7 Nights in Maui, HI

With direct flights from San Diego International Airport to Maui in just over five hours, it’s easy to see why so many San Diegans return year after year. Traveling before the busy summer rush arrives in late June comes with some serious perks: fewer crowds, more attractive hotel rates, and a much better chance of snagging reservations at Maui’s most sought-after restaurants.

Maui isn’t an island that should be experienced from a single beach chair. Each side of the island offers its own distinct personality, and exploring them all is the key to truly understanding Maui’s magic. The sun-soaked shores of South Maui invite lazy beach days and spectacular sunsets, while the lush landscapes of East Maui reward adventurers with waterfalls, rainforest scenery, and winding coastal drives. Upcountry Maui offers cooler temperatures, rolling farmland, and sweeping panoramic views, while the west side blends historic charm, oceanfront dining, and some of the island’s most memorable snorkeling spots.

One day you might be in the old western town of Makawao, and the next you could be chasing waterfalls along the Road to Hana or watching sea turtles glide through crystal-clear waters. Every region contributes its own flavor, creating a richer, more complete Maui experience.

While June marks the beginning of Maui’s dry season, the island occasionally surprises visitors with passing showers and stretches of cloud cover. Rather than a disruption, these brief moments often enhance the experience, bringing relief from the tropical heat, painting rainbows across the sky, and transforming the island’s already vibrant landscapes into even more breathtaking shades of green.

Enjoy a seven-night itinerary vetted and perfected for your enjoyment. The only two places I feel are missing on this itinerary are the Pipiwai Trail and Haleakala National Park. We ultimately chose to relax at the resort on the day we planned to visit these sites, but you likely won't want to miss these based on my research. As for me, I never have FOMO...

Day One:

Check into the Fairmont Kea Lani in Wailea, where you'll be welcomed with a fresh lei and a refreshing cup of guava juice. While the bellman takes your luggage to your room, sneak a peek at the stunning property as a teaser of what lies ahead in this five-star luxury resort.

The Fairmont offers the ultimate customer service experience from booking to check-out. Before even checking in, the concierge team was patient, responsive, and always willing to answer my many questions as they helped me plan a perfect itinerary. Upon arrival, guests are given a phone number to communicate every need to a staff member via a phone text. There is also a complimentary shuttle that takes guests to destinations throughout the Wailea area, making it super easy to get around.

With three pools (including an adults-only pool), five exceptional restaurants, a full-service spa, beachside service, and a marketplace, you'll find everything you need in this modern, newly renovated, expansive, open-air property that lets you catch a sea breeze at every turn.

The baseline rooms at The Fairmont Kea Lani are all suites, so you're guaranteed spacious accommodations. We loved our one-bedroom King bed suite with a soak-in tub and separate walk-in shower, two closets, a large balcony, and a kitchenette. You will absolutely have all the comfort you need for a wonderful seven-night stay.

After a five-hour flight and a long morning of traveling, you'll want a quick bite before dinner to hold you over. Located in the hotel's main lobby, Pilina offers sophisticated decor and a menu that showcases creative seafood and sushi dishes.

Award-winning Chef Peter Merriman's Monkeypod is just a five-minute drive from the Fairmont. This is one of Wailea's most popular restaurants and gets booked up a few weeks in advance. The staff is spot on in their timing and service; the macadamia-crusted mahi is outstanding, and the house-made cocktails are well-balanced. Mostly you'll love dining along with live music in their upbeat environment.

Day Two:

Start your day with a breakfast buffet at Humuhumunukunukuapua'a (since most people cannot pronounce this, you can just call it "humu") located at the Grand Wailea, a Waldorf Astoria property. For $65 a person, you will enjoy a pastry bar, an omelet station, a fruit and cheese bar, a hot food station, and a make-your-own Bloody Mary station. We absolutely loved the locally grown strawberries, pineapple, and watermelon as well as the homemade malasadas tossed in cinnamon sugar. Make sure to check out the main bar, which has a wrap-around counter that is a fish tank!

