9-Day Maui Model Itinerary: Scenic Drives and Resort Relaxation

4 cities | 26 attraction(s) | total distance 519 km

TIPS

This 9-day model itinerary for Maui is based on a stay in Kaanapali and is designed to let you enjoy a balanced mix of beach resort time, nature, scenic drives, and town strolling. The main points are as follows. --- Overall Concept - Area of stay: Assumes the “Kaanapali” resort area in West Maui - Style: Classic sightseeing + a bit of adventure, with a relatively relaxed schedule - Transportation: Primarily rental car recommended (tours can also be used on long-drive days) --- Overview of Each Day Day 1: Arrival & Kaanapali Stroll - After arriving at Kahului Airport, transfer to Kaanapali (about 45–60 minutes) - Walk along Kaanapali Beach to reset from jet lag and travel fatigue - Light shopping and dining at “Whalers Village” Day 2: Fully Enjoy the Kaanapali Resort - Swimming and strolling at Kaanapali Beach - Snorkeling at the northern end “Black Rock” (possible encounters with sea turtles) - Relax at the hotel pool and spa - Time your visit to enjoy cocktails at a beach bar at sunset Day 3: Lahaina Town (visiting with sensitivity to recovery status) - Stroll through the historic port town of “Lahaina” (check up-to-date information on the fire damage in advance) - Focus on reopened areas around “Banyan Tree Park” and “Front Street,” enjoying shops, cafés, galleries, and more - Be mindful of spending that supports the local economy - Return to Kaanapali in the evening and enjoy a leisurely dinner Day 4: Sunrise at Haleakala National Park - Watch the sunrise near the summit of “Haleakala” at about 3,055 m elevation - If driving on your own, a “sunrise entry reservation” is required; joining a tour is also recommended - Winter-level cold-weather gear is essential - Stop at cafés and farms in the “Kula” uplands on the way down - Rest at the hotel in the afternoon (a recovery day after the early start) Day 5: Scenic Drive on the Hana Highway - Drive the spectacular east-coast route “Hana Highway,” with its continuous curves and bridges - Take a short waterfall trail at “Twin Falls” near the beginning - Visit “Waianapanapa State Park,” famous for its black sand beach (reservations may be required) - Have lunch in the unpretentious “Hana Town” - Return to Kaanapali by evening (an itinerary that prioritizes safety and avoids overdoing it) Day 6: Grown-up Resort Time in the Southern Wailea Area - Relax at “Wailea Beach,” lined with luxury resorts - Shopping and dining at “The Shops at Wailea” - Visit the impressive, expansive “Makena Beach (Big Beach)” - Stop by supermarkets (Foodland, Safeway, etc.) on the way back to shop Day 7: Iao Valley & Kahului Area - See the valley scenery and Iao Needle at “Iao Valley State Monument,” with a light walk - Enjoy the local-town atmosphere in nearby “Wailuku” and have lunch at cafés or bakeries - Do bulk shopping and buy souvenirs at big-box stores in Kahului (Costco, Target, Walmart, etc.) - Return to the hotel in the evening and relax Day 8: Free & Buffer Day - Free time according to weather and fitness - Examples: Molokini snorkeling, whale-watching (in winter), SUP and other activities - Or simply enjoy “a day of doing nothing” at your favorite beach Day 9: Final Day & Departure - Final beach walk in the morning - After checkout, head to the airport with plenty of time (aim to arrive 2–3 hours before departure) - Last-minute shopping for coffee, macadamia nuts, etc. at Kahului Airport --- Directions for Customization - For active travelers Add more trekking on the Hana Highway or at Haleakala and include ocean activities such as Molokini tours. - For relaxed travelers Shorten long drives and add more beach and spa days to reduce travel time. - For family trips Adjust the schedule so that a long travel day is followed by a beach-only day, avoiding uneven physical strain. Overall, this is structured as a “relaxed itinerary that uses Kaanapali as a base while covering Maui’s signature spots such as Haleakala, Hana, Wailea, and Iao Valley, with rest days built in.”

Day1: Maui > Hawaii > Lahaina

3 attraction(s) · 33 km

On this itinerary, after arriving at Kahului Airport on Maui, you will transfer to the Kaanapali area by rental car or shuttle in about 45–60 minutes and enjoy a beach resort stay. After check-in, take a walk along Kaanapali Beach to unwind from the fatigue of travel while gazing at Lanai and Molokai, and have fun shopping at Whalers Village or picking up drinks and snacks at an ABC Store. Dinner is planned at a restaurant overlooking the beach, where you can enjoy Hawaii-style seafood such as mahi-mahi and ahi poke and spend a relaxing first day.

Kahului Airport

Serving the Maui area, this airport offers flights overseas & to interisland destinations.

28 km

Whalers Village

Beachside mall with boutiques, restaurants, hula lessons & other activities.

5 km

ABC Stores

Chain retailer selling island-themed apparel for the family, plus jewelry, food, home goods & gifts.

Day2: Maui

2 attraction(s) · 2 km

This is a plan to leisurely enjoy the resort around Kaanapali on Maui. In the morning, enjoy swimming and snorkeling while strolling along Kaanapali Beach, with the chance to see sea turtles near high-visibility Black Rock. In the afternoon, relax at the pools and spas of resort hotels such as the Hyatt and Sheraton, then head back to the beach in the evening to watch the sunset and savor cocktails like Mai Tais at a beach bar—a healing-focused day.

Hyatt Regency Maui Resort and Spa

Tropical-garden beach resort with outdoor pools, a day spa & water sports, plus seven restaurants.

