Maui, Hawaii, USA 14-Day Trip Itinerary

Arrival at Kahului Airport (OGG)

Arrive at Kahului Airport, pick up your rental car, and drive to your luxurious resort in Wailea.

Check into your accommodation and settle in.

Pre-book your rental car well in advance. Wailea is about a 30-40 minute drive from OGG.

Resort Pool & Beach Time

Unwind after your journey with a relaxing afternoon by the resort pool or on the beautiful Wailea Beach. Enjoy the warm sun and ocean breeze.

Grab a complimentary beach towel and find your perfect spot. Consider ordering a refreshing drink.

Sunset Dinner in Wailea

Enjoy your first Maui dinner with stunning sunset views at a restaurant in Wailea.

Options range from casual to fine dining.

Many restaurants along the Wailea coast offer fantastic sunset views. Make a reservation, especially for popular spots.

Maui Swap Meet

Explore Maui's largest open-air flea market, offering local food, crafts, souvenirs, and unique bargains.

A great way to experience local culture on a Saturday morning.

Arrive early for the best selection and to avoid crowds. Bring cash as some vendors may not accept cards.

Maui Pineapple Tour

Discover the history, culture, and cultivation of pineapples on Maui.

Learn about the process from field to plate and enjoy fresh pineapple tasting.

This tour is a sweet insight into Maui's agricultural heritage. Wear comfortable shoes and sun protection.

Afternoon at Wailea Beach

Spend a leisurely afternoon swimming, sunbathing, or trying out some watersports like paddleboarding or snorkeling directly from Wailea Beach.

Wailea Beach is consistently ranked among the best beaches in the world. Equipment rentals are often available near the major resorts.

Kihei Dinner & Nightlife

Head to nearby Kihei for a casual dinner and to experience some of the town's laid-back nightlife.

Options include local bars with live music.

Kihei offers a more relaxed vibe compared to Lahaina, with many beachfront restaurants and bars popular with locals and visitors.

Hike Maui: Waterfalls & Rainforest

Embark on a guided hike through Maui's lush rainforest, swimming beneath waterfalls and experiencing the island's natural beauty with a naturalist.

Wear water-friendly shoes, swimwear, and bring a towel. This is a moderate activity, suitable for most fitness levels.

Afternoon Spa or Pool

After your hike, treat yourselves to some well-deserved relaxation.

Parents can enjoy a spa treatment, while you might opt for some quiet pool time or a refreshing dip.

The resort spa offers a range of treatments. Book any desired spa appointments in advance.

Dinner at Leisure

Enjoy dinner at one of the resort's restaurants or explore other dining options in Wailea at your own pace.

Consider a more casual meal tonight after a day of activity.

Hawaii Nautical Snorkel Trip

Embark on an unforgettable snorkeling or whale watching tour (seasonal, but August is still good for marine life) with Hawaii Nautical, exploring Maui's vibrant underwater world.

Ma'alaea Harbor is a common departure point for boat tours. Bring reef-safe sunscreen, a hat, and a camera. Price varies per activity and boat size.

Maui Ocean Center

After your snorkel trip, visit the Maui Ocean Center, a premier aquarium showcasing Hawaii's marine life, including one of the world's largest displays of live Pacific corals.

A great way to learn more about the creatures you saw while snorkeling. Conveniently located near Ma'alaea Harbor.

Maui Sunset Cocktail Cruise

Enjoy a beautiful sunset cruise along the Maui coast, offering stunning views, cocktails, and often live music.

A perfect way to spend an evening together.

Numerous companies offer sunset cruises. Book in advance, especially for popular options. Dress code is typically resort casual.

Maui Flight Academy Experience

Take the controls of a modern aircraft with an instructor and enjoy breathtaking aerial views of Maui.

A unique and thrilling experience!

This is a hands-on experience! Be sure to book your flight time in advance. It's safe and exhilarating.

Maui Brewing Co. Tour & Lunch

Visit Hawaii's largest craft brewery for a tour and tasting.

Enjoy lunch at their brewpub and sample local beers (for those 21+).

They offer non-alcoholic options and delicious food. Check their website for tour times and availability.

Relaxed Afternoon in Wailea

Enjoy a free afternoon to relax by the pool, indulge in some last-minute resort amenities, or do some light shopping at The Shops at Wailea.

This is a good opportunity to simply unwind and soak in the Maui atmosphere before heading to your evening plans.

Upscale Wailea Dinner

Treat yourselves to a special fine dining experience at one of Wailea's exquisite restaurants, celebrating your first few days in paradise.

Make reservations well in advance for high-end restaurants. Many offer unique Hawaiian-inspired cuisine.

