Chai tour !!

Trip overview

This version gives you the most variety without feeling rushed. Kauai gives you dramatic scenery, cliffs, beaches, gardens, snorkeling, and a calmer vibe. Maui gives you a more polished resort experience, stronger dining options, easier beach days, diving opportunities, and a better New Year setup.

Fly into Lihue (LIH) Stay in Poipu on Kauai Fly Kauai → Maui Stay in Wailea on Maui Fly home from Kahului (OGG) 2 adults + 1 teen

Flight strategy

Segment	Plan
Outbound	Boston → Lihue (Kauai)
Inter-island	Lihue → Kahului (Maui)
Return	Kahului → Boston

Book this as a multi-city trip rather than round-trip. It avoids backtracking and fits the island flow much better.

Day-by-day itinerary

Dec 24

✈️ Flight from Boston

Depart Boston on Dec 24. This is your only long-haul travel day.

Evening departure recommended
Expect one or two connections depending on routing
Pack this as a travel-only day

Dec 25

✈️ Arrive in Kauai

Arrive in Kauai on Dec 25 because of the time difference. Pick up the rental car and head to Poipu for a light arrival day.

Land at Lihue Airport
Drive to Sheraton Kauai Resort
Beach walk and sunset if energy allows
Easy dinner and early night

Dec 26

🏖️ First full day in Kauai · Beach and water day

A simple first full day with low logistics and maximum enjoyment.

Morning snorkeling at Poipu Beach
Optional beginner surf lesson for the teen
Pool and beach break at the hotel
Easy sunset dinner

Dec 27

🌿 Gardens and south shore sights

Stay close to Poipu and enjoy Kauai’s lush side without a long drive.

Morning at Allerton Garden or McBryde Garden
Stop at Spouting Horn
Explore Old Koloa Town for snacks and browsing
Back to hotel for beach time

Dec 28

🥾 Scenic coastal day + Kauai hike

This is the best day to do a beautiful but manageable walk.

Maha'ulepu Heritage Trail in the morning
Views over cliffs and shoreline
Optional stop at Shipwreck Beach
Drive through the Tree Tunnel on the way back

Dec 29

🚁 Big Kauai experience day

Use this day for the island’s signature wow experience.

Choose either a Na Pali Coast helicopter tour or a boat tour
Keep the rest of the day light
Special dinner in Poipu

Dec 30

✈️ Fly to Maui

Easy travel day between islands.

Dec 31

🎉 New Year’s Eve in Maui

Keep this day relaxed so the evening feels special rather than rushed.

Wailea beach or resort pool day
Early dinner reservation
Resort or nearby New Year celebration
Fireworks or oceanfront countdown if available

Jan 1

🗺️ Road to Hana

A classic full-day Maui drive with waterfalls, jungle, dramatic road curves, and coastal scenery.

Road to Hana scenic drive
Stop at Twin Falls for a quick waterfall hike
Black sand beach at Wai'anapanapa State Park
Lunch in Hana town
Return along the same road or continue around the island

Jan 2

🌋 Haleakala

A dramatic crater landscape and summit views — a completely different side of Maui.

Haleakala National Park — sunrise or morning crater visit
Book sunrise entry permit in advance (required)
Walk the crater rim trail for sweeping views
Descend and relax for the afternoon
Final dinner in Wailea

Jan 3

✈️ Fly home

Relaxed morning, drive to Kahului Airport, and return flight to Boston.

Hotels

Kauai base

Sheraton Kauai Resort · Poipu

Best weather area on Kauai, beachfront setting, easy family base, strong sunset location, and close to south shore highlights.

Best for: easy beach access and relaxed start
Area feel: sunny, calm, family-friendly
Trip role: your Kauai home base

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Best overall Maui pick

Wailea Beach Resort – Marriott, Maui

Best balance of comfort, pools, beach access, family fit, and overall value for 3 people.

Best for: pools, waterslides, convenient Wailea base
Area feel: upscale, polished, easy dining nearby
Trip role: best practical Maui choice

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Luxury upgrade

Grand Wailea

Best if you want the resort itself to feel like a destination, with a major pool complex and a bigger wow factor.

