Island Hopping in the Caribbean with Windstar

Can a Type A travel writer with mega FOMO find happiness on a small cruise ship like Windstar?

As a former New Yorker living just two blocks from the Manhattan Cruise Terminal and Floridian with ports in every direction, I’ve experienced a handful of the larger cruise lines in my day. And you know what? I liked them all. I like having a packed schedule of crazy fun adventures. I like flashy shows and karaoke and sunrise yoga and scavenger hunts. I like pushing my limits, burning the candle at both ends and trying new things.

At least… that’s what I’ve always liked in the past.

Check out our Windstar Cruise experience!


When we booked our Windstar cruise, I was curious what it would be like to cruise on a 212-passenger ship that looks like a Barbie boat next to some of the modern sailing marvels. Limited space means there’s no Broadway shows or trapeze lessons or rock climbing. There’s only one tiny pool and two wee hot tubs, a couple of bars/lounges and two restaurants. Where most cruise lines are shooting the moon to go bigger and more grandiose every year, Windstar has remained small and cozy, focusing on its James Beard cuisine program and unique, small ports of call.

That’s not to say there’s nothing to do, but there’s just not 7,409 things to do every 15 minutes. 


We arrived on a super early flight to our port of embarkation, lovely San Juan, Puerto Rico. Rick and I did not account for this day of pre-cruise exploration, so by the time we boarded, we were sweating and sunburned like first time travelers. We walked 10 miles (literally!) around Old San Juan, from forts to parks to diners to museums. You almost wouldn’t know that the island was still feeling the effects of Hurricane Maria, because the colorful area around the cruise terminal has bounced back so quickly.

The eager and friendly Windstar staff waiting to welcome us were a sight for sore eyes (and feet!) and we were whisked away within a few minutes from check-in to our suite.


Our Suite

You know how once you fly First Class, it’s really hard to go back to Coach? That’s how I feel about our home onboard the Star Pride. Rick and I were in one of four Classic Suites. Ours was midship on Deck 6, with ample living and dining space, closets for days, a roomy balcony (tucked rather unceremoniously under a lifeboat) and a full-sized shower. I could’ve fit the rest of our immediate family in our suite and still had room. I’m not sure I could ever book an interior stateroom ever again.



What Makes Windstar Special

That Vibe Though

The most intriguing thing about the Star Pride was also the hardest to quantify for me, because honestly, how do you capture the feeling of a sailing? Everyone was just so… chill. So mellow. So unfrazzled. No one rushed around to get anywhere. There were no pushy folks at the buffets or elbows being thrown to get to the lobster station at the deck party. 

While Windstar’s price point is premium, the experience is much more laidback than you might expect. Not only are there no formal nights, there didn’t seem to be too many formal people. Rick, who chafes if I request he wear a shirt with buttons, was in his element. And frankly it was nice to not have to worry about packing gowns and shoes and jackets and whatnot. 


In just a day or two, it seemed like we were on a first name basis with the staff and the passengers — and we aren’t always the go-out-and-make-friends-with-strangers-types. Unlike some of the ships I’ve sailed on, the Star Pride was definitely not an all-night party ship. If you’ve ever accidentally booked one of the large ships during Spring Break, you know what I mean. Things can get cray-cray real fast.  

On the Star Pride, everyone seemed to be having a whale of a time in pleasant moderation.


Watersports Platform

I’ve never had the opportunity to step off the ship into the sea before until the Star Pride. After our time exploring Martinique, we dropped our stuff in the cubbies and dove right in, frolicking on the water trampoline, chasing down wayward noodles and getting to know our fellow passengers. This feature is unique to the smaller cruise ships of the world, and it’s one of my favorite amenities. 


The Warmest Staff

Wilhelm, Marius, Hubert, Tigi, Sin City, Dian, Mark Anthony and Arnel were just a few of the folks who made a lasting impression on us. Months later, we are still laughing about Tigi’s one-liners, marveling over how Wilhelm went above and beyond to make sure we had candy for our movie night and reliving via iPhone video the line dance party everyone talked about all week. 


Small Ship, Small Ports

There are benefits to sailing on a small ship that I didn’t even consider beforehand. Taking the tender to and from shore was a piece of cake. There were never any lines or crowds. I can’t say I’ve ever had an easier time in port than with the Star Pride.


And the ports we visited were often just for us. This wasn’t a trip to Nassau with 10,000+ other daily cruise passengers. In St. Lucia, we were the only ship in the bay, and we had a catered beach party on a private slice of beach. In Montserrat, we were the only ship in port. It felt like we had the place to ourselves. That’s such a rarity in cruise ports!


Daily Sail Away Ceremony & Open Bridge Policy 

On the first day as we sailed from San Juan, the staff hoisted the Windstar flag above the pool/bar area with pomp and circumstance and an evocative soundtrack. Think Game of Thrones meets the Russian Navy meets Pirates of the Caribbean. (It’s actually from Greek composer Vangelis’ 1492: Conquest to Paradise album. Yes, we listen to it at home now at pool parties.) It was curious to watch on the first day, but by the end, everyone was into it. After a few days, it became a real group moment at the Star Bar that everyone looked forward to. It’s funny how quickly we all felt like seafaring family.

Windstar Cruises is one of the only lines with an open bridge policy. For the majority of time at sea, you can pop in to the bridge to meet the captain and crew. Rick is a true Long Islander with a long history on the sea, so he had lots of smart questions for the captain about aft and stern and knots and whatnot. I just wanted to know all the juicy gossip and stories about the wackiest passengers and weirdest occurrences at sea.

