Planning a Caribbean cruise? Here is our full review of the Windstar Cruises 7 day Caribbean itinerary aboard the Star Pride. We snorkeled at Trunk Bay in St Johns USVI, explored The Baths on Virgin Gorda, and also visited St. Barts, St. Maarten, St. Kitts, and Jost Van Dyke, and ended with a private island beach BBQ.
There are vacations that are fun, and and then there are trips that shift the way you think about travel entirely. Our week onboard the Star Pride with Windstar Cruises was the second kind. It offered the perfect balance of relaxation, adventure, and small ship luxury, set against some of the most beautiful islands in the Caribbean.
As full-time travelers, we have experienced everything from driving a campervan across Australia to boutique hotels, but Windstar Cruises introduced us to a completely new style of travel: yacht style cruising that feels intimate, calm, and intentionally designed for people who want more connection and less chaos. Here is our full, honest review of our Windstar Caribbean cruise, including everything we loved about the ship, the ports, the excursions, and the unforgettable moments that made this one of our favorite trips of the year.
Why Windstar Cruises Really Is 180 Degrees From Ordinary
We had heard Windstar Cruises described as “180 degrees from ordinary,” but the meaning did not fully click until we were onboard the Star Pride. This ship carries a maximum of about 312 guests, but on our sailing there were only around 220 guests and nearly 150 crew members. That ratio alone creates a totally different energy.
From the moment we stepped on board, the atmosphere felt calm, spacious, and personal. There were no crowds, no lines, and no noise. It felt like we had walked onto a chic but understated private yacht that we were sharing with a small group of like-minded travelers.
Throughout the week, we noticed how many things set Windstar Cruises apart. The peaceful atmosphere meant there was always space to relax. Personalized service made the entire experience warm and thoughtful. The ship’s small size allowed us to dock in intimate harbors that large cruise ships cannot access. And the entire guest experience felt curated, intentional, and never rushed.
If big cruise ships overwhelm you, Windstar Cruises is the exact opposite experience. We genuinely felt like guests, not numbers.
Our First Moments On Board Windstar Cruises Star Pride
Embarkation day in San Juan, Puerto Rico was the first clue that this trip was going to be something special. There was no crowded terminal, no long check-in line, and no frantic energy. We walked up to the ship, checked in within minutes, and were immediately greeted by friendly crew members offering chilled drinks.
Inside, the ship felt warm and elegant in a way that encourages you to slow down. There is a beautiful simplicity to Windstar’s design with soft lighting, natural textures, cozy lounges with ocean views, and an atmosphere that feels more like a boutique hotel than a traditional cruise ship.
As we explored the ship, we quickly discovered lounging areas, cozy seating nooks, and quiet outdoor decks perfect for sunrise coffee or sunset drinks. Within a few hours, we already felt comfortable navigating the ship and had chosen our favorite spots.
Our Windstar Cruise Suite: A Cozy, Spacious Home at Sea
When we opened the door to our suite, our jaws honestly dropped. The Star Pride is an all suite yacht, which means every room on the ship is more spacious than a standard cruise cabin.
Our suite included a comfortable living room area, a large bed with luxe linens, plenty of storage in our walk-in closet, a bright modern bathroom with a double vanity and spacious shower, and double doors opening onto our small balcony framing endless Caribbean blue. Every morning became a ritual of waking up slowly and watching the sunrise glow across the water as we cruised towards a new island paradise. It is one of the things we miss most now that we are off the ship.
From the very first day, the crew made us feel welcome. With only 220 guests on board, everyone had the time to offer individual attention. It felt like joining a well run household where the staff genuinely enjoyed taking care of their guests. By the end of day one, we already felt at home.
Life On Board Windstar Cruises: Quiet Luxury and Real Comfort
The most unexpected part of the cruise was how restful it felt. There were no loud announcements, no overcrowded pool decks, and no pressure to pack every moment with activities. Instead, life onboard unfolded at a gentle, easy pace.
