Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii North Shore waves and palm trees overlooking the ocean Hawaii Volcanoes National Park with volcanic landscape Hanauma Bay crater with blue waters and snorkelers

Hawaii Travel Itineraries

398 itineraries · 6 trip lengths · 392 variants — routes scored by distance, days balanced by intensity

Hawaii leans heavily into nature — expect parks, scenic views, and outdoor activities throughout. A moderate mix of walking and active experiences, with a mix of self-guided and guided activities. Around 26 must-see landmarks in the mix, and options span budget to mid-range.

Top attractions include Haleakala Sunrise Experience, Na Pali Coast Boat Tour, Pearl Harbor & USS Arizona Memorial, Haleakala National Park Sunrise & Summit, Pearl Harbor National Memorial, Hawai'i Volcanoes National Park, Diamond Head Crater Hike, Hawaii Volcanoes National Park.

📅 Best Time to Visit Hawaii

Best months: April–May, September–November

Year-round destination. Whale watching December–April. Less crowded in shoulder seasons.

Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec
  • Open year-round; free timed tickets required — book well in advance
  • Open year-round; advance reservations required for non-residents
  • Open year-round; sunrise reservations required 3-7am, book 60 days ahead
  • Best May-Oct
  • Year-round. Nov-Feb for big wave season and surf competitions. Summer has calmer water for swimming. Matsumoto's open daily.

Choose Your Hawaii Itinerary

5 route options optimized for different trip lengths and travel styles

3 Days — Quick Escape

Oahu → Maui

4+ activities

Haleakala Sunrise Experience, Pearl Harbor & USS Arizona Memorial, Diamond Head Crater Hike

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5 Days — Classic Tour

Oahu → Maui → Big Island

7+ activities

Haleakala Sunrise Experience, Pearl Harbor & USS Arizona Memorial, Pearl Harbor National Memorial

View itinerary ›

7 Days — Classic Tour

Oahu → Maui → Big Island

11+ activities

Haleakala Sunrise Experience, Pearl Harbor & USS Arizona Memorial, Pearl Harbor National Memorial

View itinerary ›

10 Days — Extended Journey

Oahu → Maui → Big Island

16+ activities

Haleakala Sunrise Experience, Pearl Harbor & USS Arizona Memorial, Pearl Harbor National Memorial

View itinerary ›

14 Days — Grand Tour

Oahu → Maui → Big Island

24+ activities

Haleakala Sunrise Experience, Pearl Harbor & USS Arizona Memorial, Pearl Harbor National Memorial

View itinerary ›

Trip Lengths

Pick a length, we'll handle the routing. Every itinerary can be tweaked by style, pace, and budget.

Quick Getaways 2–4 days

Week Trips 5–7 days

Extended Trips 8–10 days

Grand Tours 11–28 days

By Travel Style

Same cities, different lens. We reshuffle activities so the trip matches what you actually care about.

Road to Hana waterfall surrounded by tropical greenery in Maui Hawaii Volcanoes National Park with volcanic landscape North Shore waves and palm trees overlooking the ocean Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii
Food & Wine

Best 7 Days in Hawaii — Food & Wine

Oahu → Maui → Big Island

7 days · 6 trip lengths available

North Shore waves and palm trees overlooking the ocean Diamond Head crater viewed from Waikiki Beach Waikiki Beach with Diamond Head volcano in background Hanauma Bay crater with blue waters and snorkelers
Walking Tours

Best 7 Days in Hawaii — Walking Tours

Oahu → Maui → Big Island

7 days · 6 trip lengths available

Hawaii Volcanoes National Park with volcanic landscape Road to Hana waterfall surrounded by tropical greenery in Maui Lahaina historic town with ocean view Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii
History

Best 7 Days in Hawaii — History

Oahu → Maui → Big Island

7 days · 6 trip lengths available

Waikiki Beach with Diamond Head volcano in background North Shore waves and palm trees overlooking the ocean Road to Hana waterfall surrounded by tropical greenery in Maui Pristine Maui beach with turquoise waters and palm trees
Art & Culture

