15 Things Families Should Know For An Amazing Havana Cruise

Posted onLeave a commentCategoriesCaribbean, CRUISE PLANNING, Itineraries, PORTS & EXCURSIONS

Over the past few years, the opportunities for regular Americans to travel to Cuba have greatly expanded. And, one of the easiest ways to visit is by sailing a cruise that stops at the Havana cruise port. Booking a cruise can certainly simplify your travel planning, but read on a for few tips to make sure that your family gets the most out of this experience.


We recently sailed on a family cruise on Royal Caribbean’s Majesty of the Seas.  The absolute highlights of the trip were our visits to the Havana cruise port! For years, I wanted to visit Cuba, but I was never  eligible to go. So once it became possible for Americans to sail on cruises that stopped in Cuba, that shot to the top of my wish list. And this year, we were finally able to pull it off.

Visiting The Havana Cruise Port

Let me preface this by saying, we had a fabulous time. Everyone in our travel party ultimately enjoyed the cruise (even the family members who were forced to arrive without any luggage due to flight mishaps). And we would all do it again.

Here are 15 things that families planning a cruise to Havana should know – some good, some fair, and some watch outs. 

1. Consider Booking Back-To-Back Cruises With Stops At The Havana Cruise Port.

At the time that we looked at booking a cruise to Cuba, the only ones we saw had relatively short itineraries of 4 or 5 days. But we usually plan our summer vacation around a 7 day cruise, so we really wanted something longer.  What we ended up doing was putting together a back-to-back itinerary. We booked a 4 night and a 5 night cruise on the same ship. We kept the same staterooms, so we still had the benefit of only unpacking once. Both legs of the cruise sailed roundtrip out of Tampa. So, for the combined 9 day itinerary, we had two different stops in Havana, plus stop in the ports of Key West and Cozumel. Also, one of the Havana stops was an overnight stop which added additional variety to the itinerary.

The original prices when we booked were very affordable compared to other Caribbean itineraries. And, we saved money booking ocean view rooms. Plus, on two occasions after we booked, our cruise specialist was able to help us take advantage of subsequent price reductions. So, overall, it was a great deal!

2. The Actual Visa Requirements and Travel Restrictions Can Be Confusing.

Americans need two important documents when sailing to Cuba. First, there’s the actual visa needed to enter the country. You can purchase those on board from the cruise line.  It was $75 per person and charged to our shipboard accounts.

In addition to a visa, Americans (or those subject to U.S jurisdiction),  must also comply with government regulations that restrict travel to Cuba. You cannot travel as a general tourist. (So, no bopping off to the beach.) Rather, you must fall within one of 12 recognized categories. If you are traveling by cruise ship, you will complete a certification at embarkation that identifies which bucket your trip falls into.

Also, we opted to purchase travel insurance, so we also had to complete a different version of a certification before we ever left home. Our travel insurance carrier required that we fax in copies a few months before we sailed. Interestingly, the version provided by the travel insurance company had much more descriptive detail as to the categories of authorized travel.

The Key Categories 

Cruise ship passengers will most likely fall under one of two categories. Either the “people to people” category or the “support the Cuban people” category.  The “people to people” category essentially requires that you participate in a tour sponsored by an authorized entity. Some of the confusion about this category likely stems from the fact that the requirements changed relatively recently, in 2017. So some of the information floating around online is no longer valid. In particular, any references you see to an ability to “self certify” under the “people to people” category is out of date.

If you book an excursion with the cruise line, you will be in full compliance with the “people to people” category.

But, you can still be in compliance even if you make excursion arrangements outside of your cruise line. The most likely applicable category would be the “support of the Cuban people” category. (This is a relevant excerpt from the certificate provided by our travel insurance company.)

Support for the Cuban people (31 C.F.R. § 515.574). […] I certify that my schedule of activities does not include free time or recreation in excess of that consistent with a full-time schedule. I also certify that the activities are of recognized human rights organization; independent organizations designed to promote a rapid, peaceful transition to democracy; or individuals and non-governmental organizations that promote independent activity intended to strengthen civil society in Cuba.

You can find more information about what “support for the Cuban people” means here at §515.574.  But be aware that pure leisure activities — such as a day at the beach — do not qualify.

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Our Ultimate Family Guide To Your Best Alaska Cruise

Posted on2 CommentsCategoriesAlaska, CRUISE PLANNING, CRUISE TIPS, Multigenerational, PORTS & EXCURSIONS

Sail Your Best Alaska Cruise

You can quickly get overwhelmed researching how to plan the best Alaska cruise for your family. This guide will help you weed through volumes of information and focus on what’s really important to you.

