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5-Day Maui Adventure: Beaches, Nightlife & Relaxed Cooking Retreat

Viewed by 107 travelers

Day 1: Arrival & Check-in

Lahaina, Maui, Hawaii on January 18, 2025

12:30PM

Flight Arrival at Kahului Airport

Arrive in Maui and pick up rental car to begin your stay on the island.
USD0, 30 minutes

1:00PM

Lunch near Airport at Coconut's Fish Cafe

Enjoy fresh and popular fish tacos at this casual eatery open daily from 11 AM to 9 PM, perfect for a quick and tasty lunch.
USD15-25 per person, 1 hour

2:30PM

Exploring Lahaina Town

Spend time wandering historic Lahaina with shops, galleries, and ocean views to enjoy pre-check-in.
USD0, 1.5 hours

4:00PM

Check-in at Airbnb

Settle into your accommodation in West Maui and relax after the day’s travel.
USD0, 1 hour

5:00PM

Beach Time at Kaanapali Beach

Unwind at the famous Kaanapali Beach for swimming and sunset views, ideal close to your Airbnb.
USD0, 2 hours

7:30PM

Dinner at Kimo's

Dine on local seafood favorites in this oceanfront restaurant near Lahaina, open until 9 PM; reservations recommended.
USD40-60 per person, 1.5 hours

9:30PM

Nightlife on Lahaina Front Street

Enjoy bars and live music in the lively front street area for a fun first night, open until late.
Varies, 2 hours
Find Hotels in Lahaina

Day 2: South Maui Beaches & Market

Kihei, Maui, Hawaii on January 19, 2025

8:00AM

Breakfast at Kihei Caffe

Start your day with hearty breakfast offerings including pancakes and loco moco, open 6 AM to 2 PM.
USD10-20 per person, 1 hour

9:30AM

Beach Time at Wailea Beach

Relax and swim at one of Maui's most beautiful beaches with calm waters and stunning scenery.
USD0, 3 hours

1:00PM

Lunch at Food Truck - Maui Tacos

Enjoy casual Mexican food from a popular mobile eatery, open until mid-afternoon.
USD10-15 per person, 1 hour

2:30PM

Visit Maui Swap Meet

Browse local crafts, produce, and souvenirs; note swap meet typically open Saturdays 7 AM to 1 PM, double check for other days.
USD0, 1.5 hours

5:00PM

Grocery Shopping & Dinner at Airbnb

Shop at a nearby Safeway or local market for groceries and cook dinner together to enjoy a relaxed evening.
Approx. USD15-25 per person, 3 hours
Find Hotels in Kihei

Day 3: Road to Hana Excursion

Maui, Hawaii on January 20, 2025

7:00AM

Depart for Road to Hana

Start your scenic drive early to fully experience waterfalls, hiking spots, and black sand beaches along the famous route.
USD0, 8 hours with breaks

12:00PM

Lunch at Hana Farms Roadside Stand

Enjoy fresh farm-to-table snacks and smoothies perfect for a picturesque picnic lunch.
USD10-20 per person, 1 hour

3:00PM

Stop at Wai’anapanapa State Park

Explore the unique black sand beach and coastal caves; park open daily 7 AM to 7 PM.
USD10 per car, 1.5 hours

5:00PM

Return to Airbnb

Relax after a full-day adventure back at your accommodation.
USD0, 2 hours
Find Hotels in Maui

Day 4: Cooking & Beach Day

West Maui, Hawaii on January 21, 2025

8:00AM

Breakfast at Airbnb

Enjoy a homemade breakfast made from local ingredients to start a relaxed day.
USD0 (groceries pre-purchased), 1 hour

10:00AM

Napili Bay Beach Visit

Spend the morning at this peaceful beach ideal for swimming and snorkeling.
USD0, 3 hours

1:30PM

Lunch at Sandwich & Brake

Enjoy a casual lunch with fresh sandwiches, open until 4 PM.
USD12-18 per person, 1 hour

3:00PM

Afternoon Rest at Airbnb

Take time to relax, nap, or prepare for the evening.
USD0, 2 hours

5:00PM

Group Cooking Dinner at Airbnb

Cook a group meal at your Airbnb using fresh local ingredients for a cozy night in.
USD0 (groceries pre-purchased), 3 hours
Find Hotels in West Maui

Day 5: Upcountry & Farewell Sunset

Upcountry Maui & Kaanapali, Hawaii on January 22, 2025

8:00AM

Breakfast at Grandma's Coffee House

Taste fresh coffee and delicious breakfast options in scenic Upcountry Maui, open 7 AM to 2 PM.
USD12-20 per person, 1 hour

9:30AM

Visit Maui Tropical Plantation

Experience a tram tour and tropical gardens; open 9 AM to 4 PM, a refreshing midday adventure.
USD25 per person, 2 hours

12:00PM

Lunch at Mill House Restaurant

Dine on fresh farm-to-table dishes in a beautiful plantation setting, open 11 AM to 3 PM.
USD25-40 per person, 1 hour

2:00PM

Relax at Kaanapali Beach

Enjoy your final beach hours swimming and basking in the sun.
USD0, 3 hours

5:30PM

Sunset Dinner at Duke's Beach House

Celebrate your last night with fresh seafood and tropical cocktails by the ocean; open until 9 PM.
USD40-60 per person, 2 hours
Find Hotels in Upcountry Maui & Kaanapali
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