Romantic Windstar Cruise — Celebrating a Milestone Anniversary Aboard Windstar’s Star Pride

Our Romantic Windstar Cruise

By Cele and Lynn Seldon

Thirty years of marriage is quite the milestone.

Fortunately, it’s been more joy than work and something we wanted to celebrate in a big way. Something filled with sunshine (we married in late-January in Richmond, Virginia!), warm weather, romantic walks along the beach, and sunsets.

After much consideration, we settled on the romance of a Caribbean cruise with Windstar Cruises.

Stunning St Lucia. * Photo: Windstar Cruises

Decisions, Decisions

A little background — we’re avid cruisers, with close to 100 cruises under our belts. And we’re seasoned travelers, with more than 30 years as full-time travel journalists.

So, it was going to be hard to come up with something unique.

We wanted something effortless, luxurious, little temptation for sightseeing, lots of beach time and Caribbean swimming, and destinations we hadn’t been to before.

After considering a South Africa cruise with Oceania, the luxuriousness of a Seabourn cruise in the Caribbean, and the all-out romance of one of Windstar’s majestic sailing vessels, we opted for a two-week sailing of the lovely Leewards aboard the spacious Star Pride, one of their newly stretched Star Class Plus all-suite motor yachts.

The anniversary couple in front of Star Pride on their romantic Windstar cruise. * Photo: Seldon Inc

Get a free quote for your dream cruise with CruiseCompete.

Our Romantic Windstar Cruise Aboard Star Pride

With capacity for only 312 passengers and suites that are a roomy 277 square feet, we thought a small ship and luxe accommodations would provide the perfect base for two weeks.

Of the 11 ports of call on the Caribbean itinerary — including many of the lesser-known islands that can only accommodate smaller ships, like Bequia, Guadeloupe, Monserrat, and Jost Van Dyke, all of which we anchored offshore and tendered to — we had never visited eight.

And so, the romance began.

Colors of the rainbow at The Baths on Virgin Gorda, BVI. * Photo: Seldon Ink

VIDEO: Cele shows us the view from the deck of Star Pride as she anchors off shore Jost Van Dyke.

Subscribe to our monthly small ship cruise email

Subscribe to QuirkyCruise.com for monthly curated newsletters highlighting our top small cruise ship reviews, round-ups & offers!

In the Beginning

With embarkation in San Juan, we opted to fly in early to get acclimated and get into the romantic mood with a stay at the Sheraton Old San Juan in the historic district, just across the street from the cruise port.

With a late checkout and a short stroll to the ship, embarkation was a breeze, with our luggage beating us to our cabin.

The anniversary couple started their anniversary cruising loving on San Juan, Puerto Rico. * Photo: Seldon Ink

Welcome to Our Suite on the Star Pride

Opening the door to our mid-level forward suite (Balcony Suite #510,) we took in the full expanse of the room.

With a king-sized bed (two twins pushed together) and full-length desk/vanity at the entrance, our eyes were immediately drawn to the wide and spacious living space beyond.

Featuring a full-sized sofa, coffee table, two club chairs with an occasional table and lamp in between, we felt right at home.

The tan whitewashed wood trim throughout and the updated taupe, blue and gray carpeting created a light and bright contemporary feel.

Many of the suites, including ours, feature French doors that open to a small balcony.

The Balcony Suite features a large living area with a French door balcony. * Photo: Seldon Ink.

There’s not enough room for furniture on the “balcony,” but it’s enough to step out and watch the sunrise or sunset, or the waves and island scenery floating by. It also allowed us to let the fresh air and sound of lapping waves fill the room.

Technology was featured in the suite in a big way, in the form of a 50-inch flat-screen television that included anything you’d need on a two-week cruise including: cruise itinerary; yacht’s location; weather; daily schedule and opening hours; restaurant hours and menus, including 24-hour room service; music, television, and on-demand movies; fitness class schedules; and more.

It was, by far, one of the most sophisticated information systems we’ve seen at sea.

Our bathroom was another stellar standout in our suite. Appropriately sized, it had double vanities and a floor-to-ceiling glass enclosed tile shower that could accommodate two (like we mentioned, we were looking for romance!).

Double vanities and a glass-enclosed tile shower were a bathroom luxury. * Photo: Seldon Ink

Although there was no bathtub, which one of us has an inexplicable affinity for, there were two spacious hot tubs on the ship — including one on Deck 5 forward, less than 100 feet from our cabin — that we enjoyed daily.

