfasts alike.
After brunch and gallery hopping, drive 20 minutes over to Wailuku. There, you’ll find Antique Freak, a treasure trove of Maui picker finds, ranging from mercury glass collections and estate jewelry to fine art, vintage clothes, and more. (On the shop’s Instagram, you can even see a walk-through of the store to get an idea of what they offer ahead of time.)
Sunday Evening
After a day of relaxing or shopping, treat yourself to a quintessential last supper: a meal at Mama’s Fish House. Pro Tip: You’ll want to book ahead. Mama’s Fish House is the most popular restaurant not only on the North Shore but in all of Maui. Reservations book out well in advance so if you see one for your desired time or even near it, grab it while you can. If you’re able to get in, treat yourself to a Mai Tai Roa Ae for a job well done and to celebrate your time in Maui. Then, peruse the curated menu of appetizers, soup, salads, entrees, and desserts.
If you opted out of sunrise at Haleakalā National Park, there’s always the option to head there for stargazing. With that in mind, you can drive 38 minutes back to Hotel Wailea or 54 minutes to the summit to take in the celestial wonders Maui has to offer. The summit is open 24 hours a day and doesn’t require a reservation outside of the 3 a.m. to 7 a.m. window, so you can always do this on a whim.
Monday Morning
Whether you’re headed home Monday afternoon or evening, one final thing you’ll absolutely want to make time for is a Ritz-Carlton Ambassadors of the Environment Cities Under the Sea snorkel sesh. A Jean-Michel Cousteau Program, this ultra-informative snorkel adventure teaches participants about Hawai‘i’s unique ocean ecosystems before guiding them to explore it firsthand.
Swimming through waters teeming with a rainbow of creatures, including humuhumunukunukuāpuaʻa (the Hawaiian state fish), Rainbow Wrasse, Moorish Idols (i.e. Gill from Finding Nemo), and Hawaiian Green Sea Turtles is an experience you’ll never forget. FYI: The Ritz-Carlton Maui, Kapalua—where you’ll meet up for the tour—is an hour from Hotel Wailea. On the way there, grab a light bite at Maui Coffee Roasters.
Monday Afternoon
As you make your way back from snorkeling, make a pit stop at Leoda’s Kitchen and Pie Shop for lunch. Nestled along the side of Honoapiʻilani Highway (AKA Highway 30), Leoda’s is easy to overlook but trust us, this is one eatery you’ll want to keep an eye out for. The Olowalu lime pie is to die for, though the eatery also offers a variety of sandwiches, burgers, and salads if you don’t want to skip straight to the sweets.
After lunch, start gearing up to go home or, if you plan to spend more time on Maui, consider incorporating some of the activities below.
More Things to Do on Maui If Time Permits
Blue Soul Maui: If you end up choosing not to stay at Hotel Wailea or you want to enjoy an outrigger canoe experience on a different day of the week, you can partake in the cultural activity by booking through Blue Soul Maui. With Blue Soul, you can look forward to a spiritual ocean experience that ties you to the water and the lands of Hawai‘i. You can choose from four outrigger tours, as well as a variety of hiking and surfing tours.
Maui Off Road Adventures: Looking for a thrill that feels a bit like Jurassic Park in real life? Maui Off Road Adventures is an ATV tour that explores miles of trails through lush terrain, accessible only via ATV or helicopter. (Just an FYI: Prepare to get muddy.)
Blue Hawaiian Helicopter Tours: Not one for mud or bumpy rides? Explore Maui’s lush landscape from above in a Blue Hawaiian Helicopter Tour.
Kapalua Ziplines: Another way to catch a thrill on land in Maui? On a zipline (or six) looming above the rainforest. At Kapalua Ziplines, 8,500 feet of ziplines are waiting to be explored. With a booking, you can also walk across Hawai‘i’s longest suspension bridge, which sits 1,600 feet above the Northwest Maui coastline.
Sail Trilogy: Another memorable dining option? The Captain’s Sunset Dinner with Sail Trilogy. The dinner cruise features a 4-course meal with a view that’s hard to beat.
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