Road to Hana waterfall surrounded by tropical greenery in Maui Pristine Maui beach with turquoise waters and palm trees USS Arizona Memorial at Pearl Harbor with American flag Haleakala crater at sunrise with clouds below the summit

Best 14 Days in Hawaii — Based in Big Island

Oahu → Maui → Big Island

14 days · 3 cities · 23 activities · route optimized by distance

Expect lots of nature — parks, scenic views, and outdoor activities. A moderate mix of walking and active experiences, with a mix of self-guided and guided activities. Includes 13 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

23+ 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
~$3,646 total · $260/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 4 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

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 3 Fri, Jul 3 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

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 $200/night Affiliate link — we may earn a commission at no extra cost to you
Day 4 Sat, Jul 4 Moderate Maui
Morning
Haleakala National Park Sunrise & Summit$~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 8 stops · Open in Google Maps ↗
Day 5 Sun, Jul 5 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

wifipoolair-conditioningbeach-access
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 $170/night Affiliate link — we may earn a commission at no extra cost to you
Day 6 Mon, Jul 6 Light Big Island
Full Day Hawaii Volcanoes National Park volcanic crater landscape
Hawaii Volcanoes National Park$~4 hrs

Explore Kilauea Caldera, lava tubes, and steam vents at this UNESCO volcanic park

$15 Verified Mar 2026 Best Apr-Oct 📍 Map
🏨 Hotel in Big Island

Kona / Hilo

wifipoolair-conditioningbeach-access
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 7 Tue, Jul 7 Moderate Big Island View on map
Morning Kealakekua Bay with snorkelers and pristine water
Captain Cook Monument Snorkeling$$~5 hrs

Snorkel Kealakekua Bay's coral reefs at the Captain Cook Monument

$130 Verified Mar 2026 Calmest May-Sep 📍 Map
Afternoon Milky Way galaxy visible above Mauna Kea observatory
Mauna Kea Stargazing Experience$$$~4 hrs

Stargaze from the 13,796-foot summit of Mauna Kea with guided telescopes

$260 Verified Mar 2026 Clearest skies Apr-Oct; tours run year-round weather permitting 📍 Map
🏨 Hotel in Big Island

Kona / Hilo

wifipoolair-conditioningbeach-access
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 $170/night Affiliate link — we may earn a commission at no extra cost to you
Day 8 Wed, Jul 8 Moderate Big Island View on map
Morning Akaka Falls cascading waterfall in tropical rainforest
Akaka Falls State Park$~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 Manta ray gliding underwater at night
Manta Ray Night Snorkel$$~2h 30m

Snorkel with giant manta rays during their nightly feeding off the Kona Coast

$140 Verified Mar 2026 Year-round; calmer ocean in summer months (Apr-Oct). Book ahead — tours sell out frequently. Sighting rate is ~90%+ year-round. Book this tour →
🏨 Hotel in Big Island

Kona / Hilo

wifipoolair-conditioningbeach-access
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 $170/night Affiliate link — we may earn a commission at no extra cost to you
Day 9 Thu, Jul 9 Full Big Island
Full Day Punalu'u black sand beach with sea turtles on the Big Island
Papakolea Green & Punalu'u Black Sand Beaches$~6 hrs

Hike to the rare green sand beach and visit Punalu'u's black sand shore with sea turtles

Year-round; drier months offer easier hiking. No fees or permits required. The shuttle service to Papakolea is unofficial/illegal — hike in only.
🏨 Hotel in Big Island

Kona / Hilo

wifipoolair-conditioningbeach-access
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 $170/night Affiliate link — we may earn a commission at no extra cost to you
Day 10 Fri, Jul 10 Moderate Big Island
Morning Waipi'o Valley lookout with lush green cliffs
Waipi'o Valley Lookout & Waimea$~3 hrs

Take in the iconic Waipi'o Valley views from the lookout and explore cowboy town Waimea

Year-round lookout access; valley road restricted since 2022 — only permitted 4WD tours allowed. Drier months (Apr-Oct) offer clearest views.
Afternoon Mauna Kea observatory under starry night sky
Mauna Kea Summit & Stargazing Tour$$$~8 hrs

Watch sunset from the 13,796-ft Mauna Kea summit, then stargaze with telescopes

$315 Verified Mar 2026 Year-round; winter months may have summit snow/ice closures. Summit road requires 4WD (most rental companies prohibit it — tours are the practical option). Children under 13 not permitted above the Visitor Station. Book this tour →
🏨 Hotel in Big Island

Kona / Hilo

wifipoolair-conditioningbeach-access
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 $170/night Affiliate link — we may earn a commission at no extra cost to you
Day 11 Sat, Jul 11 Moderate Big Island View on map
Morning
Kona Coffee Farm Tour & Tasting$~2 hrs

Tour a working Kona coffee farm and taste freshly roasted single-origin beans from the slopes of Hualalai

Year-round; harvest season (Aug-Jan) is most interesting. 📍 Map
Afternoon Black sand beach with ocean and sea turtle
Punalu'u Black Sand Beach$~2 hrs

Walk the volcanic black sand beach and spot endangered green sea turtles resting on shore

Open year-round; calmest conditions Apr-Oct 📍 Map
🏨 Hotel in Big Island

Kona / Hilo

wifipoolair-conditioningbeach-access
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 12 Sun, Jul 12 Moderate Big Island
Morning Snorkeling in clear tropical water near coral reef
Kealakekua Bay Snorkel Cruise$$~4 hrs

Snorkel the pristine coral reefs of Kealakekua Bay near the Captain Cook Monument

$155 Verified Mar 2026 Year-round; calmer seas and best visibility Apr-Oct. Morning tours are more popular — book ahead.
Afternoon Hapuna Beach white sand on the Kohala Coast
Kohala Coast & Pololu Valley Drive$~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

wifipoolair-conditioningbeach-access
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 $170/night Affiliate link — we may earn a commission at no extra cost to you
Day 13 Mon, Jul 13 Moderate Big Island View on map
Morning
Hilo Farmers Market$~2 hrs

Browse 200+ vendors selling tropical fruits, fresh poke, leis, and local crafts in downtown Hilo

Year-round; Wednesdays and Saturdays are full-scale market days. 📍 Map
Afternoon Kailua-Kona waterfront with palm trees
Kailua-Kona Historic Waterfront$~4 hrs

Explore Kona's waterfront with Hulihee Palace, Pu'uhonua o Honaunau, and coffee country

Year-round. Kona Coffee harvest season (Aug-Jan) adds extra farm activity.
🏨 Hotel in Big Island

Kona / Hilo

wifipoolair-conditioningbeach-access
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: $1,832–$2,748

Trip Budget Estimate

$3,646 estimated total per person
$260 per day
Lodging $2,290
Activities $1,171
Transport $185

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

Similar Destinations

Similar vibes, fewer crowds — destinations our algorithm rates as close matches to Hawaii.

Explore Similar Trips