Great Stops On A Caribbean Cruise In Winter

Great Stops On A Caribbean Cruise In Winter.jpg

Enjoying Great Stops On A Caribbean Cruise In Winter

We were so glad we enjoyed some great stops on a Caribbean cruise with Oceania Cruises. It was awesome to head to the Caribbean in winter and escape the cold weather at home in Toronto in Canada.

Even though we booked our Caribbean cruise only 10 days before we sailed, we planned for some great days in the Caribbean. Our day trips took us outdoors and the weather was perfect for fun in the sun. On our last day, we enjoyed a lazy beach day at the Great Stirrup Cay in Bahamas for the first time.

It was our first international trip in a long time and it finished out a busy travel year. But it was a reminder that travelling during the pandemic required planning and some extra risk management.

A Painful Trip To Miami

We planned this Caribbean cruise as a quick getaway from Toronto. We often visited Miami at the start of a cruise for an extended time. But we had obligations at home before and after this cruise. So our stop in Miami on this trip was only for one night. We always wanted to be in a cruise departure city at least one day before so we were not stressed with travel delays.

We booked an economy Air Canada flight for the short 3 hour trip to Miami. It might have been the worst and unsafest flight we have ever taken. It was a sad reminder of some of the challenges of international travel with a pandemic still raging.

By the time we arrived late in Miami, we were pretty stressed. I could not get my Uber app working so we decided to take a cab. Yet another bad learning experience. So when we did not notice that we were dropped at the wrong  JW Marriott hotel in downtown Miami, we were not surprised.

With directions in hand, we set off and rolled our suitcases the 20 minute walk to the  JW Marriott Miami. The walk was an easy one and it gave us a chance to work off some of the stress of our travel to Miami.

A Quick Stop In Miami

We were welcomed with a smile and a confirmed reservation at the JW Marriott Miami. Even though the hotel was pretty full, we were delighted with the benefits we got from elite Marriott status. We not only got the King bed we requested but we got an upgraded suite too.

JW Marriott Miami - Great Stops On A Caribbean Cruise In Winter.jpg

We usually wanted a high floor. So when we saw our room was on the 7th floor, our expectations were tempered. But when we arrived and found our room on the outdoor pool level with a walkout patio, we were excited. This was a great upgrade!

JW Marriott Miamii - Great Stops On A Caribbean Cruise In Winter.jpg

JW Marriott Miami.jpg

We collapsed and tried to let some of our bad travel day go. When we awoke in the morning, we headed downstairs for breakfast. But we quickly went back upstairs and enjoyed some time on our great patio space by the pool

JW Marriott Miamii - Great Stops On A Caribbean Cruise In Winter.jpg

JW Marriott Miami.jpg

We enjoyed a late check out and definitely wished we had planned more time in our lovely suite at the JW Marriott Miami. It would have been a great place to unwind before our Caribbean cruise in winter. But we kept the hotel in mind for a return visit when we had more time.

Looking Forward To Some Great Stops On A Caribbean Cruise

We arrived at the cruise terminal and were immediately shepherded into a long line of people waiting for their Covid-19 test before boarding. Just another of the new pandemic processes on this first international trip. By the time we finally made it on the ship our cabin was ready.

Oceania Cruises Riviera Penthouse Cabini - Great Stops On A Caribbean Cruise In Winter.jpg

Oceania Cruises Riviera Penthouse Cabin.jpg

We reviewed the onboard paperwork for our cruise. There were several senior officers onboard that we fondly remembered from previous trips with Oceania Cruises. We were not surprised when we found a change in cruise itinerary. There were several changes before we planned our Caribbean cruise. But we found our port stop in St Kitts was replaced with a day in Antigua. Last minute port changes were just one of the cruising risks we were prepared for.

A Covid-19 kit was provided for everyone. With our Oceania branded masks we wandered around the ship and found it all decorated for the Christmas holiday season. And then we headed up to our favourite spot at the barista bar for coffee. We were delighted that the coffee bar renovations added more seating and expanded the food selection.

