Best cruises seniors wil want to do over and over again

Best Cruises Seniors {Will Want to Book Over and Over}

When you take a cruise that’s really special there’s no reason you can’t or shouldn’t book the same cruise again. Maybe it was the ship that was special. Possibly it was the staff that impressed you so much. For most people who cruise, it’s the itinerary they found to be exceptional. Whatever the reason, here are some of the best cruises seniors will want to book over and over.

Hands down, the most popular cruise destination in the world is the Caribbean Sea. How can you not love the brilliant sunshine, powdery white sand, and shimmering water in a host of blue/green shades?

Best cruises seniors wil want to do over and over again
You never know what stunning vista your next Caribbean port-of-call will offer. Will you be sailing to Belize?

As a rule, the majority of these three routes are seven days in duration. If you happen to be trying a cruise vacation for the first time, seven days is the perfect amount of time to determine if a cruising vacation is all you thought it would be.

There are also three and four-day cruises, but it’s really not enough time to come to any sort of decision about cruising in general. With seven days, you might get to stop at as many as five of six islands and you will get to know what each has to offer. It also gives you time to adjust to life onboard a state-of-the-art cruise ship.

Best cruises seniors wil want to do over and over again
Many Southern Caribbean cruises will visit or originate from San Juan.

It’s important to keep in mind that a three or four-day cruise is normally a higher cost per day than a seven-day cruise. Also, they might only have two or three islands on their itinerary so you don’t really get to see too much of the amazing Caribbean Islands.

Some cruises are longer than a week. There are 10-day cruises, 14-day cruises, and even some Caribbean cruises that might be as long as three weeks. If you are new to cruising, 10 days or more might be too long. When you are on the ship you are pretty much committed to seeing the entire itinerary through.

It’s unlikely, but what happens if you discover you don’t really like cruising after four or five days and you booked a 14-day cruise? So really, the first cruise of about a week is perfect.

Most Caribbean cruises follow three main routes. You can choose the Western Caribbean, Eastern Caribbean, or the Southern Caribbean.


Most Eastern Caribbean cruises will leave from ports in Florida. Some of the most common embarkation ports in Florida are Jacksonville, Port Canaveral, Miami, and Tampa. You might also find Eastern Caribbean cruises that leave from Charleston, SC or New York City.

Best cruises seniors wil want to do over and over again
Princess Cays is an example of a cruise line private island.

Many of the cruise lines sailing the Eastern Caribbean will stop in the Bahamas. The most common island in the Bahamas is Nassau, but several cruise lines have their own private islands that can be truly spectacular. A couple of examples are Disney Cruises’ Castaway Cay or Holland America Line’s Half Moon Cay.

Most private islands will offer guests an opportunity to enjoy a host of land and water sports in a spectacular setting.

Ports-of-Call you might expect to visit on an Eastern Caribbean cruise will include Puerto Rico, St. Thomas, St. Martin, St. John. These islands are close together and most of the shore excursions are centered around beach and water activities, shopping, and simply snorkeling or sun-tanning on an amazing beach.


If you are cruising the western Caribbean, chances are you will be leaving from Florida, New Orleans, or Texas.

Normally your Ports-of-Call will include Mexico. For instance, you might stop at Cozumel or Playa Del Carmen. Key West is another popular stop, as is the Grand Cayman Islands.

Best cruises seniors wil want to do over and over again
I went for a run along this beach in the Cayman Islands

There are also several mainland Ports-or-Call that might be on a Western Caribbean itinerary. These might include Mexico, Belize or Costa Rica. Chances are you might stop at one of the larger islands like Jamaica and the Dominican Republic.

One thing to be aware of is that the islands are much further apart in the Western Caribbean, so you may not have as many Ports-of-Call as compared to the East. That being said, there are some very spectacular and varied shore excursions in the West. For example, no trip to the Grand Cayman Islands is complete without a visit to Stingray City.

Cozumel will offer you the opportunity to swim with the dolphins and this is one of the most popular shore excursions offered on Western Caribbean cruises. If Dolphins aren’t your thing, you might enjoy cave tubing in Belize, exploring Mayan ruins, or hiking through a rain forest.

