Maui 3-Day Trip Itinerary
Maui Trip - Jan 30 to Feb 1
A romantic 3-day escape to Maui, combining the breathtaking sunrise at Haleakala, charming Upcountry exploration, a vibrant luau experience, and relaxing beach time. This itinerary is designed for a couple seeking a blend of adventure and relaxation.
Arrival & North Shore Charm
Friday, January 30Arrive at OGG & Car Rental
Arrive at Kahului Airport (OGG), pick up your rental car (highly recommended for exploring Maui), and head towards your luxurious accommodation in Wailea.
Book your rental car in advance, especially during peak season. You'll need it to fully explore the island.
Driving from OGG to Wailea takes approximately 30-40 minutes.
Check into Hotel
Check into your beautiful resort in Wailea and take some time to settle in and enjoy the amenities.
Enjoy the resort's pools, beach access, and stunning ocean views upon arrival.
Explore Paia Town
Drive to the charming, bohemian surf town of Paia.
Browse unique boutiques, art galleries, and enjoy the laid-back atmosphere.
Paia is known for its windsurfing culture and historic plantation-era buildings.
Approximately 45-minute drive from Wailea to Paia.
Dinner in Paia
Enjoy dinner at one of Paia's popular restaurants, offering a range of cuisines from fresh seafood to casual fare.
Haleakala Sunrise & Upcountry
Saturday, January 31Haleakala Sunrise
Wake up early for a spectacular sunrise viewing from the summit of Haleakala volcano.
Witness the incredible color palette unfold above the clouds.
A reservation is required for vehicles entering the summit district between 3:00 AM and 7:00 AM. Book well in advance! Dress in layers, as it's very cold at the summit. Pack snacks and hot beverages.
Breakfast in Upcountry
After descending from Haleakala, enjoy a hearty breakfast in one of Upcountry Maui's charming towns like Makawao or Kula.
Maui Swap Meet
Explore the Maui Swap Meet, the island's largest open-air flea market, taking place every Saturday morning.
Hunt for local crafts, food, and bargains.
A great place to find unique souvenirs and taste local treats. Remember to bring cash for some vendors. Booking: https://www.tripadvisor.com/Attraction_Review-g60631-d2091984-Reviews-Maui_Swap_Meet-Kahului_Maui_Hawaii.html?m=66827
Hawaii Safaris in Kula
Embark on an adventure with Hawaii Safaris in Kula.
Discover unique flora and fauna and enjoy the beautiful natural surroundings of Upcountry Maui.
This can be a great way to experience a different side of Maui's natural beauty. Check for specific tour options and availability.
Dinner in Kihei
Enjoy a relaxed dinner in Kihei, offering a variety of dining options from casual eateries to fine dining with ocean views.
West Maui & Luau Experience
Sunday, February 1Explore Lahaina Town
Drive to historic Lahaina, a former whaling village.
Wander along Front Street, explore the shops, art galleries, and visit the famous Banyan Tree Park.
Lahaina offers a glimpse into Maui's past. Parking can be challenging, so consider public lots.
Approximately 1-hour drive from Wailea to Lahaina.
Lunch in Lahaina
Enjoy lunch at one of Lahaina's many restaurants, many offering scenic waterfront views.
Relax at Kaanapali Beach
Spend a leisurely afternoon relaxing on the golden sands of Kaanapali Beach, known for its beautiful waters and Cliff Diving ceremony at Black Rock.
Perfect for swimming, sunbathing, or a romantic stroll. You might spot sea turtles while snorkeling near Black Rock.
Old Lahaina Luau
Experience an authentic Hawaiian luau with traditional cuisine, music, cultural dances, and demonstrations, all by the ocean at sunset.
Book your tickets far in advance as this popular luau sells out quickly. It's a wonderful way to immerse yourselves in Hawaiian culture. Booking: https://www.tripadvisor.com/Attraction_Review-g60634-d104288-Reviews-Old_Lahaina_Luau-Lahaina_Maui_Hawaii.html?m=66827
This 3-day itinerary for Maui can be customized using our AI travel planner. Chat with our AI assistant to modify activities, adjust timings, add personal preferences, and get recommendations for restaurants, hotels, and transportation.