2 km

Sheraton Maui Resort & Spa

Upscale oceanfront property offering island-style dining & a free area shuttle, plus a pool & a spa.

Day3: Maui > Lahaina

4 attraction(s) · 8 km

On this day, you will visit the historic port town of Lahaina on Maui, observe the progress of recovery after the large-scale 2023 wildfire, and enjoy walking around the town focusing on shops and restaurants that are open. Stop by Banyan Tree Park, known for its giant banyan tree, to reflect on the town’s history, and stroll Front Street, visiting seaside cafés and galleries for lunch or coffee while browsing local art shops. In the evening, return to the hotel area in Kaanapali and enjoy a leisurely dinner nearby.

Kaanapali

6 km

Lahaina

2 km

Lahaina Banyan Court

This compact public space features a historical courthouse & Maui's oldest living banyan tree.

1 km

Front Street

Oceanside shopping & dining strip of Lahaina, also home to a park with a huge banyan tree from 1873.

Day4: Maui > Hawaii

2 attraction(s) · 12 km

On Maui, you will head to Haleakala National Park early in the morning to watch the sunrise emerging above a sea of clouds from the Summit Visitor Center at an elevation of about 3,055 meters. Dress warmly as if for midwinter and enjoy the spectacular scenery while taking care of your physical condition, then stop at the Kula uplands on the way down to linger over breakfast at cafés or farms. In the afternoon, return to the hotel and spend a relaxing time by the pool or in your room to recover from the early start—a day with plenty of breathing room.

Haleakalā Visitor Center

12 km

Kula

Day5: Maui

4 attraction(s) · 79 km

Using Kaanapali as your base on Maui, you will depart early in the morning to drive the scenic “Hana Highway” along the northeast coast. While driving this road of continuous curves and bridges, stop at highlights such as Twin Falls, where you can easily enjoy waterfalls and a jungle-like atmosphere on a short trail, and Waianapanapa State Park, famous for its black sand beach and lava caves. After tasting local food in the quaint town of Hana, you will return to Kaanapali by early evening with a relaxed schedule that avoids overexertion and rest at the hotel.

Kaanapali

47 km

Twin Falls Maui

Rainforest hiking & sightseeing spot featuring waterfalls & pools, with guided tours available.

30 km

Waiʻānapanapa State Park

Coastal park featuring black lava sand, tidal caves & native plants also has cabins for rent.

4 km

Hana

Day6: Maui > Hawaii > Kahului

6 attraction(s) · 74 km

On this day, you will head to the Wailea area in southern Maui to enjoy the calm atmosphere unique to a luxury resort. First, spend a leisurely time at Wailea Beach and stroll along the coastal walking path. Then enjoy shopping and dining at The Shops at Wailea. In the afternoon, venture further south to Makena Beach (Big Beach) to take in the powerful scenery and vast sandy shore. On the way back toward Kaanapali in the evening, stop by supermarkets such as Foodland and Safeway to stock up on fruits and snacks in preparation for relaxation time at your accommodation.

Kaanapali

39 km

Wailea Beach

1 km

The Shops at Wailea

Mall with more than 70 shops, restaurants & art galleries, with regular evening entertainment.

7 km

Makena Beach

Spacious, scenic beach ideal for swimming & snorkeling, with picnic tables & a food truck.

12 km

Foodland

Local supermarket chain with departments for produce, general groceries & Hawaiian specialties.

18 km

Safeway

Longtime supermarket chain carrying brand-name & house-label groceries, plus a deli, bakery & more.

Day7: Maui > Hawaii > Kahului

7 attraction(s) · 29 km

On this day, you will visit Iao Valley State Monument on Maui, lightly walking along the stream while enjoying the lush green valley and views of the Iao Needle. After sightseeing during the cool morning hours, move to the town of Wailuku, which retains a historic atmosphere, and enjoy lunch at local cafés and bakeries. In the afternoon, visit the shopping areas in Kahului—Costco, Target, Walmart, and others—to shop for souvenirs and Hawaii-exclusive goods. In the evening, return to the hotel and rest up for the remaining days of your trip.

Kaanapali

17 km

ʻĪao Valley State Monument

Lush, 4,000-acre valley offering hiking, sightseeing, a nature center & views of the Iao Needle.

5 km

Wailuku

4 km

Kahului

3 km

Costco Wholesale

Members-only warehouse selling a huge variety of items including bulk groceries, electronics & more.

2 km

Target

Retail chain offering home goods, clothing, electronics & more, plus exclusive designer collections.

1 km

Walmart

Day8: Hawaii

1 attraction(s) · 0 km

This day is set as a completely free and buffer day on Maui, allowing you to spend it flexibly according to the weather and how you feel. You can join activities such as snorkeling at Molokini, whale watching in winter, or stand-up paddleboarding, or spend a luxurious time doing nothing while listening to the sound of the waves at a favorite beach—enjoying Maui’s charms at your own pace.

Molokini Crater

Destination for boat & rafting excursions to a volcanic atoll known for snorkeling & diving.

Day9: Maui

2 attraction(s) · 27 km

During this 9-day trip to Maui, you will use Kaanapali Beach as your base, spending relaxed time on beach walks and snorkeling while also fully enjoying Maui’s unique great outdoors with scenic drives along the Hana Highway by rental car and sunrise/sunset viewing at Haleakala. Along the way, you’ll enjoy strolling and shopping in historic Lahaina Town and savor local gourmet food. On the final day, after soaking in the lingering memories of your trip at the beach, you will buy souvenirs at Kahului Airport and head home—an itinerary that balances active experiences and relaxation.