Take A Cruise To Cuba For The Holidays

Oceania Cruises Insignia - Cruise To Cuba For The Holidays.jpg

Heading Back To Cuba

As Canadians, we have no restrictions on to travel to Cuba. We visited Cuba for 3 different beach vacations in the past.  We knew there were lots of reasons to visit Cuba.  So when we saw Oceania Cruises had a cruise to Cuba for the holidays, we decided it was time to go back. This trip offered us a chance to cruise around Cuba to see 3 new spots (Havana, Cienfuegos and Santiago de Cuba). And two overnight stops meant we had longer stays.

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Thawing Out In Miami

The winter started early and cold in Toronto. So we headed to Miami 5 days before our cruise started. Our return to the Intercontinental Miami offered us a familiar retreat. Our sweet suite had great views out over the Port of Miami. Each day we grew more excited about our cruise to Cuba for the holidays as we watched the cruise ships come and go.

Intercontinental Miami - Cruise To Cuba For The Holidays.jpg

Intercontinental Miami Harbour View - Cruise To Cuba For The Holidays.jpg

We enjoyed being close to downtown. Every day we went out for a walk. We found art everywhere we looked. Slowly our bones warmed up. We were definitely happy to be out in the sunshine.

Miami Art - Cruise To Cuba For The Holidays.jpg

Miami Art - Cruise To Cuba For The Holidays.jpg

Miami Art - Cruise To Cuba For The Holidays.jpg

On the night before we left Miami, we were startled by big bang. We had come to recognize this as the starting bell for fireworks. We turned all the lights off in our suite. And sat back for the greatest fireworks show. Below us we saw a parade of colourfully lighted boats. We were happy to get this great send-off.

Miami Fireworks - Cruise To Cuba For The Holidays.jpg

Miami Fireworks - Cruise To Cuba For The Holidays.jpg

But the day break brought another treat. On the morning of our cruise, we were greeted to a wonderful sunrise. We watched as not one but two Oceania Cruises ships sailed into the harbour. Soon we would be on board.

Miami Sunrise - Cruise To Cuba For The Holidays.jpg

Miami Sunrise - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia and Sirena - Cruise To Cuba For The Holidays.jpg

Miami Was Decorated For The Holiday Season

We started the Christmas holiday season in Vancouver. It jump-started our holiday spirit. We are never sure how much like Christmas it will feel when we head south for the holidays. But we were immediately greeted by the Intercontinental Miami all dressed for the holiday spirit. Christmas trees and decorations were everywhere. There was even a bulk candy store to fill your stocking. When Santa came to visit, he came with his electric floor fan!

Intercontinental Miami #ICWinterWonderland - Cruise To Cuba For The Holidays.jpg

Intercontinental Miami #ICWinterWonderland - Cruise To Cuba For The Holidays.jpg

Intercontinental Miami #ICWinterWonderland - Cruise To Cuba For The Holidays.jpg

As we wandered around Miami, we found holiday decorations all around the city. It was always funny to see Christmas trees in juxtaposition with palm trees.

Miami at Christmas - Cruise To Cuba For The Holidays.jpg

We made sure to pose for our Christmas card pictures. It was great to find the holiday spirit when we visited Miami before our cruise to Cuba for the holidays.

Miami at Christmas - Cruise To Cuba For The Holidays.jpg

The Beautifully Renovated Oceania Cruises Insignia Ship

Although we had not planned it, we realized that we started the year with a cruise to the Southern Caribbean on Oceania Cruises Insignia. And would end the year on this same ship. But right before we boarded Insignia in December, it underwent a major renovation. We were excited when we realized that our cruise to Cuba for the holidays would give us an early preview of Insignia’s new look.

The new muted and elegant colours were obvious as soon as we boarded. Blue and silver tones replaced the old dark blues and reds. A peek in the dining room showed the new design that seemed to open up the room. The top level Horizons lounge had also been opened up. It truly offered horizon views from all spots.

