Cruising With Windstar In The Caribbean

Cruising With Windstar In The Caribbean.jpg

Heading Back To The Caribbean

We started the year cruising in the southern Caribbean for David’s birthday. We finished that trip with a week in St Lucia. It was great to escape the winter in Toronto. But we were not back for a month before we started to itch to head south again. We considered a large number of options. And then we came across some last minute deals. If we could move quickly, we could cruise with Windstar in the Caribbean. The cruise was in and out of San Juan, Puerto Rico. And we got 8 different islands along the way.

Cruise Ports - Cruising With Windstar In The Caribbean.jpg

We checked on availability for the cruise and put a hold on a cabin that worked for us. We then needed to figure out travel to and from San Juan. There were a few things on our U.S. shopping list so we wanted to stop in Miami on one or both ends. After considering a bunch of different options we decided to fly to Miami for 6 days. It was then an easy hop to San Juan. And we could even get a direct flight home from San Juan to Toronto. And even though we booked all the flights at the last minute, the flight prices were not prohibitively high. We were all booked to do our first cruise with Windstar in the Caribbean.

Pampered In Miami

We have started cruises in Miami before. It is an easy 3 hour flight from Toronto and there is no time change. All the major airlines cover this route so there are lots of options. Since we are still working on building airline status, we stuck with Air Canada for the short hop.

We have elite status with IHG Rewards so the choice of a hotel was simple. We headed back to the Intercontinental Miami. From the moment we reached out to them before our arrival, until the last hug goodbye, we were pampered in Miami. Our room upgrade was waiting for us when we arrived at noon. It was a sweet suite with a great view of the harbour. We caught great harbour sunrises and the full moon!

Intercontinental Miami - Cruising With Windstar In The Caribbean.jpg

Intercontinental Miami View Sunrise - Cruising With Windstar In The Caribbean.jpg

Intercontinental Miami View Moon Rise - Cruising With Windstar In The Caribbean.jpg

We booked a room with Concierge Lounge access. The breakfast and Happy Hour snacks had a good supply of protein to keep our carb cravings at bay. The Toro Toro restaurant had lots of options if we were prepared to discard portions of the meal. For 6 days at the Intercontinental Miami, we stayed true to our diet. I won’t say it was always easy!

Intercontinental Miami Concierge Club Breakfast - Cruising With Windstar In The Caribbean.jpg

Intercontinental Miami Toro Toro Burger - Cruising With Windstar In The Caribbean.jpg

The first night we got our welcome treat. We had just started a low carb diet before leaving for our vacation. One short discussion with the Concierge Lounge staff and our nightly treats had just the perfect mix we could eat. Night after night we were spoiled.

Intercontinental Miami Concierge Club Welcome Treat - Cruising With Windstar In The Caribbean.jpg

The Intercontinental Miami was a great place to enjoy a little pampering before we departed for San Juan to start our cruise with Windstar in the Caribbean.

Enjoying The Sun In Miami

Part of the reason for our stop in Miami was to warm up and get a little base tan. Even though we just returned from the Caribbean, our heat batteries were running low.

The Intercontinental Miami has a large outdoor pool on the 3rd floor. The pool was long enough to swim lengths and get a little exercise. If we were there early before the kids showed up. The pool deck had sun until about 1pm. So every day we headed to the pool for a few hours to slowly warm up.

Intercontinental Miami Pool - Cruising With Windstar In The Caribbean.jpg

Intercontinental Miami Pool - Cruising With Windstar In The Caribbean.jpg

The hotel is right on the waterfront. A short walk away we found the Bayside Marketplace and the marina. It was a busy spot on the weekend as people came and shopped, ate in the restaurants, had a drink or enjoyed the live music.

Intercontinental Miami - Cruising With Windstar In The Caribbean.jpg

Miami Bayside Marketplace - Cruising With Windstar In The Caribbean.jpg

The marina was filled with private boats of all sizes. But there were also a wide range of tour boats. Tour boats started at the water taxi level. You could buy a one way ticket or a hop on hop off ticket. Faster boats raced you around the harbour. Larger tour boats took you around a more leisurely pace. There was something for everyone.

