Morning: Depart Baltimore on an overnight flight to Honolulu, enjoying in‑flight meals and a chance to rest before the long journey. Upon arrival, collect luggage and take a shuttle to the Disney Aulani Resort in Ko Olina.
Afternoon: Check in at Aulani, unwind with a welcome drink, and explore the resort’s pool complex and beachfront. Take a leisurely walk along the Ko Olina Lagoons to stretch your legs after the flight.
Evening: Dine at the resort’s ‘AMA‘AMA restaurant, sampling Hawaiian‑inspired seafood while watching a sunset over the Pacific. Early to bed for a fresh start tomorrow.
Find HotelsMorning: Enjoy a family‑friendly breakfast at the resort, then join the “Aunty’s Garden” activity where kids learn about native plants. Afterward, relax on the golden sands of Ko Olina Beach and try paddle‑boarding.
Afternoon: Participate in the resort’s cultural workshop, crafting traditional Hawaiian leis and learning the story of the island’s mythology. Later, take a short drive to Ka‘ena Point for scenic coastal views.
Evening: Experience a magical Disney character dinner at ‘Ohana, where beloved characters mingle with guests. End the night with a stroll along the illuminated lagoon.
Find HotelsMorning: Hike the iconic Diamond Head trail for panoramic vistas of Honolulu and the Pacific; the climb takes about 1.5 hours round‑trip. Bring water and a camera for the spectacular lookout.
Afternoon: Descend to Waikiki Beach for sunbathing, surfing lessons, and a casual lunch at a beachfront café. Explore the nearby Kalakaua Avenue shops for souvenirs.
Evening: Savor dinner at House Without A Key, renowned for its live Hawaiian music and sunset views. Return to Aulani for a relaxing night swim.
Find HotelsMorning: Drive to the Polynesian Cultural Center and start the “Ali‘i Voyage” tour, discovering the cultures of Samoa, Fiji, Tonga, and more. Participate in interactive demonstrations of fire‑making and canoe building.
Afternoon: Enjoy the Center’s vibrant villages, try local snacks, and take a leisurely tram ride between them. Reserve a spot for the evening’s spectacular “Ha Ha a Mai” show.
Evening: Attend the award‑winning luau, featuring a buffet of Hawaiian specialties and a dazzling hula performance under the stars. Return to Aulani for a restful night.
Find HotelsMorning: Visit the historic Pearl Harbor complex, touring the USS Arizona Memorial and the Pacific Aviation Museum. Allocate time for the insightful audio guide and reflective moments.
Afternoon: Head north to the legendary surf spots of Waimea Bay and Sunset Beach. Watch world‑class surfers or simply enjoy the dramatic cliffs and tide pools.
Evening: Return to Aulani, enjoy a casual dinner at the resort’s poolside grill, and pack for the upcoming flight to Maui.
Find HotelsMorning: Fly from Honolulu to Kahului, Maui, then take a shuttle to your ocean‑front stay at the Kaanapali Beach Resort. Check in and settle into the tropical surroundings.
Afternoon: Stroll along Kaanapali Beach, snorkeling near the famous Black Rock and soaking up the sun. Grab a light lunch at Leilani’s on the Beach.
Evening: Explore the historic town of Lahaina, browsing art galleries and dining at the waterfront Kimo’s. Return to the resort for a nightcap on the balcony.
Find HotelsMorning: Embark on a half‑day boat tour to Molokini Crater, renowned for crystal‑clear waters and vibrant marine life. Snorkel among tropical fish and sea turtles for an unforgettable experience.
Afternoon: After returning, head to Kapalua Bay for a relaxed beach lunch and gentle waves perfect for swimming. Explore the nearby Kapalua Golf Resort grounds for a scenic walk.
Evening: Enjoy sunset cocktails at the resort’s Hula Hula lounge, followed by dinner featuring farm‑to‑table Hawaiian cuisine.
Find HotelsMorning: Depart early on the legendary Road to Hana, stopping at Twin Falls for a short hike and a refreshing dip. Continue to the black‑sand Waiʻanapanapa State Park for dramatic coastal scenery.
Afternoon: Visit the historic town of Hana, explore the Hana Lava Tube, and marvel at the towering Wailua Falls. Picnic lunch amid lush rainforest surroundings.
Evening: Return to Kaanapali, stopping at scenic lookouts for sunset photos. Unwind with a quiet dinner at the resort after a full day of adventure.
Find HotelsMorning: Ascend to the summit of Haleakalā National Park for a breathtaking sunrise above the clouds; dress warmly for the chill at 10,000 ft. Take a brief walk along the summit trail to appreciate the volcanic landscape.
Afternoon: Descend to Makawao in Upcountry Maui, exploring boutique shops and sampling local shave‑ice. Visit a nearby pineapple farm for a tasting session.
Evening: Return to the resort for a relaxed dinner, perhaps a beachfront BBQ, and share stories of the day’s highlights.
Find HotelsMorning: Explore the lush Iao Valley State Park, walking the easy trail to the iconic Iao Needle and learning about its cultural significance.
Afternoon: Spend your final hours on Kaanapali Beach, swimming or snorkeling, then pack your belongings and check out of the resort.
Evening: Catch an evening flight from Kahului back to Baltimore, carrying memories of two unforgettable Hawaiian islands.
Find HotelsTotal Estimated Cost: $300
To extend your trip, add an extra night on Maui for a relaxed day at Makena Beach or a sunrise hike on the West Maui Mountains. If you need to shorten the itinerary, combine Day 4 and Day 5 on Oahu by visiting Pearl Harbor in the morning and the North Shore in the afternoon, then skip the evening luau. On Maui, you could replace the full‑day Road to Hana with a shorter “Hana Highlights” tour (Twin Falls and Wailua Falls) to free up time for a morning surf session.