O'ahu & Maui Family Road Trip
Beach Vacations, Family Vacations, Road Trips
Trip Overview:
Bask in the warmth of Hawaii on this journey through two of its most captivating islands. Begin in Honolulu, where golden sands meet the rolling surf of Waikiki. Greet the day with a sunrise small-group adventure around O‘ahu, exploring volcanic craters, lush valleys, and sweeping coastal views that reveal the island’s wild beauty. Glide over crystal-clear waters on a glass-bottom boat, spotting tropical fish and coral gardens beneath your feet.
Unwind with a day at leisure, soaking up the vibrant beach life and local flavours of Honolulu before flying to the serene shores of Maui. From your base here, sail to the Molokini Crater, a marine sanctuary teeming with colourful fish, and swim alongside graceful sea turtles in the calm waters of Turtle Town. With another day free to relax, you might choose to wander through Maui’s charming towns, trace its scenic coastal drives, or simply let the Pacific breezes wash over you.
This island-hopping escape blends adventure, nature, and relaxation in equal measure, offering travellers a taste of Hawaii’s diverse landscapes, from volcanic peaks to coral reefs. Whether watching the sunrise over O‘ahu or floating above Maui’s marine life, each day brings a fresh way to connect with the aloha spirit before your journey home.
Highlights:
- Watch the sunrise over O‘ahu’s volcanic craters and lush valleys on a scenic island adventure.
- Stroll Waikiki’s golden sands and glide across crystal waters on a glass-bottom boat cruise.
- Fly to Maui to snorkel at Molokini Crater and swim with sea turtles in Turtle Town’s calm bay.
- Spend leisurely days exploring Maui’s coastal roads and laid-back towns rich in island charm.
- Embrace Hawaii’s aloha spirit as you journey from volcanic landscapes to vibrant coral reefs.
Included Services:
- 4 nights in moderate accommodations on Oahu
- 3 nights in moderate accommodations on Maui
- 5 days Intermediate Car Rental with unlimited mileage (Mazda 3 or similar) on Oahu
- 4 days Intermediate Car Rental with unlimited mileage (Mazda 3 or similar) on Maui
- Complete Island Small Group Adventure with Sunrise (max 7 guests)
- Shared Honolulu Glass Bottom Boat Tour (max 40 guests)
- Shared Molokini & Turtle Town Snorkel Adventure (max 60 guests)
- 1 breakfast, 1 lunch
Excluded Services:
- Car Rental insurance
- Travel insurance
- International and domestic airfare & airfare taxes
- Entrances fees to sites not explicitly listed as included
- Meals and beverages not mentioned
- Gratuities
- Items of a personal nature
- Passport and Visa fees if applicable
- Family Vacations
- Self Drive
- Snorkeling
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
Rental Car: Hertz - Honolulu Int'l Apto Honolulu Int'l Ap
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
Rental Car: Hertz - Honolulu Int'l Apto Honolulu Int'l Ap
Take advantage of calm ocean conditions and crystal-clear waters on the perfect trip for any wildlife enthusiast. Explore tropical reefs and shipwrecks that are home to honu (sea turtles), eels, reef sharks, dolphins, and schools of tropical fish. The mornings on Oahu's South Shore offer are perfect for looking through glass-bottom boat viewports. This is the most peaceful time of day to cruise on the Pacific Ocean and see the iconic Waikiki beach boardwalk. During whale watching season (November - May), humpback whales migrate through Hawaiian waters to mate and calve; you may be able to catch a glimpse or two of these majestic creatures on your cruise. We've seen them put on spectacular shows for us. You might even hear them sing!Day 4: At Leisure in Waikiki
Rental Car: Hertz - Honolulu Int'l Apto Honolulu Int'l Ap
Day 5: From O'ahu to Maui
Rental Car: Hertz - Honolulu Int'l Apto Honolulu Int'l Ap
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 & Turtle Town Snorkel Adventure
Rental Car: Hertz - Kahului Apto Kahului Ap
Come aboard the quickest single deck power catamaran on Maui, the Malolo! Molokini Crater is a wonder of the Hawaiian Islands and is seen as a "must do" while vacationing on Maui! With plenty of indoor and outdoor seating, choose your preferred spot and enjoy an uninterrupted view of the pristine blue waters of Maui! Enjoy two snorkel destinations, the translucent waters of Molokini crater are sure to leave you in awe with up to 200 feet of visibility. Then cruise to the remarkable shoreside location of Turtle Town, where "Honu" (Hawaiian Green Sea Turtle) are frequently seen enjoying the gardens of coral, that they call their home!Day 7: At Leisure on Maui
Rental Car: Hertz - Kahului Apto Kahului Ap
Day 8: Depart from Maui
Rental Car: Hertz - Kahului Apto Kahului Ap