Best for: luxury resort time and a bigger splash factor
Area feel: high-end, resort-driven, scenic
Trip role: premium Maui option

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Attractions and activities (including hikes)

Na Pali Coast

The signature Kauai experience. Best seen by helicopter for full scenery or by boat for ocean-level drama, sea caves, and possible dolphin sightings.

Open attraction

Poipu Beach Snorkeling

Easy shore snorkeling close to the hotel. Great first water activity with colorful fish, calm entries on good days, and very low logistics.

Open attraction

Snorkeling with turtles in clear blue water

Maui Snorkeling

Best easy Maui snorkeling options are Wailea Beach and Ulua Beach. These work well for a relaxed half-day without a long boat outing.

Open Ulua Beach

One Diving Day

Plan one dedicated scuba day in Maui, where dive logistics are easier. Good fit for certified divers or intro dives through local operators.

Open diving options

Road to Hana

A classic full-day Maui drive with waterfalls, jungle, dramatic road curves, and coastal scenery. Best if you want the most varied land day.

Open attraction

Haleakala

A very different Maui experience with crater landscapes and summit views. Strong alternative to Road to Hana if you want one dramatic mountain day.

Open attraction

Recommended activity mix: easy snorkeling on Kauai, one full diving day in Maui, one additional Maui snorkeling session, and one signature land day in Maui. Added: one dedicated nature hike on each island.

🌿 Recommended Nature Hikes

Kauai: Maha'ulepu Heritage Trail

Best easy coastal hike near your hotel. Dramatic cliffs, ocean views, and no long drive.

Length: 2–4 miles (flexible)
Difficulty: Easy
Best time: Morning

Open hike

Maui: Waihee Ridge Trail

One of the most rewarding hikes in Maui with ridge views, clouds, and lush greenery.

Length: ~5 miles round trip
Difficulty: Moderate
Best time: Early morning

Open hike

Restaurants near Sheraton Kauai Resort

RumFire

Best easy first-night option because it is at your hotel. Great ocean views and a low-stress arrival dinner.

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The Beach House

Iconic sunset dinner choice in Poipu. Great pick for one of your special Kauai nights.

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Red Salt

Best refined dinner near Poipu. Great for a nicer dinner without going too formal.

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Keoki’s Paradise

Family-friendly, tropical, relaxed, and fun. Good mid-trip dinner choice.

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Eating House 1849

Modern Hawaiian option with a little more energy. Nice for a flexible dinner night.

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Brennecke’s Beach Broiler

Good for a casual lunch or easy dinner after beach time. Burgers, fish tacos, and no pressure.

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Restaurants near Maui hotel area

Monkeypod Kitchen

Best overall Maui pick for your trip: lively, fun, reliable, and great for families.

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Spago Maui

One of the best New Year or celebration dinner options if you want a polished ocean-view evening.

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KOMO

Premium sushi choice in Wailea. Best for a splurge dinner.

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Lineage

Great shareable dishes and one of the more interesting casual-nice dinners in Wailea.

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Matteo’s Osteria

Excellent change of pace from seafood-heavy dinners. Good family-friendly Italian option.

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South Maui Fish Company

Best casual fresh fish stop. Great for a non-fancy lunch or easy dinner.

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Budget estimate for 3 people

Category	Estimated range	Notes
Flights	$2,400 – $4,200	Boston to Kauai, Kauai to Maui, Maui back to Boston
Hotels	$5,000 – $9,000	Holiday season pricing, 8 nights total
Rental cars	$500 – $800	One car on each island
Food	$1,200 – $2,000	Casual to comfortable dining
Activities	$800 – $1,500	Depends on helicopter tour, diving, snorkeling, and other paid activities
Total	$9,000 – $16,000+	Comfortable holiday-season range

Best value version: Sheraton Kauai Resort + Wailea Beach Resort. Best luxury version: Sheraton Kauai Resort + Grand Wailea.

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