Miami Bayside Marketplace Lift Bridge - Cruising With Windstar In The Caribbean.jpg

Miami Bayside Marketplace Tour Boats - Cruising With Windstar In The Caribbean.jpg

Miami Bayside Marketplace Tour Boats - Cruising With Windstar In The Caribbean.jpg

After 5 days at a slow, leisurely pace, we headed to the airport for the quick hop to San Juan, Puerto Rico. We were off to cruise with Windstar in the Caribbean.

Getting Settled On Our Windstar Ship

This was our first time cruising with Windstar. It was a fairly easy and quick process to get from the San Juan airport, find the ship and get boarded. But it was a very long day.  While we were up at 6am to start our travels, it was almost 5pm before we were settled into our cabin. We had thought we might tour around San Juan, but that did not happen at the start of our cruise.

San Juan Puerto Rico - Cruising With Windstar In The Caribbean.jpg

We got our first experience with a small ship on our first night out. High sea swells were created from storms in the north. The roll of the ship was enough to keep me awake for most of the night. It was a good thing that our first day was a day at sea. I needed it to recover.

The first day at sea we wandered around the ship. We found the barista and espresso machine. The front deck and jacuzzi quickly became our quiet spot to get some sun and escape. A BBQ outside was a great way to have lunch in the sun as we cruised along.

We spent some time hearing about the excursions offered on the ship. The captain’s welcome introduced us to the senior officers on board. We tried enough different food to know that we could stick to our diet on the cruise.

It was a great first day cruising with Windstar in the Caribbean.

Our First Port In St Kitts

We have done several different cruises in the Caribbean and have visited a lot of islands. But St Kitts was a new port for us. It was one of the reasons we planned our trip cruising with Windstar in the Caribbean. We debated an island tour or something more fun. Fun won out! For the morning we enjoyed our first zipline ride in St Kitts. It was a lot of fun on the 5 runs through the canopy of the rainforest.

St Kitts Zipline - Cruising With Windstar In The Caribbean.jpg

St Kitts Zipline - Cruising With Windstar In The Caribbean.jpg

We spent a little time walking around the former sugar plantation. And we saw some beautiful batik work. It gave us a chance to get our adrenaline levels down.

St Kitts Wingfield Estates - Cruising With Windstar In The Caribbean.jpg

St Kitts Wingfield Estates

We were so glad we chose to do a zipline ride in St Kitts. It was a great way to start our cruise.

Enjoy The Beach At St Barts

We visited St Barts before so we did not book an excursion. The last 2 times we visited, sailing regattas were happening and the harbour and docks were filled with ships. Cruising with Windstar in the Caribbean we found the harbour less busy.

St Barts Harbour - Cruising With Windstar In The Caribbean.jpg

We went into town and headed back to Shell Beach. It was mid-week and the beach was quite empty. The water colour was so amazing. We found a spot on the rocks as our base and ventured into the water to cool down.

St Barts Shell Beach - Cruising With Windstar In The Caribbean.jpg

It was a lazy beach day in St Barts. As we walked back to the tender dock, we walked past many of the spots we visited on prior trips. We could see some remnants of the storm damage from Hurricane Irma.

St Barts Hurricane Irma Storm Damage - Cruising With Windstar In The Caribbean.jpg

Stopping In Falmouth In Antigua

We visited Antigua twice before. Both previous times we had ventured out to tour from St. John’s where our cruise ship was docked. The Star Pride was anchored in the Falmouth Bay when we were cruising with Windstar in the Caribbean.