Destination Discovery Event

Each sailing, guests are treated to a special event somewhere along the way. Ours was a spectacularly catered Caribbean beach party in St. Lucia. We did a snuba excursion early, and then made our way to cozy, shaded lounge chairs where we sipped coconutty drinks and waded in crystal clear water. I didn’t expect to be back in St. Lucia so soon, but I’m not complaining!


Limited Kids

Kids are wonderful and I love them. Now that we all know I’m not a kid-hater, can I say just how wonderful it was to have a limited number of them onboard? There are no kids activities whatsoever, so those who do sail with Windstar are every bit as mellow and unflappable as the other passengers. Low key, self-sustaining kiddos over 7 who don’t need a lot of packaged entertainment do well here. We met the handful of youngsters throughout the week and they were awesome. 


Mishaps and Room for Improvement

If you’re a human being*, you probably already know it’s impossible for everything to go well 100% of the time. There’s not much you can do but roll with the punches on those days. And no matter how far you run from the dramas of home, you’ll find them abroad eventually if you travel long enough.

*If you’re not a human being, I have some questions for you.

I woke up sweating around 3 a.m. on the second night of our journey, somewhere between Martinique and St. Lucia. There was no power in our stateroom, so I opened the door to our balcony and let a bit of sea breeze in. At breakfast, we learned the ship was having issues with one of the power sources onboard, but expected it to be sorted out quickly. Over the next couple of days, the power was on and off, affecting the dining room schedule and the air conditioning. The captain kept passengers updated with frequent audio announcements and occasional paper updates in the rooms, but no sooner did the air conditioning start working again than the generator would fizzle and they’d have to start all over. The captain altered the itinerary so we could dock in Castries, St. Lucia, to await technicians to fly in. Ultimately we missed our day in Guadeloupe so they could make sure it was safe to carry on. 


There’s something to be said for the way a brand approaches unexpected mechanical issues like these, and Windstar did a pretty good job of keeping passengers informed and ultimately compensated. Onboard credits were offered, as were free drinks for the duration of the journey.

While I did shell out for quite a few expenses, our cabin was complimentary for this journey, so realistically I was probably less frustrated with the power situation than someone who’d perhaps paid full price. I was more stressed about the WiFi being out than anything else, because I can’t work if I can’t be online! It worked often enough that I was able to keep things afloat, so to speak.

To be frank, I was shocked at how many of our fellow passengers found the generator issues to be a fun and novel part of a travel adventure vs. a major inconvenience. I was surprised at how cavalier folks were about the mishaps, and it definitely got me thinking about how travel gives you perspective on life’s speed bumps.

Can you still have a good time if things aren’t perfect? And what does that say about you as a traveler and a person?

Short of packing up and flying home from the next port, there was not much we could do about the issues with the generator. But we were safe, well-fed and in the Caribbean for goodness sake, so there was little point in throwing a hissy. We had the drink of the day and a balcony to sleep on when the room got too warm.


That said, with the mechanical issues in play, I’m not sure we got the full Windstar experience. A taste of the yacht life was enough to convince us to try this one again in the future – ideally on one of the three ships with the gorgeous sails. Yes, we were hot and uncomfortable at times, but the pleasant attitude from the staff (who I imagine were stressed and sweaty as well) spread to all the passengers. The free rum helped, too.

I’m a big fan of folks who can make the best of things even when they’re all wrong. They make the best travelers, the best friends and the best staff. The Star Pride was full of these kinds of folks.


After a little introspection, it occurred to me that as much fun as I’ve had on cruises in the past, I do often feel like I’ve been dragged behind a truck afterward. And this is mostly my fault! There are always going to be relaxing options, like sitting by the pool or spending a day at the spa. But when I’m presented with an all-you-can-handle menu of activities from ice skating to go karting to line dancing, my FOMO kicks in and I want to do it all.

Windstar’s purposefully minimal activity schedule (and unscheduled mechanical mishaps) meant I had to slow my frenetic pace. It was hard to do at first, but by the end I had an idea of what a vacation might be like for people with an OFF switch.

Life onboard a smaller ship meant we spent more time just existing with my guy – watching the flying fish in the ship’s wake, searching for telltale signs of whales on the horizon and making friends in the pool. We didn’t spend any time deliberating over if we should go to the towel animal demonstration or the hairy chest contest or bingo. We just existed.

Maybe that’s what a real vacation is all about. 

I’ll share more about our itinerary and our favorite ports of call in a future post. In the meantime, tell me about your favorite cruise line. Do you prefer large ships with lots of activities or smaller ones with more relaxed itineraries?


As I mentioned, Windstar hosted us on this sailing. This post, as always, reflects my personal experience and opinions. 

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Tired of crowed cruise ships full of teenagers? Windstar cruises might be perfect for you. Check out my Windstar Cruise review, here! It's definitely for those who are looking for a relaxing, laid back experience. Enjoy!

Tired of crowed cruise ships full of teenagers? Windstar cruises might be perfect for you. Check out my Windstar Cruise review, here! It's definitely for those who are looking for a relaxing, laid back experience. Enjoy!

5 thoughts on “Island Hopping in the Caribbean with Windstar”

  1. Sounds like a wonderful experience. I think I’d prefer this type of cruise compared to the larger, flashier ones.

  2. I read and enjoyed your blog about the Windstar Star Pride Caribbean cruise.I was hoping you would include the average prices of the cocktails, beer, etc. you mentioned free rum when things went awry but can you tell us the price of their drinks for purchase? We are not interested in packaged beverage costs. Thanks.

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