Curator’s statement
Hawai’i is the ultimate “easy button” — perfect weather, soft beaches, and a balance of active adventure and laid-back luxury. This itinerary pairs two of Hawai’i’s most iconic islands: Maui, with its golden beaches and easy access to kid-friendly surf, and the Big Island, where lava meets luxury. Designed for families, couples, or small groups, this is a trip that blends snorkels and sunsets, volcanoes and pool time. With the right advisor, Hawai’i feels not just relaxing—it feels effortless.
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Day 1: Arrive in Maui & settle into island time
Easy beach day in Kihei—perfect sand, gentle waves, and dolphin floaties.
Fly into OGG and make your way to your home for the next few days—either a breezy condo or a private villa at Honua Kai for easy access to Kaʻanapali, or head south to Wailea for ocean views and tranquil luxury. Once you’ve checked in, keep it simple: beach walk, mai tai, and sunset. Let the stress melt off as quickly as your sandals.
Day 2: Surf’s up in Kaʻanapali
Surf school success—Kaʻanapali’s beginner break is great for all ages.
Start the day with a surf lesson from KaʻAnapali Surf Club. Operating in front of the Marriott, they’ve got one of the most beginner-friendly breaks on the island. Kids as young as five can get up on their first try, and the instructors are warm, playful, and pro-level patient. Spend your afternoon snorkeling at Black Rock or floating down your hotel’s lazy river.
Insider tip: Their digital photo package is affordable and adorable.
Day 3: Choose your own adventure - waterfalls or Lānaʻi by catamaran
Gearing up to snorkel Hulopoʻe Baz—Lānaʻi’s calm, clear waters are perfect for kids.
Option 1: Take a mini road to Hana detour. Stop at Twin Falls for a short waterfall hike and enjoy the lush beauty of the Garden of Eden without committing to the full twisty drive.
Option 2: For something unforgettable, hop aboard Trilogy’s catamaran and head to Lānaʻi. You’ll snorkel in protected waters, picnic at Hulopoʻe Bay, and explore tidepools—all with warm hospitality and incredible crew service.
Day 4: Choose chill or adventure on your last day on Maui
Use your final Maui day to do exactly what you want. Lounge by the pool, take a spa morning, or head out for a coastal walk in Wailea. Want one more adventure? Try a whale-watching cruise (in winter months) or an outrigger canoe tour. In the evening, enjoy a farewell dinner with your toes in the sand.
Day 5: Off to the Big Island for beach, lava, and wide open space
Welcome to the Big Island—lava rock coastlines, swaying palms, and sunset cocktails await.
Fly into Kona (KOA) and check into one of the Big Island’s top luxury resorts: Mauna Lani, Fairmont Orchid, or Four Seasons Hualālai. Each offers a different take on island elegance—Mauna Lani blends modern luxury with cultural history; Fairmont Orchid offers family-friendly calm and great snorkeling, and Hualālai is simply next-level. Spend your afternoon exploring the beach or pool and settling into the rhythm of this wilder, wider island.
Day 6: Cultural adventures & stargazing at Mauna Kea
From sea level to stars—the Big Island wows all day.
Spend your morning snorkeling in Pauoa Bay or exploring the fishponds and lava fields around Mauna Lani. In the afternoon, grab lunch, recharge, and then head up Saddle Road toward Mauna Kea Visitor Center. This is one of the clearest stargazing spots in the world—bring warm layers and a blanket for an unforgettable sky show.
Day 7: Volcanoes National Park day trip
Watching the lava glow at Hawaiʻi Volcanoes National Park–a moment they’ll never forget.
Today is about fire and steam. Drive across the island to Hawai’i Volcanoes National Park, where you’ll hike through lava tubes, watch sulfur vents bubble, and stand at the edge of the Halemaʻumaʻu crater. If you’re up for it, book a night in Volcano to break up the return drive.
Day 8: Poolside bliss & manta ray magic
Underwater magic: manta rays circle just beneath the surface viewable from a walk down from a luxe dinner.
Sleep in and enjoy your resort—whether it’s a beach cabana or a slow family breakfast. In the evening, get ready for one of Hawaii’s most memorable wildlife encounters: the manta ray night snorkel. Lit from below by floodlights, the graceful creatures swirl beneath the surface while you float just above.
Day 9: One last dip, then aloha for now
Your flight may be calling, but Hawai’i gives you time for one last swim. Soak in the view, sip that final cup of coffee, and start dreaming of your next island adventure.
Need to know
Hawai’i really can be easy—with the right planning, you don’t need spreadsheets, splurges, or 5-star resorts to have a 5-star experience. There are family-friendly surf breaks, reef-protected beaches, and low-key luxury stays that make it all feel seamless.
For families, I’ve personally tested every element of this itinerary with kids of different ages—from surf schools that welcome 5-year-olds to manta ray snorkels that wowed even our tweens. We’ve done waterfall hikes, lazy beach days, cultural outings, and yes, even timeshare presentations.
Don’t sleep on day trips and excursions. Some of our best memories came from unexpected adventures—sailing to Lānaʻi with Trilogy, stargazing from a volcano summit, watching lava glow at night, or snorkeling under floodlights with manta rays.
Want to mix in a budget element? Ask your advisor (me!) about ways to balance out the trip—like renting a 2–3BR villa with a kitchen at Honua Kai, or grabbing a high-value resort rate with perks on the Big Island.
Timing matters. Holiday weeks book early, but shoulder seasons (April–May and September–October) are ideal: fewer crowds, better pricing, and just as much sun.
Rental cars are essential—especially on the Big Island—and I can help you figure out the best airport logistics and even book inter-island flights.
Hawai’i doesn’t have to be fancy to be fabulous—the key is knowing where to go, when to book, and how to blend adventure with recharge time. That’s where I come in.
Travel Advisor
Lilly S.
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