πΊ Wailea / Kihei, Maui
3 nights β Jan 15β18 β 76β82Β°F (24β28Β°C)
South Maui's Wailea coast is the driest and sunniest part of the island β a perfect finale after the adventures of Ka'anapali. From here, tackle the legendary Road to Hana, explore upcountry botanical gardens, walk the oceanfront Wailea Beach Path, and close out the trip with a splurge dinner at Hawaii's most famous restaurant.
π Daily Itinerary
Day 10 β Ka'anapali to Wailea via 'Iao Valley
Friday, January 15
Morning
Check out of Ka'anapali. Drive south via Wailuku β stop at 'Iao Valley State Monument (on the route). The Needle rises 1,200 ft from the valley floor. Easy paved path, 30 min stop.
Late Morning
Maui Tropical Plantation (optional) β tram tour through working farm with coffee, cocoa, and tropical fruit. Quick stop en route.
Lunch
Tin Roof Maui in Kahului β Chef Sheldon Simeon's (Top Chef) casual lunch spot. Local plate lunches, pork belly bowls. ($30β40 for two, cash/card). Closes at 2 PM.
Afternoon
Check into Hilton Grand Vacations Club Maui Bay Villas. Explore the property β newer 2023 resort, condo-style with kitchen.
Late Afternoon
Walk the Wailea Beach Path β 1.5-mile oceanfront path connecting five beaches. Watch for turtles and whale spouts.
Dinner
Nalu's South Shore Grill β local favorite in Kihei. Casual, generous portions, great seafood and burgers. ($70β90 for two)
Day 11 β Road to Hana
Saturday, January 16
6:30 AM
Depart early for Road to Hana (Hwy 36/360). 64 miles of curves, one-lane bridges, and waterfalls. Allow 10β12 hours round trip. Fill gas tank and pack snacks.
Morning Stops
Twin Falls (mile 2, easy, free), Garden of Eden Arboretum (mile 10, $20pp, beautiful overlooks), Ke'anae Peninsula (mile 17, taro patches, dramatic coastline).
Midday
Wai'Δnapanapa State Park β black sand beach, sea caves, and blowholes. $5pp + $10/vehicle. Reservation required in advance.
Lunch
Hana town β limited options. Try Braddah Hutt's BBQ or Hana Ranch Restaurant. ($30β50 for two)
Afternoon (Optional)
PΔ«pΔ«wai Trail at 'Ohe'o Gulch (KΔ«pahulu) β 4 miles RT through bamboo forest to 400-ft Waimoku Falls. Moderate difficulty. Add 2β3 hours if doing this.
Evening
Return via same route (safer/faster than continuing past Hana). Arrive ~8 PM. Light dinner: Coconut's Fish Cafe in Kihei. ($40β50 for two)
Day 12 β Upcountry Gardens & Mama's Fish House
Sunday, January 17
π Maui Oceanfront Marathon β Jan 17, 2027
The Maui Oceanfront Marathon takes place today along West Maui's coast (Ka'anapali/Lahaina area). Distances: Marathon, Half Marathon, 10K, and 5K. If you decide to run the 5K, you'd need to adjust this day β early morning start near Ka'anapali (35 min drive from Wailea), then proceed with Kula/Mama's Fish House in the afternoon. Register on Race Roster.
If not running: No impact on today's plans β you'll be heading upcountry and east (Kula, Pa'ia), away from the West Maui road closures.
Morning
Drive upcountry to Kula Botanical Garden (30 min from Wailea). 8 acres of protea, orchids, native Hawaiian plants, koi ponds, and a tabletop garden. $12pp. Cooler temperatures up here β bring a light layer.
Late Morning
Ali'i Kula Lavender Farm (5 min from botanical garden). Walk through lavender fields with views of the central valley and ocean. Gift shop has lavender honey, sachets, and scones.
Afternoon
Return to Wailea. Pool time, Wailea Beach, or spa treatment at the resort. Rest up for the big dinner.
Dinner β¨
Mama's Fish House β the ultimate splurge finale. Legendary Maui restaurant since 1973. Fresh-caught fish (menu names the fisherman and where it was caught). Thatched-roof oceanfront setting on Pa'ia's north shore. ($300β400 for two with wine). Reserve 2β3 months ahead. 45-min drive from Wailea β worth every mile.
Day 13 β Departure
Monday, January 18 (MLK Day)
Morning
Optional: Kihei Caffe breakfast (famous for massive omelets and banana mac-nut pancakes, $30β40 for two, cash only, opens 5 AM). Or enjoy one last hotel breakfast on the lanai.
Late Morning
OGG airport is 25 min from Wailea. Return rental car, check in. Allow extra time β MLK Day may mean busier airport.
