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Pros and Cons of a Fall Cruise and a Winter Cruise

There are many pros and cons of a fall cruise or a winter cruise. No matter the season, you’ll be guaranteed a fabulous time on your cruise vacation.

We mostly travel in the shoulder season and for us, it’s quite possibly the best time to vacation. There are a few destinations we have yet to experience because summer would be the best time. Eventually, we will shuffle around our vacation time. For now, a fall cruise is our favorite time to vacation.

So, if you’re contemplating a vacation off-season, here are some pros and cons of a fall cruise and a winter cruise to mull over.

featured blog image | fall cruise or winter cruise

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Fall Cruise and Winter Cruise

11 Pros of a Fall Cruise and a Winter Cruise

1. Summer is over…

Kids are back to school. Which means fewer children on the ships. Take my word for it, it makes a huge difference on the ship.

2. Adults get time to play

Did I mention that the kids are back in school? It’s the adult’s turn to plan a romantic cruise without the kiddos.

3. Fewer crowds

Don’t know about you, but I prefer not to be bumping into everyone on the pool deck or waiting in long lines to get food.

Pros and cons for a fall and winter cruise Pin design for Pinterest

4. You can save money

Prices drop because summer is over and the demand for those family vacations isn’t as high. Best time to take advantage of discounted cruise rates.

5. Experience the magic of the fall season

Depending on where you’re cruising from or to (Canada or New England), you’ll be able to experience the fall foliage in all its glory. Think of all the beautiful colors of fall.

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6. The Caribbean is the best escape…

The temperatures start to drop and you’re looking to escape it, you can cruise to warmer and tropical weather. Escape to the Caribbean and enjoy a pina colada on the beach.

7. The warm weather is just right

The heat in the Caribbean and Mexico isn’t as harsh as it is in the summertime. Still hot enough to sunbathe and frolic at the beach.

8. Explore Europe in the off-season

View of Palma de Mallorca, Spain from cruise balcony

Just like a land vacation, it’s the best time for a European cruise. The weather is just starting to call down the beginning of the fall and the sights are slightly less crowded.

9. Australia & New Zealand cruise

The seasons in Australia and New Zealand are opposite from ours here in the US. Therefore, our Fall is their Springtime and our Winter is their Summertime.

Time to take a winter cruise through the New Zealand Fjords!

10. Hurricane season ends on Nov 30th

If you refused to plan that trip to the Caribbean or Mexico because of the possibility of a hurricane ruining your cruise itinerary (always buy cruise insurance), don’t worry because hurricane season ends on Nov 30th.

You can plan that winter cruise! Leave the snow behind for some white sand and turquoise views of the ocean.

11. Holiday cruising

Have you ever experience cruising during a holiday?

  • Thanksgiving
  • Christmas
  • Hanukkah
  • New Year’s Eve

After reading about the festivities on the ships, it is on my bucket list and you should add it to yours too.

Imagine the magic of the holiday decor around the ship! The Christmas trees, the massive gingerbread houses, and full spreads of delicious foods without having to lift a finger in the kitchen. Don’t know about you, but not having to bust my ass in the kitchen is definitely a plus for me!

Ringing in the New Year with family and a new set of friends in the middle of the ocean with some bubbly and the band playing in the background.

Ahh, it all sounds like a magical celebration!

christmas tree and decor on cruise stairs and atrium
Christmas photos provided by my queen of cruising friend, Kim!
Doesn’t this look festive and fun?

7 Cons of a Fall Cruise and a Winter Cruise

1. No cruises to Alaska

You won’t be able to enjoy this Alaskan view from a cruise ship after September.

Cruises to Alaska come to a halt as the season ends in September. We’ve been dying to go on an Alaskan cruise, but haven’t yet planned a summer vacation to do so.

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2. Hurricane season

Hurricane season continues until the end of November. If you book a cruise to Mexico or the Caribbean, you’ll be stalking the weather channel and praying no hurricanes will disrupt your vacation.

It happened to us and we had the wrong cruise insurance to protect us. We lost a lot of money and we had to rebook a last-minute cruise – which turned out to be one of our favorite cruises – but we still learned a valuable lesson.

