New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

AI Travel Planner

Ultimate 14-Day Hawaiian Island Adventure

Ultimate 14-Day Hawaiian Island Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Oahu's Highlights

Morning
Begin your Hawaiian adventure with a hearty breakfast at Duke's Waikiki, known for its oceanfront dining. Afterward, take a stroll along the famous Waikiki Beach and enjoy the morning sun.
Afternoon
For lunch, savor the fresh seafood at Nico's Pier 38. Spend your afternoon exploring the historic Pearl Harbor and the USS Arizona Memorial. Continue to the serene Byodo-In Temple for a cultural experience.
Evening
As the sun sets, dine at La Mer at Halekulani, offering exquisite French cuisine with ocean views. End your day with a vibrant performance at the Waikiki Starlight Hawaiian Luau.
Bedtime
Find amazing hotels in Oahu.

North Shore and Luau Experience

Morning
Enjoy a breakfast at Rainbow Drive-In, a local favorite known for its plate lunches. Head to the North Shore and visit the famous Banzai Pipeline and Sunset Beach.
Afternoon
Have lunch at Giovanni's Shrimp Truck, an iconic spot on the North Shore. Afterward, explore the quaint town of Haleiwa and its charming shops and galleries.
Evening
Dine at Haleiwa Joe's Seafood Grill and indulge in the catch of the day. Conclude your evening with the Te Au Moana Luau at the Wailea Beach Marriott Resort, featuring traditional Polynesian dance and music.
Bedtime
Find amazing hotels in Oahu.

Historical Sites and Scenic Views

Morning
Start with breakfast at Musubi Cafe Iyasume, offering a variety of Japanese rice balls. Visit the Iolani Palace, the only royal palace in the United States, and the Honolulu Museum of Art.
Afternoon
For lunch, head to Morimoto Asia Waikiki and enjoy the innovative Asian cuisine. Spend your afternoon at the Hanauma Bay, a renowned snorkeling spot, and later take a drive to the scenic Diamond Head for a panoramic view of the island.
Evening
Dine at Roy's Waikiki Beach and savor the Hawaiian fusion dishes. Cap off the night with a leisurely walk on the Waikiki Beach under the moonlight.
Bedtime
Find amazing hotels in Oahu.

Maui's Magnificent Waterfalls and Beaches

Morning
Begin your Maui journey with breakfast at The Gazebo Restaurant at Napili Shores, known for its macadamia nut pancakes. Fuel up for a day of adventure.
Afternoon
After breakfast, head to the lush Iao Valley and the iconic Iao Needle. For lunch, enjoy the fresh catch at Paia Fish Market Restaurant.
Evening
Dine at Mama's Fish House, one of Maui's most renowned restaurants, where you can enjoy the sunset with a cocktail in hand and the sound of waves in the background.
Bedtime
Find amazing hotels in Maui.

Road to Hana and Beyond

Morning
Wake up early and grab a quick breakfast at Kula Lodge & Restaurant before embarking on the famous Road to Hana. Enjoy the journey with its breathtaking views, waterfalls, and hidden beaches.
Afternoon
For lunch, stop at Nutcharee's Authentic Thai Food in Hana and indulge in some spicy and flavorful dishes. Afterward, continue your exploration, visiting Wai'anapanapa State Park and the stunning Ohe'o Gulch (Seven Sacred Pools) in the afternoon.
Evening
As the day winds down, have dinner at Casanova Italian Restaurant & Deli in Makawao, and enjoy some delicious Italian cuisine. End the day with a relaxing stroll on the beach or a drink at a local bar.
Bedtime
Find amazing hotels in Maui.

Upcountry Maui and Sunset Views

Morning
Start your day with breakfast at La Provence, a charming French bakery in Kula. Afterward, visit the Maui Ocean Center to explore the marine life of Hawaii.
Afternoon
Have lunch at Makawao Sushi & Deli, and then spend your afternoon horseback riding in the picturesque Makena or visiting the serene Maui Lavender Farm.
Evening
Dine at Spago in Wailea and enjoy the stunning sunset views. After dinner, take a walk on the Ka'anapali Beach and experience Maui's nightlife.
Bedtime
Find amazing hotels in Maui.

Kauai's Natural Wonders

Morning
Begin your day with breakfast at The Dolphin Restaurant, Fish Market & Sushi Lounge. Then, head to the majestic Napali Coast for a morning hike or boat tour.
Afternoon
For lunch, enjoy the fresh seafood at Kauai Grill with panoramic views of the island. Spend your afternoon at the Waimea Canyon, often referred to as the "Grand Canyon of the Pacific."
Evening
Dine at Tidepools and indulge in a romantic dinner set amidst a breathtaking lagoon. End your day with a peaceful walk on the Poipu Beach.
Bedtime
Find amazing hotels in Kauai.