So Why Cruise Alaska?

The massive glaciers and stunning marine wildlife provide a unique backdrop for a family cruise. The natural wildlife both in sea and on land is its own attraction – humpback whales, Orcas, sea otters, seals, sea lions, wild salmon, moose, grizzly, and polar bears. And, Alaska also has the largest population of bald eagles in the country. In addition to numerous wildlife viewing opportunities, you’ll find many outdoor adventures. Stunning mountain hikes, dog sledding, fishing, kayaking, and various helicopter excursions only scratch the surface of what’s available.

Very few cruise experiences can compare to the fun and excitement of an Alaskan cruise.  More than one million cruisers make that trip every year. And, more than half of the visitors to Alaska arrive by cruise ship. Not surprisingly, it is also a top destination choice for multigenerational family travel


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Alaska is one of the most exotic cruises you can take while still being in the United States (right up there with Hawaii). But, unlike Hawaii, Alaska’s vastness and unique topography make it quite challenging to master for the typical family traveler. It is literally frontier country. Millions of acres of untamed wilderness and only a smattering of cities/towns. And, some towns can only be reached by air or water.

So, a cruise may be the only viable option for most people for seeing Alaska. It is almost certainly the most affordable option. 

 

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That Time I Foolishly Forgot Our Family Passports

Posted onLeave a commentCategoriesCaribbean, CRUISE TIPS
Forgotten Family Passports - photo of sad woman with bag sitting by wall with head in hands
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You may have seen the recent news stories about an elderly couple who packed their family passports in their luggage and were ultimately not allowed to board their Norwegian cruise.  

Left at the dock and looking for a refund from a cruise line

Norwegian Cruise Line changes course, offers couple apology, refund, and ‘dream’ trip

A few years ago, I faced a similar unfortunate circumstance while booked on a different cruise line and had a much better outcome.

I arrived at Port Canaveral with my party of four prepared to board our Disney cruise.  Our party included my 4-month old infant son, and a young adult cousin who had recently graduated from college.  Neither the baby nor my cousin had passports.  And, due to circumstances beyond our control, it was not possible to obtain passports for either of them before the cruise.  But, I felt confident that we had everything we needed.  I had fully researched the requirements for a closed loop cruise.  And, I had gathered all of the requisite paperwork in an organized folder ready to present.

Unfortunately, I had been so focused on making sure I had all of the right paperwork gathered for those of us who did not have passports – that I forgot to actually retrieve the passports for folks who did.

Related Post: How To Conquer Family Cruises Without Passports

I quickly developed an intensely sick feeling in the pit of my stomach when the guys taking luggage reminded us to keep our passports with us. I suddenly realized that I didn’t even have mine at all. Both my passport and my oldest son’s passport were still tucked away at home. One thousand miles away. In a lock box to which I had the only keys. And, those keys were on my person.   (In my partial defense, we had recently moved which is why the passports were in an actual lockbox in the first place.)

I proceeded to the cruise check-in desk to see what could be done.  It was a Saturday.  All government offices were closed. The prospects seemed bleak to me.  But, the cruise personnel did not seem particularly surprised or concerned about my predicament.  They conferred with a supervisor.  According to the supervisor,  I should find a copy of the missing family passports or of our birth certificates and have them faxed or emailed to me.  The desk agents could print them out there. And, I would be allowed to board.  

After a couple of hours of frantic emails and phone calls, I managed to get someone who was able to go to my house, retrieve the relevant birth certificates (which were not in a lock box) and scan and email them to me.  The cruise personnel deemed our documents adequate, and allowed us to board.  We were some of the very last guests to board, but at least we made it.

When it came time to reenter the U.S., I explained what happened to the customs agent and presented the “copy” of my certified birth certificates.  He shook his head and waved us through with a relatively mild “tut, tut, tut”.  Under the circumstances, I was happy to make that particular walk of shame.

Lessons learned from this particular mis-adventure:
  • Gatekeepers (whether cruise line supervisors or customs agents) have some discretion to help you work out problems – so stay optimistic.
  • If you have made a packing list or trip checklist, actually take a final look at it before walking out the door.
  • Keep digital copies of important documents readily available (e.g., Evernote, Google Docs, etc.).

Have you shown up at the pier missing family passports or something else important?  Share your experience in the comments.