Always buy your own cruise insurance.

3. Kids are in school

Kids are in school for the most part, so family vacations are put on hold until the next break.

4. Seasonal weather

Rainy day at Coxen Cole Cruise Port, Roatan
Rainy day in Roatan

The weather may or may not cooperate. Some islands are in their rainy seasons. Like Roatan, every time we visit in the fall we were told that it’s typical for that time of year. In Europe, it gets cold, so forget sunbathing.

5. Rough seas

If the weather isn’t cooperating that most likely means rough seas. It’s not fun for anyone.

6. Low tourist season

During high seasons, all shops are open and all excursions are available. In low tourist seasons, you won’t have the same options.

7. High cruise fares during the holiday season

A family vacation during the Thanksgiving and Christmas holidays sounds like a blast, but the cruise fares are high yet again. Ugh.

Did you decide on a fall cruise and a winter cruise? What season do you love to vacation or cruise?

Why do you love or hate cruising in the fall or winter?

Don’t forget to share the love on Pinterest:

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Vivienne Lindley

Tuesday 27th of August 2019

I’ve never tried cruising but your posts definitely make me consider it. Alas shoulder season is out of the question as I’m a teacher - maybe I need a new profession! ?


Tuesday 27th of August 2019

Oh, you can do a Christmas cruise! Then come back to tell me all about it. :D

It's so nice to hear from you! I hope you're doing well. I had no idea that you are a teacher, which is so awesome! Thank you for teaching our kids.


Monday 26th of August 2019

Great post, Kathy! Got a lot of travel tips for our next vacation. My hubby and I are thinking of trying a longer cruise someday. Thanks:)


Monday 26th of August 2019

Based out of NY you should look into a Bermuda cruise. Of course, they say that the best time to go there is between May and Sept as it's the nicest weather. So that's off from my fall and winter recommendations, haha. Still, though, it's an easy one to take from NY or Boston. We are going to Bermuda in 2021 - yup, already booked.

Hope you get to plan that cruise soon. I think it's a great way to get a vacation in without the pressure of having to do and see everything.

Macey @ Brine & Books

Sunday 25th of August 2019

My grandparents went on so many cruises after they retired, and after they came back with so many pictures of the travels, I always wanted to do the same when I grew up! I'd love to be in England during Christmas one year, and since my dream is to get married during December, and England my honeymoon, maybe I can perfectly combine all of that together :') I'd LOVE to go to NZ when it's their summer as well; that's been one of my dreams since falling in love with the LOTR movies as that's where so much of the trilogy was filmed, and NZ is just gorgeous!


Monday 26th of August 2019

What a beautiful memory of your grandparents. Love how they shared their travels with you.

I love how you have your future honeymoon planned and I have to say, it's a solid plan. Christmas in Europe just sounds so ideal for some reason. It's my hope to experience something similar in the future too.

When I see photos of NZ, I am simply floored so I get it. I remember the LOTR movies and the film locations are spectacular. I'm not a campervan kind of person but that's my dream for New Zealand to do a road trip in a campervan. It just seems like one of those countries that you'll see more of by exploring it via road trip.

Thanks so much for reading and commenting!

Cristina - Memories of the Pacific

Saturday 24th of August 2019

I was on a cruise with my husband once in August and we didn't love the experience. Maybe it's a better idea to go in fall or winter!


Sunday 25th of August 2019

Definitely give it a try and see if it makes a difference. I always say the cruise ship and cruise line can make or break your vacation, but so can the season. If you are worried about hurricane season, check out cruises to Aruba, Bonaire, and Curacao, they are outside of the hurricane belt.


Thursday 22nd of August 2019

Great comparison!

Lauren Elena

Saturday 24th of August 2019

Great post Kathy! It’s so helpful to know about all this stuff and take it into consideration before planning a trip like this. A cruise around a holiday does sound like such a fun idea! It would be so festive! Love that idea! Even though I’m still hesitant about going on a cruise, I love reading all your posts on them. It would be a great way to see some cool places and have everything at your disposal. I just have to get over my fear of being on the water for an extended amount of time.???‍♀️