Explore Maui in 5 days (Luxury)

Rough USD planning ranges for this luxury travel style in Maui — lodging, meals, activities, and getting around for a 5-day trip.

Accommodation: $220–400 per night. Food: $90–150 per day. Activities & tours: $80–160 per day. Transport: $60–110 per day (car share, transit, or short transfers).

Typical daily total: $420–680. Typical 5-day total: $2,100–3,400. Season, fuel, and booking lead time can push either end of the range.

Day 1 of this 5-day Maui itinerary links stops best covered with short drives around Hana.

Start with breakfast at Freshies Maui — Great · highly reviewed · Makawao, HI Vibe / cuisine: Restaurant. A great spot at Makawao, HI — useful when you want a crowd-tested meal without gambling on a random reservation.

Continue on to ʻOheʻo Gulch — a well-reviewed sight that rewards a slow visit.

Break for lunch at Hali'imaile General Store — Great · highly reviewed · Makawao, HI Vibe / cuisine: Hawaiian. A great spot at Makawao, HI — useful when you want a crowd-tested meal without gambling on a random reservation.

Begin at Waiʻānapanapa State Park — This stunning park offers dramatic coastal scenery with black sand beaches and sea caves. It's a must-see for its unique geological formations and breathtaking ocean views.

Close the day around Wailua Falls — Wailua Falls is a stunning, easily accessible waterfall on the Road to Hana. It's a perfect quick stop to admire the natural beauty of Maui. — about 7.2 mi from the previous stop.

If you want a guided option nearby, consider Viator Exclusive: Maui Tropical Rainforest Small Group Tour. From $268.00.

Continue on to Haleakalā National Park — a well-reviewed sight that rewards a slow visit.

Wind down with dinner at The Restaurant at Hotel Wailea — Good · highly reviewed · 555 Kaukahi St Vibe / cuisine: Restaurant. A good spot at 555 Kaukahi St — useful when you want a crowd-tested meal without gambling on a random reservation.

Day 2 of this 5-day Maui itinerary links stops best covered with short drives.

Start with breakfast at Kula Bistro — Great · highly reviewed · Kula, HI Vibe / cuisine: Hawaiian. Enjoy a taste of Hawaiian cuisine at Kula Bistro, a local favorite with a high Google rating.

Continue on to Upper Waikani Falls — a well-reviewed sight that rewards a slow visit.

Break for lunch at Monkeypod Kitchen by Merriman - Wailea, Maui — Good · highly reviewed · Kihei, HI Vibe / cuisine: Hawaiian. Enjoy delicious Hawaiian cuisine at Monkeypod Kitchen by Merriman, a great spot to relax after exploring Wailea.

Begin at Haleakalā National Park — Haleakalā National Park offers breathtaking sunrise and sunset views from its summit. It's a must-visit for its unique volcanic landscape and stunning panoramic vistas.

Close the day around Haleakalā Summit — Witness a breathtaking sunrise or sunset from the summit of Haleakalā, an iconic dormant volcano. The panoramic views from this elevation are truly unforgettable. — about 6.4 mi from the previous stop.

If you want a guided option nearby, consider Maui Private Half-Day Road to Hana Tour With Snacks 2026. From $299.00.

Wind down with dinner at Le Bazaar Maui — Excellent · highly reviewed · Kihei, HI Vibe / cuisine: Moroccan. An excellent spot at Kihei, HI — useful when you want a crowd-tested meal without gambling on a random reservation.

Day 3 of this 5-day Maui itinerary links stops best covered with short drives around Paia.

Start with breakfast at Momona Bakery And Coffee Shop — Great · highly reviewed · Kahului, HI Vibe / cuisine: Coffee shop. A great spot at Kahului, HI — useful when you want a crowd-tested meal without gambling on a random reservation.

Continue on to Jungle Zipline Maui-HI — a well-reviewed sight that rewards a slow visit.

Break for lunch at Tin Roof Maui — Great · highly reviewed · Kahului, HI Vibe / cuisine: Hawaiian. Pricing: Dinner ~$21 per person. Tin Roof Maui offers a taste of authentic Hawaiian cuisine, perfect for a meal before or after your festival fun.

Begin at Ho'okipa Beach Park — Ho'okipa Beach Park is a world-renowned spot for windsurfing and watching the sunset. It's a great place to observe skilled athletes and enjoy the beautiful coastal scenery.