After a big breakfast, walk off some calories and check out the expansive grounds of the Grand Wailea, complete with striking, tropical landscaping, a large koi pond, beautiful lagoons, outdoor caves, and even its very own seaside chapel!

Just an eight-minute walk from the Grand Wailea Hotel, you'll find The Shops at Wailea, an upscale outdoor shopping center featuring seventy retail shops, restaurants, and galleries. Depending on how much shopping you'll be inspired to do, you can easily get lost strolling the shops for a couple of hours.

Once you're done with all that shopping, head back to the hotel and throw on your swimsuit. Then, head over to Maluaka Beach, even the locals don't know about it!

When we arrived, roughly only a dozen people were sharing this slice of Paradise with us. An unknown stretch of sand with the island of Lanai straight ahead into the horizon, a small section of clustered lava rocks, and lush tropical trimming facing the clear blue waters.

An absolute highlight was swimming with a large sea turtle as he swam beside us in the shallow - make sure to bring your goggles or snorkeling gear to catch these magical creatures underwater!

All that walking, shopping, and swimming will work up your appetite. Head over to the adults-only pool at the Fairmont, order some delicious cocktails (I opted for the mezcal-spiced hibiscus margarita, which was way spicier than I expected), and chill out with your drinks and company; you are on vacation, after all!

Oh- make sure to order the dynamite fries made with Yukon Gold potatoes, spicy aioli, sweet soy sauce, furikake, green onion, and pickled ginger - these are insanely good!

The Fairmont beachside decor disappoints with its vinyl strap chaise lounges, but the natural beauty of the Pacific Ocean makes up for it. The ocean was fierce on the day that we visited, making for a perfect outdoor nap as we fell asleep to the waves crashing.

End your day with a beautiful sunset and a delicious dinner at Koast, whose culinary team masterfully turns to local Hawaiian resources to create a small menu with flavorful results. The butter lettuce salad is so simple in its base of ingredients: thinly shaved kholrabi and turnip in a pink peppercorn vinaigrette, but the freshness packs in a tremendous amount of flavor. Similarly, the cauliflower lightly fried with garlic and mint, the dry-aged Wagyu in homemade rigatoni, and the charred sweet potato topped with smoked yogurt and macadamia nut dukkah will blow you away.

Day Three:

No visit to Hawaii is complete without ordering at least one acai bowl. Manana Market at the Fairmont's lower level makes a pretty delicious one to start an early day of excursions!

Once you've eaten, make the thirty-minute drive to Maalaea Harbor to meet your private sail captains with Ali'i Nui Sailing Charters. Be prepared for a choppy ride towards Molokini Crater, but once you arrive at this reef bursting with colorful fish, you'll forget about the bumps on the way. Booking a morning tour is best as the waves are calmer and the crowds are smaller. Renting a private boat lets you customize your explorations while offering the added convenience of a clean bathroom on board. A jump in the water at Turtle Town is a must - we swam with four sea turtles!

You'll be hungry after the sail, and luckily Haven's Harborside Fish & Chop House is right at the harbor waiting for you to disembark. We were worried the food would be "eh" as most restaurants along harbors cater to tourists. We were wrong. The poi falafel sandwich and ahi tuna sandwich were insanely good. Not a crumb was left on our plates. Not one crumb. And their Mai Tai is the best on the island.

After lunch, we arranged a private driver through R & L Taxi to drive us around Maui.

First stop- the colorful and lively surf town of Paia. You'll fall in love with the boho-chic vibe, well-curated designer shops, bright storefronts, and adorable eateries. You'll also love strolling the sidewalks, doing a little shopping, and enjoying a cup of Tobi's famous shaved ice in the traditional rainbow flavor.