We spent days lounging by the pool, reading on quiet decks, sipping mocktails at sunset, and soaking in the hot tub while watching the islands drift by. The ship never felt busy, even at midday.
Service remained exceptional throughout the entire sailing. Crew members remembered our names by day two and greeted us like friends. Bartenders knew our favorite drinks, and servers always made sure we had everything we needed. It felt personal without ever being intrusive.
Star Pride also offers wonderful amenities including a gym with ocean views, a spa with a sauna and relaxation rooms, an infinity style pool, hot tubs, a water sports platform, and multiple bars and lounges. Some days we enjoyed long stretches of reading or sunbathing. Other days we went from a morning workout to a spa session to an afternoon nap by the pool. The balance of activity and rest was perfect.
Dining on Star Pride: Fresh, Relaxed, and Incredibly Memorable
Dining on the Star Pride quickly became one of our favorite parts of the cruise. Windstar Cruises takes a relaxed but elevated approach to food, and every meal felt intentionally prepared without being overly formal. We loved starting our days with slow breakfasts overlooking the water, sampling fresh seafood at lunch, and enjoying beautifully plated dinners as the sun dipped behind the Caribbean horizon. The atmosphere was always calm and unhurried, and we never once waited for a table.
One of the most romantic moments of our entire trip was the morning we ordered room service breakfast and enjoyed it in our robes. The crew delivered a gorgeous spread of fruit, pastries, and made-to-order dishes right to our suite. We ate beside our large balcony as the ship glided across turquoise water, and it felt like the perfect embodiment of small ship luxury: peaceful, private, and completely unrushed.
Evenings onboard were especially memorable. Some nights we chose a cozy indoor dinner with sea views, and other nights we dined under the stars at the Star Bar with warm breezes and soft candlelight. The menus were creative and often reflected the flavors of the Caribbean, and every dish felt fresh and thoughtfully prepared. It was the kind of dining experience that made each evening feel special without requiring anything more than a comfortable outfit and a good appetite.
Service elevated everything. The staff quickly learned our preferences, made thoughtful recommendations, and consistently went above and beyond to make each meal enjoyable. Whether we were grabbing a casual poolside lunch, savoring a romantic dinner, or indulging in dessert that we technically didn’t have room for, every dining moment with Windstar felt like a highlight of the day.
Our Caribbean Itinerary with Windstar Cruises: Beautiful Islands and Unforgettable Excursions
One of the biggest perks of sailing with Windstar Cruises is the ability to visit smaller, more intimate ports that large cruise ships cannot reach. Here is a look at our itinerary and the excursions we experienced along the way.
St. John, USVI: Snorkeling at Trunk Bay
This day was one of the highlights of our entire week. We joined a Windstar Cruises excursion to Trunk Bay, which is known as one of the most beautiful beaches in the Caribbean. The water is crystal clear and turquoise, and the snorkeling was incredible. We spent the morning swimming above coral reefs, spotting colorful fish, and floating in warm, calm water. It was the perfect blend of adventure and relaxation.
St. Barts: Pure French Caribbean Elegance
St. Barts felt like stepping into a postcard. The island has a glamorous, French influenced energy that makes even a simple walk feel special. After tendering ashore, we spent a little time exploring the marina area, wandering through boutiques, and enjoying the upscale but relaxed vibe of Gustavia.
After some light shopping, we headed to Shell Beach, one of the island’s most famous beaches known for its soft, crushed-shell shoreline and stunning turquoise water. It is an easy walk from town, and the scenery alone is worth the visit.
We spent the rest of the afternoon at Shellona Beach Club, which instantly became one of our favorite spots of the entire cruise. The atmosphere was dreamy and chic with comfy loungers, great music, and warm Caribbean breezes. We ordered a couple of drinks, relaxed in the shade, and enjoyed incredible views of the bay. It was the perfect combination of luxury and laid back island living, and we could have stayed there for hours.
St. Barts ended up being one of the islands we said, “We have to come back here someday,” and a big part of that was the perfect, relaxing beach day at Shell Beach and Shellona.
