O'Brien Family  ·  Adventure Awaits

KauaiThe Garden Isle

Seven days on the North Shore — sea caves, jungle rivers,
helicopter canyons, and doing absolutely nothing.

June 21 — June 28, 2026
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Home Base & Wheels
Hale Hina
Airbnb · Wainiha, North Shore
Hale Hina
3 Bedrooms  ·  3.5 Baths  ·  Steps to Kepuhi Beach  ·  ★ 4.73
Explore the House & All 50 Photos
Turo · Pick up Lihue Airport
Cadillac
Escalade ESV
Luxury full-size SUV. Seats all seven comfortably with surfboards, beach gear, and luggage for a week on the North Shore.
Full-size luxury SUV 7 passenger capacity Pick up on arrival, June 21
🚙
View on Turo
🌊
Day 2 · Booked
Nāpali Zodiac
Sea caves, dolphins, open-water snorkeling off the Na Pali cliffs
🚁
Day 6 · Booked
Jurassic Falls Heli
Island Helicopters · Land at the base of a waterfall in the wilderness
🚣
Day 3 · Booked
Secret Falls Kayak
Wailua River paddle + muddy rainforest hike to a 120-foot waterfall
🏄
Days 4–7
5 Soft-Top Rentals
Pine Trees / Waioli Beach Park · Hanalei Bay's gentlest break
🥾
Day 5
Kalalau Trail
First 2 miles to Hanakāpīʻai Beach · Rugged, muddy, jaw-dropping
🍧
Non-Negotiable
Wishing Well Shave Ice
Hanalei · Get the large · Every single day if you want
7
Days on Kauai
5
Surfboards Rented
120′
Secret Falls
3
Booked Excursions
1
Helicopter Landing
∞
Shave Ice
01
Day One · June 21, 2026

Arrival &
North Shore Setup

Lihue Airport → Costco → Hanalei → Hale Hina, Wainiha

Kauai North Shore
Arrival Day
Hale Hina beach view
1:00 PM
Land at Lihue Airport
Pick up the Cadillac Escalade ESV. Load everyone up — it's a 45-minute drive north to paradise.
Logistics
2:00 PM
Costco or Safeway Stock Run
Drinks, breakfast food, grill supplies, snacks for the whole week. This single stop saves you all seven days.
Logistics
4:30 PM
Arrive at Hale Hina
Unpack, claim your rooms, walk down the garden path to Kepuhi Beach out front. Let the vibe fully sink in.
Evening
Dinner on the Lanai
5-minute walk to Hanalei — Hanalei Poke or Pat's Taqueria (the truck by the pier). Takeout back to the lanai.
🍽 Food
02
Day Two · June 22, 2026

The Sea Caves

Nāpali Coast Zodiac Raft Expedition & Snorkeling

Na Pali Coast cliffs
✓ Booked
Ocean aerial Kauai
10:15 AM
Drive into Hanalei
Check in for the tour. Sunscreen, water shoes, leave valuables at Hale Hina — you are going to get completely drenched.
11:00 AM
Nāpali Coast Zodiac Raft Expedition
Massive sea caves with crashing swells inside, spinner dolphins, and open-water snorkeling off the Na Pali cliffs. Nothing like it on earth.
✓ Booked
3:30 PM
Return to Hale Hina — Total Downtime
Pool, ocean, nap. The kids will need it. You will need it. This is by design.
Recover
03
Day Three · June 23, 2026

The Jungle River

Wailua River Kayak & Hike to Secret Falls

Secret Falls waterfall
✓ Booked
Kayaking river Kauai
6:15 AM
Early Drive to Wailua River
45 minutes south. Get the coffee going before you leave. The sunrise drive is the warm-up.
7:00 AM
Kayak & Hike to Secret Falls
Paddle the Wailua River, then a muddy, root-covered trek through rainforest to a 120-foot waterfall. Shoes destroyed. Worth it.
✓ Booked
1:00 PM
Lunch on the Way Back North
Fish tacos at Sleeping Giant Grill — or noodles at Hamura Saimin, a legendary Kauai institution since 1952.
🍽 Food
Afternoon
Wishing Well Shave Ice + Rest
Stop in Hanalei for a massive shave ice. Then home to nap, read, or float. You've done enough today.
🍧 Treat
04
Day Four · June 24, 2026

Surf & Sand

Hanalei Bay · Pine Trees · BBQ Night at Hale Hina

Surfing Hanalei Bay
Surf Day
Tropical ocean bay
Morning
Sleep In. Late Breakfast on the Deck.
No alarm. Coffee, fruit, eggs. Watch the ocean from the lanai. This is what a real vacation feels like.
Chill
10:30 AM
Pick Up 5 Surfboard Rentals
Drive into Hanalei for soft-top rentals. Multi-day rate for the rest of the week.
Midday
Pine Trees — Waioli Beach Park
Gentle waves, sandy bottom. Hanalei Bay's most forgiving break. Paddle out, wipe out, repeat. All afternoon.
Evening
Fire Up the Gas BBQ at Hale Hina
Good thing you loaded up at Costco on Day 1. Grill night on the lanai.
🔥 BBQ
05
Day Five · June 25, 2026

Hāʻena &
Tunnels

Kalalau Trail → Tunnels Beach Snorkeling

Kalalau Trail sea cliffs
Book Pass 5/25
Tunnels Beach clear water
⚡ 6 AM ET
Secure Hāʻena State Park Parking + Pass
Book at exactly 6:00 AM ET on May 25. Sell out in minutes. Set an alarm. Do not miss this one.
⚠ Book May 25
8:30 AM
Walk into Hāʻena State Park
Two minutes from Hale Hina — you could literally walk the beach from the house.
Morning
Kalalau Trail — First 2 Miles
Rugged, muddy, jaw-dropping. Massive sea cliffs, hanging valleys, and a wild beach at the end. Bring poles, embrace the mud.
1:00 PM
Tunnels Beach Snorkeling
Offshore reef blocks the summer swell — calmest, clearest water on the island. Sea turtles, tropical fish, coral gardens. Best snorkeling on Kauai.
🐠 Snorkel
06
Day Six · June 26, 2026

The Jurassic
Helicopter Ride

Island Helicopters → Anini Beach → Celebration Dinner

Helicopter over Kauai
✓ Booked
Kauai aerial canyons
Morning
Drive South to Lihue Airport
45 minutes. Early start for best light and clearest mountain visibility before afternoon clouds roll in.
Midday
Island Helicopters — Jurassic Falls Tour
Circle the island. Fly deep into the Na Pali canyons. Step off the helicopter at the base of a waterfall in the middle of the wilderness. The trip highlight for the kids and for you.
✓ Booked
Afternoon
Anini Beach on the Way Back North
Calmest, shallowest water on Kauai. Perfect for floating and recovering from the sensory overload.
Float
Evening
Celebration Dinner in Hanalei
Bar Acuda for tapas, or Ama for ramen with mountain views. Book 2 weeks in advance.
🥂 Celebrate
07
Day Seven · June 27, 2026

Last Call on
the North Shore

No schedule. All waves. One more sunset at the Hanalei Pier.

Hanalei Pier sunset
Free Day
Tropical sunset ocean
All Day
No Rigid Schedule
The surfboards are still yours. Move freely between Hale Hina, Hanalei Bay, and the roadside fruit stands.
Free
Daytime
Local Fruit Stands & Wandering
Mango, lilikoi, papaya from the roadside. Drive around, find the places you haven't been. Let the kids lead.
Sunset
Final Sunset at the Hanalei Pier
Watch the sun drop behind the mountains over the bay. There is no better last image of a Kauai trip than this pier at golden hour.