Oceania Cruises Riviera Lobbyi - Great Stops On A Caribbean Cruise In Winter.jpg

Oceania Cruises Riviera Lobby.jpg

Oceania Cruises Riviera Barista Coffee Bar.jpg

Oceania Cruises Riviera Barista Coffee Bar.jpg

The port of Miami receded behind us as we cruised out. We were excited about the fun stops on a Caribbean cruise that awaited us.

Oceania Cruises Riviera Miamii - Great Stops On A Caribbean Cruise In Winter.jpg

Snorkelling In Gustavia, St Barts

The first port stop was in Gustavia, St Barts. The colourful port was a familiar sight from when we visited Gustavia several times before. So for our day trip we booked a short snorkelling excursion.

Gustavia St Barts Snorkeli - Great Stops On A Caribbean Cruise In Winter.jpg

The ship tender dropped us on the dock and we walked to the fast RHIB boat for our excursion. The snorkelling boat took us just into the harbour at Gros Islet. From there we even had a view of our ship at anchor.

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We followed the snorkelling leader into the water and explored the rocky undersea world. It was a great day for some water exercise and we saw some things as we snorkelled.

Gustavia St Barts Snorkel.jpg

Gustavia St Barts Snorkeli - Great Stops On A Caribbean Cruise In Winter.jpg

Gustavia St Barts Snorkeli - Great Stops On A Caribbean Cruise In Winter.jpg

St Barts was a fun one of the stops on a Caribbean cruise. This cruise excursion provided our first Caribbean water sports and activities. We were excited for our other planned water outings.

A Champagne and Lobster Catamaran Trip In Antigua

When we boarded the ship and found that Antigua was a new port stop on this cruise, we headed to the destination centre and checked out the available excursions. We again looked for an outdoor excursion for fun Caribbean water sports and activities.

Antigua Catamaran Tour.jpg

On our cruise around South America we visited Antigua. And since the champagne and lobster catamaran trip we did on that trip was so good, we booked and did this again with Mystic Cruises.

It was a short walk along the dock to the Explorer catamaran and then we were out on the water for the day. Once out of the harbour, the sails were raised.

Antigua Catamaran Tour.jpg

Antigua Catamaran Tour.jpg

We had several beach stops along the way. And were joined by the Mystic catamaran when we anchored for lunch. We enjoyed the beach while the crew cooked an amazing bbq lobster lunch. Local rum, beer and champagne were kept flowing.

Antigua Catamaran Tour Mystic Cruisei - Great Stops On A Caribbean Cruise In Winter.jpg

Antigua Catamaran Tour Mystic Cruise.jpg

Antigua Catamaran Tour Mystic Cruisei - Great Stops On A Caribbean Cruise In Winter.jpg

We had a perfect sunny and warm day for a catamaran trip along the coast in Antigua. Another of our fun stops on a Caribbean cruise in winter.

A Lazy Day In St Lucia

St Lucia was the next port on our Caribbean cruise. This was the only port when we cruised that had specific Covid-19 pandemic requirements in place. Anyone who wanted to leave the ship needed to be tested and had to be on an approved tour.

We visited St Lucia by cruise ship many times. And also stayed on the island for several stays at Sandals Resorts. So we decided we would not book an excursion and planned to enjoy a sunny day on the ship.

We were entertained as we watched the ship dock in Castries. There were already two cruise ships docked and for awhile the captain thought we might be anchored out in the bay. But when cleared, our captain showed his skill as he parked in between the two ships and easily put us on the dock. Even as our large ship entered harbour, a small catamaran decided they had time to squeeze between the ships!

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Castries St Lucia Porti - Great Stops On A Caribbean Cruise In Winter.jpg

Once docked we had a great view out over the port as we watched airplanes land at the nearby airport.

