A Thoughtful Way to Experience Hawaii: 17 Nights Around the Islands

Posted on by Kenneth Reece, Agent of Modern Travel Professionals

Hawaii has a way of staying on people’s bucket lists for years. The islands feel familiar, yet completely different from anywhere else in the U.S.—with dramatic landscapes, deep cultural roots, and a sense of calm that’s hard to replicate.

One beautiful way to experience Hawaii is on a 17-night Circle Hawaii cruise, sailing roundtrip from San Diego aboard Holland America Line’s Koningsdam. This sailing departs January 9, 2027, and offers a relaxed, immersive way to see several Hawaiian islands in one journey.

The Itinerary: Hawaii, Island by Island

This Circle Hawaii itinerary includes visits to multiple islands, each with its own personality and scenery. Ports typically include:

  • Honolulu (Oahu) – rich in history, culture, and iconic sights
  • Kahului (Maui) – known for its beaches, scenic drives, and laid-back feel
  • Nawiliwili (Kauai) – lush, green, and often called the “Garden Isle”
  • Hilo and Kona (Big Island) – offering volcanoes, black-sand beaches, and coffee country

There is also a stop in Ensenada, Mexico on the return journey, adding a little extra variety to the trip.

Instead of flying between islands, you unpack once and let the ship do the traveling. You wake up in a new place ready to explore—without airports, luggage transfers, or changing hotels.

Sea Days That Feel Meaningful

The journey to and from Hawaii includes several sea days, and on a sailing like this, those days are very much part of the experience.

Holland America is known for using sea days intentionally, especially on longer voyages. Guests can expect enrichment programming that highlights Hawaiian culture, history, and traditions, along with live music, performances, and activities that help set the tone for the destination ahead.

Sea days are also when many travelers truly relax—sleeping in, enjoying leisurely meals, spending time on deck watching the ocean, or finding a favorite lounge and settling in with a good book.

Life Onboard the Koningsdam

Koningsdam is a Pinnacle-class ship, designed with an elegant, contemporary style and a strong focus on music, comfort, and space. She feels refined without being formal and offers a nice balance between activity and quiet corners.

Onboard highlights include:

  • Multiple dining venues, from casual to specialty restaurants
  • Comfortable lounges and live music venues
  • A spacious spa and fitness center
  • A Library
  • Pools and outdoor deck areas perfect for sea days
  • Evening entertainment on the World Stage

It’s a ship well suited for longer journeys, where settling into a rhythm matters just as much as the destinations themselves.

What Is Included with “Have It All”

This sailing is offered with Holland America’s Have It All promotion, which bundles several popular amenities into one package. While inclusions can vary slightly, this promotion typically includes:

  • A beverage package
  • One or more specialty dining experiences
  • Shore excursion credit
  • Wi-Fi package

Having these items bundled together makes the experience more seamless and helps many travelers enjoy their cruise without worrying about adding extras as they go.

Why Cruising to Hawaii Is Such a Great Option

Hawaii is made up of islands that feel very different from one another. Cruising allows you to experience that variety in a single trip—lush landscapes, volcanic terrain, historic towns, and coastal scenery—without the logistics of island hopping.

A longer itinerary like this also gives you time to slow down. There’s room to explore, rest, learn, and truly enjoy the journey, not just rush from one highlight to the next.

For travelers who want Hawaii to feel like a vacation, not a checklist, a cruise like this offers a wonderful balance of discovery and relaxation.

Interested in learning more?

This 17-night Circle Hawaii cruise aboard Koningsdam, departing January 9, 2027, currently starts at around $8,800 per couple for a balcony stateroom with the Have It All promotion. It’s a wonderful option for travelers who like a longer, more relaxed journey with the chance to see several islands in one trip. (prices can & do change, email me for a current quote)

That said, it’s just one of many ways to experience Hawaii. Depending on how you like to travel, there may be other Hawaiian cruise itineraries, a stay at Aulani, A Disney Resort & Spa, an escorted tour, or a land-based island stay that fits you even better.

If you have questions, would like a personalized quote, or want to talk through which Hawaii experience makes the most sense for you, feel free to email me anytime. I’m always happy to help you explore the options and find the one that feels just right.

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Published by Kenneth Reece, Agent of Modern Travel Professionals

Hi, I’m Kenneth Reece — and I help make unforgettable vacations feel effortless. With 50 cruises under my belt (and more in the works!), I specialize in bucket-list travel experiences for grown-up travelers who want something a little more meaningful, a little more personal, and a lot more fun. Whether you're cruising the blue waters of the Caribbean, exploring the stunning coastlines of Alaska, or soaking in the magic of Europe one cobblestone street at a time — I’m here to help you plan a trip you’ll always remember. Lately, river cruising has completely captured my heart. There’s just something special about waking up each morning in a new European town, with your floating boutique hotel waiting to take you to the next charming stop. I love pairing these river cruises with guided land tours for a perfect balance of sightseeing and relaxation. Princess Cruises has long been one of my favorites at sea, but I’ve sailed with many cruise lines and know how to match each client with the right one for them. I’ve also experienced the Disney magic around the world — from Disneyland and Walt Disney World to Tokyo and Paris — and I bring that same sense of wonder and thoughtful planning into everything I do. Whether you're celebrating a milestone, traveling solo, or just need help making sense of all the choices out there, I’m here to be your guide. I love helping clients as much — or as little — as they prefer. From the first conversation to the moment you return home, you’ll know someone has your back. Let’s make your next trip easy, exciting, and completely tailored to you.