Pristine Maui beach with turquoise waters and palm trees USS Arizona Memorial at Pearl Harbor with American flag Road to Hana waterfall surrounded by tropical greenery in Maui North Shore waves and palm trees overlooking the ocean

Best 3 Days in Hawaii — Winter

Oahu → Maui

3 days · 2 cities · 4 activities · route optimized by distance

A mix of food & wine, adventure, and nature. Mostly low-effort and walkable, with a mix of self-guided and guided activities. Includes 3 must-see landmarks across Oahu and Maui.

Highlights: Pearl Harbor & USS Arizona Memorial, Haleakala National Park Sunrise & Summit, Mama's Fish House, North Shore & Haleiwa Town

Arriving Wed, Jul 1 Change

Your Route — ordered to minimize backtracking

4+ activities scored and ranked · route optimized across 2 cities

Where you'll stay
Hotel in Oahu · From $180/night +1 more
See lodging →
Trip cost
~$635 total · $212/day
See budget →
Top picks
Pearl Harbor & USS Arizona Memorial, North Shore & Haleiwa Town, Haleakala National Park Sunrise & Summit
See itinerary →

Day-by-Day Schedule — heavy and light days alternate so you don’t burn out

Oahu

Oahu 2 stops · Open in Google Maps ↗
Day 1 Wed, Jul 1 Full Oahu View on map
Morning USS Arizona Memorial at Pearl Harbor with American flag
Pearl Harbor & USS Arizona Memorial$~4 hrs

Tour the USS Arizona Memorial and Pearl Harbor visitor center

Open year-round; free timed tickets required — book well in advance 📍 Map
Afternoon
North Shore & Haleiwa Town$~4 hrs

Watch world-class surfers at Pipeline, explore Haleiwa, and grab shave ice at Matsumoto's

Year-round. Nov-Feb for big wave season and surf competitions. Summer has calmer water for swimming. Matsumoto's open daily.
🏨 Hotel in Oahu

Waikiki / Kailua

wifipoolair-conditioningbeach-access
Travelers book: Outrigger Waikiki $220-380/nightPark Shore Waikiki $150-250/nightWaikiki Beachside Hostel $60-100/night
Book Hotel in Oahu from $180/night Affiliate link — we may earn a commission at no extra cost to you
Oahu → Maui
1h 30m ~$100 Inter-island flight from Honolulu to Kahului (40min)

Maui

Maui 2 stops · Open in Google Maps ↗
Day 2 Thu, Jul 2 Full Maui View on map
Morning
Haleakala National Park Sunrise & Summit$~4 hrs

Watch sunrise from the 10,023 ft summit of Haleakala, then hike the otherworldly volcanic crater trails.

$30 Verified Mar 2026 Year-round. Sunrise reservations required (3am-7am). Summit temps near freezing — bring layers.
Afternoon
Mama's Fish House$$$~2 hrs

Dine on fresh-caught Hawaiian fish at Maui's most iconic oceanfront restaurant in Paia

$125 Verified Mar 2026 Year-round; lunch and dinner service daily. 📍 Map
🏨 Hotel in Maui

Wailea / Lahaina / Kihei

wifipoolair-conditioningbeach-access
Travelers book: Grand Wailea $300-500/nightMaui Ocean Pavilions $180-300/nightPaia Inn Hotel $150-250/night
Book Hotel in Maui from $200/night Affiliate link — we may earn a commission at no extra cost to you
Day 3 Fri, Jul 3 Maui
Checkout & Depart

Check out of your hotel, grab a final breakfast, and head to the airport. Safe travels from Maui!

Where You’ll Stay

Estimated total: $304–$456

Trip Budget Estimate

$635 estimated total per person
$212 per day
Lodging $380
Activities $155
Transport $100

Estimates based on listed activity prices and hotel rates. Actual costs vary by season, availability, and personal spending.

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