Ultimate 29-Day Hawaiian Adventure Itinerary

Start your day with a visit to the Honolulu Zoo, where you can encounter a diverse range of tropical animals. Afterward, enjoy a hearty breakfast at Cinnamon's at the Ilikai, known for its delicious pancakes and island-style dishes.

Post breakfast, immerse yourself in the rich marine life of Hawaii at the Waikiki Aquarium. For lunch, head to Tikis Grill & Bar and savor their Pacific Rim cuisine in a relaxed, beachfront setting. Spend the rest of the afternoon lounging at the serene Kapiolani Park, enjoying the ocean breeze and the Diamond Head backdrop.

As the sun sets, indulge in a luxurious dinner at Le'ahi Bar & Grill, offering a menu inspired by the island's diverse culinary heritage. After dinner, take a cultural journey at the Polynesian Cultural Center, where you can witness traditional island arts, crafts, and performances from various Pacific cultures.

Embark on an early morning hike to the summit of Diamond Head, one of Hawaii's most famous landmarks. Enjoy the panoramic views of Waikiki and the sparkling Pacific Ocean. After the hike, refuel with a delicious breakfast at SWIM Restaurant & Bar, offering a modern, ocean-inspired menu.

Spend your afternoon exploring the upscale boutiques and eateries at Ala Moana Center, one of the largest open-air shopping centers in the world. For lunch, dine at Tropics Waikiki, where you can enjoy a variety of island-inspired dishes in a casual, tropical ambiance.

Experience the vibrant colors, music, and dance of the islands at an authentic Hawaiian luau. Enjoy a traditional feast and live entertainment at Germaine's Luau, where you'll learn about the history and culture of Hawaii through captivating performances.

Begin your day with a visit to the Iolani Palace, the only royal palace on American soil. Explore the rich history of Hawaii's monarchy and its impact on the islands. For breakfast, enjoy the local favorites at Bar Maze, known for its innovative cocktails and island-inspired dishes.

After the palace, take a guided tour of the Honolulu Museum of Art, home to a diverse collection of Asian, European, Pacific, and American art. For lunch, head to Bevy, a trendy spot offering a menu of contemporary, globally inspired cuisine in a stylish setting.

Conclude your day with a relaxing sunset cruise along the Waikiki coastline. Enjoy the breathtaking views of the city skyline and Diamond Head while sipping on cocktails and savoring appetizers. For dinner, indulge in the fresh catch of the day at Uncle Bo's Pupu Bar & Grill, known for its seafood and lively atmosphere.

Explore the lesser-known gems of Oahu by visiting the serene Lanikai Beach on the windward side of the island. After soaking in the tranquility, enjoy a delightful breakfast at Murphy's Bar & Grill, a local favorite known for its Irish hospitality and hearty meals.

Post-breakfast, take a scenic drive to the Byodo-In Temple nestled in the Valley of the Temples. Experience a moment of serenity at this replica of a 900-year-old Japanese temple. For lunch, head to Splash Bar and enjoy the laid-back beach vibe with a menu featuring fresh salads, sandwiches, and tropical drinks.

As the day winds down, visit the Kualoa Ranch for an unforgettable experience. Choose from activities such as a movie sites tour, horseback riding, or an ATV adventure to explore the stunning landscapes that have been featured in numerous films and TV shows. For dinner, enjoy the farm-to-table cuisine at Smith & Kings, located in the heart of Kakaako's vibrant arts district.

Take a leisurely morning stroll at the Waiola Shave Ice, a local favorite spot for a refreshing treat. Enjoy a classic shave ice with your choice of flavors. Afterward, indulge in a sumptuous breakfast at Osoyami Bar and Grill, offering a fusion of Japanese and local flavors.

Spend your afternoon exploring the trendy boutiques and art galleries in the Kakaako neighborhood. For lunch, visit Stinger Rays Tropical Bar and Grill and enjoy their tropical-inspired dishes in a laid-back setting. After lunch, continue your retail therapy at the Ward Village, home to a variety of shops and eateries.

Relax and unwind with a spa treatment at Moana Lani Spa at the Moana Surfrider, A Westin Resort & Spa. After pampering yourself, savor a sophisticated dinner at Ferguson's Irish Pub, known for its warm hospitality and extensive whiskey selection. End the evening with a nightcap at the pub or take a moonlit walk on the beach.

