Review of Windstar Cruises: What it's like cruisin' the Caribbean

Review of Windstar Cruises: What to expect while cruisin’ the Caribbean

The hot Caribbean sun warmed my skin as I stood on our suite’s spacious balcony aboard Windstar Cruises’ gleaming Star Pride, the ocean breeze fanning the white sails of the boats gliding by below.

Across the gem-toned water a mosaic of tiled, orange roofs was framed by rolling green hills dotted with palm trees, a hallmark of postcard-perfect Terre-de-Haut island which is part of Guadeloupe’s Îles des Saintes.

Noticeably absent from this idyllic scene: any other cruise ships, guaranteeing that our group of just 204 passengers would have the island mostly to ourselves that day–an advantage of small ship cruising.

Review of Windstar Cruises
Looking out at Terre-de-Haut, Guadeloupe

Moments like this are the Windstar difference: the opportunity to dock in remote harbours which are inaccessible to most vessels, visit off-the-beaten-path destinations, enjoy elevated experiences like fine dining, curated wine lists and luxe amenities, then cap off the day with a front row seat to mesmerizing sunsets as you sail off to a new port to enjoy it all over again tomorrow.

From what to expect onboard to helpful tips for organizing your own trip, here’s everything you need to know about the sailing experience and my honest review of Windstar Cruises.

Globe Guide note: This Windstar review is based on my personal experience which is quite varied; this was my eighth cruise, and I’ve done everything from tiny sailboats to river cruises, expedition ships and ocean liners in South America, the Caribbean and Europe. As always, hosts have no editorial influence on articles.

Windstar Cruises itineraries

The carefully-crafted itineraries are what initially sold me on booking with Windstar Cruises.

I love the idea of waking up in a new country every day and only having to unpack once, but as someone who gets seasick easily boats can be tricky–especially if three full days of a weeklong trip are spent at sea which is common with larger cruise lines who like to keep passengers on board so they’ll spend money at bars and casinos.

Old San Juan, Puerto Rico

Instead, Windstar focuses on the destinations which means more time in each port so guests can actually spend time exploring each country, even staying as late as 10 p.m. in some spots.

We only spent one day at sea during our Caribbean voyage, which meant getting to see six new countries…and way less seasickness.

Getting to watch sunset in St. George’s, Grenada since the yacht didn’t leave until 10 pm
San Juan, Puerto Rico

Windstar’s yachts only hold 148-342 passengers which allows for a much more intimate experience where you’ll get to know other guests and staff, and ships are able to dock in or anchor near ports that almost no one else can thanks to their compact size.

No large boats can dock in Terre-de-Haut, Guadeloupe

While Windstar Cruises specializes in the South Pacific and sails pretty much everywhere except Antarctica, I was wowed by the options for their Caribbean cruises which offer stops most other cruise lines don’t and are tough to get to otherwise: think St. Barth’s, Les Saintes in Guadeloupe, and charming Bequia in St. Vincent and the Grenadines.

We opted for the one-week Windward Islands Surf & Sunsets itinerary, which pairs nicely with the San Juan & The Virgin Islands itinerary for those with extra time (the two week trip is called Lovely Leewards, and looks incredible!)

Terre-de-Haut, Guadeloupe

Amenities on Windstar Star Pride

Windstar Cruises has six yachts in their fleet, including the newly stretched and refurbished Star Pride which we travelled on.

Three of them are sail-powered, and the romantic, serene experience of quietly sailing past remote islets in far-flung destinations helped it rank as the world’s best midsize-ship ocean cruise line.

Star Pride guests enjoy all-inclusive dining at the five restaurants, and there’s also a cafe in the Yacht Club which is a great place to curl up with a coffee and watch sunrise through the panoramic windows, or relax with a glass of wine and a puzzle in the evening.

The Yacht Club on Star Pride
The Yacht ClubThe Yacht Club

The expansive pool deck has a jacuzzi, small infinity pool and plenty of sun loungers, and there’s another whirlpool on the fifth floor at the bow of the boat.

A modern gym and spa area are on the seventh floor, and along with treatments like massages, body wraps and facials there’s a steam room and sauna that all guests are free to use.

The gym on Star Pride
The gym

Multiple bars, a boutique, reception area, screening room and lounge round out the amenities on Star Pride, and in certain ports a watersports platform is rolled out for guests to enjoy complimentary activities like snorkeling, kayaking, SUPs and a water trampoline.

The spa

Review of Windstar Cruises rooms

I knew this trip was going to impress as soon as I saw our room.

We were in an Ocean View Suite, and despite it being one of the ‘smaller’ ones it still had a comfortable queen size bed (which can be split into two twins), desk, and a completely separate sitting area complete with a large window, minibar, TV and storage.

