3 days you’ll remember in Wailea, Hawaii.
Wailea is where laid-back luxury meets natural splendor on Maui’s sun-kissed southern coast. Think soft golden beaches, swaying palms, and some of the island’s most upscale resorts—all balanced by the aloha spirit and a slower rhythm that invites pure ease. Mornings are for snorkeling with sea turtles, afternoons for scenic drives or spa bliss, and evenings for oceanfront dining as the sun melts into the Pacific.
This Foresyte itinerary was curated to help you experience Wailea’s breezy sophistication and island magic, one unforgettable moment at a time.
Let’s take it from the top.
Itinerary inspired by the Foresyte community.
📍 Sunset Serenity
Day 1: Monkeypod Kitchen
“Famous for its handcrafted cocktails, lilikoi foam mai tais, and locally sourced, flavor-packed plates.”
Day 1: Dinner @ Molokini Crater
“Snorkel inside a volcanic caldera where tropical fish and crystal-clear waters create an underwater wonderland.”
Day 2: The Pint and Cork
“A cozy gastropub with a sleek Hawaiian twist, whiskey flights, gourmet bites, and easygoing charm.”
Day 2: Lunch @ Keawakapu Beach
“Less crowded and endlessly peaceful, this soft-sand stretch is your go-to for barefoot tranquility.”
Day 2: Matteo’s Osteria
“Rustic Italian in the heart of Wailea, housemade pastas, rich sauces, and a wine list worth lingering over.”
Day 2: Dinner @ Kea Lani
“All-white arches and breezy luxury, the Fairmont Kea Lani invites you into its world of island indulgence.”
Day 3: Brunch @ Sea Scooter
“Zip beneath the waves with a motorized sea scooter, part James Bond, part tropical dream come true.”
Day 3: Lobby Lounge
“Settle in with live Hawaiian music, ocean views, and a signature cocktail at this luxe resort mainstay.”
Day 3: Bites @ Mokapu Luau
“An immersive evening of island culture, think hula, fire dancing, and a farm-to-fork Hawaiian feast.”
Day 3: Ka’Ana Wailea
“Fine dining elevated with Maui-grown ingredients, ocean vistas, and a taste of elegance under the stars.”
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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