I personally cruised both the Eastern and Western Caribbean several times. One year I decided to do both. The cruise line I booked with would do the Western Caribbean one week and then the Eastern Caribbean the next week, and alternate between the two for the entire season. I decided to do both. I kept my same cabin and just stayed on the ship when everyone else disembarked.

Best cruises seniors wil want to do over and over again
You will always know when you are in Curacao by the colorful buildings lining the shore.

The beauty of this is that I got to cruise with a whole new set of passengers. Not only that, I had the opportunity to visit about nine ports-of-call. My thinking was that the second week was a bargain because I flew from Calgary, Canada to Miami, Florida.

One of the biggest expenses associated with cruising for many people is flying to and from the embarkation/disembarkation city. Since I was already there, I only paid for the flight once to basically go on two different cruises.

I had been on many cruises, so I had no reason to hesitate when it came to going on what amounted to a 14-day cruise. There was no doubt in my mind that I would enjoy it.

So might you as well. Check out the 35% savings on the Caribbean, Mexico, Hawaii, and Asia Cruises featured by Princess Cruises.


I have to say my best cruise ever was a 10-day cruise on the Carnival Jubilee. It has been out of service now for a few decades. It was a smaller ship compared to the line of sister ships that followed.

Best cruises seniors wil want to do over and over again
Try and make it to the Guadeloupe Carnival if you can

Those ships included the Fascination, Sensation, Ecstasy, inspiration, Elation, and Paradise. Over the years I sailed on four of these ships as well.

The Jubilee was on one of its last voyages before being taken out of service. This was a one-time cruise itinerary that I was fortunate enough to stumble onto.

We set sail out of Miami and headed South. In those ten days, we stopped at nine islands. It’s not often you will ever find a cruise like this. We started out in the US Virgin Islands. Of course, we went to St. Thomas, the duty-free shopping capital of the Caribbean.

We also made stops in St. Martin, St. John, and St. Barts(Bartholomew). There were two ports-of-call that I was lucky enough to visit as I would never manage to find a cruise ship after that with the same islands on their itinerary. It was the spice islands of Grenada and Guadeloupe.

I still remember stepping onto the island of Guadeloupe and the aroma of fresh pepper, cinnamon, vanilla, and all the other spices wafting in the warm Caribbean air from the open-air Saint-Antoine market in Pointe-à-Pitre.

Best cruises seniors wil want to do over and over again
Try and visit the spice islands of Grenada and Guadeloupe if at all possible

The stall owners all wore ample dresses and madras headscarves. They spoke nothing but French, but also spoke the international language of smiles and laughter and were a treat to bargain with even though we never understood each other.

I regret never getting to see the Guadeloupe Carnival. One year I plan on going for a land stay for a few weeks during carnival.

From Pointe-à-Pitre to Basse-Terre to Grand-Bourg de Marie-Galante, numerous parades with shimmering costumes and exuberant masks will entrance the entire crowd big, and small! Especially since they all are lulled by the rhythm of drums, percussions, and songs.

But wait, we had some other amazing Southern Caribbean Islands to visit. We stopped at the ABC islands Aruba, Bonaire, and Curacao. They were all stunningly beautiful. Eventually, I would go back to St. Thomas and St. Martin four times and Aruba five times. I have to say that next to Guadeloupe, Aruba was my favorite island.

How can you not love the snow-white sand of Palm Beach? When you walked across the sand it would come up to your ankles and be like a fine powder.


So where are you planning to go for your next cruise? The Caribbean, Alaska, Mexican Riviera, Panama Canal, Hawaii, Europe, Tahiti or Cuba?

Check out all the Landmark cruise options available at Princess Cruises.

Don’t miss out on the Best. Sale. Ever. For the first time ever, Princess Cruises is offering guests a fare that includes drinks, Wi-Fi, and gratuities when they book a cruise or cruisetour. Book today!

The options are endless and an argument can be made for any of these cruise ship destinations. If you have never been on a cruise, you don’t know what you’re missing.

