How many days is this Hawaii itinerary?

7 days visiting Oahu, Maui, Big Island, with routes optimized by distance.

How much do hotels cost on this Hawaii trip?

Hotels average $170-$200/night based on mid-range options. See our day-by-day hotel picks with booking links.

What cities are included in this Hawaii itinerary?

Oahu, Maui, Big Island — ordered to minimize backtracking between stops.

Pristine Maui beach with turquoise waters and palm trees

Kilauea crater with volcanic steam at Hawaii Volcanoes National Park

Hanauma Bay crater with blue waters and snorkelers

Diamond Head crater viewed from Waikiki Beach

Best 7 Days in Hawaii — Workcation

Oahu → Maui → Big Island

7 days · 3 cities · 6 activities · route optimized by distance

A mix of nature and adventure. A moderate mix of walking and active experiences, mostly at your own pace. Includes 6 must-see landmarks across Oahu and Maui and Big Island.

Highlights: Hawai'i Volcanoes National Park, Diamond Head Crater Hike, Road to Hana Scenic Drive, Road to Hana Scenic Drive, Hanauma Bay Snorkeling

Arriving Wed, Jul 1 Change

Your Route — ordered to minimize backtracking

Waikiki Beach with Diamond Head volcano in background

Oahu 3 nights

Road to Hana waterfall surrounded by tropical greenery in Maui

Maui 2 nights

Hawaii Volcanoes National Park with volcanic landscape

Big Island 1 night

6+ 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

~$1,385 total · $198/day

See budget →

Top picks

Diamond Head Crater Hike

See itinerary →

Make It Yours

Each option links to a pre-built itinerary with a different focus.

📅 Trip Length

3 days 5 days 7 days 10 days 14 days 21 days

⚙ More Options

🎼 Rhythm

Classic Slow Travel Workcation

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

Morning

Remote work morning — find a café or coworking space

Afternoon

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

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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 Light Oahu

Morning

Remote work morning — find a café or coworking space

Afternoon

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 Light Oahu

Morning

Remote work morning — find a café or coworking space

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

Oahu → Maui

1h 30m ~$100 Inter-island flight from Honolulu to Kahului (40min)

Maui

Maui 2 stops · Open in Google Maps ↗

Day 4 Sat, Jul 4 Full Maui

Morning

Remote work morning — find a café or coworking space

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 5 Sun, Jul 5 Light Maui

Morning

Remote work morning — find a café or coworking space

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 6 Mon, Jul 6 Full Big Island

Morning

Remote work morning — find a café or coworking space

Afternoon

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 7 Tue, Jul 7 Big Island

Checkout & Depart

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