Falmouth Harbour Antigua - Cruising With Windstar In The Caribbean.jpg

Falmouth Harbour Antigua - Cruising With Windstar In The Caribbean.jpg

We considered returning to Antigua Paddles for a kayak and snorkelling adventure. But there was no pickup from Falmouth. We figured we would need to pay a driver for a full day to get there and back. None of the ship’s tours were of interest so we planned to head to the dock and see what water sports might be available.

We had not realized how small the town of English Harbour actually was. There were a few small cafes and restaurants. We saw many people sitting in cafés looking for wifi. But not really much else.

English Harbour Antigua - Cruising With Windstar In The Caribbean.jpg

Nelson’s Dockyard was a longer walk and it was frankly too hot for us to head that way. We saw signs for water sports but nobody was open. Finally we just walked around the harbour and looked at the boats. We have been toying with the thought of buying a boat. Sailboat or yacht is still up for debate. But we knew that most of the large super yachts in this harbour were well out of our price range.

English Harbour Antigua Boats - Cruising With Windstar In The Caribbean.jpg

English Harbour Antigua Super Yachts - Cruising With Windstar In The Caribbean.jpg

It was a good thing that the Marina sports deck was open on the ship when we returned. David immediately jumped in to test out the trampoline. The seas were really rough and did not look totally safe. So I resisted the urge to jump in. But I was able to capture David’s antics.

Star Pride Marina Deck - Cruising With Windstar In The Caribbean.jpg

Star Pride Marina Deck - Cruising With Windstar In The Caribbean.jpg

Walk The Hills Of Guadaloupe

The morning we were scheduled to arrive in Guadaloupe, I opened my offline map and tried to match up the points of reference from the printed map we had been given. Even the island looked to be a different shape. As I puzzled this out, David pointed out that we were not really going to the main island of Guadaloupe. But rather we were anchoring off of the smaller island of Terre-De-Haute.

When we landed, we were pleasantly surprised to find a great small town. There were small shops, coffee shops, a great gelato spot and restaurants along the main street.

We had been told that the best beach was at Pompierre on the other side of the island. It was supposed to be a mile walk. What we found was a walk close to two miles each way with quite steep hills coming and going. We definitely got our exercise to walk to the beach. We really wished we had rented a scooter like so many others did. At one point we stopped on the hill and could see our cruise ship far off in the distance.

Guadaloupe Terre de Haute Les Saintes Town - Cruising With Windstar In The Caribbean.jpg

As we neared the beach, there was a gale force wind sandblasting us. While there was a little bit of shelter from the wind on one end of the beach, the rest was quite exposed. A few people were swimming but most like us sat and contemplated a swim.

Guadaloupe Terre de Haute Les Saintes Pompierre Beach - Cruising With Windstar In The Caribbean.jpg

It was a good thing we had entertainment. And we had been forwarded! Goats and chickens wandered from group to group looking for handouts. If towels and bags were left unattended, they were free game to be rooted through.

Guadaloupe Terre de Haute Les Saintes Pompierre Beach Chickens - Cruising With Windstar In The Caribbean.jpg

Guadaloupe Terre de Haute Les Saintes Pompierre Beach Chickens - Cruising With Windstar In The Caribbean.jpg

Guadaloupe Terre de Haute Les Saintes Pompierre Beach Goats - Cruising With Windstar In The Caribbean.jpg

On the walk back, we passed the small local church. In town we stopped for an espresso at the gelato stop. There were some things we found hard to pass up on our cruise ship diet. We looked longingly at the gelato but stayed firm in our resolutions. The nuts on top of the gelato did not fool us into thinking this would be low carb!

Guadaloupe Terre de Haute Les Saintes Town Church - Cruising With Windstar In The Caribbean.jpg

Guadaloupe Terre de Haute Les Saintes Town Gelato - Cruising With Windstar In The Caribbean.jpg

Our stop on Terre-De-Haute gave us a chance to stretch our legs and walk the small island. It was another great small port cruising with Windstar in the Caribbean.

