North Shore waves and palm trees overlooking the ocean USS Arizona Memorial at Pearl Harbor with American flag Waikiki Beach with Diamond Head volcano in background Hanauma Bay crater with blue waters and snorkelers

Best 14 Days in Hawaii — Based in Oahu

Oahu → Maui → Big Island

14 days · 3 cities · 25 activities · route optimized by distance

A mix of nature and adventure. A moderate mix of walking and active experiences, with a mix of self-guided and guided activities. Includes 15 must-see landmarks across Oahu and Maui and Big Island.

Highlights: Haleakala Sunrise Experience, Pearl Harbor & USS Arizona Memorial, Pearl Harbor National Memorial, Haleakala National Park Sunrise & Summit, Hawai'i Volcanoes National Park

Arriving Wed, Jul 1 Change

Your Route — ordered to minimize backtracking

25+ 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
~$3,174 total · $227/day
See budget →
Top picks
Pearl Harbor & USS Arizona Memorial, Diamond Head Crater Hike, Pearl Harbor National Memorial
See itinerary →

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

Oahu

Oahu 10 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 Diamond Head crater viewed from Waikiki Beach
Diamond Head Crater Hike$~2h 30m

Hike to the summit of iconic Diamond Head crater for panoramic views

$5 Verified Mar 2026 Open year-round; advance reservations required for non-residents 📍 Map
🏨 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 $180/night Affiliate link — we may earn a commission at no extra cost to you
Day 2 Thu, Jul 2 Moderate Oahu View on map
Morning
Pearl Harbor National Memorial$~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 Hanauma Bay crater with blue waters and snorkelers
Hanauma Bay Snorkeling$$~3 hrs

Snorkel in a protected marine sanctuary with abundant tropical fish

$25 Verified Mar 2026 Calmest May-Sep 📍 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 $180/night Affiliate link — we may earn a commission at no extra cost to you
Day 3 Fri, Jul 3 Moderate Oahu View on map
Morning
Diamond Head State Monument Hike$~2 hrs

Hike to the summit of Diamond Head crater for 360-degree views of Waikiki and the Pacific

$5 Verified Mar 2026 Year-round. Cooler months (Oct-Apr) are ideal for the hike. Online reservation required for non-residents.
Afternoon Waikiki Beach shoreline with hotels and Diamond Head
Waikiki Beach$~4 hrs

Relax on world-famous Waikiki Beach with shopping and dining

Warm and swimmable year-round; calmest May-Sep 📍 Map
🏨 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
Day 4 Sat, Jul 4 Moderate Oahu
Morning
Hanauma Bay Snorkeling$$~3 hrs

Snorkel with tropical fish in a volcanic crater bay, Oahu's top marine preserve

$25 Verified Mar 2026 Year-round (Wed-Sun only). Summer has calmer water and best snorkeling visibility. Closed Mon-Tue. Online reservation required.
Afternoon
Waikiki Beach & Kalakaua Avenue$~3 hrs

Swim, surf, and stroll the golden sands of Waikiki Beach with Diamond Head as your backdrop

Year-round. Summer months (Apr-Oct) have calmer surf. Free Friday night fireworks at Hilton Hawaiian Village.
🏨 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 $180/night Affiliate link — we may earn a commission at no extra cost to you
Day 5 Sun, Jul 5 Moderate Oahu View on map
Morning
North Shore & Haleiwa Town$~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.
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

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 $180/night Affiliate link — we may earn a commission at no extra cost to you
Day 6 Mon, Jul 6 Moderate Oahu View on map
Morning Lanikai Beach with pristine white sand and turquoise water
Lanikai Beach$~3 hrs

Relax on one of Hawaii's most beautiful and quieter beaches

Calm water year-round; parking limited, arrive early 📍 Map
Afternoon North Shore big waves and surfers during winter swells
North Shore Beach & Surf Culture$~3 hrs

Experience legendary surfing beaches and casual beach town atmosphere

Surf Nov-Feb 📍 Map
🏨 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
Day 7 Tue, Jul 7 Moderate Oahu View on map
Morning Kualoa Ranch windward valley with Ko'olau mountains
Kualoa Ranch Movie Tour & Activities$$~3 hrs

Explore legendary movie set locations and windward coast scenic views

$63 Verified Mar 2026 Open year-round; book 2-3 weeks ahead in peak season 📍 Map
Afternoon
Historic Honolulu & Iolani Palace$$~4 hrs