Best 7 Days in Hawaii — Art & Culture

Oahu → Maui → Big Island

7 days · 6 trip lengths available

Waikiki Beach with Diamond Head volcano in background Palm trees overlooking a sandy beach in Maui, Hawaii Hanauma Bay crater with blue waters and snorkelers Road to Hana waterfall surrounded by tropical greenery in Maui
Family Friendly

Best 7 Days in Hawaii — Family Friendly

Oahu → Maui → Big Island

7 days · 6 trip lengths available

Pristine Maui beach with turquoise waters and palm trees Road to Hana waterfall surrounded by tropical greenery in Maui Kilauea crater with volcanic steam at Hawaii Volcanoes National Park USS Arizona Memorial at Pearl Harbor with American flag
Romantic

Best 7 Days in Hawaii — Romantic

Oahu → Maui → Big Island

7 days · 5 trip lengths available

Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii Haleakala crater at sunrise with clouds below the summit Road to Hana waterfall surrounded by tropical greenery in Maui Kualoa Ranch windward valley with Ko'olau mountains
Photography

Best 7 Days in Hawaii — Photography

Oahu → Maui → Big Island

7 days · 6 trip lengths available

Waikiki Beach with Diamond Head volcano in background Hanauma Bay crater with blue waters and snorkelers Road to Hana waterfall surrounded by tropical greenery in Maui Diamond Head crater viewed from Waikiki Beach
Adventure

Best 7 Days in Hawaii — Adventure

Oahu → Maui → Big Island

7 days · 6 trip lengths available

North Shore waves and palm trees overlooking the ocean Pristine Maui beach with turquoise waters and palm trees Hanauma Bay crater with blue waters and snorkelers Road to Hana waterfall surrounded by tropical greenery in Maui
Nature

Best 7 Days in Hawaii — Nature

Oahu → Maui → Big Island

7 days · 6 trip lengths available

Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii North Shore waves and palm trees overlooking the ocean Diamond Head crater viewed from Waikiki Beach Waikiki Beach with Diamond Head volcano in background
Vegan & Plant-Based

Best 7 Days in Hawaii — Vegan & Plant-Based

Oahu → Maui → Big Island

7 days · 5 trip lengths available

Hawaii Volcanoes National Park with volcanic landscape Road to Hana waterfall surrounded by tropical greenery in Maui Diamond Head crater viewed from Waikiki Beach North Shore waves and palm trees overlooking the ocean
LGBTQ+ Friendly

Best 7 Days in Hawaii — LGBTQ+ Friendly

Oahu → Maui → Big Island

7 days · 5 trip lengths available

Waikiki Beach with Diamond Head volcano in background Hawaii Volcanoes National Park with volcanic landscape Haleakala crater at sunrise with clouds below the summit Pristine Maui beach with turquoise waters and palm trees
Gluten-Free

Best 7 Days in Hawaii — Gluten-Free

Oahu → Maui → Big Island

7 days · 5 trip lengths available

Pristine Maui beach with turquoise waters and palm trees Kilauea crater with volcanic steam at Hawaii Volcanoes National Park Lush green valley with dramatic mountain peaks in Hawaii Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii
Solo Travel

Best 7 Days in Hawaii — Solo Travel

Oahu → Maui → Big Island

7 days · 6 trip lengths available

Workation

Best 7 Days in Hawaii — Workation

7 days

Nightlife

Best 7 Days in Hawaii — Nightlife

7 days

Combined Interests

Two themes, one trip. Activities scored for both interests so nothing feels forced.

