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

Viewed by 85 travelers

Day 1: Arrival & Beach Relaxation

Lahaina, Maui, Hawaii on January 18, 2025

9:00AM

Arrival at Kahului Airport

Arrive in Maui and pick up rental car to drive to your Airbnb in West Maui near Lahaina, perfect for beach access and nightlife.
USD0, 1 hour

11:00AM

Beach Time at Kaanapali Beach

Enjoy the pristine sands and swimming at Kaanapali Beach, one of Maui's best beaches with abundant amenities and wave-free swimming areas.
USD0, 3 hours

2:00PM

Lunch at Leoda's Kitchen and Pie Shop

Savor fresh sandwiches, salads, and homemade pies at this local favorite, open daily from 10 AM to 6 PM.
USD15-25 per person, 1 hour

3:30PM

Relax & Settle into Airbnb

Unwind at your Airbnb to get settled in and unpack before the evening.
USD0, 1.5 hours

5:00PM

Nightlife at Lahaina Front Street

Explore the vibrant nightlife with bars, live music, and restaurants, open into late night typically until 11 PM or later.
Varies, 3 hours

8:00PM

Dinner at Kimo's

Enjoy fresh seafood and Hawaiian specialties at this popular oceanfront restaurant open until 9 PM; make reservations in advance.
USD40-60 per person, 1.5 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 options including pancakes and loco moco, open from 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 views.
USD0, 3 hours

1:00PM

Lunch at Food Truck - Maui Tacos

Enjoy casual Mexican food with fresh local ingredients from a popular food truck open until mid-afternoon.
USD10-15 per person, 1 hour

2:30PM

Visit Maui Swap Meet

Browse local crafts, fresh produce, and souvenirs at this market open Saturdays, 7 AM to 1 PM (verify for Sunday availability ahead).
USD0 entry, 1.5 hours

5:00PM

Return to Airbnb for Cooking Night

Shop for groceries at local stores (e.g., Safeway in Kahului) and prepare dinner at the Airbnb kitchen for a relaxed evening.
Approx. USD15-25 per person for groceries, 3 hours
Find Hotels in Kihei

Day 3: Road to Hana Day Trip

Maui, Hawaii on January 20, 2025

7:00AM

Road to Hana Drive

Embark early on the scenic and famous Road to Hana, exploring waterfalls, black sand beaches, and small hikes along the way.
USD0, 8 hours with stops

12:00PM

Lunch at Hana Farms Roadside Stand

Grab fresh, local food and fruit smoothies from the roadside stand, perfect for a picnic lunch during the trip.
USD10-20 per person, 1 hour

3:00PM

Visit Wai’anapanapa State Park

Explore the park’s black sand beach and sea caves; park open daily from 7 AM to 7 PM.
USD10 per car, 1.5 hours

5:00PM

Drive Back to Airbnb

Return in the evening to relax from the day’s adventures.
USD0, 2 hours
Find Hotels in Maui

Day 4: Airbnb Cooking & Local Beach

West Maui, Hawaii on January 21, 2025

8:00AM

Breakfast at Airbnb

Enjoy a leisurely homemade breakfast to start your day fresh using local ingredients.
USD0 (groceries pre-purchased), 1 hour

10:00AM

Walk or Swim at Napili Bay

Relax on one of Maui’s peaceful beaches ideal for swimming, snorkeling, and sunbathing.
USD0, 3 hours

1:30PM

Lunch at Sandwich & Brake

Light casual lunch featuring sandwiches and local fixings, open till 4 PM.
USD12-18 per person, 1 hour

3:00PM

Free Time / Nap at Airbnb

Return to Airbnb to rest, read, or enjoy your accommodations before evening plans.
USD0, 2 hours

5:00PM

Cook Dinner at Airbnb

Prepare a delicious group dinner using local fresh produce and seafood bought earlier.
USD0 (groceries pre-purchased), 3 hours
Find Hotels in West Maui

Day 5: Upcountry & Sunset

Upcountry Maui & Kaanapali, Hawaii on January 22, 2025

8:00AM

Breakfast at Grandma's Coffee House

Enjoy fresh coffee and hearty breakfast dishes located in Upcountry Maui, open daily 7 AM to 2 PM.
USD12-20 per person, 1 hour

9:30AM

Visit the Maui Tropical Plantation

Tour this working plantation with gardens, tram rides, and a chance to learn about island crops. Open 9 AM to 4 PM.
USD25 per person, 2 hours

12:00PM

Lunch at the Plantation's Mill House Restaurant

Savor farm-to-table dishes with island flavors in a beautiful plantation setting, open 11 AM to 3 PM.
USD25-40 per person, 1 hour

2:00PM

Afternoon at Kaanapali Beach

Return to enjoy final beach time swimming and relaxing on this iconic Maui beach.
USD0, 3 hours

5:30PM

Sunset Dinner at Duke's Beach House

Cap your trip with beachfront dining featuring fresh fish and tropical cocktails, open until 9 PM.
USD40-60 per person, 2 hours
Find Hotels in Upcountry Maui & Kaanapali
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