For the 50+ Traveler

Palm trees, coconuts, pineapples, and tropical sunsets. Have you been dreaming of a Hawaiian cruise? Hawaii is one of those bucket-list places that people save and plan to visit for years. All too often, people book the cruise of a lifetime without considering some extremely important items that can make or break their level of satisfaction with the cruise. These decisions are as important, if not more important, than which cruise line you book with.

I’ve visited Hawaii and I’ve done a fair amount of cruising. I’ve also talked with dozens of people who have booked that bucket-list trip and been disappointed because they hadn’t considered what a cruise to Hawaii would entail. They only thought about hula dancers, beaches, tropical drinks, and all the fun they would have. Every cruise includes all of these, but there are many things that make cruising to Hawaii successful.

While the Hawaiian Islands are beautiful and a place that I feel every traveler should visit at least once in their life, cruising to Hawaii is not always the best solution.

Before you book your cruise to Hawaii there are some things you need to consider and some options that might better serve your needs.

1. Is This Your First Cruise?


If this will be your first cruise, then select another cruise. Not that you will not love Hawaii, but a 12- or 15-day cruise is not the best choice for someone who has never cruised before. Select a five- or seven-day cruise and see if you enjoy it before taking a longer cruise. When you cruise to Hawaii, it includes five or six days in a row at sea, and it can be more than some people can handle, especially when it’s a first cruise. Who knows if you will get sea sick or go stir crazy when all you see is the ocean for several days?

I have a relative who booked a cruise to Hawaii to celebrate their retirement. They had never cruised and thought they would love to see Hawaii that way. Once they arrived in Hawaii they enjoyed seeing the islands, but they hated being at sea. They felt they were never going to see land again, they were claustrophobic, and it basically turned them against cruising. I would hate for that to happen to you. So take my advice and if it is your first cruise, don’t plan to go to Hawaii.

Another option is to fly to Hawaii and board a ship there. Cruise to the various islands over a week, and then fly home.


If the answer is no, it is not your first cruise, and you have enjoyed other shorter cruises, then a Hawaiian cruise might be perfect for you. But before you book, consider the following questions as well.

2. Do You Have Significant Time Off?


If you answered yes, then a Hawaiian cruise might be the ideal cruise for you. You will need to plan to be away for at least 12 to 13 days if you are cruising one way then visiting the islands and flying home. If it is a round-trip cruise, then you need to plan for at least 15 to 20 days depending on the itinerary.


If you aren’t fortunate enough to have extended time off, you can fly to and from Hawaii and take a seven-day cruise around the islands. Be aware these are long flights and you would still need at least nine days away from your job to make this kind of trip happen.

If you can’t get nine days away, your best option is to select another destination. Wait till you have more time to enjoy a Hawaiian cruise.

The coast of Hawaii.

3. Do You Get Seasick?


If you suffer from sea sickness, five or six days at sea to Hawaii will more or less ruin your vacation. Your best bet if you still wish to cruise is to fly to Hawaii and then cruise around the islands. Most of the cruising will be at night and you will be off the ship during the day. Once your cruise is complete, you would fly back to the states.


If you don’t suffer from seasickness, then you should be good to cruise to Hawaii if all the other factors line up!

4. Do You Enjoy Sea Days?


If the answer is yes, then leaving the West Coast for a cruise to Hawaii might be the perfect vacation for you. You will have at least five or six days at sea. Not everyone can handle seeing nothing but water for five days. But if that sounds heavenly to you, then go for it. These consecutive sea days give you plenty of time to participate in all the fun ship activities, visit the spa, relax, and read a good book.

If it is a round-trip cruise, you will have 10 or 12 days at sea. That is a lot of sea days. If you enjoy them, then you will love a round-trip Hawaiian cruise.


If you answered no, then skip cruising to Hawaii. You still have the option of flying there, cruising around the islands, and flying home. Everyone that I talked to who didn’t enjoy a Hawaiian cruise listed the number of sea days as being the worst part of the experience.

5. Do You Enjoy Long Flights?


If you are good with long flights, then you can fly to and from Hawaii and board a ship there to cruise from island to island. This usually entails a seven- or nine-day cruise. You get to spend a day or two at each island and then fly back home.

You also have the opportunity to cruise one way and fly the other, which might be a good option. These cruises are usually 10 to 12 days.

Many people who do this choose to fly over and then spend a few days touring Honolulu and then board the ship to visit all the other islands. Or they do their touring after the cruise and before flying home. This is a great option if your schedule is flexible and you can take the time to spend a few extra days.


If you hate long flights, your choices are to cruise one or both ways, or opt for cruising to a different location.

6. Do You Want To Spend Multiple Days On Each Island?


Spending multiple days on each island is more conducive to a land vacation that includes airfare from island to island. Usually on a cruise ship, you have just one day at each location, and, at the most, two days in prime locations. This is long enough to see highlights or focus on one specific area or tour, but not long enough to see everything you might want to experience if you have a lot of Hawaiian spots in mind.


If you are good with a single day on each island and seeing one main attraction, then a cruise would be a perfect option for you. Many people have visited the islands multiple times and do not feel the need to spend a lot of time on each.

A small cruise ship docked in Hawaii.

7. Do You Want To Visit The Majority Of The Islands?


A Hawaiian cruise is a wonderful option if you desire to visit most of the islands. You can cruise from island to island and get a feel for each. You travel between islands while you are sleeping, so there's no wasted time. Cruising all the islands is great for learning which island you want to return to and visit for a longer period of time -- or just for seeing as much as possible during your bucket-list vacation.


If you only want to visit one island and enjoy everything there, then cruising is not a good option for you.

8. Do You Enjoy Packing And Unpacking?


Plane hopping from island to island might be enjoyable for you if you don’t mind packing and unpacking every day or so. I’ve done this on a 14-day trip. We had seven days in Honolulu and then divided seven days between the other islands with two or three days on each. While it was a fantastic trip and I enjoyed every minute, a great deal of our time the second week was spent packing up, going to the airport, flying to the next island, and then unpacking and settling into our new hotel. Doing that three times within a week eats up a great deal of your time.


Cruising around the islands is a great option if you want to unpack just once. You move from island to island at night and then you have all day to enjoy the sites at each island without packing and unpacking. You can enjoy this on all the Hawaiian cruise options we’ve covered.

9. Are You Comfortable On Small Planes?


Island hopping by plane might be a perfect solution if you are comfortable on small aircrafts.


Cruising will be a better option if you don’t like small planes.

Once you have considered these questions and are sure that you want to cruise to Hawaii, then you can consider how many days you wish to be gone and make an educated choice about which option is best for your personal needs.

Hawaii is a beautiful state, and I hope you get to visit. Just take the time to make sure you enjoy how you are getting there and how you see the islands so your bucket-list trip is one full of great travel memories.

Want to read about the one Hawaiian island you won’t get to visit? Here are 11 fascinating things to know about Hawaii’s forbidden island.