St Lucia Beach BBQ

Before cruising with Windstar in the Caribbean, we did a southern Caribbean cruise and got off the ship for a week in St Lucia. We had considered spending the day at the Sandals Grande Resort right beside where we were anchored. But we never did get that set up.

St Lucia Sandals La Toc - Cruising With Windstar In The Caribbean.jpg

This was our fourth time in St Lucia and we did not feel the need to book an excursion. Windstar set up a great beach BBQ and we just enjoyed some beach time. The BBQ feast had lots of selection so we had no trouble staying true to our low carb diet.

St Lucia BBQ Beach Party Pigeon Island National Park - Cruising With Windstar In The Caribbean.jpg

St Lucia BBQ Beach Party Pigeon Island National Park - Cruising With Windstar In The Caribbean.jpg

St Lucia BBQ Beach Party Pigeon Island National Park - Cruising With Windstar In The Caribbean.jpg

St Lucia BBQ Beach Party Pigeon Island National Park - Cruising With Windstar In The Caribbean.jpg

St Lucia BBQ Beach Party Pigeon Island National Park - Cruising With Windstar In The Caribbean.jpg

For our exercise that day, we donned our snorkel gear and swam out along the cliff underneath Fort Rodney. Once we cleared the jetty, the waters were much clearer and we could see the small fish in the rocks. The waves and current provided us with a great workout.

St Lucia Snorkel Pigeon Island National Park - Cruising With Windstar In The Caribbean.jpg

St Lucia Snorkel Pigeon Island National Park - Cruising With Windstar In The Caribbean.jpg

St Lucia Snorkel Pigeon Island National Park - Cruising With Windstar In The Caribbean.jpg

St Lucia Snorkel Pigeon Island National Park - Cruising With Windstar In The Caribbean.jpg

Windstar did a great job in setting up the BBQ, beach chairs and watersports for the day on the beach. It certainly looked like people had a fun time even if they didn’t book an excursion.

Grenada Under The Sea

Grenada was the only port where we actually tied up at the dock. Since Star Pride was a smaller ship, we tied up at the cruise port in the main harbour. It was an easy walk into town if people wanted to explore St. George’s.

Grenada Cruise Terminal - Cruising With Windstar In The Caribbean.jpg

This was our third time to Grenada. On our first visit we explored the island for an 8 hour tour. On our second visit on our recent southern Caribbean cruise, we enjoyed the opportunity to snorkel on the underwater statues.

For this visit we booked scuba diving in Grenada. We had two good scuba dives in great visibility. A great way to enjoy a visit to Grenada.

Grenada Scuba Diving - Cruising With Windstar In The Caribbean.jpg

Grenada Scuba Diving - Cruising With Windstar In The Caribbean.jpg

Grenada Scuba Diving - Cruising With Windstar In The Caribbean.jpg

It was a late night in port. Windstar took advantage of being tied up to host a great deck BBQ on the ship. There was so much food all night long. We had no problem on our low carb diet finding meat and seafood to get us stuffed. There was a steel band playing through the evening that kept the guests entertained.

Windstar Star Pride BBQ Night - Cruising With Windstar In The Caribbean.jpg

Windstar Star Pride BBQ Night - Cruising With Windstar In The Caribbean.jpg

Windstar Star Pride BBQ Night - Cruising With Windstar In The Caribbean.jpg

It was a great day in Grenada.

A Day Off In Bequia

On our southern Caribbean cruise, we visited St Vincent and the Grenadines. We took a catamaran excursion to Bequia Island. It was a great spot to snorkel. On this trip, we anchored right outside of Port Elizabeth in Bequia. We saw our snorkelling spot off the nose of the ship. It was funny to be back at this tiny port twice in the same season.

Port Elizabeth Bequia St Vincent - Cruising With Windstar In The Caribbean.jpg

We continued to marvel at the number and variety of boats we saw in our ports. In Bequia we saw a large number of ferries docked. On our last visit to Bequia, we learned that many people commuted from Bequia to Kingstown for school or work.