St. Maarten: A Classic Caribbean Day
St. Maarten ended up being one of our most surprising and memorable days because we packed in two totally different but equally fun experiences. We started the morning at the island’s most famous (and most thrilling) spot: Maho Beach, where planes land just a few feet overhead. And yes, it is just as wild in person as it looks on the internet.
We timed our visit perfectly and got to watch a Boeing 737 fly directly over us as it descended toward the runway. The sound, the wind, the energy: it is an experience you truly cannot get anywhere else, and we were buzzing for a good hour afterward.
After our aviation adrenaline rush, we crossed to the French side of the island for a totally different vibe and spent the rest of the afternoon relaxing at Orient Beach. This area feels quieter, more refined, and beautifully European. The beach is long and wide with soft sand, gentle waves, and plenty of space to stretch out.
We had a leisurely beach day, enjoyed the warm water, and soaked up the sunshine before heading back to the ship. It was the perfect balance of excitement and relaxation, and one of our favorite days of the entire itinerary.
St. Kitts: Lush Landscapes and Island Charm
St. Kitts was one of those islands that immediately pulls you in with its dramatic scenery. As we approached the port, we were surrounded by lush green mountains, rolling hills, and bright blue water. It felt like we were sailing straight into a tropical postcard.
We spent the morning exploring a bit of the island’s history and coastline, taking in viewpoints that seemed to stretch on forever. St. Kitts has this beautiful mix of Caribbean charm and quiet natural beauty. Even a simple drive offers spectacular moments, with palm trees swaying over old stone walls, colorful island homes along the roads, and mountain peaks rising sharply in the distance.
After our exploring, we wandered near the port, browsed a few local shops, and enjoyed the easy pace of island life. But what we loved most about this day was actually choosing to return to the ship early. One of the biggest perks of small ship cruising is how enjoyable the onboard experience is, and we wanted to savor more of it.
We headed back to the Star Pride in the early afternoon and enjoyed a peaceful stretch of quiet ship time. We swam in the pool, soaked in the hot tub, and spent a long, relaxing session in the spa’s sauna and relaxation area. With so many guests still ashore, it felt like we had the ship almost entirely to ourselves. It was the perfect midweek reset and one of those simple, blissful vacation moments that we still talk about.
St. Kitts offered the perfect blend of adventure ashore and serenity onboard, and it ended up being one of the most balanced and memorable days of our cruise.
Jost Van Dyke: The Perfect Beach Day
Jost Van Dyke was one of those quintessential Caribbean days that felt like a tropical dream from start to finish. As soon as we arrived, the water looked almost unreal, with bright turquoise stretching out in every direction and soft white sand lining the entire shore.
We took the tender in and headed straight to the island’s most legendary spot: the Soggy Dollar Bar. This beach bar is famous for inventing the Painkiller cocktail, and for its fun, easygoing atmosphere where people swim up from their sailboats, dry off in the sun, and stay for hours without realizing how much time has passed.
We grabbed a couple of diet cokes, found a shady spot near the water, and spent the day swimming, relaxing, and soaking up the lively beach vibe. Between the music, the laughter, the warm water, and the postcard-perfect scenery, it was impossible not to fall completely in love with this island.
What we loved most about Jost Van Dyke was how carefree it felt. No agenda, no rush, no pressure to do anything except enjoy the moment. It was the kind of beach day that you replay in your mind long after the trip is over, and it perfectly captured the magic of Caribbean island life.
Virgin Gorda: The Baths
Virgin Gorda was a day we had been looking forward to since the moment we booked this cruise, and it completely exceeded every expectation. The Baths are one of the most iconic natural wonders in the Caribbean, and seeing them in person was truly breathtaking. Even the tender ride toward shore felt special, with the granite boulder formations slowly coming into view as we approached the island.
The excursion began with a scenic drive across Virgin Gorda, which gave us beautiful views of the island’s hills, coastline, and quiet residential areas. Everything felt lush and peaceful, a perfect warm-up to what was waiting for us at The Baths.