Start your day with a visit to the Koko Crater Railway Trail, a challenging hike with rewarding views. After the hike, enjoy a hearty breakfast at Pint and Jigger, known for its craft beer selection and elevated pub fare.

Explore the local food scene with a guided Hole-in-the-Wall Food Tour. Sample a variety of dishes from hidden gems and neighborhood favorites. For a more relaxed afternoon, visit the Honolulu Beerworks for a brewery tour and tasting. For dinner, indulge in the innovative cuisine at Livestock Tavern, where you can enjoy dishes made with locally sourced ingredients in a stylish, industrial-chic setting.

Experience the vibrant nightlife of Honolulu at The Republik, a popular venue for live music and entertainment. Check their schedule for any upcoming performances or events. End the night with a visit to Scarlet Honolulu, a stylish nightclub with a rooftop bar, offering panoramic views of the city and the ocean.

Begin your day with a moment of reflection at the Diamond Head State Monument. Take a quiet hike to the summit and enjoy the panoramic views of the island. After the hike, enjoy a peaceful breakfast at Yard House, known for its extensive menu and wide selection of draft beers.

Spend a serene afternoon at the Manoa Falls, where you can take a leisurely hike through the lush rainforest to reach the majestic waterfall. After the hike, head to The Nighthawk for a late lunch and enjoy their elevated comfort food in a cozy, retro-inspired setting.

As the day comes to a close, take a drive up to Tantalus Lookout and witness the breathtaking panoramic views of Honolulu and the surrounding landscape. For dinner, enjoy the casual elegance of MW Restaurant, known for its innovative, farm-to-table cuisine and extensive wine list.

Arrive in Maui and start your day with a sumptuous breakfast at Longhi's Lahaina, where you can enjoy oceanfront dining with a menu featuring fresh, local ingredients. After breakfast, take a relaxing walk on the golden sands of Kaanapali Beach, one of Maui's most famous beaches.

For lunch, head to Mama's Fish House, a Maui institution known for its fresh seafood and Polynesian-inspired dishes. After lunch, explore the charming town of Lahaina, with its historic sites, art galleries, and boutique shops. Don't miss the opportunity to visit the Banyan Tree Park, home to one of the largest banyan trees in the world.

Witness a stunning Maui sunset at Napili Bay, a picturesque and serene spot. Then, indulge in a memorable dinner at Merriman's Kapalua, where you can savor farm-to-table cuisine in an elegant, plantation-inspired setting. End your evening with a stroll under the stars at the Whalers Village, enjoying the ocean breeze and the sound of the waves.

Begin your day with a scenic drive to Haleakalā National Park, where you can witness the breathtaking sunrise from the summit of the dormant volcano. After the sunrise, enjoy a hearty breakfast at Kula Bistro, known for its delicious pastries and local coffee.

Explore the upcountry area of Maui, visiting the Ali'i Kula Lavender Farm and MauiWine in Ulupalakua. Enjoy the fragrant gardens and a wine tasting experience with panoramic views of the island. For lunch, indulge in the gourmet sandwiches and salads at La Provence, a hidden gem in Kula.

As the day winds down, head to Paia, a charming town with a bohemian vibe. Enjoy the eclectic shops and art galleries before having dinner at Mill House Restaurant, located on the grounds of the Maui Tropical Plantation. Savor the innovative dishes made with ingredients sourced from the plantation, surrounded by lush tropical greenery.

Embark on the iconic Road to Hana adventure, a full-day journey filled with breathtaking scenery, lush rainforests, and stunning waterfalls. Pack a picnic breakfast from Cafe des Amis in Paia, known for its delicious crepes and paninis, and enjoy it at one of the scenic stops along the road.

Take your time exploring the various attractions along the Road to Hana, including Waianapanapa State Park, Hana Lava Tube, and the cascading Waimoku Falls. For lunch, stop at Nahiku Marketplace [1164] and sample the local food trucks offering fresh, island-style cuisine in a relaxed, tropical setting.

After a full day of adventure, relax and enjoy a well-deserved dinner at Mala Ocean Tavern in Lahaina. The restaurant offers a diverse menu with a focus on sustainable, local, and organic ingredients, as well as a great selection of wines and cocktails. End your evening with a leisurely walk on the lively streets of Lahaina, taking in the historic charm and vibrant nightlife.