Oceania Cruises Insignia Renovated Grand Dining Room - Cruise To Cuba For The Holidays.jpg

We were excited to see the changes in the cabins. The lighter colours seemed to brighten these rooms too. Glass and chrome made the room sparkle. In the reconfigured bathroom, there seemed to be more room with glass doors on the shower. The tvs were replaced with smart tvs for access to entertainment and information.

Oceania Cruises Insignia Renovated Cabins - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Renovated Cabins - Cruise To Cuba For The Holidays.jpg

On our cruise to Cuba for the holidays, we were delighted to see the renovated Insignia ship.

We Celebrated The Holiday Season Onboard

And given it was the Christmas cruise, the ship was beautifully decorated for the holiday season. We were onboard Oceania for Easter when we cruised across the Atlantic from the Caribbean to Lisbon. Oceania always did a great job of decorating for the holidays.

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A large table of gingerbread houses reminded us of the gingerbread house contest we just saw in Vancouver. Carollers sang holiday music. And we got holiday treats like hot chocolate that overflowed with whipped cream. On Christmas day, we even got a visit from Santa!

Oceania Cruises Insignia For Christmas - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia For Christmas - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia For Christmas - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia For Christmas - Cruise To Cuba For The Holidays.jpg

If we did not step outside into the hot weather, we might not know we were headed south for a cruise to Cuba for the holidays.

Welcomed Back Like Family

If you read our blog, you know we have done a lot of Oceania Cruises trips. We like the smaller ships like Insignia for the personal touch we have always found. It was not long before we saw familiar faces. And we were welcomed with hugs.

When we read the senior officer list, many of the names were new to us. But we were happy to find that we knew several people in leadership roles in the food and beverage department. This certainly ensured we had a delightful trip. On a cruise ship known for its food, you spend a lot of time eating and drinking. And every single time we ate or ordered wine, we were welcomed with a smile and by name.

We were also delighted to find that chef Mario was the Executive Chef. Oceania Cruises always has the best cuisine at sea. But Mario always takes that responsibility personally. Mario’s cooking classes at sea were always great education and entertainment.

Oceania Cruises Insignia Cooking Demo - Cruise To Cuba For The Holidays.jpg

On our travels in 2018, we tried a number of different cruise lines. They took us to new and fascinating destinations in 2018. But it did feel like we had come home when we boarded Oceania Cruises Insignia to cruise to Cuba for the holidays.

A Day In Key West

We have been to Key West for a week long vacation. And it has been a common port stop on our Caribbean cruises. But it is alway great to return to Key West. And we did get the absolute best sunrise as we docked.

Key West Sunrise - Cruise To Cuba For The Holidays.jpg

We enjoyed a lazy morning on the ship. And then headed into the downtown area. Due to damage to downtown docks, the number of cruise ships to Key West has been limited. And we were docked in the Navy yard. So that meant we had to take a shuttle into downtown. But there was never a shortage of trains or trolleys lined up to ferry people into town.

Key West was busy with two cruise ships in port. The bars were often standing room only. The shop keepers tried to draw people in. It was fun as we wandered a little to see the town dressed up for Christmas.

Key West Christmas Decorations - Cruise To Cuba For The Holidays.jpg

Key West Christmas Decorations - Cruise To Cuba For The Holidays.jpg

Key West Christmas Decorations - Cruise To Cuba For The Holidays.jpg

And then we headed to our favourite Key West stop. We could not visit and miss a trip to Kermit’s Key Lime Pie Shop. And the delicious frozen key lime pie slice covered in dark chocolate. It was definitely worth the walk.

Key West Kermits Key Lime Pie - Cruise To Cuba For The Holidays.jpg

Key West Kermits Key Lime Pie - Cruise To Cuba For The Holidays.jpg

We watched the sun set as the sailboats and watercraft headed out on their sunset cruises. It was time for us to cruise to Cuba for the holidays.

