A Wailea itinerary should leave room for sandy feet, a long lunch and a sunset you don’t have to rush. Spend the morning on the coast, then choose a few of these beach walks, cultural activities, restaurants and nearby adventures.
Build a Wailea itinerary around one main outing
Wailea’s beaches, resort restaurants and shopping are close together, but Mākena and Kīhei outings need driving time. Start with the experience you most want, then fit the rest around it.
- A relaxed day: walk the coastal path, have lunch, then browse the Shops at Wailea and its galleries.
- An active day: book a guided kayak trip or a round of golf in the morning, followed by a quiet afternoon.
- An evening out: choose a luau, a Mulligans show or dinner at Monkeypod. Give that reservation the evening.
1. Kayak along the South Maui coast
Seeing the shoreline from a kayak gives you a different view of South Maui, with lava points, beaches and Haleakalā rising behind the coast. Aloha Kayaks Maui and Hawaiian Paddle Sports are options for a guided outing.
Choose a trip that fits your paddling experience and swimming ability. Follow your booking confirmation for the launch location, arrival time and equipment. If snorkeling is included, ask how much time you’ll spend in the water and what support the guide provides.
During whale season, a kayak whale-viewing tour adds another reason to look offshore. Wildlife sightings are a bonus, never a promise. Use Boss Frog’s Maui Snorkel Report alongside local advice and your guide’s assessment of the conditions.
2. Reserve a Wailea luau evening
Make a luau the main event rather than squeezing it between other bookings. Wailea options include Te Au Moana at Wailea Beach Resort, Feast at Mōkapu at Andaz and the Grand Wailea Luau.
The settings, menus and performance styles differ. Te Au Moana serves a three-course meal family-style at the table, with Hawaiian and Polynesian music and dance beside the ocean. Compare the seating and meal format, mention dietary needs when booking, and arrive with time to enjoy the setting before the show.
3. Slow down at Maui’s Best Massage
Maui’s Best Massage & Spa makes a good anchor for a quieter afternoon. The studio is in the Island Surf Building at 1993 South Kīhei Road, Suite 19, a drive north from Wailea.
Choose from services such as lomi lomi, deep tissue, hot stone or couples massage, and discuss your preferences with the therapist. Book ahead for a particular time or a side-by-side couples appointment. The business also offers limited South Maui outcall service, which you can arrange directly if you’d prefer an appointment at your accommodation.
4. Browse the Shops at Wailea and Kush Fine Art
The Shops at Wailea is an easy place to combine lunch, boutiques and a gallery visit. You can spend an hour looking around or build an afternoon around the events calendar, which includes activities such as lei poʻo making, ʻukulele lessons and hula.
Stop at Kush Fine Art & Jewelry for Vladimir Kush’s imaginative paintings, prints, sculpture and jewelry. The gallery’s metaphorical scenes reward a slower look, and there’s no need to turn the visit into a shopping marathon.
Check the day’s activity listing before you arrive, especially if you’re bringing children for a class. Leave time afterward to wander the open-air courtyards or get something to eat.
5. Catch a show at Mulligans on the Blue
Mulligans on the Blue pairs a pub setting and ocean views with live entertainment in the hills above the coast. It’s a good choice when you’d rather settle into one place for dinner and a show.
Choose the evening by the entertainment calendar. Opening hours and performances vary by day, and some events have separate tickets. Check whether your booking includes a table or whether you should make a dinner reservation as well.
6. Book the Wailea golf course that fits your game
Wailea Golf has three distinct courses: Gold, Emerald and Blue. Gold brings a more demanding layout, Emerald has broad ocean views and tees for a range of players, and Blue winds through the Wailea resort area.
Let the round anchor your active Wailea itinerary. Check tee times, club rentals and the aeration schedule before booking. If you’re new to golf, a lesson at the academy can be more enjoyable than committing to a full round straight away.
7. Visit Mākena’s Big Beach
Drive south for the wide sand and dramatic shoreline at Mākena Beach, commonly called Big Beach. It’s a beautiful place for a walk or time on the sand, even when swimming isn’t on the plan.
The state park information warns of dangerous shorebreak. Ask the lifeguards about the day’s conditions and keep well clear of breaking waves. Check the park hours and entry and parking charges before leaving Wailea.
8. Take an unhurried coastal walk
The Wailea coastal path is one of the easiest ways to enjoy the area without filling the day with reservations. Follow the shoreline past beaches and resort gardens, pause for the view, then turn around whenever you’ve had enough.
An early walk is a pleasant start before lunch or shopping. Bring water and sun protection, and choose a stretch that suits your group. Surfaces, slopes and steps vary along the route, so anyone needing a step-free outing should check the specific section first.
Use the signed public access routes and remember that resort pools, loungers and other private facilities are for their guests.
9. Stop at Monkeypod Kitchen for a mai tai
Monkeypod Kitchen at the Wailea Gateway Center is known for its mai tai with honey-lilikoi foam. It’s a fun stop for lunch or dinner when you’d like a break from the beachfront resort restaurants.
Build the visit around a meal rather than chasing a particular discount. The Gateway Center is uphill from the coast, so plan transport between stops. If cocktails are part of the evening, arrange a driver or a ride back to your accommodation.
10. Explore the lava coast near La Perouse
Beyond Mākena, the Hoapili Trail near La Perouse crosses a rugged landscape of sharp lava, ocean views and historic stone features. This is a very different outing from the paved Wailea path, with little shade and uneven footing.
Go early, wear sturdy shoes and carry water. Follow state trail information and posted access rules, stay on the authorized route and leave walls and cultural features untouched.
The lava landscape is part of Haleakalā’s volcanic story. The U.S. Geological Survey dates the volcano’s most recent eruption to between about 1480 and 1600. Give yourself time to appreciate the coast without pushing farther than the heat or footing allows.
Where to base your Wailea itinerary
The Fairmont Kea Lani offers suites and villas near Polo Beach, with dining and cultural activities on the property. Choose the accommodation category for the space and features your group needs.
For a condo or villa stay, compare Wailea Ekolu, Wailea Ekahi, Wailea Elua and Hoʻolei Villas. Look at the actual rental’s location, walking route to the beach and room layout. An uphill condo, beachfront complex and villa near a resort each make for a different daily routine.
We’re a small group of full-time Maui residents that LOVE exploring and writing about what we think is the best place on Earth: The Island of Maui, Hawaii! Expect many more articles, reviews, photos and videos of Maui and all of the Hawaiian Islands. ALOHA!
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