Port Elizabeth Bequia St Vincent Boats - Cruising With Windstar In The Caribbean.jpg

Port Elizabeth Bequia St Vincent Boats - Cruising With Windstar In The Caribbean.jpg

Port Elizabeth Bequia St Vincent Ferries - Cruising With Windstar In The Caribbean.jpg

We took the opportunity to enjoy the empty ship. The deck chairs and pool were empty. It was quiet everywhere. The lounge was a great refuge to get a cappuccino and work on pictures and blog posts. This was exactly the relaxing day we wanted.

A Great Day Sailing In Martinque

We booked a catamaran excursion in Martinique. We spent a great with the sails our going along the coast. Several times we stopped to snorkel in a sheltered bay.

Catamaran Sailing Martinique Diamond Rock - Cruising With Windstar In The Caribbean.jpg

Catamaran Sailing Martinique Diamond Rock - Cruising With Windstar In The Caribbean.jpg

Catamaran Sailing Martinique Diamond Rock Snorkel - Cruising With Windstar In The Caribbean.jpg

The crew was great. They constantly looked for things for us to see along the say. There was a great local feast served onboard.  We were certainly glad we chose to see a little of Martinique by catamaran.

Catamaran Sailing Martinique Diamond Rock - Cruising With Windstar In The Caribbean.jpg

Catamaran Sailing Martinique Diamond Rock Bat Cave - Cruising With Windstar In The Caribbean.jpg

Catamaran Sailing Martinique Diamond Rock - Cruising With Windstar In The Caribbean.jpg

A Great Time Cruising With Windstar In The Caribbean

We visited 8 great islands cruising with Windstar in the island. We did a great shore excursion in St Kitts to zipline over the rainforest. In Grenada we enjoyed a day scuba diving. Our catamaran experience in Martinique was a great day on the sea. In other ports we walked to see the sights, enjoyed the beaches or the quiet ship. It was just the relaxing vacation we had hoped for.

Windstar Star Pride Jacuzzi - Cruising With Windstar In The Caribbean.jpg

We said goodbye to Puerto Rico as we flew out. It was still cold at home in Toronto. But we got a great sunset view as we came close.

WestJet Flying Home From San Juan - Cruising With Windstar In The Caribbean.jpg

WestJet Flying Home To Toronto - Cruising With Windstar In The Caribbean.jpg

This first cruise with Windstar was a great way to taste test this cruise line before we head to Japan with them in the fall.

Have you tried cruising with Windstar in the Caribbean? How did you find the Windstar experience?

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About TravelAtWill 405 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!

22 Comments

  1. What could possibly be next? Around the world maybe?
    We leave for Machu Picchu and Galapagos in May. ATW in January. Then Silverseas Antarctica Jan 2020. Life is Good.
    Greg

    • Greg, Sounds like you guys have amazing travels coming up. We are off in two weeks with OAT to Eastern Europe. Will let you know how that goes and if there are any tips for you. We then have China and Japan booked for the fall. Send me the Antarctica info. It is still a far off plan for us but interested to see what you picked after all your research. Linda

  2. The Intercontinental Miami hotel sounds amazing. That’s so sweet they gave you low carb options and the pool looks amazing! Cant’ believe your cruise went 8 places. Seems like you really enjoyed it! Hoping to get to St Kitts soon so will definitely checkout that zip lining!

    • Steph and Zack, We love to stay at the Intercontinental Miami. The service has always been great and the location is good for walking the waterfront. It was our first trip to St Kitts and our first ziplining experience. Next time we will see more of the island. Linda

  3. I can understand wanting to recharge your heat batteries. It has been a cold winter for us and I could use some hot days near a pool. Great underwater pictures! My wife and I have only been on one cruise and we were in the ocean near hurricane Katrina. After reading your great experience, I feel like trying the high seas out again.

