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7 Days. 4 Islands. One Unforgettable Hawaii.

Most people who dream about Hawaii end up putting it off. The planning feels complicated, the options are overwhelming, and it's hard to know if what you're booking is actually worth what you're paying.

This trip solves that.

The Pride of America is the only cruise ship that sails Hawaii year-round — no sea days, no detours, no flying between islands on your own. Just four of the most beautiful islands in the world, one after another, with everything handled and nothing left to chance.

Oahu. Maui. The Big Island. Kauai.

Each island has its own personality, its own landscapes, and its own moments that stay with you long after you're home. This itinerary puts all four within reach — and gives you enough time on each one to actually experience it.

This is a planning template. Every detail — your cabin, your flights, your pace, your experiences — gets built around you. Fill out the form below and we'll take it from there.

Itinerary

  1. Trip Details

    1. New Cruise

    2. Room Options

    3. Norwegian Cruise Line — Free at Sea™ Cruise Package

  2. Departure

  3. Honolulu, Hawaii, United States

  4. Kahului-Maui, Hawaii, United States

  5. Kahului-Maui, Hawaii, United States

  6. Hilo, Hawaii, United States

  7. Kailua-Kona, Hawaii, United States

  8. Nawiliwili, Hawaii, United States

  9. Nawiliwili, Hawaii, United States

  10. Debarcation Day

  11. Fly Home

Full Itinerary

  • Why This Trip Works

    • No sea days — Every morning you wake up at a new island. The ship moves while you sleep
    • Four islands in one trip — Oahu, Maui, the Big Island, and Kauai. No inter-island flights to book, no luggage to recheck, no logistics to manage
    • The right ship — The Pride of America was built specifically for Hawaii. Every port, every schedule, every experience on board is designed around the islands
    • Two nights on Maui and Kauai — The two most requested islands get two days each. Enough time to go beyond the surface
    • Fully personalized — This isn't a package you pick off a shelf. Your cabin, your flights, your excursions, and your dates are all confirmed specifically for you

  • What's Included at a Glance

    • Round-trip flights from your home airport
    • 7-night cruise aboard Pride of America
    • Pre-cruise hotel stay in Honolulu (1–2 nights)
    • All airport and pier transfers
    • NCL Free at Sea package — unlimited beverages, specialty dining, Wi-Fi, and shore excursion credits
    • Shore excursions selected and confirmed for your travel style
    • Post-cruise Honolulu extension (optional)
    • Full planning support from start to finish

    Pricing varies based on travel dates, cabin category, and flight selection. All figures are confirmed at time of booking — nothing is locked in until you're ready.

  • This Is Just the Starting Point

    What you're looking at is a framework — a carefully built starting point designed to show you what this trip can be. The islands, the ship, the flow of the itinerary — those are the foundation.

    Everything else gets built around you.

    Your travel dates. Your cabin. Whether you want an active excursion day or a quiet beach morning. Whether you're traveling as a couple, with family, or on your own. Whether you want to extend the trip with a few extra days in Honolulu or head straight home after the cruise.

    Fill out the form and that conversation starts. No pressure, no commitment — just a chance to find out what this trip looks like when it's built specifically for you.

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Your Advisor

Jessica Gray

Superbly Justifiable Travel Services

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jessica@sj-travels.com

833-933-8747