L’Occitane en Provence amenities and plush bathmats and towels were the bathroom cherries on top.

VIDEO: Cele shows us around their Star Pride Balcony Suite, below.

The Stretch of the Star Pride

These updated bathrooms were among the many enhancements that were part of Windstar’s $250-million Star Plus initiative, which transformed the three Pride Class ships purchased from Seabourn in 2019 to the new and improved Windstar Star Class ships.

In addition to new bathrooms in all suites, other enhancements that came about were an additional 50 suites in an 84-foot “stretch” of the ship; two new three-bedroom Owner’s Suites; two new restaurants; an elevated infinity pool and whirlpools, as well as expanded deck space; a reimagined and enlarged spa and fitness center; new engines and generators; and new tenders and tender loading areas.

An elevated infinity pool and whirlpool were part of the Star Class initiative . * Photo: Seldon Ink

Some of the other public spaces that weren’t part of the initiative seemed a bit dated like pillars in the show lounge that obstructed our view and hallways that were fairly antiseptic with little artwork or color and were often cluttered with cabin steward cleaning supplies and vacuums.

But overall, the enhancements outweighed those minor distractions in a big way.

Setting Sail on a Romantic Windstar Cruise

With a romantic evening sail-away from San Juan, past the somber lights of the majestic Castillo San Felipe del Morro, we were happy that we had opted for the “All-In” package.

Not only did we not have to think twice about spending more for that sail away cocktail — or almost any cocktail, beer, or wine, for that matter — but our “All-In” package also came with unlimited wi-fi and all shipboard gratuities.

And since we had opted for the two-week itinerary, laundry was also included.

We were starting to think that we might not have to pay for anything else during our anniversary celebration. Which certainly helped to set the mood.

RELATED: Anne Kalosh reports how the Windstar trio would be stretched.

RELATED: Dana Freeman reviews her Star Breeze cruise in the Caribbean.

Sailing Companions on our Romantic Windstar Cruise

Our fellow passengers were very much a like-minded group of active mid-60s to mid-70-year-old couples, making us feel at home.

Many were from the north and Midwest who were escaping the winter cold for a dose of Caribbean sunshine. The majority seemed to be Windstar loyalists and had chosen this particular cruise for the ship’s size or its itinerary, although we did come across several couples who were celebrating a milestone birthday or anniversary, as well as a couple of young couples on their honeymoon.

Chris and Floyd McKeag from Hilton Head Island, South Carolina (we were surprised by how many fellow South Carolinians were on board) were on their third Windstar sailing.

According to Chris, “Small ship sailing allows mooring in smaller ports. We especially like not arriving with the mega ships.”

Romantic Dining on Star Pride

To jump-start our celebration, we made a reservation for dinner at one of Star Pride’s newest restaurants, Cuadro 44 by Anthony Sasso.

Cuadro 44 by Anthony Sasso features a chef’s counter and community table. * Photo: Seldon Ink

Not just part of the Star Plus initiative, Cuadro 44 is also part of Windstar’s partnership with the James Beard Foundation.

The Spanish-inspired cuisine at Cuadro 44 by Anthony Sasso was a popular dining choice. * Photo: Seldon Ink

Created by James Beard Foundation-recognized chef, Anthony Sasso, with his 13-year career at the 10-time Michelin-starred restaurant Casa Mono, the intimate Spanish-inspired dining venue — including a convivial chef’s counter and community table — Cuadro 44 was a delicious way to start our romantic cruise.

The chef’s counter at Cuadro 44 by Anthony Sasso provides front row seats to all of the culinary action. * Photo: Seldon Ink

With a two-week cruise, there was plenty of time to experience all six complimentary dining options on Star Pride.

Although, occasionally, it was a challenge to get a reservation in the specialty dining rooms.

From breakfast in bed and lunch and a movie with 24-hour room service, to lavish brunches and lunches in the Veranda buffet overlooking the sparkling Caribbean waters, our other dining options included: international cuisine in the lush Murano-glass filled Amphora dining room

Amphora dining room features international dining and dishes by James Beard Foundation chefs. * Photo: Seldon Ink

James Beard Foundation chefs are featured nigthly in all dining venues. * Photo: Seldon Ink

We also enjoyed barbecued, smoked and rotisserie delicacies from the global grilling authority, Stephen Raichlen at the outdoor Star Grill — conveniently located adjacent to the Star Bar; romantic alfresco dining at Candles, featuring steaks, chops and more under the stars; and light bites and elevated coffee and tea concoctions throughout the day at Yacht Club Café.