Castries St Lucia Port.jpg

Castries St Lucia Porti - Great Stops On A Caribbean Cruise In Winter.jpg

For our day in port we booked massages and enjoyed the mostly empty sundecks. We could not have had a more relaxing day!

Oceania Cruises Riviera Castries St Lucia Porti - Great Stops On A Caribbean Cruise In Winter.jpg

Even when there were great stops on a Caribbean cruise, we knew we did not have to get off the ship at every port. Sometimes we just needed to enjoy the floating luxury we had at sea.

Snorkelling And Beach Fun In St Maarten

The next port was a return visit to St Maarten for us. We did many fun things on stops at this cruise port and decided to book another fun water activity for this stop. We walked down the dock in Philipsburg to the Golden Eagle catamaran.

As the catamaran pulled out of the bay, we looked back and saw the three cruise ships docked. We were happy we saw the cruise business back on the Caribbean islands.

Philipsburg St Maarten Catamaran.jpg

Our first stop was a snorkelling stop. We found an interesting array of things underwater at this spot.

Philipsburg St Maarten Catamaran Snorkel.jpg

Philipsburg St Maarten Catamaran Snorkeli - Great Stops On A Caribbean Cruise In Winter.jpg

Philipsburg St Maarten Catamaran Snorkeli - Great Stops On A Caribbean Cruise In Winter.jpg

We moved further down the coast under sail and got of view of St Maarten from the water. The ship anchored in a sandy bay. We swam around and enjoyed a cold local Carib beer in the sun.

Philipsburg St Maarten Catamaran.jpg

Philipsburg St Maarten Catamarani - Great Stops On A Caribbean Cruise In Winter.jpg

Philipsburg St Maarten Catamaran.jpg

Philipsburg St Maarten Catamaran.jpg

When our time was up, the anchor on the Golden Eagle catamaran was pulled up and we headed back to the dock. Definitely a perfect day for fun water sports and activities in St Maarten. This was another of the great stops on a Caribbean cruise.

Wandering In San Juan, Puerto Rico

We got our first view of San Juan, Puerto Rico as we cruised in. We recognized the old fort on the hill and as we came around the corner got a good view of the port area.

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San Juan was another of the stops on a Caribbean cruise we visited many times. So we booked no excursions and just wandered around the town. The cruise port had large signs reminding people about Covid-19 precautions and their role to protect the local people.

San Juan Puerto Ricoi - Great Stops On A Caribbean Cruise In Winter.jpg

San Juan Puerto Rico.jpg

San Juan Puerto Ricoi - Great Stops On A Caribbean Cruise In Winter.jpg

We walked along the old town streets. Everywhere we walked we found colour and design.

San Juan Puerto Rico.jpg

San Juan Puerto Rico.jpg

San Juan Puerto Ricoi - Great Stops On A Caribbean Cruise In Winter.jpg

San Juan Puerto Rico.jpg

For a coffee break, we found the Cuatro Sombras Cafe. This was a regular stop on our visits to San Juan. David bought some coffee for home. And we got iced coffee drinks to take out.

San Juan Puerto Rico Cuatro Sombras Coffee.jpg

San Juan Puerto Rico Cuatro Sombras Coffee.jpg

On a Caribbean cruise in winter, we found lots of holiday cheer in the ports we visited.

A Relaxing Beach Day At Great Stirrup Cay

The final port on our Caribbean cruise in winter provided a fun beach day on the private island of Great Stirrup Cay in the Bahamas. This was a private island is owned by Norwegian Cruise Lines. And since we were the only cruise ship in that day, we had the deserted island all to ourselves.

Great Stirrup Cay Bahamasi - Great Stops On A Caribbean Cruise In Winter.jpg

Great Stirrup Cay Bahamasi - Great Stops On A Caribbean Cruise In Winter.jpg

We loved the idea of a relaxing day at the beach. We took our snorkel gear and were delighted when we found the Sir Nicholas Nuttall Coral Reef Sculpture Garden underwater.