Gardens, Waterfalls, and Luau

Morning
Enjoy a delightful breakfast at Cafe Portofino, and then visit the spellbinding Smith Family Garden Luau to immerse yourself in Hawaiian culture.
Afternoon
Have lunch at Postcards Cafe and spend your afternoon at the serene Wailua Falls and the Fern Grotto.
Evening
Dine at The Beach House Restaurant and witness a stunning sunset over the ocean. Conclude your day with the Luau Kalamaku, featuring a theatrical show with fire dancing and traditional Polynesian performances.
Bedtime
Find amazing hotels in Kauai.

Summits, Stars, and Waterfalls

Morning
Start with breakfast at Kona Brewing Co. Pub & Brewery and then head to the summit of Mauna Kea for a breathtaking view above the clouds.
Afternoon
For lunch, enjoy the casual atmosphere and fresh seafood at Huggo's Restaurant. Afterward, visit the majestic Akaka Falls and the lush Hawaii Tropical Botanical Garden.
Evening
Dine at Brown's Beach House Restaurant and enjoy the oceanfront setting. Later, experience the world-class stargazing at Mauna Kea Observatory, one of the best places for astronomy.
Bedtime
Find amazing hotels in Big Island.

Volcanoes, Coffee, and Snorkeling

Morning
Have breakfast at CanoeHouse and then explore the otherworldly landscape of Volcanoes National Park. Witness the active Kilauea volcano and visit the Thurston Lava Tube.
Afternoon
Enjoy a lunch with a view at Lava Lava Beach Club and then take a tour of the Mountain Thunder Coffee Plantation to learn about Kona coffee production. End your afternoon with a relaxing snorkel at Kahaluu Beach Park.
Evening
Dine at Merriman's Waimea and savor the farm-to-table cuisine. If you're lucky, you might catch live music at the Blue Dragon Restaurant & Spa while enjoying a cocktail.
Bedtime
Find amazing hotels in Big Island.

Waterfalls, Whales, and Sailing

Morning
Start with breakfast at Under the Bodhi Tree and then witness the breathtaking Rainbow Falls. Continue to Boiling Pots and the Pe'epe'e Falls for a morning of waterfall exploration.
Afternoon
For lunch, enjoy the fresh catch at Three Fat Pigs and then head out for a guaranteed whale watching experience at A-Bay. Later, relax on a sailing adventure with Body Glove Cruises.
Evening
Dine at Monkeypod Kitchen by Merriman - Wailea and indulge in the farm-to-table menu. Cap off the night with a cocktail at South Shore Tiki Lounge, known for its vibrant atmosphere and live music.
Bedtime
Find amazing hotels in Big Island.

Kohala Coast's Highlights

Morning
Enjoy breakfast at The Fish Hopper Seafood and Steaks, and then set out for a morning of snorkeling at the pristine Hapuna Beach or Makalawena Beach.
Afternoon
Have lunch at Uncle's Awa Bar & Farmers Market and then explore the beautiful Pu'uhonua o Honaunau, also known as the Place of Refuge. Visit the nearby Two Step for some of the best snorkeling on the island.
Evening
Dine at Kona Brewing Co. - Kailua Kona Pub & Brewery and sample their craft beers. End your day with a stroll through the Kailua-Kona Village, exploring the shops and galleries.
Bedtime
Find amazing hotels in Big Island.

Kohala Waterfalls and Sunsets

Morning
Start with breakfast at The Canoe House and then embark on a tour of the Kohala Waterfalls. Enjoy the lush landscapes and refreshing cascades.
Afternoon
For lunch, visit Island Lava Java and then spend your afternoon at the Pololu Valley. Explore the black sand beach and the valley's stunning views.
Evening
Dine at Hawi Gallery & Bite Club and then catch the beautiful sunset at Hapuna Beach, followed by some stargazing at the beach or a visit to a local bar for live music.
Bedtime
Find amazing hotels in Big Island.

Leisurely Day in Kona

Morning
Enjoy a leisurely breakfast at Daylight Mind Coffee Company - Waterfront, and then spend your morning exploring the shops and historical sites of Kailua-Kona Village.
Afternoon
For lunch, visit Kona Brewing Co. - Kailua Kona Pub & Brewery and then relax at the Kahaluu Beach Park, one of the best
Evening

Top Oahu Travel Videos

Adjacent Cities

kayakFind the right stay during your trip.
Got a question about your trip?