Afternoon/Evening
Fly OGG β connecting city β TPA. Aloha, Hawaii. πΊ
ποΈ Attractions
'Iao Valley State Monument
β β β β β 4.6 (4,800+)Sacred valley where King Kamehameha won a decisive 1790 battle. The 'Iao Needle (KΕ«kaemoku) rises 1,200 feet from the valley floor. Lush emerald walls, stream, and short botanical loop. Best visited in the morning before clouds roll in.
Road to Hana
β β β β β 4.7 (8,500+)One of the world's most scenic drives. Waterfalls around every bend, lush rainforest, black sand beaches, and dramatic coastal cliffs. Start early (7 AM), pack snacks, and don't rush β the journey IS the destination.
Kula Botanical Garden
β β β β β 4.4 (650+)8-acre upcountry garden at 3,300 ft elevation. Proteas, orchids, native koa trees, koi ponds, and an aviary. Cooler temperatures make for pleasant walking. Smaller and more intimate than the coastal gardens β feels like a secret hideaway.
Wailea Beach Path
β β β β β 4.8 (2,200+)Oceanfront walkway connecting five crescent beaches along the Wailea coast. Turtles bask on rocks, whale spouts visible offshore, and the path passes by resort gardens and lava formations. Beautiful at sunrise or sunset.
Maui Tropical Plantation
β β β β β 4.3 (1,400+)Working plantation with coffee, cocoa, coconut, papaya, and tropical flowers. Tram tour explains Hawaiian agriculture. Country store sells fresh fruit, local coffee, and macadamia nuts. Good quick stop between Ka'anapali and Wailea.
π¨ Hotels
Hilton Grand Vacations Club Maui Bay Villas
$250β350/night
β β β β β 4.4 (900+)Opened 2023 β one of Maui's newest properties. Condo-style suites with full kitchen, washer/dryer, and lanai. Modern finishes, multiple pools, close to Wailea Beach Path. Perfect for the final stretch β cook breakfast, save money for Mama's Fish House.
Wailea Beach Resort β Marriott
$350β450/night
β β β β β 4.5 (5,400+)Directly on Wailea Beach with ocean-view rooms. Multiple pools including an adults-only infinity pool. Recently renovated. Central Wailea location with easy access to The Shops at Wailea and the beach path.
Grand Wailea, A Waldorf Astoria Resort
$500β700/night (luxury alternative)
β β β β β 4.4 (8,200+)Iconic Wailea luxury resort with 40-acre grounds, massive pool complex (9 pools!), waterslides, and world-class spa. Hilton Honors points eligible (Waldorf Astoria brand). If you want to end the trip in grand style.
π½οΈ Restaurants
Mama's Fish House β¨ Splurge Dinner
β β β β β 4.7 (6,200+)Hawaiian Seafood β’ Oceanfront β’ Legendary
$300β400 for two (with wine)
Hawaii's most famous restaurant, operating since 1973. The menu names each fisherman and where the catch was landed that day. Thatched-roof Polynesian setting on a coconut-palm beach in Pa'ia. Sunset seating is unforgettable. Reserve 2β3 months ahead β this is a pilgrimage, not just dinner.
Nalu's South Shore Grill
β β β β β 4.5 (1,800+)American-Hawaiian β’ Seafood β’ Sports bar
$70β90 for two
Local favorite in Kihei's Azeka shopping center. Generous portions, excellent fish tacos, burgers, and daily fresh catch specials. Lively atmosphere, good beer selection. No pretense β just great food at fair prices.
Coconut's Fish Cafe
β β β β β 4.7 (3,600+)Seafood β’ Fish tacos β’ Casual
$40β50 for two
Best fish tacos on Maui β consistently top-rated. Fresh local fish, creative preparations (macadamia-crusted, blackened, coconut-crusted). Small casual spot in Kihei. Perfect light dinner after the Road to Hana. Expect a short wait at peak times.
Tin Roof Maui
β β β β β 4.7 (1,900+)Hawaiian plate lunch β’ Pork belly β’ Noodles
$30β40 for two
Chef Sheldon Simeon's (Top Chef Season 10 & 14) casual counter-service spot in Kahului. Signature dry mein noodles, garlic shrimp, and pork belly bowls. Local ingredients, big flavors, small prices. Lunch only (10:30 AM β 2 PM). On the route from Ka'anapali to Wailea.
π Opera & Events
South Maui is quieter on the performing arts front, but the Maui Arts & Cultural Center (MACC) in Kahului is 25 min away, and Wailea's resort scene offers live Hawaiian music nightly.
Maui Arts & Cultural Center (MACC) β Kahului
β β β β β 4.7 (320+)25 min from Wailea. Check mauiarts.org for January 2027 programming. The Castle Theater hosts concerts, dance, and visiting artists throughout the month.