Great Stirrup Cay Bahamas Snorkel.jpg

Great Stirrup Cay Bahamas Snorkeli - Great Stops On A Caribbean Cruise In Winter.jpg

Our day at Great Stirrup Cay was probably the most relaxing of the stops on a Caribbean cruise. A great way to enjoy some Caribbean water fun and to finish our trip.

Great Stirrup Cay Bahamasi - Great Stops On A Caribbean Cruise In Winter.jpg

Much To Do Cruising In Addition To Great Stops On A Caribbean Cruise

It was a long time since our last cruise when we got stranded by the pandemic on our trip around South America. And we were still some of the more cautious passengers on this cruise ship while Covid-19 still raged. But we still enjoyed our time on the ship.

The onboard entertainment kept brought us music in multiple venues. We loved the quiet time after dinner when we enjoyed the Sync Session band in the lounge. The Rock The Boat outdoor party let us enjoy the warm evening weather outside and some great music too.

Oceania Cruises Riviera Entertainment.jpg

Oceania Cruises Riviera Entertainment Sync Sessioni - Great Stops On A Caribbean Cruise In Winter.jpg

The food onboard Oceania Cruises remained exceptional. We found a quiet spot outside when we could. Being in the Caribbean meant lots of fresh seafood. And we made sure we got all our favourites when we ate at the Red Ginger Asian restaurant.

Oceania Cruises Riviera Terrace.jpg

Oceania Cruises Riviera Terrace.jpg

Oceania Cruises Riviera Red Gingeri - Great Stops On A Caribbean Cruise In Winter.jpg

We always loved to attend the wine tasting events when we cruised. On this cruise we attended the Mediterranean Jewels wine tasting and pairing led by the Head Somellier We tasted a great selection of wines and loved learning about how the tastes varied with food. We were delighted when we learned more about our favourite Brunello red wine varietal.

Oceania Cruises Riviera Mediterranean Jewels Wine Tastingi - Great Stops On A Caribbean Cruise In Winter.jpg

Oceania Cruises Riviera Mediterranean Jewels Wine Tastingi - Great Stops On A Caribbean Cruise In Winter.jpg

Oceania Cruises Riviera Mediterranean Jewels Wine Tasting.jpg

When we needed to enjoy some quiet time, we watched a colourful sunrise or sunset at sea. Or just had a treat on our balcony.

Oceania Cruises Riviera Chocolate Butlersi - Great Stops On A Caribbean Cruise In Winter.jpg

Oceania Cruises Riviera Sunrise.jpg

Oceania Cruises Riviera Sunrise.jpg

We sure enjoyed everything about our Caribbean cruise in winter. And we were happy to be back at sea.

A Better Flight Home To Toronto

We were always up early as we cruised back into Miami. We had a great view of the city all lit up when we left. And it was still dark and lit up as we returned.

Oceania Cruises Riviera Miamii - Great Stops On A Caribbean Cruise In Winter.jpg

Oceania Cruises Riviera Miamii - Great Stops On A Caribbean Cruise In Winter.jpg

It was an easy departure from the ship and we took an Uber to the Miami Airport. Air Canada did not have dedicated airport lounge in Miami. But with our upgraded ticket to Business Class for our return flight to Toronto, we got access to the partner lounge for Turkish Airlines. We sure enjoyed a mostly quiet spot and finished the wait for our flight.

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We knew the flight was late so we stayed in the lounge until we saw the airplane arrive. When we finally boarded and settled in we were so happy we upgraded our tickets. What a difference in the flight home from the horrid trip down to Miami.

Air Canada Rouge.jpg

Our passage through customs was fast with our Nexus passes. Even with changed pandemic requirements, our flight was not subject to mandatory testing on arrival. And we luckily were not pulled over for a random test.

