Ultimate 16-Day Oceanfront Adventure in Maui, Hawaii Itinerary

Start your day with a hearty breakfast at The Mill House, surrounded by the lush plantation. Post breakfast, embark on an exciting Ma'alaea Harbor Whale Watching Catamaran Cruise to witness the majestic humpback whales in their natural habitat.

After the cruise, enjoy a delightful lunch at Three's Bar & Grill, known for its fusion of Hawaiian, Southwestern, and Pacific Rim cuisine. Spend your afternoon at the Maui Ocean Center, where you can explore the fascinating marine life of Hawaii.

Dine at The Beach House Bar & Grill and indulge in their fresh seafood while enjoying the ocean breeze. Cap off the evening with a walk on the beach or a visit to the Maalaea Harbor to see the boats returning from their day's adventures.

Have a grab-and-go breakfast from Guava Tree Bar & Grill as you prepare for a full day of adventure. Start early and drive the famous Road to Hana (Hana Highway), making stops at the Pua'a Ka'a State Wayside Park and other scenic spots.

Enjoy a picnic lunch at the beautiful Wai'anapanapa State Park, where you can explore the black sand beach and the stunning coastal views. Continue your journey and visit the mesmerizing Oheo Gulch (Seven Sacred Pools) in the afternoon.

As you head back, stop at Pailolo Bar & Grill for a relaxing dinner. Reflect on the day's adventures and enjoy the laid-back atmosphere of the oceanfront restaurant.

Enjoy a breakfast with a view at Lokelani Pool Bar within the Grand Wailea resort. Post breakfast, drive up to the serene Ali'i Kula Lavender Farm where you can immerse yourself in the fragrant lavender fields and enjoy the panoramic upcountry vistas.

For lunch, visit KAPA Bar & Grill and savor their farm-to-table dishes. Afterward, take a guided tour of the Hali'imaile Pineapple Farm to learn about the island's sweetest export and enjoy some fresh pineapple treats.

Dine at The Pint & Cork in the evening, a cozy pub-style restaurant with a wide selection of beers and comfort food. Wind down with a stroll in the upcountry, taking in the cool mountain air and the starry night sky.

Start your day with a breakfast at The Beach House Bar & Grill, then spend the morning at the beautiful Makena Beach, also known as "Big Beach," where you can relax on the golden sands and take a dip in the clear waters.

For lunch, head to Haui's Life's A Beach and enjoy their casual beachside dining. Afterward, continue to Paia, a charming town with unique shops and a laid-back vibe. Explore the town and grab a coffee at one of the local cafes.

Experience the Te Au Moana Luau at the Wailea Beach Resort, where you'll be treated to a traditional Hawaiian feast and a spectacular Polynesian show. It's a perfect way to immerse yourself in the island's culture and hospitality.

Enjoy a breakfast at Diamonds Bar & Grill before heading out for a morning of snorkeling. Join the South Maui AM Snorkel to Coral Gardens or Molokini Crater tour and explore the vibrant marine life and coral formations.

After the snorkeling adventure, have a satisfying lunch at The Mill House and then visit the Molokini Crater itself, a partially submerged volcanic crater that now offers some of the best snorkeling in Maui.

Dine at Mulligans on the Blue, an oceanfront restaurant with live music and a menu featuring a blend of Irish and local flavors. Enjoy the sunset views and the relaxed atmosphere.

Start with breakfast at The Beach Club Restaurant & Bar and then head to the airport for an exhilarating Central Maui Two-Island Scenic Helicopter Flight to Molokai. Witness the dramatic sea cliffs, waterfalls, and the untouched beauty of Molokai from the air.

After the helicopter tour, have a leisurely lunch at Lava Rock Bar & Grill and spend the afternoon at the Maui Tropical Plantation, where you can take a tram tour and learn about the island's agriculture.

Enjoy a special dinner at Pau Huaka'i, a restaurant known for its innovative cuisine and oceanfront dining experience. Relax and reminisce about the day's aerial and terrestrial adventures.

Fuel up with breakfast at The Mill House before heading to the North Maui 7 Line Zipline Adventure with Ocean Views. Soar through the lush valleys and enjoy panoramic ocean views as you zip from one platform to another.

