7-Nights Oahu & Maui Family Road Trip - Beach Vacations, Family Vacations, Road Trips from $1,584

Day 1: Welcome to Honolulu

Rental Car: Hertz - Honolulu Int'l Apto Honolulu Int'l Ap

Hotel: Aston at the Waikiki Banyan (3 Star Rating)

The family-friendly hotel enjoys an ideal location, just a few steps from world-famous Waikiki Beach. It features the largest recreation deck in Waikiki with a heated swimming pool, children's playground, tennis and basketball court, putting green, snack bar and barbecue area. The Waikiki Aquarium and the Honolulu Zoo are within a short stroll. The hotel offers spacious suites; each of the rooms has air conditioning, a living room, a kitchen and a bathroom. The standard amenities of most rooms include a balcony. Further bookable amenities include separate bedrooms and a safe. For relaxation, hotel provides besides the outdoor pool, spa and indoor heated pool, the Jacuzzi and sauna, and for the actives one a workout in the gym is the most recommended.. The seasonal snack shop offers snack food. The perfect choice for any vacation, the hotel boasts spectacular beaches, outstanding service, and thrilling activities.

Day 2: Complete Island Small Group Adventure with Sunrise

Get ready for the ultimate Oahu adventure! This small group tour sets off just before sunrise and is designed for all travelers alike, offering a 10-hour journey to Oahu's hidden gems. Start your adventure at Sandy Beach with a stunning Oahu sunrise - perfect for unforgettable photos. Travel the Kaiwi shoreline, stopping at lookouts to capture postcard-perfect views; look out for rainbows year-round and whales in winter! Experience the breathtaking Ko'olau Mountains, a photographer's dream. Stop for breakfast at Kalapawai Market, an island favourite since 1932 (not included). Savour a famous Leonard's Bakery malasada, a must-try local treat (included). Visit the serene Byodo-In Temple, where you can snap photos and ring the bell for luck (admission included). Explore Kualoa Beach Park with views of "Chinaman's Hat" and some of the mountains featured in Jurassic Park. Stop at a local fruit stand to enjoy fresh, tropical fruits (not included), and later relax in the peaceful cove at Kawela Bay with an aim to spot turtles. End your tour in the charming town of Hale'iwa, home to local food trucks and vibrant galleries. More than a small group tour, it's your chance to preserve your Hawaii memories in style. The tour is professionally led by a local guide and crafted to provide unrivaled photo opportunities at every turn. With a maximum of only seven passengers, it is a personalized experience in an intimate small group setting.

Day 3: Honolulu Glass Bottom Boat Tour

Enjoy the beauty of Oahu's South Shore on a cruise departing from Kewalo Basin Harbor toward Leahi (Diamond Head). Aboard the Haleiwa Queen, discover the Pacific Ocean floor while cruising over vibrant tropical reefs and one of Hawaii's popular shipwrecks. Glass-bottom viewing ports offer glimpses of honu (sea turtles), eels, reef sharks, dolphins, and schools of colourful tropical fish. During whale-watching season (November-May), migrating humpback whales may be spotted in Hawaiian waters as they mate and calve. Lucky sightings may include spectacular displays or the chance to hear their songs.

Day 4: At Leisure in Waikiki

Waikiki needs no itinerary, it has a rhythm entirely its own, and a day spent wandering at leisure is rarely anything but wonderful. The beach itself is the natural starting point; iconic, yes, but no photograph quite captures the experience of Diamond Head framing the shoreline in person. The calm, warm water invites an easy morning swim or, for the adventurous, a first attempt at stand-up paddleboarding amid the gentle surf. Kalakaua Avenue rewards an unhurried afternoon of browsing, international names sit alongside local boutiques and galleries, while the beachfront bars and restaurants make a compelling case for a long, leisurely lunch. As the sun drops toward the Pacific, find a spot facing west; Waikiki sunsets have been stopping people in their tracks for well over a century, and for good reason.

Day 5: From O’ahu to Maui

Rental Car: Hertz - Kahului Apto Kahului Ap

Hotel: Aston Kaanapali Shores (3 Star Rating)

When you stay at Aston Kaanapali Shores, you are joining our ohana - our family. The friendly and knowledgeable staff at our Kaanapali resort not only make you feel at home, but are also happy to guide you to Maui's most coveted destinations. Our guest activities desk can arrange anything from snorkeling and parasailing adventures to visits at natural pools and historical Hawaiian sites.

But you don't have to leave our resort to have an exciting vacation! Grab breakfast, lunch, or dinner at the Beach Club Restaurant & Bar. Take a dip in one of our two heated freshwater pools. Book an appointment at the salon & spa, get in a workout at the fitness center, or utilize our tennis, pickleball, and shuffleboard courts. Please note that beach and ocean conditions at the resort change with the seasons.

Day 6: Molokini Crater & Turtle Town Snorkeling

Cruise to Molokini Crater aboard Malolo, a comfortable 55-foot catamaran, for one of Maui's most popular snorkeling adventures. Explore the crystal-clear waters of this extinct volcanic crater, where visibility often exceeds 100 feet and vibrant coral reefs are home to tropical fish, green sea turtles, manta rays, reef sharks, and other marine life. After snorkeling at Molokini, continue to a second site, either Turtle Town or Coral Gardens, depending on ocean conditions, for another chance to discover Maui's incredible underwater world and spot Hawaiian green sea turtles. Perfect for families and first-time snorkelers, this unforgettable excursion combines spectacular scenery, abundant marine life, and two of Maui's premier snorkeling locations for an amazing day on the water.

Day 7: At Leisure on Maui

Maui offers a wealth of experiences for a day at leisure, and the challenge lies only in choosing where to begin. Lahaina's historic waterfront provides a natural morning anchor, the old whaling town's art galleries, heritage buildings, and excellent cafe stops reward a gentle wander. For something truly unforgettable, the drive along the Road to Hana is as much an experience as a journey, waterfalls, jungle valleys, and black sand beaches unfold around every curve, and the drive itself is best taken slowly and without a schedule. The switchbacks of Haleakala are worth an afternoon, whether you're watching the volcanic crater landscape shift in the changing light or simply enjoying the extraordinary perspectives it offers over the island below. Come evening, the western coast around Wailea sets a magnificent scene for dinner as the sun sinks into the Pacific.

Day 8: Depart from Maui