Hawaiian Island Cruises

1 Cruise
2 Offers
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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A small group of cruise travelers seen hiking on the Hawaiian Island of Lanai's cliffside shoreline with golden mountains behind them Get aboard this cruise to Lanai.
Trips, Tours & Cruises

Hawaii Island Hopping by Small Ship

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1 Cruise
2 Offers

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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8 Day Cruise
Hawaiian Seascapes Cruise

This unique 8-day, 4-island itinerary offers discovery of Hawaii's rich traditions and natural wonders, including a thrilling night snorkel. Experience the beauty of the Pacific Ocean aboard the 36-guest Safari Explorer adventure yacht.

Special Offer
From $5900USD
Jan Feb Mar Apr May Nov Dec
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A group of passengers seen from behind on the bow of a ship looking at the Hawaiian Islands shoreline

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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.

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Hawaii Cruises 2024 & 2025

Small ship Hawaii cruises in 2024 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 2025 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

“Cruising Hawaii offers an efficient way to reach many of the islands.”

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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Book with the confidence that comes from experience.

100+ combined years of experience, 7 continents explored, decades of expedition cruising around the world & here to help you find & book your dream trip.

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Travel Guides

Planning Hawaiian Island Cruises Today

Get in Touch with an Expert

AdventureSmith travelers as well as our expert staff have been aboard small Hawaiian Island cruises and can help guide your trip planning. Read on to get a feel for your ship and activity choices, as well as the region and the striking tropical landscape and culture that await you. We share fun and personal stories from our Hawaiian Island cruises to help you learn more about what it’s like to be on a unique Hawaii island hopping cruise. These reviews can inspire and inform, whether you are planning a Hawaii honeymoon, a getaway with friends or an active family trip. Let these tales can inspire your own Hawaii interisland cruise and know what to anticipate.

Expert Review • August 2nd, 2024
Expert Review: Cruising Small in Hawaii

An AdventureSmith expert shares her experience on the 8-day Hawaiian Seascapes cruise aboard the 36-guest Safari Explorer, plus read more reviews from our travelers who've cruised the Aloha State.

Travel Journal • September 24th, 2014
Active Adventures on My Hawaii Cruise

As I drift off to sleep I begin to dream of the amazing experiences that I couldn't even have imagined only seven days ago. I dream of diving with manta rays, of Pele, the goddess of fire, of paddle boarding at Shark's Fin Cove and swimming in the cool water under the cascading falls of Moâ'oula.

Travel Journal • September 22nd, 2014
Our Hawaii to Moloka'i Honeymoon Cruise

What’s the first question a newly-married couple gets? “Where did you guys go on your Honeymoon?” We are outdoorsy and adventurous. We enjoy hiking and getting out there, we want to experience things that others could only read about. We didn't want to completely rough it on our honeymoon but we also didn't want the resort or the 2,000 person cruise ship.

Expert Review • May 31st, 2024
Expert Aboard: Safari Explorer Review

From Hawaii to Alaska this vessel offers year-round exploration and adventure. Get an experts firsthand take on their favorite cabins and tips for getting the most out of your experience aboard.

Testimonials

What Travelers Say About Their Hawaiian Island Cruises

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Special Offers

Small Ship Hawaii Cruise Deals

Contact Us for More Ways to Save

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.

Our Expertise

Our Experts Are Your Quickest Way to Tropical & Hawaiian Islands Cruises

Get a Personalized Recommendation

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 2024 and 2025, 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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