    • Chris, It has been a brutally long winter in Toronto. So I too needed to recharge my sun batteries regularly. We love to head underwater whenever we get a chance. Our underwater camera broke on this trip so we are looking for a new one. Hope it works as well as the old one. It must have been a rough experience on a cruise during Katrina. Weather may be unpredictable, but not that rough! We love to cruise in the Caribbean. Linda

  4. Great post – I felt like watching a TV show thinking what is next. I somehow enjoyed the empty ship day part the most as I sometimes take days off from the vacation itself when vacationing and I feel a little guilty about it but it feels so good.

    • Burcu, I am glad you found the post entertaining and it drew you through our travels. I never feel guilty anymore when I take a down day. Especially when I am cruising on a ship with lots to do. I do have to remind myself that it is a vacation! Linda

    • Nicola, We were happy to add a bunch of new ports on this Caribbean cruise. The stops were all a bit different but all interesting. It is still cold in Toronto so I too wish I were back on a beach! Linda

  5. I’ve heard good things about the Windstar ships, and your cruise definitely lives up to those expectations. Looks like you got a great deal for having the flexibility to book last minute, and that you were able to sort flights and some time in Miami to take advantage of the deals really well. Loving the look of the range of islands you visited too.

    • Kavita, We were happy that we got to try Windstar in the Caribbean. It was a great itinerary with some new islands that we had not yet visited. We were indeed lucky to get flights at the last minute. It helped make this vacation happen. Linda

  6. That looks like such a great vacation. We lived on Martinique for a year and it was one of my very favorite places ever. Visiting all of those islands would be so much fun, although I would probably want to eat fruit and snorkel on every island.

    • Kathleen, Martinique must have been great for a year. We got just a taste test but it was one of the new islands we visited that we really would like to return to. We were glad we did a mix of lazy days and more exciting excursions. It was meant to be a relaxing break. We loved the chance to snorkel whenever we could. Linda

  7. A great way to escape winter by having a cruise in a tropical destination like the Caribbean. Being pampered in Miami, having great food and engaging in those water activities are sure fun ways to beat the winter blues. Also, island-hopping in 8 locations was a lovely feature of the whole adventure.

    • Ash, Living in Toronto we need to escape to a warmer destination on a regular basis. Our stop in Miami not only pampered us but also warmed us up! It was a great Caribbean itinerary. Always great to see new islands. Linda

  8. What a great trip, especially with the weather so crappy here in Toronto. The only place I’ve been on your itinerary was Terre-De-Haute. I went there when I was in Guadeloupe and like you, ended up doing a humungous walk. I’m so jealous you got to see St Bart’s. And St Lucia is high on my list too. Really a great itinerary of so many islands I want to see.cc

    • Carol, It was definitely a winter to escape Toronto. We enjoyed our walk in Terre-de-Haut but just wished the beach was calmer when we got there. We love St Lucia. This was our 4th visit. One for your list for sure. Linda

  9. It sounds like you found a good deal. I have never been on a cruise.I always thought I might get bored but it seems you can have fun and do activities. I should give it a try at least for a few days to start with then expand it to one month or so 🙂

    • Mansoureh, We have been on a lot of cruises and have never been bored. The ports always have lots of options for activities. And there is lots to do on a ship. My bigger problem is taking downtime when I am cruising! I would suggest you try a cruise that has destinations that you might want to visit. The cruise would give you a taste test. Linda

  10. What an amazing itinerary! I just got back from a Western Caribbean cruise. It was my first, and I have nothing to compare it to. But getting to explore different ports, go snorkeling, and eat great food were some of the highlights — just like yours! Your underwater photos were beautiful; especially the shot of an octopus. So glad to hear that a Windstar cruise is well-recommended!

    • Tami, I am glad you enjoyed your Western Caribbean cruise. We did that a few years ago and loved the chance to see the Western side too. Amazing how many stops there are and how different they all are. Thanks for your comments on our underwater photos. We love to share the part of the world that many people don’t see. Watch for the coming blog that looks more at Windstar as a cruise line. Linda

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