5-Day Maui Itinerary: Relaxation, Beach Time & Easy Dining with Rental Car

Day 1: Arrival & Rental Car

Lahaina, Maui, Hawaii on January 18, 2025

12:30PM

Arrival at Kahului Airport and Rental Car Pickup

Arrive in Maui and pick up your rental car right at the airport to enjoy flexible and easy travel throughout your stay.
USD0 (car rental fees apply), 45 minutes

1:30PM

Drive to Airbnb in West Maui

Head to your Airbnb accommodation in Lahaina or nearby to settle in and relax after your journey.
USD0, 45 minutes

3:00PM

Relax at Airbnb

Unwind at your Airbnb with time to freshen up and enjoy the amenities.
USD0, 2 hours

5:00PM

Dinner at Lahaina Fish Co.

Enjoy a fresh, casual seafood dinner with ocean views just a short drive or walk from your Airbnb; open until 9 PM.
USD30-50 per person, 1.5 hours

7:00PM

Evening Stroll on Front Street

Take a leisurely walk through the charming streets of Lahaina to enjoy shops and ambiance without the need for late nightlife.
USD0, 1 hour
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Day 2: South Maui & Cooking

Kihei, Maui, Hawaii on January 19, 2025

8:00AM

Breakfast at Kihei Caffe

Start your day with classic Hawaiian-style breakfast offerings in Kihei, open from 6 AM to 2 PM.
USD10-20 per person, 1 hour

9:30AM

Beach Time at Wailea Beach

Relax and swim at this beautiful beach with calm, clear waters ideal for your group.
USD0, 3 hours

1:00PM

Lunch at Food Truck - Maui Tacos

Enjoy casual, tasty Mexican food from a popular local food truck for a quick bite, open until mid-afternoon.
USD10-15 per person, 1 hour

2:30PM

Grocery Shopping for Airbnb Cooking

Shop at nearby Safeway or local market in Kihei to stock up on ingredients for cooking dinner together.
USD15-25 per person, 1.5 hours

5:00PM

Cook Dinner at Airbnb

Enjoy a relaxed evening cooking a meal together in your fully equipped kitchen with quality local ingredients.
USD0 (groceries pre-purchased), 3 hours
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Day 3: Road to Hana Day

Maui, Hawaii on January 20, 2025

7:00AM

Depart for Road to Hana

Begin your scenic adventure early with your rental car to explore waterfalls, lush forests, and beaches.
USD0, 8 hours with stops

12:00PM

Lunch at Hana Farms Roadside Stand

Take a break for fresh smoothies and light bites made with local produce.
USD10-20 per person, 1 hour

3:00PM

Visit Wai’anapanapa State Park

Hike and enjoy the stunning black sand beach and lava tube caves within the park, open daily 7 AM to 7 PM.
USD10 per car, 1.5 hours

5:00PM

Return to Airbnb

Rest after your full day road trip and relax for the evening.
USD0, 2 hours

7:00PM

Dinner Takeout at Paia Fish Market

Order casual seafood takeout to enjoy at your Airbnb for an easy dinner after travel day.
USD20-30 per person, 1 hour
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Day 4: Relax & Cook

West Maui, Hawaii on January 21, 2025

8:00AM

Breakfast at Airbnb

Enjoy homemade breakfast with local ingredients and good coffee to start an easy day.
USD0 (groceries pre-purchased), 1 hour

10:00AM

Visit Napili Bay Beach

Spend the morning at a beautiful quiet beach with opportunities for swimming and snorkeling.
USD0, 3 hours

1:30PM

Lunch at Sandwich & Brake

Stop for fresh sandwiches and salads in Napili, open until 4 PM.
USD12-18 per person, 1 hour

3:00PM

Relaxation Time at Airbnb

Rest in the afternoon, read, or lounge by the pool if available at your accommodation.
USD0, 2 hours

5:00PM

Group Dinner Cooking at Airbnb

Cook one final group dinner together, celebrating with your fresh local ingredients and memories.
USD0 (groceries pre-purchased), 3 hours
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Day 5: Upcountry & Farewell

Upcountry Maui & Kaanapali, Hawaii on January 22, 2025

8:00AM

Breakfast at Grandma's Coffee House

Enjoy fresh brewed coffee and breakfast amid Upcountry Maui’s countryside, open 7 AM to 2 PM.
USD12-20 per person, 1 hour

9:30AM

Tour Maui Tropical Plantation

Take a leisurely tram tour through lush tropical gardens, open 9 AM to 4 PM.
USD25 per person, 2 hours

12:00PM

Lunch at Mill House Restaurant

Enjoy farm fresh cuisine in a lovely plantation setting, open 11 AM to 3 PM.
USD25-40 per person, 1 hour

2:00PM

Relax at Kaanapali Beach

Spend your last afternoon enjoying Maui’s iconic beach with relaxing ocean views.
USD0, 3 hours

5:30PM

Farewell Dinner at Duke's Beach House

Celebrate your Maui trip with a memorable sunset dinner featuring local seafood and tropical cocktails, open until 9 PM.
USD40-60 per person, 2 hours
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