Resort Check-in

Check into your luxurious accommodation in Kapalua, settling in and enjoying the resort's amenities.

Enjoy the facilities and breathtaking views offered by your resort.

Relax on Ka'anapali Beach

Spend a relaxing afternoon on the renowned Ka'anapali Beach, famous for its golden sands and clear waters. Enjoy swimming, sunbathing, or a leisurely stroll.

Look out for cliff diving ceremonies at Black Rock (Pu'u Keka'a) around sunset.

Dinner in Lahaina

Enjoy dinner at one of the many restaurants in historic Lahaina town, offering a variety of cuisines and oceanfront dining options.

Consider making reservations, especially for oceanfront spots.

Skyline Hawaii Zipline

Experience an exhilarating 8- or 11-line zipline course, gliding high above Ka'anapali's coastal landscape with expansive ocean views.

Take a break mid-tour at a treehouse.

Book in advance. Wear closed-toe shoes. Views of Maui's untouched lands and the Pacific Ocean.

Lunch in Lahaina

Grab a casual lunch in Lahaina town, perhaps trying some local Hawaiian fare or fresh seafood.

Explore Old Lahaina Town

Wander through the historic streets of Old Lahaina, a former whaling village.

Discover art galleries, shops, and cultural landmarks like the Old Lahaina Banyan Tree and Lahaina Harbor.

Consider visiting the Baldwin Home Museum for a glimpse into missionary life.

Evening Stroll & Dinner

Enjoy a leisurely evening stroll along Front Street, perhaps catching a sunset, followed by dinner at a restaurant overlooking the ocean.

Hawaii Nautical Ocean Experience

Embark on an unforgettable ocean experience, such as a snorkeling tour, whale watching (seasonal), or a scenic coastal cruise with Hawaii Nautical. Explore Maui's rich marine life.

Hawaii Nautical offers various tours. Choose based on interest (snorkeling, catamaran cruise). Book in advance.

Maui Swap Meet

Visit Maui's largest open-air flea market, taking place every Saturday morning.

Hunt for local food, crafts, and unique bargains.

A great place to find local souvenirs and try Hawaiian street food. Arrive early for the best selection.

Maui Ocean Center

Explore Hawaii’s marine life at the Maui Ocean Center, home to one of the world’s largest displays of live Pacific corals.

A fantastic educational and immersive experience.

Great for all ages. Pre-booking tickets online is recommended.

Dinner in Kihei

Enjoy a casual dinner in Kihei, known for its laid-back atmosphere and diverse dining options, after your visit to the Ocean Center.

Maui Pineapple Tour

Discover the history, culture, and hard work behind Hawaii's iconic pineapple.

Enjoy a guided tour through the fields and a fresh pineapple tasting.

Located in Upcountry Maui. Wear comfortable shoes and sun protection.

Lunch in Makawao

Enjoy a charming lunch in the paniolo (Hawaiian cowboy) town of Makawao, known for its unique shops and local eateries.

Maui Brewing Co. Visit

Head back towards Kihei to visit Maui Brewing Company, Hawaii's largest craft brewery.

Enjoy a tasting flight or a pint on their lanai (patio).

They also offer tours of the brewery. Great for sampling local brews.

Resort Dinner & Relaxation

Enjoy a relaxed evening with dinner at one of your resort's restaurants or a nearby eatery, unwinding after a day of exploration.

Maui Flight Academy

Take the controls of a technologically advanced aircraft for a unique and thrilling flight experience over Maui, offering breathtaking aerial views.

Experience a modern aircraft with a parachute system for ultimate safety. Booking well in advance is essential.

Lunch in Kahului

Enjoy a casual lunch in Kahului, the island's commercial hub, after your exciting flight experience.

Afternoon Resort/Beach Relaxation

Return to your resort for an afternoon of relaxation.

Enjoy the pool, a spa treatment (optional, extra cost), or simply lounge on the beach near your hotel.

Take advantage of the resort's amenities for a tranquil afternoon.

Sunset Dinner in West Maui

Indulge in a special sunset dinner in the West Maui area, perhaps at a restaurant offering stunning ocean views to mark the end of this segment of your trip.

Maui Pineapple Tour

Discover the history and culture of pineapples in Hawaii with a guided tour through the fields.

Enjoy fresh pineapple tastings and learn about the harvesting process.

Book online in advance to secure your spot. Wear comfortable shoes and bring sun protection. This is an enriched activity from TripAdvisor.

Lunch in Makawao

Enjoy a casual lunch in the charming paniolo (Hawaiian cowboy) town of Makawao.

Explore local eateries offering fresh, farm-to-table options.

Makawao offers a variety of cafes and restaurants. Try fresh local ingredients.