Next, we drove over to Twin Falls. Expecting a 1.5-mile trail to the falls, we packed our sneakers and changed out of our flip-flops in the car. We paid the $20 entrance fee and were told the falls were a five- to ten-minute walk from the parking lot. Turns out, our driver took us to the easy route- for those who prefer to take the hike, make sure you park at the right entrance. Nevertheless, the falls were pretty, and the swimming hole below them was open for a dip. You shouldn't go out of your way to check out Twin Falls, but if you follow my itinerary, they are along the route and worth the quick stop.

Our next stop was in Makawao, known for its Cowboy heritage, making it a historic town. It's a charming little place packed with galleries, cafes, and restaurants. To taste a unique flavor of Maui's ranching roots, it's worth spending a couple of hours in this Upcountry Maui town.

As a long day of discovery comes to an end, after getting ready for the evening ahead, make sure to catch the Fairmont's nightly sunset conch-blowing ceremony to learn about Hawaii's heritage, followed by a stunning sunset off the property's coast.

To truly appreciate the Fairmont's breathtaking grounds, take a walk around once the sun has set and everything has a new glow.

End your already perfect day with an outstanding dinner at Ko Restaurant. You'll be talking about this meal for days. From cocktails to dessert and everything in between, we were inspired by each dish. For my vegetarian readers, Ko offers a vegetarian menu. Blending flavors from Hawaii’s diverse plantation-era cultures, each dish feels both creative and deeply rooted in local tradition. The thoughtful presentation and warm hospitality make Ko a dining experience that lives up to its reputation. Ko gets the prize for our best meal on Maui.

Must order: sizzling tofu agedashi, makeke salad, ginger-steamed opakapaka and crispy wok-fried lobster tail, vegetarian homemade udon noodles, and the maui mocha mai'a brulee.

Day Four:

Ease into the day at the Fairmont's Kei Lani open-air restaurant and dive into its buffet that boasts a spread of everything you can dream of for $65 per person. Cheeses, pastries, make-your-own-poke-bowl, frittatas, pancakes, french toast, oatmeal, yogurt parfaits, omelette station, noodle bar, miso soup... It's a perfect spread!

You'll want to enjoy the Fairmont's amenities in between sightseeing. My own personal itinerary balances enough chill days with days of exploration. Today, consider planting yourself poolside or beachside, soaking up some vitamin D, and sipping on refreshing cocktails.

Mid-day, head over to the South Maui Gardens in Kihei around lunchtime to eat at one of their many food trucks in the Kihei Food Oasis packed with every kind of cuisine imaginable in the most attractive setting. Seriously, if you're a foodie, you'll get lost in the many award-winning options, picnic tables tucked in the lush landscaping, and colorful trucks. South Maui Gardens are so enticing and beautifully laid out, not only with food trucks but with artisan vendors, a butterfly conservatory, wild chickens running around, and even a community tortoise that survived a recent fire. There's loads to do here; don't miss this part of Maui!

Count on another memorable dinner while in Maui as you dine al fresco at Ferraro's at the Four Seasons. The evening's special grilled local swordfish over sweet corn polenta topped with peperonata was perfectly prepared and will leave you wanting more.

Set against the backdrop of Wailea’s stunning coastline, Ferraro’s pairs exceptional cuisine with one of the island’s most romantic sunset views. The combination of impeccable service, fresh local ingredients, and an unforgettable oceanfront setting makes this a meal you’ll be talking about long after your trip ends.

DAY FIVE:

Everyone's first visit to Maui must include a Road to Hana experience. This famous road has 59 one-way bridges and over 600 curves! If you get easily car sick, this may not be the right experience for you. For our time in Hana, we booked Primo VIP to guide us on an eight-hour adventure.

The Road to Hana is much more than a scenic drive; it's a full-day adventure through some of Maui's most breathtaking and untouched landscapes. From hidden waterfalls to black-sand beaches and panoramic ocean views, each stop offered a glimpse into the island's natural beauty.