Four Seasons Wailea β Live Music
β β β β β 4.8 (4,200+)Even if you're not staying here, the lobby bar features live Hawaiian slack-key guitar most evenings. Free to enjoy with a cocktail purchase. Beautiful grounds worth walking through at sunset.
πΈ Wine & Cocktail Bars
Maui Brewing Company β Kihei
β β β β β 4.3 (3,200+)Craft beer, cocktails, pub food
$30β50 for two (drinks + appetizer)
Maui's flagship craft brewery. 36 taps of house-brewed beer including Bikini Blonde, Coconut Hiwa Porter, and rotating seasonal IPAs. Full restaurant with good pizza and fish tacos. Casual, lively atmosphere. 10 min from Wailea.
Humble Market Kitchin Bar β Wailea
β β β β β 4.5 (1,100+)Craft cocktails, wine, Asian-inspired bar bites
$40β60 for two (drinks + small plates)
At Wailea Beach Resort. Creative cocktail program by a former Nobu mixologist. Asian-Hawaiian fusion small plates pair beautifully with their signature drinks. Upscale but not stuffy.
ποΈ Small Shops & Museums
The Shops at Wailea
β β β β β 4.3 (800+)Upscale open-air mall with local art galleries, Hawaiian jewelry, ABC Stores for essentials, and boutiques. Tuesday evening farmer's market (3β6 PM) features local produce, crafts, and food trucks. Live music on weekends.
Ali'i Kula Lavender Farm
β β β β β 4.5 (1,600+)13.5 acres of lavender at 4,000 ft with panoramic views. Gift shop sells lavender honey, scones, body products, and sachets. Beautiful photography spot. Combine with Kula Botanical Garden for a full upcountry morning.
π Running Routes & Hiking
Wailea Beach Path
Paved oceanfront path connecting five crescent beaches along the Wailea coast. Passes luxury resorts, rocky lava outcroppings, and elevated viewpoints perfect for whale watching. Flat and smooth β ideal for a morning jog or walk. Start from your hotel and head south toward Polo Beach or north toward Keawakapu.
Kihei Shoreline Run (N. Kihei to Kamaole)
Run along Kihei's connected beaches from North Kihei through South Kihei to Kamaole Beach Parks IβIII. Mix of beach sand and sidewalk/bike path. Flat, open ocean views the whole way. Multiple entry/exit points let you customize distance. Great for longer runs.
PΔ«pΔ«wai Trail (Hike β Road to Hana Day)
4-mile round trip through a towering bamboo forest to 400-ft Waimoku Falls in the KΔ«pahulu section of HaleakalΔ National Park. The bamboo forest section is magical β dense, creaking groves blocking out the sky. Moderate with some muddy sections and stream crossings. One of Maui's best hikes, best combined with your Road to Hana day.
π― Extras
Maui Oceanfront Marathon, Half Marathon, 10K & 5K
Sunday, January 17, 2027 β During Your Stay!
Annual oceanfront race along West Maui's coast. Point-to-point course with ocean views the entire way. The 5K is an out-and-back from the finish line area near Ka'anapali/Lahaina. 1,000β5,000 participants. Eco-friendly event (reusable speed cups).
Further Reading
Destination Guides & Resources
- Lonely Planet β Maui β Comprehensive travel guide with practical tips
- AllTrails β Maui β Trail maps, reviews, and GPS navigation for all hikes
- Hawaii Guide β Maui β Detailed local guides, updated regularly
- Go Hawaii β Maui (Official Tourism) β Official Hawaii tourism board
- Pride of Maui Blog β Local activities and insider tips
- Road to Hana Guide β Detailed mile-by-mile guide for the Hana Highway (Day 11)
π Transport
Key Distances from Wailea
| OGG Airport | 25 min (17 mi) |
| 'Iao Valley | 35 min (18 mi) |
| Kula Botanical Garden | 30 min (15 mi) |
| Road to Hana start (Pa'ia) | 45 min (25 mi) |
| Mama's Fish House (Pa'ia) | 45 min (25 mi) |
| Kihei town center | 10 min (4 mi) |
| Maui Brewing Company | 10 min (5 mi) |
Car Tips
Same Maui rental from Ka'anapali continues through Wailea (Jan 10β18 total). Return to OGG on departure day. For Road to Hana: fill the tank in Pa'ia (last gas), start by 7 AM, download offline maps (no cell service past mile 10).
Road to Hana Tips
- Reserve Wai'Δnapanapa State Park in advance β $5pp + $10/vehicle, limited slots
- Start by 7 AM to avoid traffic and have time for all stops
- Fill gas in Pa'ia β no reliable stations until Hana town
- Bring snacks, water, and motion sickness meds if needed
- Return the same way (Highway 360) β the "back way" past Hana is rough and rental companies may not cover it
- Allow 10β12 hours round trip with stops