Waikiki Beach with Diamond Head volcano in background USS Arizona Memorial at Pearl Harbor with American flag Kilauea crater with volcanic steam at Hawaii Volcanoes National Park Pristine Maui beach with turquoise waters and palm trees
Food & Wine & Walking Tours

Best 7 Days in Hawaii — Food & Wine & Walking Tours

Oahu → Maui → Big Island

7 days · 4 trip lengths available

North Shore waves and palm trees overlooking the ocean USS Arizona Memorial at Pearl Harbor with American flag Haleakala crater at sunrise with clouds below the summit Road to Hana waterfall surrounded by tropical greenery in Maui
Art & Culture & Food & Wine

Best 7 Days in Hawaii — Art & Culture & Food & Wine

Oahu → Maui → Big Island

7 days · 5 trip lengths available

Waikiki Beach with Diamond Head volcano in background North Shore waves and palm trees overlooking the ocean Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii Kilauea crater with volcanic steam at Hawaii Volcanoes National Park
Food & Wine & Nature

Best 7 Days in Hawaii — Food & Wine & Nature

Oahu → Maui → Big Island

7 days · 4 trip lengths available

Hawaii Volcanoes National Park with volcanic landscape Road to Hana waterfall surrounded by tropical greenery in Maui Diamond Head crater viewed from Waikiki Beach Haleakala crater at sunrise with clouds below the summit
Food & Wine & Vegan & Plant-Based

Best 7 Days in Hawaii — Food & Wine & Vegan & Plant-Based

Oahu → Maui → Big Island

7 days · 5 trip lengths available

North Shore waves and palm trees overlooking the ocean Hanauma Bay crater with blue waters and snorkelers Waikiki Beach with Diamond Head volcano in background Hawaii Volcanoes National Park with volcanic landscape
Food & Wine & Gluten-Free

Best 7 Days in Hawaii — Food & Wine & Gluten-Free

Oahu → Maui → Big Island

7 days · 5 trip lengths available

Pristine Maui beach with turquoise waters and palm trees Waikiki Beach with Diamond Head volcano in background Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii Kilauea crater with volcanic steam at Hawaii Volcanoes National Park
Photography & Walking Tours

Best 7 Days in Hawaii — Photography & Walking Tours

Oahu → Maui → Big Island

7 days · 5 trip lengths available

Waikiki Beach with Diamond Head volcano in background Hawaii Volcanoes National Park with volcanic landscape Haleakala crater at sunrise with clouds below the summit Pristine Maui beach with turquoise waters and palm trees
Adventure & Walking Tours

Best 7 Days in Hawaii — Adventure & Walking Tours

Oahu → Maui → Big Island

7 days · 4 trip lengths available

North Shore waves and palm trees overlooking the ocean Pristine Maui beach with turquoise waters and palm trees Hanauma Bay crater with blue waters and snorkelers Road to Hana waterfall surrounded by tropical greenery in Maui
Nature & Walking Tours

Best 7 Days in Hawaii — Nature & Walking Tours

Oahu → Maui → Big Island

7 days · 4 trip lengths available

North Shore waves and palm trees overlooking the ocean Hawaii Volcanoes National Park with volcanic landscape Hanauma Bay crater with blue waters and snorkelers Kilauea crater with volcanic steam at Hawaii Volcanoes National Park
Family Friendly & History

Best 7 Days in Hawaii — Family Friendly & History

Oahu → Maui → Big Island

7 days · 3 trip lengths available

Pristine Maui beach with turquoise waters and palm trees Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii North Shore waves and palm trees overlooking the ocean Haleakala crater at sunrise with clouds below the summit
Art & Culture & Family Friendly

Best 7 Days in Hawaii — Art & Culture & Family Friendly

Oahu → Maui → Big Island

7 days · 4 trip lengths available

Hawaii Volcanoes National Park with volcanic landscape Hanauma Bay crater with blue waters and snorkelers Kilauea crater with volcanic steam at Hawaii Volcanoes National Park Road to Hana waterfall surrounded by tropical greenery in Maui
Family Friendly & Romantic

Best 7 Days in Hawaii — Family Friendly & Romantic

Oahu → Maui → Big Island

7 days · 4 trip lengths available

Road to Hana waterfall surrounded by tropical greenery in Maui Waikiki Beach with Diamond Head volcano in background Diamond Head crater viewed from Waikiki Beach North Shore waves and palm trees overlooking the ocean
Family Friendly & Photography