Some Great Stops On A Caribbean Cruise In Winter

We sure enjoyed some great stops on a Caribbean cruise in winter. It was a fun way to finish our great travel year in 2021.

We were so happy to be back at sea. The ports offered lots of outdoor water fun as we enjoyed the sun and warmth. It was good returning to ports we visited before. And we loved the chance to visit the Great Stirrup Cay in Bahamas for the first time.

This Caribbean cruise was a major milestone for our Oceania Cruises loyalty status. It moved us up in loyalty points and status. But it also meant we earned a free cruise. We were busy planning that cruise trip.

We had such a good time cruising again that we returned to Toronto and started to plan for more cruising in 2022!

Have you had some great stops on a Caribbean cruise? Did you escape cold weather for a Caribbean cruise in winter?

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About TravelAtWill 669 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!

70 Comments

  1. It is definitely a great idea to go on a Caribbean Cruise in winter when you’re living in Canada! OMG, too bad about the stressful trip to Miami. I do know how well traveled you are and when you say that it was your worst flight ever, I can’t imagine how horrible it would have been! Thankfully the upgraded suite in JW Marriot sounds like a good finishing touch to the nightmare of flight. Champagne and Lobster Catamaran lunch sounds absolutely pampering! A lazy day resting in the ship at St.Lucia sounds nice. Coral Reef underwater sculpture garden is very intriguing.

    • We were so glad we did our Caribbean cruise – even with a few hiccups along the way. The stops on the cruise were great. And it was so good being back onboard a cruise ship.

  2. I can see the joy in your faces – it must feel good to be cruising again. Such adventures you have. I’d take the relaxing St Lucia any day. I was there decades ago and loved that tiny island. The wine tasting activity on board would be exactly what I would love to do.

  3. So sorry to hear that the start of the trip in Miami was a bit of a strain. But am glad the rest of it was amazing. I loved all your snorkeling adventures – those would have been my highlight for sure. I loved San Juan as a town – it is so quirky and colorful. As always. lovely tips included.

  4. This sounds like a super relaxing trip, and much needed after the trials of getting to Miami. I had a girls trip to Antigua postponed due to COVID and we still haven’t rescheduled. I will for sure encourage the catamaran trip on the coast, champagne and lobster is a bonus!

  5. I think you really love traveling in a cruise ship. I like seeing you got to explore several islands in the Caribbean during the cruise and both of you look so happy. Gone was the bad experience in the beginning of your cruise. As always, you got to eat the best cruise food ever. That grilled lobster looks so delicious! I think they will ask me to move to another table if I was there. hehe..

  6. This is just a perfect way of relaxation and rejuvenation! Riding a cruise ship is really one of my dreams — offering fun in a family-friendly atmosphere with good food and entertainment all in one unique location. What a delightful escape!

  7. Im sitting here in Belgium and absolutely freezing! But reading your latest trip to the Caribbean has made me yearn for the sun! It sounds like an absolutely amazing cruise and something I would absolutely adore, especially to visit all the incredible Caribbean islands. So magical!

  8. That cruise sounds like so much fun! I would love to go snorkeling in those blue waters! I went on a similar Caribbean cruise many years ago and had the best time!

  9. There were challenges initially for you, but as they say, all is well that ends well. The cruise line had great plan for the stops and also the cruise has great amenities. Wine tasting event while on cruise sounds exquisite.

  10. Sorry to hear that your flight to Miami was stressfull. I never thought much about cruises, but I guess it is an advantage, that once you are “cleared” for the ship, you do not have to deal with COVID regulations that much. I have never been to the Caribbean – but it looks lovely and dreamlike on all the pictures.

  11. A Caribbean cruise sounds like a ton of fun! I would love to go Snorkelling in Gustavia, St Barts – that sounds like a blast. San Juan is also one of my favorite places, so it would be great to go back.

