Hawaii — Multi-Island Adventure, a luxury journey by Kennedy Holidays
Island Hopping12 Nights / 13 Days

Hawaii

Multi-Island Adventure

United States · Hawaiian IslandsApril to OctoberIsland-hopping + Nature + Culture

Journey overview

Volcanoes, waterfalls, sunrise summits and secluded beaches — a detailed multi-island journey across four of Hawaii's most distinct landscapes.

  • Big Island — Hawaiʻi Volcanoes National Park and dramatic lava coastlines
  • Maui — the Road to Hana and sunrise above the clouds at Haleakalā
  • Oahu — Pearl Harbor, Waikiki and the surf culture of the North Shore
  • Lanai — a secluded finish among sea cliffs and the Garden of the Gods

Signature experiences

Volcanoes NPRoad to HanaHaleakalā SunrisePearl HarborNorth ShoreLanai Sea Cliffs

Route overview

Big Island
Kona, Volcanoes NP
3 Nights
Maui
Road to Hana, Haleakalā
4 Nights
Oahu
Waikiki, Pearl Harbor, North Shore
3 Nights
Lanai
Garden of the Gods
2 Nights
Day by day

The full itinerary

    • Arrive at Kona International Airport (KOA) and pick up your rental car
    • Explore Kailua-Kona town: Hulihe'e Palace and the Kona Farmers Market
    • Relax at Kahalu'u Beach Park (great for snorkelling and spotting turtles)
    • Dinner: fresh seafood at Jackie Rey's Ohana Grill or Umekes Fishmarket Bar & Grill
    • Early drive to Hawai'i Volcanoes National Park (approx. 2 hrs)
    • Visit the Kilauea Visitor Center for updates
    • Walk the Thurston Lava Tube and hike the Kilauea Iki Trail crater rim
    • Visit the Steam Vents and Sulfur Banks
    • Visit Rainbow Falls in Hilo town
    • Drive east to Akaka Falls State Park and hike to the 442 ft waterfall
    • Explore Punalu'u Black Sand Beach and look for sea turtles
    • Optional snorkelling at Kealakekua Bay or kayak to Captain Cook Monument
    • Morning flight Kona (KOA) to Kahului, Maui (OGG), approx. 45 min
    • Pick up your rental car at Kahului Airport
    • Visit the Lahaina Historic Trail (Whalers Village)
    • Explore Lahaina Town: Front Street shops, Banyan Tree Park, Lahaina Harbor
    • Dinner: fish tacos at Paia Fish Market or upscale dining at Lahaina Grill

    Travel: Flight KOA → OGG · approx. 45 min

    • Drive the Road to Hana (start early)
    • Highlights: Twin Falls, Wai'anapanapa State Park (black sand beach), Seven Sacred Pools (Ohe'o Gulch), Hana town
    • Optional stops: Wailua Falls, Hamoa Beach
    • Pack snacks or eat at roadside stands; dinner back in Lahaina or Hana
    • Early morning: Haleakālā National Park sunrise (reserve permit in advance)
    • Morning: explore the summit area and hike the Sliding Sands Trail (optional short hike)
    • Afternoon: visit Makawao Town for local art galleries and paniolo (cowboy) culture
    • Morning: snorkel at Molokini Crater (book boat tour early) or Turtle Town off the Makena coast
    • Afternoon: relax on Kaanapali Beach or Wailea Beach
    • Optional spa treatment or golf
    • Dinner at Monkeypod Kitchen or Mama's Fish House (reservation recommended)
    • Morning flight Maui to Honolulu (OGG to HNL, approx. 40 min)
    • Rental car, or rely on rideshare / public transport in Oahu
    • Visit Pearl Harbor National Memorial (USS Arizona Memorial, Battleship Missouri)
    • Walk around Downtown Honolulu and Chinatown

    Travel: Flight OGG → HNL · approx. 40 min

    • Drive to the North Shore (approx. 1 hr)
    • Visit famous surf spots: Waimea Bay, Banzai Pipeline and Sunset Beach
    • Visit Waimea Valley botanical garden and waterfall hike
    • Grab a shrimp plate lunch at the food trucks in Kahuku
    • Hike up Diamond Head Crater (1.5–2 hrs round trip)
    • Relax on nearby beaches (e.g. Kaimana Beach)
    • Visit Iolani Palace, the King Kamehameha Statue and the Hawaii State Capitol
    • Explore the Honolulu Museum of Art or shop at Ala Moana Center
    • Morning ferry from Maui (Mā'alaea Harbor) to Lanai (approx. 45 min)
    • Rent a 4x4 vehicle on Lanai
    • Visit Keahiakawelo (Garden of the Gods) rock formations
    • Explore Lanai City: quaint shops and the Lanai Culture & Heritage Center
    • Dinner at Lanai City Grill or Blue Ginger Cafe

    Travel: Ferry · approx. 45 min

    • Morning: Hulopoe Bay for snorkelling and possible dolphin sightings
    • Off-road adventure to Shipwreck Beach (requires 4x4)
    • Afternoon: relax at the hotel or explore local art galleries
    • Dinner: Nobu Lanai (if staying at Four Seasons) or casual local spots
    • Morning ferry back to Maui, or flight from Lanai Airport to Honolulu / Kona
    • Connect to your international flight home

Experience highlights

Hawaiʻi Volcanoes National Park in Hawaii — Kennedy Holidays

Hawaiʻi Volcanoes National Park

The Kilauea Visitor Center for updates, the Thurston Lava Tube, the Kilauea Iki Trail crater rim, Steam Vents and Sulfur Banks.

Road to Hana in Hawaii — Kennedy Holidays

Road to Hana

A full day of Twin Falls, Wai'anapanapa State Park's black sand beach, the Seven Sacred Pools at Ohe'o Gulch and Hana town.

Haleakalā Sunrise in Hawaii — Kennedy Holidays

Haleakalā Sunrise

A pre-dawn drive to the summit (permit reserved in advance), the optional Sliding Sands Trail, then upcountry Makawao's galleries and paniolo culture.

Let Kennedy Holidays Craft Your Journey

Every journey can be tailored around your pace, preferences and travel style.

Download the Full Itinerary

The complete branded Hawaii itinerary, exactly as our travel designers prepared it.

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Make this Hawaii journey yours.

Dates, hotels, pace and add-ons — all tailored. Talk to a Kennedy Holidays travel designer.

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