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Hawaiian Island Cruises

1 CRUISE 4 DEALS

See the Hawaiian Islands as few do—from the outside in, sailing from island to island on a small ship cruise. Hike remote shorelines and snorkel at sea as you cruise Molokai, Lanai, Maui and Hawaii.

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Hawaii Island Hopping by Small Ship

With tens of millions visiting the Aloha state each year, take a Hawaii island hopping cruise for an entirely new, off-the-beaten-path travel experience. Maybe you have been to Hawaii before, but never like this. While day cruises are common, overnight Hawaiian Island cruises are few and far between. Staying aboard a small ship offers unique opportunities to travel in an efficient and effortless way while never missing a sunset. Leave airport travel and hotel bag-packing behind to go Hawaii island hopping in style and ease.

Our Hawaiian Island cruises reach ports and locations that are off-the-beaten path and away from the typical Hawaii cruise destinations. These relaxed, intimate and active Hawaii small ship cruises may just offer the new spin on Aloha luxury you’ve been searching for. Your itinerary is flexible and not available to larger ships, making this Hawaii interisland cruise experience uncrowded, unrushed and full of active adventure exploring remote locales by foot, kayak, sailboat, paddleboard and motor launch.

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Hawaii Small Ship Cruises with AdventureSmith

We offer the most unique, intimate way to visit Hawaii—by yacht. Let us take you there with efficiency and ease. Why book your Hawaii interisland cruise with AdventureSmith Explorations?

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Personalized

Work with one Adventure Specialist to prepare for your Hawaii island hopping cruise.

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Experience

We can match you with the best Hawaiian cruise & timing thanks to our years of experience.

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Active

Snorkel, whale watch, hike, kayak & paddleboard all in one trip, included in the cost.

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Value

We're here to help you save with our partnerships & exclusive Hawaii cruise deals.

Three yellow kayaks paddle off the coast of Maui on a Hawaiian Islands cruise

Hawaii Cruises 2026 & 2027

Small ship Hawaii cruises in 2026 are hotter than ever thanks to travelers seeking more exclusivity and remoteness for their travels. Be among the few to cruise Hawaii. Our specialists make it easier than ever to go Hawaii island hopping. Skip the crowds and logistics of air travel and island hop Hawaii by small ship cruise. Our team can assist you with your trip this year, or Hawaii cruises in 2026 and beyond. 

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Luxury Hawaii Cruises & Private Yacht Charters

Through AdventureSmith and our expertise with small ship cruising worldwide, you have the power to choose from scheduled Hawaii small ship cruises in Hawaii or design your own Hawaii island hopping charter cruise for an even more intimate experience with your small group. Let our award-winning experts skilled in pairing travelers with the right ship at the best price create the perfect Hawaii boat cruise for you. Think fresh-caught fish and tropical shorelines just for your group! Luxury Hawaii cruises are hard to find with mostly big ships and day cruises dominating the waters. Let us steer you to the best Hawaiian Island cruises that tap into authentic Aloha.

Seared ono fish on a plate with white wine and a Hawaiian Island shirt in the background

Year-Round Hawaii Island Hopping

In Hawaii, winter is warm and summer is warmer. Even in “winter,” temperatures are regularly in the 80s, making it an incredible destination for year-round Hawaiian Island cruises. While rain is common, your small ship captain can navigate to windward and leeward sides of islands to take advantage of unique microclimates and steer you away from rain storms. Taking a Hawaii island hopping cruise can truly ensure you land in the best weather during your vacation. Want to Learn More About Hawaii's Climate?

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What Travelers Say About Their Hawaiian Island Cruises

Read Our Expert Review

  • “This Was a Perfect Fit!”

    We wanted to experience the different islands of Hawaii, and we love water adventures, so this was a perfect fit!

    Roberta L. Spring Lake, MI

    OVERALL 5.0/5
    LODGING 4.0/5
    MEALS 5.0/5

  • “Really Enjoyed the Trip Overall”

    We are not cruise-shippers, normally preferring independent travel, but this is a great way to get under the skin of Hawaiian culture and wildlife on several islands, and away from the crowds.

    Edward M. London, UK

    OVERALL 5.0/5
    LODGING 5.0/5
    MEALS 4.0/5

  • “Simply Fantastic”

    We loved the luxury of the cruise, combined with the various active adventures. Perfect!

    Cathy B. Holly Park, NV

    OVERALL 5.0/5
    LODGING 5.0/5
    MEALS 5.0/5

  • “Beyond Excellent!”

    The guides were always enthusiastic, considerate of all passengers' abilities and extremely knowledgeable. The entrees were always fresh and locally sourced. Thank you Arielle for your help and quick response to questions.

    Barbara C. Baltimore, MD

    OVERALL 5.0/5
    LODGING 5.0/5
    MEALS 5.0/5

  • “A Well Tuned Adventure”

    The trip leaders were all excellent. Friendly, accommodating, helpful, fun. No request was ever too much, unless it was unsafe.

    Pamela G. Toronto, ON

    OVERALL 5.0/5
    LODGING 5.0/5
    MEALS 5.0/5

  • “A Blissful Contrast to the Touristy Experience”

    We've always wanted to see Hawaii but didn't want resorts or large cruise ships. This trip was very active, yet relaxed and intimate -- perfect for us.

    Ann P. Evansville, IN

    OVERALL 5.0/5
    LODGING 5.0/5
    MEALS 5.0/5

Small Ship Hawaii Cruise Deals

Our experienced team can help you find the latest discounts, explain the ins-and-outs of Hawaiian Island cruises and secure your dream Hawaii interisland cruise at the best rate. From early-booking deals to discounts on new routes, browse our current deals on cruises around Hawaii for ways to save. While our options skew more toward luxury Hawaii cruises due to the ship accommodations, remote access and included activities, we do know how to land you Hawaii cruise deals if you are looking for them. The best Hawaiian cruise is one where you experience the authentic Aloha State at a relaxed pace, not just rush by as a tourist on the least expensive route.
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Our Experts Are Your Quickest Way to Tropical & Hawaiian Islands Cruises

Not much beats Hawaii island hopping, but this iconic place is not our only tropical destination to small ship cruise. Our experts are just a phone call or email away to assist you narrow down all the options worldwide. We're here to help you find Hawaii cruise deals and Hawaii cruises 2026 and 2027, or to explore other remote island chains. Contact us to receive a personalized recommendation on the best Hawaiian cruise or Pacific Islands sailing for your travel style, budget and timing needs, or head to our Trip Finder to do your own research. Our team can assist with a personalized look at which Hawaii small ship cruises will be best for you.
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