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Our First Port In Cuba Was Havana

We enjoyed our taste test of colourful Havana. It was great to drive around the city and see the historic sites. A stop at Fusterlandia showed us an amazing colourful tile neighbourhood.

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Fusterlandia Havana Cuba - Cruise To Cuba For The Holidays.jpg

A walking tour of old town Havana provided us with an interesting mix of grand architecture, history and statue art.

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Street Art Havana Cuba - Cruise To Cuba For The Holidays.jpg

We were glad to visit Havana on our cruise to Cuba for the holidays.A chance to see Havana was certainly one of our reasons to visit to Cuba.

But nature decided that our Cuba plans needed to be mixed up. Gale force winds and a major storm kept us in port for a few extra hours. And the path of the storm caused the captain and head office to re-assess the path around Cuba. In the end, safety won out and the path and our ports was reversed.

We Climbed The Hills Of Santiago De Cuba

When we arrived in Santiago de Cuba, we left the ship and wandered on our own. It did not take us long to realize that the old part of town was a steady walk up. But we were already committed! At the top of the hill we stopped in a local coffee shop. But a cold beer tasted way better to me after the hill climb. We then wandered around to see the sights in the main squares of Santiago de Cuba.

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Bacardi Museum Santiago de Cuba - Cruise To Cuba For The Holidays.jpg

We wandered down the Jose Antonia Saca walking street. On all sides of the street we found shops and more of the colourful outdoor art and architecture we had come to expect in Cuba.

Enramadas Buildings Santiago de Cuba - Cruise To Cuba For The Holidays.jpg

Enramadas Street Art Santiago de Cuba - Cruise To Cuba For The Holidays.jpg

At the bottom of the street, we saw our ship in the harbour. A short walk took us back through the port. It was great to see a little of Santiago de Cuba on our cruise to Cuba for the holidays.

Our Last Port In Cuba Was Cienfuegos

We only toured the town of Cienfuegos for one day as we wanted to take Christmas Day off. A start in the Cemetery de Reina provided a beautiful look at the history and folk lore of the town.

Cienfuegos Cemetery de Reina Enramadas Cuba - Cruise To Cuba For The Holidays.jpg

When we drove along the water, we got a view of the crystal clear water and views along the shore. Interesting and artistic buildings lined the streets.

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The main Jose Marti Square is the heart of this UNESCO town. It was great to sit in the park and explore the buildings that ring this town square.

Jose Marti Square Cienfuegos Buildings Cuba - Cruise To Cuba For The Holidays.jpg

Jose Marti Square Cienfuegos Buildings Cuba - Cruise To Cuba For The Holidays.jpg

On Boxing Day, we left Cienfuegos and stayed on deck for the sail out. It was our last view of land on our cruise to Cuba for the holidays. We left wanting to see more. But knew we could always plan a return trip.

Castillo de Jagua Cienfuegos Cuba - Cruise To Cuba For The Holidays.jpg

We Ate And Drank Well Sailing With Oceania Cruises

As Canadians, we can visit Cuba any time we want. So we did not pack our days in Cuban ports with tours. We used the cruise to Cuba for the holidays as a bit of taste test of some new spots we had not visited. And the rest of the time we enjoyed our five star resort aboard Oceania Cruises Insignia!

Oceania is known for its great food. Under Boris’ leadership, every detail was under the watchful eyes of the food and beverage team. Sasa, Duda and Philip always made sure we ate well at every opportunity. At every interaction we felt the customer service focus that Oceania is known for. We ate well throughout our cruise to Cuba for the holidays.

Oceania Cruises Insignia Food and Wine - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Food and Wine - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Food and Wine - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Food and Wine - Cruise To Cuba For The Holidays.jpg

On this cruise to Cuba for the holidays, we cleared out the ship’s stock of 2010 bottles of our favourite Brunello. We were so spoiled by the perfect vintage year, that when we had to open a 2012 bottle, we decanted that bottle on our last night to bring back some of the 2010 taste.