Start your day with a visit to the Maui Ocean Center, where you can explore the fascinating marine life of Hawaii through interactive exhibits and live animal encounters. After the ocean center, enjoy a delightful breakfast at Paia Fish Market Southside, known for its fresh seafood and casual, beachy atmosphere.

Spend your afternoon snorkeling at Molokini Crater, a partially submerged volcanic caldera known for its crystal-clear waters and diverse marine ecosystem. Take a guided snorkel tour and witness colorful fish, coral, and maybe even some sea turtles. For lunch, enjoy a picnic on the boat provided by the tour company.

After a day in the water, relax and enjoy a sunset sail along the coast of Maui. Many companies offer sunset cruises with live music, appetizers, and open bar. For dinner, head to Sarento's on the Beach in Kihei, where you can dine with a panoramic view of the ocean and enjoy their award-winning Italian cuisine.

Explore the charming upcountry town of Makawao, known for its paniolo (Hawaiian cowboy) history and vibrant arts scene. Enjoy a leisurely breakfast at Casanova, a local favorite serving up delicious Italian fare in a cozy, rustic setting.

Visit the Hali'imaile Distilling Company for a tour and tasting of their handcrafted, locally made spirits. Afterward, have lunch at The Restaurant at Hotel Wailea, where you can indulge in a farm-to-table dining experience with panoramic ocean views.

Conclude your day with a unique stargazing experience at the Haleakalā Observatory. Join a guided tour or venture on your own to witness the breathtaking night sky from the summit of Haleakalā. For dinner, enjoy the casual elegance of Maui Brewing Co. Kihei, where you can pair their craft beers with a menu of island-inspired pub fare.

Start your day with a relaxing breakfast at Koiso Sushi Bar in Kihei, a hidden gem known for its authentic, high-quality sushi. After breakfast, take a morning stroll on the soft sands of Makena Beach, also known as "Big Beach," and enjoy the panoramic views of the coastline.

Spend your afternoon exploring the unique and vibrant marine life at Ahihi-Kinau Natural Area Reserve. Snorkel in the clear waters and observe the colorful fish, coral, and perhaps even some sea turtles. For lunch, visit Monkeypod Kitchen by Merriman, where you can savor their farm-to-table dishes and refreshing cocktails in a laid-back, open-air setting.

As the sun begins to set, head to La Perouse Bay and take a short hike to the lava fields, where you can witness the rugged beauty of the volcanic landscape against the backdrop of the ocean. For dinner, enjoy the upscale, contemporary Hawaiian cuisine at Nick's Fishmarket Maui in Wailea, and toast to another beautiful day in paradise.

Enjoy a leisurely breakfast at Spago, located in the Four Seasons Resort Maui at Wailea. After breakfast, take a drive to the Iao Valley State Park, where you can explore the lush, green valley and learn about its historical and cultural significance.

For lunch, head to Star Noodle in Lahaina, known for its delicious noodle dishes and Asian-inspired small plates. After lunch, spend the afternoon exploring the shops, galleries, and historical sites of Lahaina, one of the most popular tourist destinations on the island.

Enjoy a memorable dinner at Fleetwood's on Front St., a restaurant and rooftop bar owned by rock legend Mick Fleetwood. Savor the fresh seafood and steaks while enjoying live music and panoramic views of the ocean. After dinner, take a stroll along Front Street, where you can experience the vibrant nightlife and entertainment options of Lahaina.

Start your day with a delicious breakfast at Hali'imaile General Store, a renowned restaurant in the upcountry. After breakfast, drive to the Archie Kalepa Surf School in Haiku and take a surfing lesson from the experts. Whether you're a beginner or an experienced surfer, the North Shore waves offer a thrilling experience.

After catching some waves, refuel with a casual lunch at Paia Bowls, a local favorite known for its healthy and refreshing acai bowls and smoothies. Spend the rest of the afternoon exploring the eclectic shops and art galleries of Paia, and if you're interested in windsurfing, visit the nearby Ho'okipa Beach Park to watch the pros in action.

For dinner, enjoy the laid-back atmosphere and fresh, locally sourced cuisine at Flatbread Company, also located in Paia. After dinner, head to Maui Arts & Cultural Center in