  12. I enjoyed reading through your well written blog post! It felt like I was traveling with you. I can imagine your frustration in going through a bad flight and being dropped at the wrong Marriot. That upgraded accommodation looks so nice but it’s a pity you had only one night there. The snorkeling, the catamaran lunch and the on-board entertainment sound brilliant. I have not been to the Carribean yet but must try this cruise some day. 🙂

  13. What great winter cruises in the Caribbean! I would love to go snorkeling in St Maarten to admire the underwater world and sculptures. Also, a champagne and lobster trip in Antigua seems to be the perfect idea for the winter holidays. I also add to my bucket list the Sir Nicholas Nuttall Coral Reef Sculpture Garden underwater. It’s a fabulous place!

  14. Glad to know you still had a great trip despite the hiccups. I think Great Stirrup Cay is still my favorite stop over. Glad to know you were able to enjoy the island to yourselves.

  15. Your snorkeling pictures are great! I love water excursions of any kind. Thank for sharing your Caribbean cruise adventures. I can’t wait to take a cruise again, it’s been ages. I am so glad that cruising has returned.

    • Water excursions are always our favourite. Even more important when on this trip we wanted to be outside as much as possible. Some great stops on this cruise. We were so very happy to be back at sea.

  16. No on a cruise, but we are headed to the Caribbean in May to Antigua and Turks and Caicos. I have-not been to either island and am really looking forward to returning to the caribbean. You always make it look so perfect!

  17. There are so many places to visit in the Carribean. It has been a while since I’ve cruised there but it is brilliant for a winter escape

  18. What an awesome winter escape! I LOVED the snorkeling around the sculpture garden. Very interesting. The BBQ lobster looks so delicious. I have never been to the Carribbean, but would love to go one day.

  19. I’m really pleased you got to get to the warmer climes for your Caribbean cruise again this year. I am also back in the region so read this post with interest. Looks like you had an amazing time, despite the disappointing start in Miami.

  20. So sorry you had a bad start to your trip. Once on the cruise ship though it looks amazing! And the snorkelling seems out of this world. I’ve never really considered a cruise before, but your posts are slowly convincing me!

    • I am happy that our cruising posts may make you consider a Caribbean cruise. It was a fun way to explore so many great ports. And offered such great underwater sights.

  21. I love the picture of you in the water with the Carib! It is interesting to read about what cruising was like during the pandemic. I certainly am jealous of your escape from the cold.

  22. I’m glad your travel bad luck fell on the front end of your trip. Sounds like you had a great experience once you were safely onboard the ship. I’ve always wanted to go on a cruise but feel so hesitant with the pandemic. This post made me feel like it really is still a viable option.

    • It took us a long time to get back on a cruise ship. But once we got settled, we were so glad we planned this Caribbean cruise. I think there are ways to protect yourself on a cruise … and as you travel. But it is not always stress free.

  23. Those chocolate covered strawberries look adorable! What a magical way to soak up the sunset! These stops look incredible! A Caribbean cruise sounds like the perfect way to spend the winter months! Thanks for the great guide!

  24. It sounds like your trip had a rubbish start, but just got better and better! It’s nice to see you looking so relaxed in the photos later in the cruise! Your cabin looks amaaaazing too! I always assumed rooms on cruise ships would be smaller than that!

  25. It sound like a great idea to take Caribbean Cruise In winter. It looks like except of some pitfalls you have had a lot of fun. I must take some cruise in near future! Thanks for sharing!

  26. We also love to get away from the gray winter here in the PNW for a sunny destination, so I’ll have to keep this post in mind for future vacation plans. What a rough start to your trip! That upgraded room at their Marriott in Miami looked amazing though. San Juan, Puerto Rico sounds like an especially fun stop! Really enjoyed reading this article 🙂

    • For those of us living a bit further north, a Caribbean cruise is indeed a good escape. It sure refreshed us! Loved all the ports on this trip. Hope you get to try it one day.

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