Oceania Cruises Insignia Wine - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Wine - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Wine - Cruise To Cuba For The Holidays.jpg

We definitely ate and drank well on our cruise to Cuba for the holidays.

On A Sea Day We Learned More About New World Wines

Wine tastings are one of our favourite ways to enjoy a sea day with Oceania Cruises. We discovered some great Italian wines on a trans-Atlantic cruise. A classic European wine pairing class when we cruised in the Southern Caribbean provided more fun and education. On this trip, we did the wine tasting to learn more about new world wine countries.

There were five red wines for us to try from regions like Australia, New Zealand, Chile and California. As we went through the wine tasting, we learned a little about the wines we tried and about the regions they came from.

Oceania Cruises Insignia Wine Tasting - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Wine Tasting - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Wine Tasting - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Wine Tasting - Cruise To Cuba For The Holidays.jpg

With the wines we had a variety of food pairings. The food tray included seared tuna, a beet and goat cheese snack, scallops, lamb and rare beef. Each wine had a specific pairing. But it was fun to try other things to see what else worked.

Oceania Cruises Insignia Wine Pairing - Cruise To Cuba For The Holidays.jpg

Other than his favourite Brunello, David does not like many red wines. We keep doing the red wine pairings to find new good options for him. This time around, he did like the Two Hands Shiraz from Australia. While I liked that one too, I liked the Craggy Range Pinot Noir and the Don Melchor Cabernet Sauvignon just a bit more.

On our cruise to Cuba for the holidays, it was fun to do a wine pairing and find new wines we liked.

We Enjoyed A Relaxing Time Aboard Oceania Cruises Insignia

We spent time on our cruise to Cuba for the holidays just relaxing. I even managed to read a few books! We did not set an alarm once during our holiday cruise. David enjoyed his time playing different games onboard the ship to collect his ship board points. He earned enough points for two shirts for us!

Oceania Cruises Insignia Games for Points - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Games for Points - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Games for Points - Cruise To Cuba For The Holidays.jpg

For Christmas day, we splurged on a pampering day. Who can argue with starting your day with a nice relaxing massage. I went even further and had my hands and toes decorated. Afternoon Tea late in the day added another relaxing point to our day. Before we joined most of the ship’s passengers in the Grand Dining Room for a wonderful Christmas turkey dinner.

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Oceania Cruises Insignia Afternoon Tea - Cruise To Cuba For The Holidays.jpg

Oceania Cruises Insignia Christmas Turkey - Cruise To Cuba For The Holidays.jpg

It was great to enjoy such a luxurious and pampering stay on our cruise to Cuba for the holidays.

Our Cruise To Cuba For The Holidays Was A Relaxing Break

We had a really busy travel year in 2018.  There are so many reasons to visit Cuba.  But a relaxing break with a cruise to Cuba for the holidays was the great way to end the year. We enjoyed our first view of Havana. And the chance to get a taste test of two more ports in Cuba – Santiago de Cuba and Cienfuegos. The overnight stays provided the opportunity to see more and to enjoy the night life.

Travelling to Cuba by cruise ship as Canadians proved a bit confusing. There were a bunch of rules and restrictions that would not have applied if we travelled to Cuba on our own from Canada.

We used our trip as a great way to unwind. It was wonderful to enjoy the holiday festivities on the ship. We started 2019 all raring to go! Before we left the ship we booked a series of new cruises. Stay tuned for more adventures in the Baltic and a cruise to the Faroe Islands, Iceland and Greenland in 2019. We will top that off with a 53 day trip around South America in 2020. How is that for a tease!

Is Cuba on your travel wish list? Do you want to follow us on a cruise to Cuba for the holidays?

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About TravelAtWill 494 Articles
Travel blogger and photographer! Scuba diving, luxury cruising, chocoholic, sea and sunshine addicts, camera attached and just generally curious! Join us on our adventures!

