North Shore waves and palm trees overlooking the ocean Road to Hana waterfall surrounded by tropical greenery in Maui Waikiki Beach with Diamond Head volcano in background Hapuna Beach white sand on the Kohala Coast

Best 5 Days in Hawaii — Winter

Oahu → Maui → Big Island

5 days · 3 cities · 8 activities · route optimized by distance

A mix of nature, history, and food & wine. Mostly low-effort and walkable, with a mix of self-guided and guided activities. Includes 5 must-see landmarks across Oahu and Maui and Big Island.

Highlights: Pearl Harbor & USS Arizona Memorial, Pearl Harbor National Memorial, Haleakala National Park Sunrise & Summit, Mama's Fish House, Akaka Falls State Park

Arriving Wed, Jul 1 Change

Your Route — ordered to minimize backtracking

8+ activities scored and ranked · route optimized across 3 cities

Where you'll stay
Hotel in Oahu · From $180/night +2 more
See lodging →
Trip cost
~$1,196 total · $239/day
See budget →
Top picks
Pearl Harbor & USS Arizona Memorial, North Shore & Haleiwa Town, Pearl Harbor National Memorial
See itinerary →

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

Oahu

Oahu 3 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

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Travelers book: Outrigger Waikiki $220-380/nightPark Shore Waikiki $150-250/nightWaikiki Beachside Hostel $60-100/night
Book Hotel in Oahu from $180/night Affiliate link — we may earn a commission at no extra cost to you
Day 2 Thu, Jul 2 Moderate Oahu View on map
Morning
Pearl Harbor National Memorial$~4 hrs

Visit the USS Arizona Memorial and Pearl Harbor museums honoring the 1941 attack

$1 Verified Mar 2026 Year-round. Book USS Arizona tickets 60 days ahead on Recreation.gov. Closed on Thanksgiving, Christmas, and New Year's Day.
Afternoon
Traditional Hawaiian Luau$$~3 hrs

Experience an authentic Hawaiian feast with hula, fire dancing, and kalua pig under the stars

$120 Verified Mar 2026 Year-round; book ahead for Friday and Saturday shows. 📍 Map
🏨 Hotel in Oahu

Waikiki / Kailua

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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 3 Fri, Jul 3 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

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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
Maui → Big Island
1h 15m ~$85 Inter-island flight from Kahului to Kona or Hilo (30min)

Big Island

Big Island 2 stops · Open in Google Maps ↗
Day 4 Sat, Jul 4 Full Big Island View on map
Morning Akaka Falls cascading waterfall in tropical rainforest
Akaka Falls State Park$~1h 30m

Hike a short loop trail to the 442-foot Akaka Falls through tropical forest

$5 Verified Mar 2026 Open year-round; waterfall most impressive after rain 📍 Map
Afternoon Hapuna Beach white sand on the Kohala Coast
Kohala Coast & Pololu Valley Drive$~4 hrs

Drive the Kohala Gold Coast from Hapuna Beach to Pololu Valley Lookout with historic stops

Year-round; Kohala Coast averages only 9 inches of rain per year.
🏨 Hotel in Big Island

Kona / Hilo

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Travelers book: Fairmont Orchid Hawaii $350-600/nightKona Tiki Hotel $140-250/nightUncle Billy's Hilo Bay Hotel $100-150/night
Book Hotel in Big Island from $170/night Affiliate link — we may earn a commission at no extra cost to you
Day 5 Sun, Jul 5 Big Island
Checkout & Depart

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

Where You’ll Stay

Estimated total: $584–$876

Trip Budget Estimate

$1,196 estimated total per person
$239 per day
Lodging $730
Activities $281
Transport $185

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

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