The Star Grill at dinnertime. * Photo: Windstar Cruises

We are typically big fans of the main dining room experience. And, Amphora was no exception. We enjoyed the conviviality and din of the space, but as is typical in large dining rooms serving many at once, the meals were often a bit rushed.

The delicacies of Star Grill were tasty, with unique offerings like smoked wild game, rotisserie char siu pork and grilled fish and jerk chicken. However, with a personal preference for being served for dinner versus heading to the buffet, we generally found ourselves enjoying these offerings for lunch.

Star Grill features grilled, smoked and rotisserie dishes for lunch and dinner. * Photo: Windstar

Candles was a lovely alfresco way to offer a true steakhouse experience and we enjoyed their lamb chops, filet mignon, seafood spear trio of scallops, salmon and shrimp and bone-in Tomahawk veal chop on several visits.

The weather, however, was occasionally a challenge with winds and brief showers that had us taking cover in the indoor space. They also offered a unique gourmet salt trio at the table which screamed out for bread service, of which there was none.

Many others agreed with our assessment of the onboard dining.

“We found the food on the ship was excellent in all of the restaurants,” said McKeag. “The menus were consistently creative and oh-so-delicious.”

If the standard all-included dining wasn’t enough, Windstar took us on a magical culinary excursion with their once-per-week signature onboard barbecue.

With food and tables set on the pool decks and live entertainment brought in from the islands, we feasted on suckling pig, paella, lobster, and delectable island delicacies.

Freshly made paella was a highlight of the once-per-week signature onboard barbecue. * Photo: Seldon Ink

The once-per-week signature onboard barbecue was a highlight for us. * Photo: Seldon Ink

VIDEO: Below is a quick look at the deck BBQ fun!

Fun Once-a-Week Beach BBQ

We were also treated to a beach barbecue once per week where they brought everything — including the kitchen sink — to a stunning beach locale

Pigeon Island, St. Lucia, was the scene on our first week, with Prickly Pear National Park on Virgin Gorda, BVI playing host on our second week.

In both cases, we dined on grilled specialties and refreshing salads under thatched umbrellas, as with the sounds of steel drums wafted wafting by.

The beach barbecue was one of this anniversary couple’s favorite meals. * Photo: Cele Seldon

Water sports and toys, including snorkeling gear, kayaks, stand-up paddle boards, swimming noodles and more, along with the sparkling azure Caribbean waters were the perfect backdrop for dessert.

Complimentary water sports were available at the beach barbecue and off the watersports platform while anchored. * Photo: Seldon Ink

Romantic Windstar Cruise Sea Day

With our first full day being at sea, we took full advantage of the ship — sleeping in, room service breakfast, and taking in some sun overlooking the infinity pool and hot tub on the top deck filled the morning.

The infinity pool and whirlpool were popular with this anniversary couple. * Photo: Seldon Ink

Starting the cruise off right with a sea day filled with pool time and Bloody Marys. * Photo: Seldon Ink

We then enjoyed a cooking demonstration by the charming Executive Chef, Nilesh Kavinde, before enjoying an alfresco lunch at Star Grill.

The afternoon was full of romance as we took our first-ever merengue dancing lesson from the Entertainment Manager, Sin (is there anything more romantic than dancing with your soulmate?), watching an on-demand movie with a bottle of champagne in our cabin.

Then we enjoyed a romantic dinner for two in Amphora, including the tasty salmon dish that the chef demonstrated earlier in the day, duck a l’orange, and a magnificent bittersweet chocolate soufflé for a shared dessert.

Life on Star Pride

With the rest of our itinerary generally featuring small Caribbean ports of call (the small size of Windstar ships allows for more out-of-the-way destinations and quieter ports than the mega liners), we quickly got into a groove.

Breakfast in the cabin or in the Veranda, catching up on some work in the Yacht Club (the recently upgraded high-speed Starlink internet access provided some of the fastest internet we’ve seen at sea), working out in the fitness center, or enjoying a spa treatment (Lynn loved his 90-minute bamboo massage while Cele tried to erase a few years with a penetrating facial) provided many morning options when we didn’t book a shore excursion.

The Yacht Club was a great spot to curl up with a book or enjoy a light bite and hot beverage. * Photo: Seldon Ink

Shore Excursions on our Caribbean Windstar Cruise

We did, however, take advantage of several shore excursions.

