Wailea: The Heart of Maui – A Destination Like No Other

Relax at Wailea Beach

Wailea Beach is the epitome of island beauty. The calm waters are perfect for swimming or snorkeling, and the golden sand is soft underfoot. With several high-end resorts surrounding the beach, you’ll have access to a variety of activities right at your fingertips, whether it’s lounging in the sun, kayaking or taking a walk along the coastline. This is the perfect place to relax, unwind and watch a gorgeous sunset.

Zip-lining at Pi'iholo Ranch

If you’re looking for an adrenaline rush, zip-lining at Pi'iholo Ranch is a must. Soar above lush valleys, dense forests and rugged terrain, all while soaking in panoramic views of the island’s diverse landscapes. The zip-line courses here offer both excitement and breathtaking beauty — two things that Wailea does perfectly. The guides are friendly and knowledgeable, ensuring an experience that’s as fun as it is memorable.

Explore the Wailea Beach Path

This scenic, paved path runs along the coast and connects several of Wailea’s most beautiful beaches and resorts. Whether you walk, jog or bike, you’ll be treated to stunning views of the ocean, as well as tropical landscaping and beachfront resorts. It’s the perfect way to explore the area at your own pace and enjoy all the natural beauty Wailea has to offer.

Golf at Wailea Golf Club

For golf lovers, Wailea Golf Club is a dream. With three championship courses, each offering amazing views of the ocean and lush greenery, it’s the perfect place to play a round while taking in some of the most beautiful scenery in Hawai'i. Whether you’re a seasoned pro or a casual golfer, Wailea’s courses provide a challenge and an experience that’s hard to beat.

Snorkel at Molokini Crater

Just off the coast of Wailea, Molokini Crater is one of Maui’s most popular snorkeling spots. This crescent-shaped island is a submerged volcanic caldera, offering clear waters and incredible marine life. Whether you’re a first-time snorkeler or a seasoned pro, the experience here is unforgettable. Take a boat tour out to Molokini and immerse yourself in the crystal-clear waters, where you’ll swim alongside vibrant coral reefs and tropical fish.

Sunrise at Haleakalā National Park

Though Haleakalā is a bit of a drive from Wailea, sunrise at Haleakalā is one of those experiences that stays with you forever. It’s an early wake-up call, but trust me — it’s totally worth it. You’ll drive up to the summit (or I can help you arrange a local guide to handle the logistics and the driving!) and find yourself watching as the sky bursts into vibrant colors, with the sun rising over the island’s volcanic landscape. It’s a humbling, almost surreal moment, and the views from the top are absolutely breathtaking. Afterward, don’t rush — take time to explore the park’s trails. Whether you’re in the mood for a short walk or a more serious hike, the scenery is mesmerizing at every turn. Haleakalā is one of those places that makes you feel like you’re on top of the world.

Day trips

• Explore the Road to Hana: The Road to Hana is another one of those experiences that stays with you long after you’ve left. The drive itself is a work of art — curvy roads lined with waterfalls, lush rainforests and black sand beaches. Make it a day trip and take your time to stop at the little hidden gems along the way, like the famous Wainapanapa State Park. Or, better yet, let me help you hire a local driver to handle the tough roads and show you the real Road to Hana from someone who knows best!

• Go whale watching: If you’re visiting between December and April, whale watching in Maui is a magical experience. Each year, thousands of humpback whales migrate to Maui’s warm waters to give birth and raise their calves. The best way to see these majestic creatures is by boat, and there are a number of tours that take you right into the heart of the action. There’s something awe-inspiring about seeing these gentle giants up close.

Ferraro’s Bar e Ristorante

Located at the Four Seasons Resort, Ferraro’s offers fresh Italian cuisine with an unbeatable oceanfront view. Whether you’re there for a casual lunch or a romantic dinner, the setting is as stunning as the food. Pro tip: Make a reservation right before sunset so you can experience the nightly blowing of the pu (conch shell) and torch lighting.

Mama’s Fish House

Although it is located outside of Wailea, Mama’s Fish House is a Maui institution and well worth the drive. Located on a beautiful beachfront, it serves up the freshest fish, caught daily by local fishermen. The laid-back vibe and fantastic food make it a must-visit during your stay. Pro tip: Mama’s books up FAST — make a reservation well in advance, or set those Resy alerts to snag a last-minute table.

Merriman’s

For an upscale dining experience, Merriman’s in Wailea offers farm-to-table cuisine with an ocean view. The restaurant specializes in local ingredients, and the setting is elegant and relaxed. Perfect for a special evening out.

The Restaurant at Hotel Wailea

For a romantic, upscale dining experience, The Restaurant at Hotel Wailea is where you want to go. The farm-to-table dishes are creative, flavorful and highlight the best of local ingredients. The ambiance is intimate, and the views of the ocean at sunset are breathtaking.

Paia Fish Market

A local favorite for fresh seafood, Paia Fish Market (with three locations on Maui) offers tasty dishes at great prices. It’s perfect for a casual bite after a day of exploring Wailea or the Road to Hana. The laid-back vibe and fresh fish make it a must-try.

Ululani’s Shave Ice

No trip to Maui is complete without indulging in some shave ice. Ululani’s is the gold standard, offering a variety of flavors made from natural syrups. The texture of their shave ice is perfect — light and fluffy — making it the ideal treat to cool off after a day of exploring.

Leoda’s Kitchen and Pie Shop

Leoda’s Kitchen and Pie Shop is a cozy, charming spot for delicious comfort food, and their pies are legendary. Whether you’re in the mood for savory dishes like their famous pot pie or something sweet, like the coconut cream pie, you’ll find something to satisfy every craving here.