First stop: Ho'okipa Beach Park to view the wild sea turtles. Watching these gentle giants bask along the shoreline is an unforgettable way to begin your Road to Hana adventure. Hoʻokipa is one of the best places on Maui to observe Hawaiian green sea turtles in their natural habitat.

Next on the itinerary, a stop in Ke'anae at Aunty Sandy's for her famous banana bread baked onsite since 1984. Warm, moist, and packed with fresh local bananas, it's easy to see why this beloved roadside treat has become a must-stop tradition on the Road to Hana.

While you're enjoying the warmth of the banana cake, head over to the Ke'anae Peninsula to see the volcanic stones and rock formations that hug the aqua coast. The landscape is magnificent.

As you're driving the windy roads on the Road to Hana, you'll spot many magical waterfalls along the way. Take a moment to appreciate the beauty in each one.

For a chance to get closer to waterfalls and swim in their swimming holes, make a stop at Pua'a Ka'a - but wear your water shoes; the rocks are slippery and sharp.

If you have a sweet tooth too, definitely stop by Hana Gold Cacao Plantation. This former papaya farm now has over 2,000 cacao trees and makes small-batch chocolate products right on-site.

Next on the route, you'll want to check out the famous black sand beach in Wainapanapa State Park. If you've been to Iceland's Reynisfjara Black Beach, you are likely to be unimpressed by the black beach in Maui - small and crowded. Nevertheless, it is pretty cool to see a coast with black sand! There is also a cliff walk with stunning overlook points that you should not miss.

The town of Hana is small, as in tiny. There is a post office, a small market, some food trucks, and a restaurant called The Hana Ranch Restaurant. Avoid the restaurant at all costs; the food was terrible. Hana Market, a bit up the road, is a popular spot for tourists with a souvenir shop and a restaurant. We walked right through the market, crossed the street, and ran over to Island Cow Cuddles. Now, $25 per person to pet cows might seem steep, but your ticket price is kinda like a donation towards the rescued cows, and you do get to brush the cows and pet the cows for as long as you'd like. They're so darn cute!

Kau Mahina offers a nice spot to stretch, use clean public restrooms, while enjoying sweeping views of the Keʻanae Peninsula and the coastline.

There are more than fifty waterfalls along the Hana Highway, and many of them are right off the road. You'll be chasing waterfalls your entire drive.

There are plenty of overlook points throughout Hana. Make sure to pull over as often as you can to take in the unfathomable beauty you'll find yourself surrounded by.

The "Painted Forest" refers to a stunning grove of rainbow eucalyptus trees whose shedding bark reveals bright streaks of vibrant green, blue, purple, and orange. They are quite a work of art and are a great last stop on your way out of Hana.

A day packed with eight hours of exploration and discovery is guaranteed to work up your appetite. Nick's Fishmarket at the Fairmont will hit the spot with its elegant interior, fresh seafood dishes, and attractive wine selection. The grilled octopus with gnochi and olives is perfection.

Tip: ask for a booth in advance; there are only two in the main dining area.

When in Maui, you'll want to make watching the sunset a part of your daily routine. Just because sunsets in Maui are extra special... you'll see, you won't want to miss them, and you'll find yourself planning your evenings around them.

Day Six:

Explore the west side of Maui for a taste of a different landscape, clearer waters, and different weather. West Maui is known to get more rain than Wailea, has a larger density of hotels, thus more populated, and is also famous for its unbelievably crystal clear waters with incredible snorkeling. We found swimming on the west side of the island more enjoyable.

As you leave Wailea, make sure to stop at the Olowalu Look Out Point known for its perfect vantage point to spot humpback whales during season along with the surrounding islands that hug Maui.

Next, plant yourself on the sand in Ukumehame Beach Park where you'll have the coast all to yourself, shared only by a couple of crabs and Salvador Dali-esque trees that grow out of the sand. The landscape reminded me of the more dramatic one on Jekyll Island, simply stunning.