In St. Lucia, we opted for a five-hour catamaran cruise to the Pitons. Passing many fishing villages along the coast, we were awed by the stunning views of the Petit and Gros Pitons rising majestically over 2,600 feet above the sea.

Then in St. Thomas, we set sail on a champagne catamaran tour to St. John National Park — the site of our honeymoon 30 years ago (almost to the day). Along with snorkeling in the pristine waters of the U.S. Virgin Islands, champagne toasts and many photo opps, it was the perfect way to celebrate.

The happy couple aboard the Adventuress catamaran in St. John National Park, USVI (the site of their honeymoon 30 years ago!). * Photo: Seldon Ink

And no trip to Virgin Gorda, BVI is complete without a visit to The Baths National Park. The massive granite boulders, powdery white sand and crystal-clear waters of the Caribbean gives romance a new meaning and was a highlight of our trip.

The caves of The Baths in Virgin Gorda, BVI was the perfect background for an anniversary photo. * Photo: Seldon Ink

On days when we didn’t go on a shore excursion, we’d enjoy lunch onboard and then head onto whatever magical island we were visiting, for a walkabout, some time at the beach, or a hike to varied forts and attractions.

VIDEO: Another day in paradise, below see the view from the decks of Star Pride off-shore Jost Van Dyke.

Whether a walk on the beach and swim in Bequia; a hike up to Fort Napolean in Les Saintes, Guadeloupe; an anniversary lunch in St. Barth’s; or a bite-off-more-than-we-can-chew hike to Foxy’s Taboo in Jost Van Dyke, BVI, it was always a welcome adventure at our own pace.

The anniversary couple toasting to 30 years at Joel Robuchon in St. Barth’s on their anniversary. * Photo: Seldon Ink

Romantic Evenings on a Windstar Cruise Were Habit Forming

Early evenings were often filled with cocktail hour while listening to trivia or Name That Tune at Star Bar (where there was always a raucous crowd competing bellied up to the bar) or trying out our newly learned dance moves on the dance floor in the Compass Rose lounge — typically highlighted by another magical sunset — followed by a romantic dinner in one of the varied venues.

We did find the entertainment options a bit lacking. There were two options all day every day — either a duo singing themed cover tunes or a four-piece band with vocalist also playing cover tunes, also often themed like Beatles night, music of the 60s, 70s or 80s, and Love Songs. We would have loved another option of classical music or jazz, but we usually found another couple or two to chat with most evenings, or simply got lost in our own thoughts.

After dinner, we often enjoyed a nightcap on the open deck, listened to music in the lounge, watched the crew talent show (we laughed until we cried at the synchronized swimming routine), watched a movie in our suite, or, well, need we say more.

We were celebrating our anniversary after all.

Sunsets were magical from the deck of the Star Pride. * Photo: Seldon Ink

Romantic Windstar Cruise Facts

The Lovely Leewards 14-night itinerary is actually two one-week cruises taken back-to-back.

Starting in San Juan, Puerto Rico, the ship visits:

• St. George’s Grenada (berth)
• Bequia (anchor)
• Pigeon Island, St. Lucia (anchor)
• Les Saintes, Guadeloupe (anchor)
• Phillipsburg, St. Maarten (berth)
• San Juan, Puerto Rico (berth)
• Charlotte Amalie, St. Thomas (berth)
• Gustavia, St. Barts (anchor)
• Little Bay, Monserrat (anchor)
• Phillipsburg, St. Maarten (berth)
• Great Harbour, Jost Van Dyke, BVI (anchor)
• Virgin Gorda, BVI (anchor)
• San Juan, Puerto Rico (berth)

The Star Pride’s watersports marina at the stern can be used in many Caribbean ports where there is a safe anchorage. * Photo: Windstar Cruises

Interested in This Romantic Windstar Cruise?

Our cruise was called “Star Collector: Lovely Leewards,” and cruise-only fares start at $4,799 per person and all-inclusive fares start at $5,956 per person (and include open-bar, tips and WiFi).

For cruise-only fares, Internet is not included in the fares, with three options available:

• $60 (for a basic email plan, with 200 MB of data)
• $120 (for the surfing plan, with 500 MB of data)
• $490 (for unlimited Internet access on a 14-night cruise)

Here’s a link to Windstar’s various onboard WifI packages and gifts.

And click HERE for more info on booking this cruise.

Don’t miss a post about small-ship cruising, subscribe to QuirkyCruise.com for monthly updates & special offers!  

© This article is protected by copyright, no part may be reproduced by any process without written permission from the author. All Rights Reserved. QuirkyCruise.com.