Take Me Back: Wailea
My initial forays to Maui always landed me in Ka’anapali, on Maui’s northwestern shores. Here, you’ll find Maui tourism at its best, thanks to quintessential island activities and attractions. But when I stumbled onto Wailea — rumors of the island’s best dining led me there — I fell in love with its quaint, yet upscale, village setting and country club vibe.
Wailea spans about 1500 acres along Maui’s dependably sunny southwestern shoreline, nestled between the blue Pacific and the Haleakala volcano. This resort destination is a playground, with myriad golf and watersports options and plenty of world-class shopping and dining. But it’s Wailea’s wonderful sense of place — an inescapable feeling that there’s magic in this enchanting corner of Maui — that keeps those of us who’ve discovered it coming back.
The core of the Wailea experience is connected by a 1.5-mile seaside path lined with natural flora and fauna. The sunset views from here are breathtaking and it takes you past deluxe oceanfront resorts that have drawn celebs, families and honeymooners alike for years. My family loves the Fairmont Kea Lani for its comfort — it’s the only all-suite property on the island — as well as island-inspired dining at Ko and plenty of complimentary cultural activities.
At the AAA 5-Diamond Four Seasons Resort Maui, the kids love late nights in the decked-out game room; you can reserve the adults-only Serenity Pool for a spectacular private experience, complete with a dinner menu you customize with the executive chef. We love our Grand Wailea stays for the beautiful sprawling grounds and an awesome pool complex (complete with water elevator) that keeps us busy for hours.
The waterfront path, which draws a steady flow of joggers and strollers, also leads to the Shops at Wailea, where comfy eating spots, island-inspired galleries and tony fashion stores converge. The rest of Wailea offers something for everyone, from thriving family-run restaurants (check out Manoli’s Pizza Company) to world-class spas. Don’t want a hotel? There are hundreds of private rental townhouses, condos and villas to choose from.
Outdoors enthusiasts love Wailea: There’s plenty of tennis, biking and hiking here. This is the only resort in Hawaii with three championship golf courses,, and the ocean views from each one make these fairways as stunning as they are challenging. The area’s biggest fun zone — the balmy ocean and five distinct beaches — is impossible to avoid, with everything from tucked-away snorkeling spots to educational canoe experiences.
Travelers flock to Wailea during summer and holidays, but I recommend visiting in the fall, when the crowds are thinner, the prices are lower and the weather is still idyllic. Wailea’s year-round average temp is 82 degrees, and there’s less rain here than other parts of Maui. For the best value, consider the lull between Thanksgiving and Christmas.
Wailea is less than a 30-minute cab ride from Kahului Airport (OGG); on some trips, we’ve opted to stay put on Wailea and have avoided renting a car altogether. If you do want to venture out, Lahaina is about 40 minutes away and about an hour’s drive will get you to Ka’anapali.
Keep an eye out for events that’ll make a Wailea visit even more enticing, including Restaurant Week every May and November and the star-studded Maui Film Festival every June.
Here’s an exclusive Wailea vacation that’s for Travelzoo members only: three nights at the AAA 4-Diamond Grand Wailea, with flights from multiple departure cities, for $999!