Best 3 Days in Hawaii — Family Friendly & Photography

Oahu → Maui

3 days · 4 trip lengths available

North Shore waves and palm trees overlooking the ocean Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii Road to Hana waterfall surrounded by tropical greenery in Maui Haleakala crater at sunrise with clouds below the summit
Adventure & Family Friendly

Best 7 Days in Hawaii — Adventure & Family Friendly

Oahu → Maui → Big Island

7 days · 4 trip lengths available

Waikiki Beach with Diamond Head volcano in background Hanauma Bay crater with blue waters and snorkelers Pristine Maui beach with turquoise waters and palm trees Kilauea crater with volcanic steam at Hawaii Volcanoes National Park
Family Friendly & Nature

Best 7 Days in Hawaii — Family Friendly & Nature

Oahu → Maui → Big Island

7 days · 4 trip lengths available

Pristine Maui beach with turquoise waters and palm trees Hanauma Bay crater with blue waters and snorkelers North Shore waves and palm trees overlooking the ocean Diamond Head crater viewed from Waikiki Beach
Photography & Romantic

Best 7 Days in Hawaii — Photography & Romantic

Oahu → Maui → Big Island

7 days · 4 trip lengths available

Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii Hawaii Volcanoes National Park with volcanic landscape Kilauea crater with volcanic steam at Hawaii Volcanoes National Park Pristine Maui beach with turquoise waters and palm trees
Nature & Romantic

Best 7 Days in Hawaii — Nature & Romantic

Oahu → Maui → Big Island

7 days · 4 trip lengths available

Hawaii Volcanoes National Park with volcanic landscape Road to Hana waterfall surrounded by tropical greenery in Maui Hanauma Bay crater with blue waters and snorkelers North Shore waves and palm trees overlooking the ocean
Adventure & Photography

Best 7 Days in Hawaii — Adventure & Photography

Oahu → Maui → Big Island

7 days · 4 trip lengths available

Kilauea lava flowing into the Pacific Ocean on Big Island Hawaii North Shore waves and palm trees overlooking the ocean Diamond Head crater viewed from Waikiki Beach Waikiki Beach with Diamond Head volcano in background
Nature & Photography

Best 7 Days in Hawaii — Nature & Photography

Oahu → Maui → Big Island

7 days · 4 trip lengths available

Hawaii Volcanoes National Park with volcanic landscape Road to Hana waterfall surrounded by tropical greenery in Maui Hanauma Bay crater with blue waters and snorkelers North Shore waves and palm trees overlooking the ocean
Adventure & Nature

Best 7 Days in Hawaii — Adventure & Nature

Oahu → Maui → Big Island

7 days · 6 trip lengths available

Pristine Maui beach with turquoise waters and palm trees Hawaii Volcanoes National Park with volcanic landscape Haleakala crater at sunrise with clouds below the summit Road to Hana waterfall surrounded by tropical greenery in Maui
Art & Culture & History

Best 5 Days in Hawaii — Art & Culture & History

Oahu → Maui → Big Island

5 days · 1 trip lengths available

Waikiki Beach with Diamond Head volcano in background Kealakekua Bay with snorkelers and pristine water USS Arizona Memorial at Pearl Harbor with American flag Kilauea crater with volcanic steam at Hawaii Volcanoes National Park
History & Photography

Best 14 Days in Hawaii — History & Photography

Oahu → Maui → Big Island

14 days · 1 trip lengths available

By Pace

Relaxed means fewer cities and more breathing room. Fast packs in more stops. We re-optimize the route either way.

Skip a Theme

Not your thing? We rebuild the itinerary without activities tagged with that theme.

Travel Rhythm

Slow down or work remotely — the itinerary adapts to your pace of life.

By Season

Activities reshuffled for the best experiences each season — cherry blossoms in spring, beaches in summer, foliage in autumn, snow in winter.

City Focus

Spend more time in one city — the route rebalances around your base.

More Options

Different airport, different budget — the route adjusts automatically.