Break for lunch at Mama's Fish House — Seafood — Mama's Fish House is a renowned seafood restaurant known for its fresh catches and beautiful oceanfront setting. It's a perfect spot to enjoy a memorable meal after exploring the charming town of Paia. — about 0.8 mi from the previous stop.

Continue on to Maui Tropical Plantation — Maui Tropical Plantation offers a glimpse into the island's agricultural heritage with its lush grounds and diverse plant life. It's a great spot to learn about local flora and enjoy a peaceful escape from the beach scene. — about 11.4 mi from the previous stop.

Wind down with dinner at Le Bazaar Maui — Moroccan — Experience the unique flavors of Moroccan cuisine at Le Bazaar Maui, a highly-rated spot in Kihei. — about 14.3 mi from the previous stop.

Wind down with dinner at Merriman's Kapalua — Great · highly reviewed · Lahaina, HI Vibe / cuisine: Restaurant. A great spot at Lahaina, HI — useful when you want a crowd-tested meal without gambling on a random reservation.

Day 4 of this 5-day Maui itinerary links stops best covered with short drives.

Start with breakfast at Nalu's South Shore Grill — Great · highly reviewed · Kihei, HI Vibe / cuisine: Hawaiian. Pricing: Dinner ~$18 per person. A great spot at Kihei, HI — useful when you want a crowd-tested meal without gambling on a random reservation.

Break for lunch at Mama's Fish House — Excellent · highly reviewed · Paia, HI Vibe / cuisine: Seafood. Mama's Fish House is a renowned seafood restaurant in Paia, known for its fresh, locally sourced ingredients and beautiful oceanfront setting. It's a perfect spot to enjoy a delicious meal after exploring the charming town.

Begin at Upper Waikani Falls — Upper Waikani Falls, also known as the "Little Niagara of the East," is a stunning natural attraction worth a stop on your journey. Its picturesque cascades offer a beautiful photo opportunity and a refreshing natural spectacle.

Close the day around ʻOheʻo Gulch — Experience the stunning natural beauty of the Seven Sacred Pools at ʻOheʻo Gulch, a breathtaking series of waterfalls and pools cascading down the mountainside. — about 13.2 mi from the previous stop.

Wind down with dinner at Mala Ocean Tavern — Great · highly reviewed · Lahaina, HI Vibe / cuisine: American. A great spot at Lahaina, HI — useful when you want a crowd-tested meal without gambling on a random reservation.

Day 5 of this 5-day Maui itinerary links stops best covered with short drives around Wailuku.

Celebrate with a $100 resort credit at The Ritz-Carlton Maui, Kapalua — Upgrade upon arrival, if available Early check-in and late checkout, if available Breakfast daily for two per bedroom Complimentary Wi-Fi.

Continue on to ʻĪao Valley State Monument — a well-reviewed sight that rewards a slow visit.

Begin at Nakalele Blowhole — Nakalele Blowhole is a stunning natural attraction on Maui's northwest coast. Witness the powerful ocean spray erupting from the lava rock formations for a truly memorable experience.

Continue on to Makaluapuna Point — Makaluapuna Point offers stunning coastal views and a chance to explore the rugged Hawaiian shoreline. It's a great spot for a scenic walk and to appreciate the natural beauty of Maui. — about 4.5 mi from the previous stop.

Break for lunch at Mala Ocean Tavern — American — Enjoy American cuisine at this popular Lahaina spot. — about 11.5 mi from the previous stop.

Wind down with dinner at Merriman's Kapalua — Dinner ~$95 per person — Enjoy a meal with a view at Merriman's Kapalua. — about 5.4 mi from the previous stop.

Break for lunch at Ula’Ula Cafe — Excellent · highly reviewed · Wailuku, HI Vibe / cuisine: Hawaiian. An excellent spot at Wailuku, HI — useful when you want a crowd-tested meal without gambling on a random reservation.

Wind down with dinner at 808 Old Town — Good · highly reviewed · 2051 Main St Vibe / cuisine: Restaurant. A good spot at 2051 Main St — useful when you want a crowd-tested meal without gambling on a random reservation.