After checking in with our guide, we made our way down the path toward the beach. The moment the giant granite boulders appeared between the trees, we both said, “Oh wow.” Photos simply do not prepare you for how massive and majestic they are in real life.
Our tour led us through the famous trail of twisting pathways, narrow rock passages, and shallow tidal pools that make The Baths so unforgettable. At times, we were climbing over boulders; other times we were ducking under them or holding onto ropes as we navigated natural rock slides and sandy ledges. The light streamed in through cracks in the rocks, creating glowing blue pools and shafts of golden sunlight. It felt like being inside a natural cathedral carved by the sea.
Every turn brought a new moment that made us stop, look at each other, and say, “Can you believe this?” The mix of adventure and beauty made the whole experience feel like we were exploring a hidden world.
The trail eventually opened onto Devil’s Bay, a stunning cove surrounded by smooth boulders and impossibly clear water. We spent time swimming, relaxing on the soft sand, and soaking in the scenery. The water was calm and warm, and the entire bay had this serene, untouched quality that made it hard to leave.
One of the things we loved most about going with Windstar Cruises’s excursion was the pacing. We never felt rushed, and the group size was small enough that we could take our time, explore at our own speed, and enjoy moments without crowds pressing behind us. Our guide was knowledgeable and patient, pointing out unique rock formations, explaining the geology, and giving us time to fully experience it.
Visiting The Baths was easily one of the most memorable parts of the entire cruise. It had the perfect blend of adventure, beauty, and peaceful Caribbean charm, and it is an absolute must if you sail this itinerary. When we think back on our favorite travel moments of this cruise, this day will be at the top of the list.
Windstar’s Signature Beach BBQ
As if exploring The Baths were not magical enough, Windstar Cruises somehow managed to make the day even better. After our tour wrapped up and we returned to the tender pier, the crew transported us to a quiet stretch of beach on Virgin Gorda for Windstar’s signature private island beach BBQ.It was the perfect transition from adventure to relaxation.
The moment we stepped onto the sand, we could feel the fun, laid back energy. The crew had transformed the beachfront into a beautiful island gathering spot, complete with shaded tables, grilling stations, colorful umbrellas, and music floating through the breeze. There was a festive atmosphere without feeling crowded or overwhelming, and everything was done with the same thoughtful Windstar touch we had seen all week.
The food was incredible. The crew grilled fresh seafood, chicken, hamburgers, and island inspired dishes, and there was a full spread of salads, fruit, sides, and desserts. After climbing through the boulders at The Baths, sitting under the shade of a palm tree with a plate of delicious food and a cold drink felt like pure bliss.
We spent the afternoon swimming, relaxing on the sand, and enjoying the warm Caribbean water. Guests from our ship floated on pool noodles, snorkeled in the shallows, or lounged in beach chairs while the crew checked in to make sure everyone was happy and hydrated. It had the relaxed, unhurried feeling of a private island picnic with friends.
What made the BBQ even better was how smoothly the entire day flowed. The timing of The Baths excursion followed by a beach party created one of the most memorable days of the whole cruise. It truly embodied what we loved most about Windstar: a perfect blend of adventure, comfort, beauty, and thoughtful experiences that never feel rushed.
Who Would Love This Windstar Cruise
This Windstar Cruises Caribbean itinerary is ideal for travelers who love a peaceful, uncrowded onboard experience, personalized service, beautiful ports, and a blend of relaxation and soft adventure. It is especially perfect for empty nesters, honeymooners, couples seeking a romantic getaway, and anyone who prefers boutique style travel over mega ship chaos.
By the end of our week aboard the Star Pride, we felt rested, inspired, and already planning when we could sail with Windstar again. This cruise reminded us how special slow, intentional travel can feel. Windstar delivered on everything it promised, and this itinerary remains one of our favorite trips to date.
If you have questions about our sailing or want help planning your own Windstar adventure, feel free to message us on Instagram @jetsetpetersons. And if you want to save on flights for your next Caribbean trip, check out our flight deal service at JetsetClub.co.