The Caribbean is a great place to start and to visit over and over again. It doesn’t even have to be overly expensive if you plan your cruise out of peak season. Better still, there are many cruise ship bargains available if you are patient and are flexible in your travel arrangements.

Would you like to share your thoughts on this topic? Feel free to leave a comment at the bottom of this page.


8 comments / Add your comment below

  1. This looks absolutely breathtaking. I was talking to my father earlier today and he has been “retired” for around 10 years, however he has still been working every day. He has now decided to full time retire but he was a bit worried about what to do each day because he does not want to sleep the days away. I am definitely taking him on a cruise across the Caribbean  and how convenient that it is a senior cruise. He loves traveling, loves the sun so what better way to celebrate with one of the best senior cruises.

    Thank you so much for the information that you have provided about the destinations and the lengths of the trips.  

    1. Thank you very much for your comment. I’m pretty sure your father would enjoy cruising. It’s a great way to see new places and meet people from all over the world.

      It’s amazing how many seniors cruise. On my very first cruise, I was about forty and I was one of the youngest on the ship. Holland America Cruise Lines would be an excellent choice for your day. It’s very classy and most senior people prefer this line.

      Carnival, for instance, has a much younger clientele, so a lot of partying and drinking. I love Carnival when I was a lot younger, but now I would be one of the oldest on the ship.

  2. Hi Ray, I must say that this article is very helpful and informative. Cruising is somehow my hobby as I enjoy traveling with my family across the summer. I would like to go to some private island but honestly, I don’t know how expensive that can be. Your images are so beautiful, I would like to visit all those places haha. I will seriously think about the Bahamas.

    1. Thanks for your comment, Daniel. Cruising is not as expensive as many people think. Imagine if you were paying to stay in a hotel for a week and had five-star dinners every night. As well as, breakfasts, lunches, and snacks. This is all included.

      There are extras to pay for, but it’s up to the individual how much they want to spend on shopping, photographs, drinking, playing in the casino, Shore excursions, and massage etc. These you will pay extra for. Personally, I never drank a lot, never bought the professional photographs, and didn’t shop at the onboard shops that much. As a result, I found cruising to be a very good deal.

  3. You paint a beautiful picture, one that I feel I could step into. As you were describing the smells, it was as if I was there smelling them with you. A cruise is on the ‘bucket’ list which is why I am starting to explore the various options around the world. Thinking about it now would give us time to plan the finances if we were to venture across the vast waters to the Caribbean. Being in Europe it might be more prudent to ‘cruise’ closer to home. Having, at least, a small understanding of the amenities of the modern day cruise ship I wouldn’t mind starting out in the Scandinavian area, breathtaking and not just because of the cold. Saying all that, the beautiful beaches, glorious weather and exotic food tend to sway me further afield. Decisions, decisions.

    1. Thank you for your comment. There are some amazing cruises in Europe. Actually, I’m in the same situation as you as I live in Canada. It would take a very long flight to get to Europe and that’s the only reason I have never been on a European or Scandinavian cruise.

      I’m continually amazed at the low prices they have for European cruises. I think it has to do with the fact that the cruise lines realize that it’s a long way to fly, and if they want to attract North American travelers, they would have to offer great prices.

      Having said that, however, over the many cruises I have taken, I had the opportunity to meet many Europeans who made the flight to Miami and sailed out of there in order to spent time in the beautiful Caribbean.

  4. The insight you shared about shorter cruises versus longer cruises is great!  We are looking at getting my parents a cruise for their 40th wedding anniversary and I was thinking a shorter cruise may be best since they have never been on one.  Now we will definitely go with the 7 day cause I hope this will lead to them taking more.  

    For newbies to cruises, would you recommend the Eastern or Western?  Not sure if it would be better to have longer periods on the ship between the Port-to-Calls or not…

    Thank you again for your insight and help!

    1. Thank you for your comment! Chances are your parents would love their cruise experience.

      I would recommend the Western Carribean cruise that would take them down to St.Thomas, USA Virgin Islands. Every cruise line has slightly different itineraries. I don’t really recommend Jamaica as they are pretty aggressive with tourists.  Jamaica would most likely be included on an Eastern Caribbean cruise.

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