Hawaii Safaris Exploration

Embark on a unique agricultural or nature tour through Kula's scenic landscapes, offering insights into local flora and fauna. This offers a different perspective on Maui's natural beauty.

Contact Hawaii Safaris directly for tour details and availability. This is an enriched activity from Google Places.

Scenic Drive Kula

Take a leisurely drive through the scenic Kula region, enjoying panoramic views of Maui, the Pacific Ocean, and the slopes of Haleakala.

Consider a stop at Ali'i Kula Lavender Farm.

The lavender farm has a small shop and beautiful gardens, offering a peaceful experience.

Dinner in Wailea

Return to Wailea for a relaxing dinner after your Upcountry explorations.

Enjoy fine dining or a casual meal at one of the resort area's many restaurants.

Reservations recommended for popular spots.

Early Start for Hana

Begin your full-day adventure on the scenic Road to Hana.

An early start helps avoid crowds and allows more time for stops along the way. Grab breakfast and snacks for the road.

Pack essentials: snacks, water, sunscreen, bug spray, swimwear, towels. Download offline maps as cell service is spotty.

Explore Hana Highlights

Experience the famous Road to Hana, stopping at various waterfalls (e.

g., Twin Falls, Wailua Falls), black sand beaches (e.g., Wai'anapanapa State Park), lush botanical gardens, and scenic overlooks. Take your time to enjoy the natural beauty.

Plan your stops in advance. Many attractions require a short hike. Wai'anapanapa State Park often requires reservations.

Lunch in Hana

Enjoy a casual lunch at one of the many roadside stands or small cafes in Hana.

Options include food trucks serving fresh local cuisine.

Cash is often preferred at many roadside vendors.

Return Drive to Wailea

Begin your return journey from Hana to Wailea.

The drive can be long, so ensure you have sufficient daylight and are well-rested.

Consider driving the 'reverse' route for different views or continuing past Hana towards the 'backside' for a more adventurous and less-trafficked route (check road conditions first).

Relaxed Dinner in Wailea

After a long day on the Road to Hana, enjoy a well-deserved, relaxed dinner in Wailea.

Opt for a comfortable setting to unwind.

Casual dining options are abundant in Wailea/Kihei.

Hawaii Nautical Boat Tour

Enjoy a morning out on the water with Hawaii Nautical.

Choose from snorkeling, whale watching (seasonal), or a scenic coastal cruise to admire Maui's beauty from the sea.

Book in advance. Wear swimwear and bring a towel. Check with Hawaii Nautical for age restrictions on certain tours. This is an enriched activity from TripAdvisor.

Lunch in Ma'alaea

Grab a fresh seafood lunch or a casual meal near Ma'alaea Harbor after your boat tour.

Enjoy views of the harbor and ocean.

Several cafes and restaurants are located around the harbor.

Maui Brewing Company Visit

Head to Maui Brewing Company for a brewery tour and tasting.

Enjoy locally crafted beers (for parents) and a lively atmosphere. They also offer food and non-alcoholic options.

Tours often require reservations. The taproom is family-friendly. This is an enriched activity from TripAdvisor.

Farewell Dinner in Wailea

Savor a memorable farewell dinner at one of Wailea's exquisite restaurants.

Reflect on your incredible Maui journey over a delicious meal.

Consider making reservations well in advance for high-end restaurants. Many offer stunning sunset views.

Post-Dinner Drinks/Music

Enjoy some light evening entertainment or cocktails at a lounge within your resort or a nearby bar in Wailea.

A relaxed atmosphere to enjoy the last night.

Many resorts have live music or elegant bars suitable for both parents and a 19-year-old.

Leisurely Breakfast

Enjoy a final leisurely breakfast at your resort or a favorite local cafe, soaking in the last moments of your Maui vacation.

Take advantage of any resort breakfast options or try a popular local brunch spot.

Last-Minute Souvenir Shopping

If time permits, do some last-minute souvenir shopping for gifts or mementos of your trip at the resort shops or nearby boutiques.

Consider local crafts, coffee, or macadamia nuts.

Hotel Checkout

Complete the checkout process at your resort.

Ensure all your belongings are packed and ready for departure.

Confirm your airport transfer or rental car return arrangements.

Travel to Kahului Airport (OGG)

Allow ample time for travel from Wailea to Kahului Airport (OGG), approximately 30-45 minutes without heavy traffic.

Return your rental car if applicable, or take a pre-booked shuttle/taxi. Factor in potential traffic.

Airport Check-in & Security

Proceed with check-in and security at Kahului Airport (OGG).

Ensure you arrive well in advance of your flight.

Domestic flights recommend arriving 2 hours prior, international 3 hours. Verify TSA guidelines.