Skip Ka'anapali, Visit Wailea As a Southern California native, 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 resorts and activities. But Wailea, a quaint village setting with a country club vibe on Maui's southwestern coast, eventually became one of my favorite discoveries. You'll find some of the state's best properties here, from the Fairmont Kea Lani to the Four Seasons Maui to the newly-opened Andaz Maui; the Japanese-inspired Hotel Wailea, set uphill, is a wonderful cost-friendly alternative. There's great shopping, world-class golf on three lush courses and lots of celeb-spotting opportunities. But there are plenty of small wonders to discover here, too, from tucked-away snorkeling spots to thriving family-run restaurants. And the quaintness of it all – the core of the Wailea experience is connected by a 1.5-mile seaside path lined with natural fauna – is remarkable.
Skip the Poi, Eat the Pasta In Wailea, the local cuisine is awe-inspiring. But would you believe that some of the neatest spots to grab a bite here have an Italian flair? At the Fairmont Kea Lani, Caffé Ciao is a classic trattoria, where breads and desserts are baked onsite, where gelato is scooped all day and where you can order an Italian custom picnic basket for your afternoon at the beach. Capische, at Hotel Wailea, is Italian fine dining at its best, offering an al fresco ocean view setting, a martini bar and ocean-sourced fare – from ahi to ono –treated with classic Mediterranean style. For a more casual Italian meal, check out family-friendly Manoli's Pizza Company, where the homemade meatballs, sauces and breads are always molto benne.
Skip the Restaurant, Get Delivery It's tough to leave the beach to go stock up on groceries, right? Then get it delivered. Maui Grocery Service lets you order online from stores like Safeway, Whole Foods and Costco. Deliveries to the main resort areas are made within 24 hours – by 6 p.m. if you order by 8 a.m. – and the $39 fee even covers unpacking and putting your groceries away in your hotel room or condo. Aloha Grocery touts itself as a delivery concierge and delivers pre-set, custom and themed grocery packages to resorts and vacation rentals in Kihei, Wailea and Makena.
Skip the Mai Tai, Sip the Wine Tedeschi Vineyards is Maui's only commercial winery, dating back to the 1970s and located on the slopes of Haleakala. Several wines are made from pineapple, naturally, and the red blends and sparklers sell well; their Maui Brut was poured during President Reagan's inauguration in 1981. To be fair, this is not where you come to taste the best wine in the country; it is, however, a destination that wows with its natural beauty and a rare spot to try wines grown on volcanic soils.