26 Comments

    • Warren, As I understand it, Americans have to keep a record of what they do when they are in Cuba (a log was provided). There are restrictions on who you can use for a “person to person” tour (e.g. must be an American tour company). And there is a long list of places where you cannot spend money. All of the rules are provided by the cruise company. They keep the record for all tours you do with the cruise company. I am NOT the expert. If you are travelling, you need to check as the rules change regularly too. Linda

  1. Funny how last night, I dreamt I was on a magical cruise alone then I read a news about a cruise ship returning in the middle of the trip because lots of the passengers were food poisoned and there is this article of yours! I still would like to experience going on a cruise and see Cuba 🙂

    • Christopher, So many different ways to experience cruising. Many people don’t think they will like it. But they may not have found the kind of cruise that works for them. Hope you get to visit Cuba. Linda

  2. Another great reason to be a Canadian. As if Justin wasn’t a good enough reason 😉 The cruise looks like it had a lot of delicious food on offer.

  3. I didn’t realize there are cruises going to Cuba. How lucky to have such a great view of the new years fireworks! Good to see that Key West has recovered from the hurricane

  4. I wouldn’t have thought about a cruise for Christmas but it looks like you had a great time! Cuba is a fascinating country, I’m glad you got some time to explore by yourselves – I still haven’t been to Santiago de Cuba but Havana and Cienfuegos were great!

  5. Wow you are so lucky that as a Canadian, you can visit Cuba anytime. Cuba is one of my dream destination and until I read this post, I didn’t know that you can take the cruise from Miami to Cuba. I think I will opt the cruise too! It’s great to relax and have unlimited food while they also provide so many activities on Oceania Cruises Insignia. I would definitely enjoy exploring the colourful Havana and Santiago de Cuba. But the place I want to visit the most is the beautiful Cemetery de Reina in the town of Cienfuegos. I really can’t wait to experience it myself, hopefully sooner rather than later. Thanks for sharing this and happy new year! 🙂

    • Debbie, I am glad this helped you to understand that taking a cruise to Cuba would be a great idea. Certainly we love to enjoy all the things that a cruise ship offers. Hope you get to visit Cuba! Linda

  6. What a lovely way to end your busy year of traveling. Wow, the food on the cruise looks amazing. This is some of the best I have seen. The activities seem like so much fun, I would definitively have signed up for the wine pairing as well. Being in Cuba for the new year…wow. Glad to hear your 2019 will involve so many places I’d love to visit – Faroe island and Greenland. Can’t wait to read about those adventures. Best wishes for the new year!

    • Rosemary, The food on Oceania is definitely one of the big reasons we travel with them. We do love doing wine tastings at sea. We are trying to sort out 2019 plans. And will share them soon. Linda

  7. Now this is a different kind of trip. I never considered that there was a cruise to Cuba. Not only you get to see Cuba but the other places along the way – all from a different perspective. Add to that the fun time on the cruise. Good to see that you had a blast celebrating your holiday onboard.

    • Ami, We like to use cruises as a way to taste test different destinations. For us, this cruise brought us some new destinations we had not visited before. And as you say, the cruise ship experience was great for the holidays. Maybe a cruise is in your future one day. Linda

  8. I’ve stumbled upon your post at the perfect time – I have been trying to plan a trip to the Caribbean Islands and have been totally confused as to which one to select in terms of the cruiseline as well as the itinerary. I haven’t heard as much about Oceania cruises to be honest, as I have of Royal Caribbean. But it seems like a beautiful ship! Also, I’d love to cover Cuba as a destination – Havana looks amazing and Santiago de Cuba as well. Oh, and Miami is so beautifully decorated for the holiday season!

    • Medha, I always love when I find a blog post right when I am thinking about a destination. We have cruised with Oceania before and knew we would have a great ship experience. This was great to add some new Cuba destinations for us. Hope you get your cruise picked. And you have a great time! Linda

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