Explore Iolani Palace, Chinatown, and the Bishop Museum in Hawaii's capital city

$27 Verified Mar 2026 Year-round. Iolani Palace closed Sundays and Mondays. Book palace tickets online in advance — no walk-ups.
🏨 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 $180/night Affiliate link — we may earn a commission at no extra cost to you
Day 8 Wed, Jul 8 Moderate Oahu
Morning
Windward Coast Drive$~4 hrs

Drive the dramatic Windward Coast past Ko'olau cliffs, Byodo-In Temple, and pristine beaches

$7 Verified Mar 2026 Year-round. Windward side gets more rain; summer months are drier. Byodo-In Temple open daily 8:30 AM-4:30 PM.
Afternoon
Kualoa Ranch Adventure Tours$$$~4 hrs

Explore the Jurassic Park valley on ATV, horseback, or movie-site tours at Kualoa Ranch

$125 Verified Mar 2026 Year-round. Drier months (Apr-Oct) are best. Book popular tours 2-3 weeks ahead. Book this tour →
🏨 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 $180/night Affiliate link — we may earn a commission at no extra cost to you
Day 9 Thu, Jul 9 Moderate Oahu View on map
Morning
Oahu Poke Bowl Crawl$~2 hrs

Sample Hawaii's iconic raw fish dish at the island's top poke shops from Waikiki to the North Shore

$15 Verified Mar 2026 Year-round; fresh ahi tuna is always available. 📍 Map
Afternoon
Manoa Falls Trail Hike$~2 hrs

Hike through a tropical rainforest to the tallest accessible waterfall on Oahu

Year-round. Drier summer months have less mud. The rainforest gets frequent showers; bring a light rain jacket.
🏨 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 $180/night Affiliate link — we may earn a commission at no extra cost to you
Day 10 Fri, Jul 10 Moderate Oahu View on map
Morning
Honolulu Poke Bowl Tour — Naturally Gluten-Free, Oahu$~1 hr

Eat fresh ahi poke with rice and tamari at Honolulu's best poke shops — Hawaii's naturally gluten-free power bowl

$16 Year-round 📍 Map
Afternoon
Polynesian Cultural Center$$~5 hrs

Experience six Polynesian island cultures through villages, performances, and a luau dinner show

$65 Verified Mar 2026 Year-round. Closed Sundays. Evening show packages (Ali'i Luau + Ha) are the most popular. Book 10+ days ahead. Book this tour →
🏨 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 3 stops · Open in Google Maps ↗
Day 11 Sat, Jul 11 Full Maui View on map
Morning Haleakala crater at sunrise with clouds below the summit
Haleakala Sunrise Experience$$~3 hrs

Watch sunrise above the clouds from a dormant volcano summit

$30 Verified Mar 2026 Open year-round; sunrise reservations required 3-7am, book 60 days ahead 📍 Map
Afternoon Waterfall along Road to Hana with rainforest
Road to Hana Scenic Drive$~8 hrs

Drive the famous winding coastal road past waterfalls and rainforests

$30 Verified Mar 2026 Best May-Oct 📍 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 $200/night Affiliate link — we may earn a commission at no extra cost to you
Day 12 Sun, Jul 12 Moderate Maui
Morning
Haleakala National Park Sunrise & Summit$~4 hrs

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

$30 Verified Mar 2026 Year-round. Sunrise reservations required (3am-7am). Summit temps near freezing — bring layers.
Afternoon
Road to Hana Scenic Drive$~10 hrs

Drive the legendary 64-mile coastal highway through rainforests, waterfalls, and black sand beaches.

Year-round but drier months (Apr-Oct) offer better road conditions. Winter rains can cause rockslides and closures.
🏨 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
Maui → Big Island
1h 15m ~$85 Inter-island flight from Kahului to Kona or Hilo (30min)

Big Island

Big Island 1 stop · Open in Google Maps ↗
Day 13 Mon, Jul 13 Full Big Island
Full Day Kilauea crater with volcanic steam at Hawaii Volcanoes National Park
Hawai'i Volcanoes National Park$~5 hrs

Explore Kilauea's craters, lava tubes, and Chain of Craters Road at this UNESCO World Heritage Site

$30 Verified Mar 2026 Open year-round 24/7. Drier months (Apr-Oct) best for hiking. Evening visits may reveal lava glow at Halema'uma'u. Construction project may affect some summit trails.
🏨 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 14 Tue, Jul 14 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: $1,896–$2,844

Trip Budget Estimate

$3,174 estimated total per person
$227 per day
Lodging $2,370
Activities $619
Transport $185

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

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