How to fold Wailea, Hawai‘i into your trip.
Wailea works beautifully as both a standalone retreat and the grounding, restorative anchor to a wider Maui itinerary.
Start your mornings slowly, barefoot on the sand before the sun fully rises, or sitting on your lanai with a cup of Kona coffee as the ocean shifts from gray-blue to bright turquoise. After breakfast, drift toward the oceanfront path and wander between Wailea’s beaches: Ulua, Mokapu, Wailea, Polo. Each has its own feel, and exploring them gives your day a gentle, unhurried rhythm. Midday is perfect for snorkeling in one of the sheltered coves, paddleboarding over calm water, or simply sinking into a cabana and letting the sun warm everything back into place. If you want to explore beyond the resort envelope, drive south to the lava fields of Makena, a stark, cinematic landscape of black rock and deep-blue coastline that looks nothing like the beaches just minutes away. Or head mauka (toward the mountains) to discover upcountry cafés, small farms, and sweeping views across the valley. Return to Wailea in the late afternoon for its most perfect hour: when the entire coastline glows amber, the ocean turns glassy, and the world feels briefly suspended. Evenings unfold however you want them to, a slow dinner under open skies, a quiet walk along the shore, or simply listening to the ocean from your balcony. Wailea doesn’t demand anything from you. It opens space. It restores. It reminds you what it feels like to breathe differently.
Three days you'll remember.
📍 Sunset Serenity
Day 1: Dinner @ Lobby
Settle in with live Hawaiian music, ocean views, and a signature cocktail at this luxe resort mainstay.
Day 2: Molokini Crater
Snorkel inside a volcanic caldera where tropical fish and crystal-clear waters create an underwater wonderland.
Day 2: Lunch @ Pint and Cork
A cozy gastropub with a sleek Hawaiian twist, whiskey flights, gourmet bites, and easygoing charm.
Day 2: Keawakapu Beach
Less crowded and endlessly peaceful, this soft-sand stretch is your go-to for barefoot tranquility.
Day 2: Dinner @ Osteria
Rustic Italian in the heart of Wailea, housemade pastas, rich sauces, and a wine list worth lingering over.
Day 3: Brunch @ Kea Lani
All-white arches and breezy luxury, the Fairmont Kea Lani invites you into its world of island indulgence.
Day 3: Sea Scooters
Zip beneath the waves with a motorized sea scooter, part James Bond, part tropical dream come true.
Day 3: Mokapu Luau
An immersive evening of island culture, think hula, fire dancing, and a farm-to-fork Hawaiian feast.
Wailea Itinerary FAQ.
What are the best things to do in Wailea on a weekend trip?
Swim or snorkel at Wailea Beach, enjoy a luxury spa treatment, explore the Shops at Wailea, tee off at a championship golf course, or take the coastal Wailea Beach Path.
When is the best time to visit Wailea for a weekend getaway?
Wailea enjoys sunny weather year-round, but the best months are April, May and September, November for fewer crowds and ideal beach conditions.
Where should I stay in Wailea for a weekend trip?
Consider luxury resorts like the Four Seasons or Grand Wailea for world-class amenities, or opt for a boutique beachfront stay for a more intimate vibe.
Is Wailea a good place for couples on a weekend trip?
Absolutely, Wailea is one of Maui’s most romantic areas, perfect for couples seeking relaxation, upscale dining, sunset strolls, and serene beach time.
What are the top restaurants to try in Wailea on a weekend visit?
Try Monkeypod Kitchen for fresh island fare, Ferraro’s for oceanfront Italian, and Lineage for modern Hawaiian cuisine with flair.
How do you get around Wailea during a weekend trip?
Renting a car is best for exploring beyond Wailea, but the area itself is walkable and many resorts offer shuttles or bikes for local transportation.
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