Road to Hana — Embark on a luxurious private tour along the famous Road to Hana, experiencing Maui's breathtaking natural beauty and unique culture. This tour offers a personalized journey through lush rainforests and scenic landscapes. Consider a private tour for a more intimate and customized experience of the Road to Hana.

Haleakala — Explore the wonders of Haleakala with a private tour, offering a unique perspective on Maui's volcanic landscapes and rich history. This experience is designed for indulgence and memorable exploration.

West Maui Mountains — Take a breathtaking helicopter tour over the West Maui Mountains, offering stunning aerial views of the island's dramatic terrain. This adventure provides a unique perspective on Maui's natural splendor. Helicopter tours departing from Kahului offer flights through the West Maui Mountains.

Iao Valley — Iao Valley is a significant site featuring the iconic Iao Needle, lush gardens, and important cultural landmarks. It's recommended for sightseers, families, and casual adventurers. Combine a visit to Iao Valley with Haleakalā for a comprehensive tour that includes volcano summit views, the Iao Needle, gardens, and cultural sites.

Browse tours on Viator · Browse tours on TourRadar

The Hana Highway (Road to Hana) — This iconic 64-mile route is Maui's most famous scenic drive, winding through lush rainforests and past cascading waterfalls. You'll encounter vibrant scenery and panoramic ocean views along its approximately 600 curves and 50 bridges. Leave early to avoid crowds. Pack snacks, water, and bug repellent. Download offline maps as cell service is limited. Stop at roadside stands for fresh fruit, coconut candy, and banana bread.

The Piilani Highway (Back Road to Hana) — For a more adventurous experience, this rugged route follows Maui's southern coast, offering dramatic lava fields and sweeping, untouched ocean vistas. It's a less-traveled alternative to the traditional Road to Hana. Check weather conditions before you go, as parts of the road can be narrow and rough. Visit Kaupo General Store for local snacks. Bring a camera to capture the unique landscapes.

Haleakalā Crater — Venture upcountry to the summit of Maui's dormant volcano for a different kind of scenic drive, climbing above the clouds for unforgettable sunrise or sunset views. The drive passes through scenic ranchlands and offers views of Haleakalā National Park. Book sunrise reservations in advance if needed. Dress warmly as temperatures at the summit are significantly cooler. Explore the nearby towns of Kula and Makawao afterward.

Distinctive Airbnb-style villas and scenic stays (4.5★+, 100+ reviews) for a private luxury base.

Modern Beautiful Renovated Maui Vista — Well-reviewed Pricing: from $203. Amenities: Wifi; Dedicated workspace; Free parking on premises; Air conditioning; Kitchen. Perks: Beach gear included; Complimentary parking. This newly renovated condo is just a minute's walk from Charley Young Beach and offers easy access to other beautiful shores, making it a perfect base for your Maui beach escape. Enjoy the convenience of included beach gear, complimentary parking, and a walkable location with plenty of dining and shopping nearby.

Beautiful Modern Remodeled Maui Banyan Suite — Well-reviewed Pricing: Typical nights from ~$263. Amenities: Wifi; Air conditioning; Washer; Dryer; Kitchen; Dedicated workspace. Perks: Self check-in; Walkable; Mountain view; Beach access; Two outdoor swimming pools; Tennis courts. This modern, remodeled condo is just steps from Kamaole Beach Park II and offers a comfortable stay with amenities like a full kitchen and WiFi. Enjoy the resort's pools, spas, and tennis courts, or explore the nearby beaches.

Maui, Scenic View 1 bedroom. — Well-reviewed Amenities: internet; cable television; DVD/Blu-ray player; telephone; balcony/lanai; partial kitchen. Perks: self check-in; walkable area; garden view; no resort fees; pool; hot tub. Enjoy spacious comfort at this Maui resort, featuring lush gardens, waterfalls, and a pool. It's a scenic and walkable area with an on-site restaurant and convenience store for a convenient stay.

Beautiful 2 bedroom, 2 bath Condo in Maui Hawaii! — Well-reviewed Amenities: Wifi; Free driveway parking on premises; Shared outdoor pool; Kitchen; Self check-in; Drip coffee maker. Perks: Shared beach access; Walkable area; Tropical garden view. This beautiful 2-bedroom condo in Kihei offers a fantastic location, just across the street from Kamaole Beach Park III. It's a guest favorite, known for its walkability and proximity to both South Kihei and Wailea.