After the adrenaline rush, have a casual lunch at The Beach House Bar & Grill and then visit the historic town of Lahaina for some shopping and exploring. Don't miss the famous Banyan Tree Park.

Dine at South Shore Tiki Lounge for a fun and lively atmosphere, and then take a South Maui Sunset Prime Rib or Mahi Mahi Dinner Cruise to end the day with a memorable ocean sunset.

Start with breakfast at Monkeypod Kitchen by Merriman - Wailea, Maui, and then visit the Maui Ocean Center to learn about the marine life of Hawaii. Take your time exploring the exhibits and the open ocean tank.

For lunch, head to Mulligans on the Blue and enjoy their oceanfront dining. Post lunch, take a guided tour of the Maui Tropical Plantation and learn about the various fruits and crops grown on the island.

Dine at The Mill House for a farm-to-table experience with panoramic views of the plantation. After dinner, enjoy the live entertainment at The Pint & Cork with a wide selection of beers and spirits.

Have breakfast at The Beach Club Restaurant & Bar and then join the South Maui Whale Watch Kayaking and Snorkel Tour in Kihei. Paddle along the coast and keep an eye out for the majestic humpback whales during the season.

After the kayak tour, enjoy a casual lunch at Three's Bar & Grill and then spend the afternoon at Kihei, exploring the shops, cafes, and the relaxed beach vibe.

Dine at The Beach House Bar & Grill and enjoy their fresh seafood with ocean views. End the day with a walk on the beach or a visit to the Maalaea Harbor to see the boats returning from their day's adventures.

Start with breakfast at Diamonds Bar & Grill and then head to the historic town of Lahaina. Explore the shops, art galleries, and historic sites such as the Lahaina Banyan Court Park.

For lunch, enjoy the oceanfront dining at Lava Rock Bar & Grill and then visit the Lahaina area beaches for some relaxation and water activities.

Experience the Royal Lahaina Luau (Myths of Maui Luau) for an evening of traditional Hawaiian music, dance, and cuisine. It's a perfect way to immerse yourself in the island's culture and history.

Have breakfast at The Mill House and then embark on a journey to the summit of Haleakalā Crater. Experience the otherworldly landscapes and the breathtaking views from the highest point on Maui.

After descending from the crater, enjoy a hearty lunch at Guava Tree Bar & Grill and then visit the Pipiwai Trail in the Haleakalā National Park. Hike through the bamboo forest and be rewarded with the majestic Waimoku Falls.

Dine at The Beach House Bar & Grill and witness a stunning Maui sunset. Reflect on your journey as you enjoy the ocean breeze and the colors of the sky.

Enjoy a leisurely breakfast at The Beach Club Restaurant & Bar and then spend the morning at your resort, taking advantage of the amenities and the oceanfront setting.

For lunch, have a beachside meal at The Beach House Bar & Grill and then indulge in some spa time with an ocean view. Unwind and pamper yourself with a massage or a rejuvenating treatment.

Dine at Monkeypod Kitchen by Merriman - Wailea, Maui and enjoy their innovative cocktails and dishes. Reflect on your Maui journey and savor the flavors of the island.

Have a final breakfast at The Mill House and then take a last walk on the beach, collecting ocean memories and bidding farewell to the island.

For lunch, enjoy the oceanfront dining at The Beach House Bar & Grill and then spend some time at the Maalaea Harbor, reminiscing about the ocean adventures and watching the boats come and go.

Dine at Monkeypod Kitchen by Merriman - Wailea, Maui for a memorable farewell dinner. Raise a glass to Maui and the ocean, and cherish the moments you've had on the island.

Begin your extended stay with breakfast at The Beach Club Restaurant & Bar, and then set out for a day of island exploration.

Enjoy a leisurely lunch at The Beach House Bar & Grill, and then visit the Maalaea Harbor to consider an additional ocean excursion or simply to admire the boats and the ocean views.

Dine at Monkeypod Kitchen by Merriman - Wailea, Maui and relax with the sounds of live music and the flavors of the island.