Continue heading north up the west coast for a dip in Kāʻanapali Beach. It's clear, warm water and marine life will keep you in the water for hours.

You'll need to refuel after all the snorkeling, swimming, and sun. The Gazebo is this side of the island's institution for breakfast (and lunch). Lines are notorious, yet people do not mind the long wait. The portions are large, the view is spectacular, and yes, the food is worth the wait (especially the banana macadamia pancakes!).

Note: cash only.

Tip: Lines are reduced substantially after the breakfast rush. We arrived at 11:00 am and only waited 20 minutes to be seated.

Just a couple of minutes away from The Gazebo is Napili Bay - an uncrowded and picturesque bay with turquoise waters, abundant sea life, and soft, golden sand. This was hands down our favorite beach in Maui.

At this point, you've spent a good chunk of your day swimming and may want to enjoy the ocean from a different perspective. The Kapalua Coastal Trail spans approximately 1.5 miles, taking thirty minutes to complete, on a mostly paved boardwalk. The views of the Pacific Ocean and the coast are breathtaking.

Make sure to hit Island Vintage Coffee while on this side of Maui for their well-loved matcha drinks and acai bowls, an ideal way to cool off after a nice walk.

Once you've enjoyed a nice shower and some downtime in your spacious hotel room, enjoy another yummy dinner on Maui, an island that does not disappoint in the culinary scene. Ka’ana Kitchen at The Andaz is a solid choice. We dined on their patio as live music played and the sun set over the Pacific. The ambience, in an idyllic vacation setting, paired with food that equally stands out. The kitchen sources all its ingredients from more than a dozen local farms - the freshness exudes in each bite.

DAY SEVEN:

My one complaint about the Fairmont is that guests are allowed to hold pool chairs for hours before actually using them. During our stay at the hotel, we weren't able to snatch poolside seating at the adults-only pool. On our last full day on the property, I was determined to be poolside and, along with everyone else, and claimed our chaises by 8:00 a.m to ensure a coveted spot by the pool.

Once you've had enough sun and poolside fun, throw on your cover-up and head over to Ko. Sunday brunch at The Fairmont is a beloved tradition and an experience not to be missed. An impressive array of beautifully presented dishes is accompanied by live music, creating the perfect atmosphere for a leisurely meal. Settle in, savor each delicious bite, and enjoy a relaxing afternoon that captures the spirit of island living.

Because you earned those poolside chaises, don't give them up. Instead, give in to a full day by the pool basking in the sun and sipping on refreshing drinks. You'll be extra pleased when the pool staff serves you your cocktails in the pool. Every vacationer needs at least one full day doing absolutely nothing.

For a perfect start to the evening, head to Pilina for happy hour and settle in with one of their refreshing $12 coconut lavender mojitos. Pair your cocktail with the ahi tuna, beautifully presented with crispy garlic chips, bright yuzu, and delicate microgreens. The combination of fresh island flavors, creative cocktails, and a relaxed atmosphere makes this an ideal pre-dinner stop.

For dinner, Aurum impressed us with a creative menu that draws inspiration from cuisines around the world. We enjoyed an Indian-inspired cauliflower dish bursting with bold flavors, pillowy Italian gnocchi, and a perfectly prepared Asian-style grilled cabbage, each showcasing the kitchen's inventive approach to dining.

Vegetarians will especially appreciate the diverse selection of thoughtfully crafted dishes, making Aurum one of Maui's most welcoming and satisfying restaurants for plant-forward dining.

Walk off those dinner calories on a stunning stroll along the Wailea Beach Path. Enjoy a beautiful golden sunset along the Maui coast. As the sun dipped below the horizon during our walk, it painted the sky in brilliant shades of gold, providing the perfect ending to a week filled with unforgettable experiences. Our last night was just like a Maui sunset - beautiful, memorable, and leaving us already looking forward to the next one.