Find stays on VRBO · Find stays on IHG Hotels & Resorts · Find stays on Expedia · Find stays on Booking.com

Fine dining and standout restaurants (4.5★+, 500+ reviews) near Maui for this luxury itinerary.

Le Bazaar Maui — Excellent · highly reviewed · Kihei, HI Vibe / cuisine: Moroccan. Experience the unique flavors of Moroccan cuisine at Le Bazaar Maui, a highly-rated spot in Kihei.

Mama's Fish House — Excellent · highly reviewed · Paia, HI Vibe / cuisine: Seafood. Mama's Fish House is a renowned seafood restaurant known for its fresh catches and beautiful oceanfront setting. It's a perfect spot to enjoy a memorable meal after exploring the charming town of Paia.

Mala Ocean Tavern — Great · highly reviewed · Lahaina, HI Vibe / cuisine: American. Enjoy American cuisine at this popular Lahaina spot.

Kamaole Beach III — This beach in Kihei is a great spot for families and boogie boarding. It's known for having soft sand perfect for sandcastles and is often reliable for producing suitable waves for boogie boarding, especially in the afternoons. Look for suitable waves for boogie boarding in the afternoons when the wind and surf usually pick up. Source: paradise-found-in-maui.com

Baby Beach — There are multiple beaches named Baby Beach on Maui, known for their perfectly calm waters. A lava rock shelf near the shore blocks waves, creating a safe pool for babies and toddlers to play in. One notable location is in Lahaina, and another is at Maui's Baldwin Beach Park on the North Shore. Source: paradise-found-in-maui.com

Honolua Bay Marine Reserve — This is one of the top choices for snorkeling directly off the beach. While not a sandy beach, it's excellent for exploring underwater life. Source: paradise-found-in-maui.com

Honolua Bay — Honolua Bay is a beautiful spot on the west side of Maui, perfect for exploring the ocean.

Iao Valley State Monument — This is a must-visit spot in Maui, located in the West Maui Mountains. The iconic needle stands 1,200 feet tall and offers spectacular photo opportunities. While you can enjoy the views from a lookout, a path also leads down to the stream for a more adventurous experience. Reservations are required, so plan ahead.

Waiheʻe Ridge Trail — This challenging 4.3-mile trail offers sweeping views of green mountains, the blue ocean, and distant waterfalls. It's described as a rewarding hike with stunning scenery from beginning to end.

Makamakaole Falls Trail — This 3-mile trail features 13 stream crossings and leads to two waterfalls, offering a chance to cool off. It's a classic Hawaiian waterfall hike.

Spend-based hotel perks and premium credit card travel benefits tied to Maui — lounge access, dining and event credits, transport upgrades, and exclusive booking extras. Confirm current card and property terms before you rely on them.

Hyatt Regency Maui Resort & Spa | The Hotel Collection — Each eligible FHR booking includes … two, (2) a $100 credit towards eligible charges, (5) room upgrade upon arrival when available, and (6) complimentary Wi-Fi. Source: americanexpress.com

Hyatt Regency Maui — Retreat to a spacious, pristine Maui suite featuring a private lanai with glass balcony and breathtaking beach views, or choose a tranquil hotel room Source: hyatt.com

Maui Resort Rooms & Suites — Check-in/-out Times. Check-in Time: 4:00 PM Check-out Time: 12:00 PM · Early Arrivals and Late Departures. Source: fourseasons.com

The Ritz-Carlton Maui, Kapalua — This luxury resort in Kapalua, Maui, offers a magical experience with over 70 weekly curated activities celebrating Hawaiian culture, wellness, and nature. Enjoy redesigned rooms and suites with island-inspired design and tropical views. Consider upgrading your stay to include The Ritz-Carlton Club Lounge for exclusive service, a private lounge, and personalized experiences. Daily access passes are available for purchase, pending availability. Source: ritzcarlton.com

Kapalua — Kapalua on Maui is a destination known for its vibrant colors, captivating perspectives, and magical experiences, inviting guests to embrace life's fullness. It's a place to restore yourself to nature and enjoy the sacred ground. Explore the 70+ weekly curated experiences that celebrate Maui's culture, wellness, and natural splendor. Take advantage of 25 percent savings on stays of four nights or more. Source: ritzcarlton.com