An Ocean View suite on Star Pride
An Ocean View suite on Star Pride

At 277 square feet it was larger than most cabins I’ve had on other ships, not to mention the extra perks you don’t usually see: a full walk-in closet, and a modern bathroom with two sinks, a full bathtub and cushy bath mats.

An Ocean View suite on Star Pride

Similar room types on the Star Pride all-suite ship are the Balcony Suites, Deluxe Suites and Star Balcony Suites which have small French balconies with a door that can be opened to let in the fresh air, and the Classic Suites with private verandas.

All suites include luxe L’Occitane amenities, robes, slippers, fresh flowers and a fruit basket which is replenished throughout the week.

An Ocean View suite on Star Pride

But wait…it gets better.

Mid-way through the week, we were treated to a surprise upgrade to one of the biggest suites: the Owner’s Suite Midship.

Owner’s Suite Midship
The dining room in the Owner’s Suite Midship

Boasting a private balcony, living room, dining area, bar, huge bedroom with a seating area and library, a gorgeous walk-in closet and not one but two bathrooms, it’s the ultimate luxury on the high seas.

There are two of these suites on board, which also have the option to connect with the adjoining Star Balcony suites making them a great option for families and groups.

Star Pride also has a pair of rooms called Owner’s Suite Forward, with some of the best views thanks to their location at the front of the yacht.

A curved wall of panoramic windows and a large private balcony allows sunlight to stream in, and 575 square feet of space includes a seating area, small dining space and two bathrooms.


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Dining on Windstar Ships

Another thing that elevates the Windstar experience are the culinary offerings.

Tapas at Cuadro 44

Partnering with the acclaimed James Beard Foundation, the inventive menus showcase creative dishes dreamed up by all-star chefs, often with local ingredients.

All dietary restrictions can be accommodated, and on some sailings guests are invited to join the chef at a local market to select the produce, herbs and spices that will be used in that night’s meal.

Star Pride has a handful of restaurants: fine dining at Amphora, buffet and plated options at Candles and Veranda, relaxed lunches at the rooftop Star Grill, and the phenomenal Cuadro 44 which features Spanish-style tapas.

The Star Grill

Our day in St Lucia included a beachfront barbecue, and in Grenada the pool deck was transformed into a late night feast complete with spit-roasted pig, a steel drum band and a spirited dance party under the stars.

Exploring with Windstar: Reviews of the excursions

With Windstar Cruises putting such an emphasis on experiences and destinations, it’s no surprise there are plenty of options when it comes to excursions.

About half a dozen different tours are offered each day, and during our Caribbean trip those included scenic drives around islands, scuba diving, catamaran snorkeling tours, learning how to race a sailboat, exclusive tours of historic forts, rum tasting, aerial tram tours and waterfall hikes.

The fun open air taxi transportation during a Windstar Cruises tour in Bequia, St Vincent
Exploring Grenada
Exploring San Juan, Puerto Rico

They’re run by local operators, and prices range from about $70-$250 per tour. Unlike some other cruise lines Windstar doesn’t offer any complimentary ones, so keep that in mind when budgeting for a trip.

A refreshment station set up on shore for the exclusive use of Windstar Cruises’ guests

That said, there’s no pressure at all to book any of them, and many of the islands are easy to explore on your own if you choose.

The Windstar team also prepares an overview of each island that includes recommendations about its history, the top places to see and eat, and a FAQ section outlining things like currency and taxi information.

Terre-de-Haut, Guadeloupe
When there isn’t a dock in port, guests are shuttled to shore on these boats

Are Windstar Cruises expensive?

Windstar Cruises’ price points are very reasonable considering the more intimate, higher-end experience of their yachts versus the mega-cruise ships with thousands of people on board.

Looking down at the Star Pride in Terre-de-Haut, Guadeloupe

There are two options available: cruise only, and all-inclusive. Cruise-only fares include all meals, 24-hour room service, non-alcoholic beverages, access to the watersports platform and snorkel rentals.

For only about $100 per day extra, the all-inclusive plan adds wi-fi, unlimited beer, wine and cocktails, and all gratuities (for the record we still ended up tipping more as the staff are so incredible!)

I appreciated how it never felt like we were trying to get ‘upsold’ on anything, and also noticed that Windstar doesn’t seem to mark up the price of the land tours they offer.

For example, we booked a fun river tubing excursion in Grenada, and it was offered for the same price as it would have been to book through a company like Viator or GetYourGuide.

River tubing in Grenada

They also have great last-minute deals online, promotions for repeat visitors, reduced single supplements and sometimes offer steep discounts for passengers looking to extend their trip and continue on with the next sailing.

Bequia, St Vincent

Windstar Cruises reviews: The hits and misses

I was seriously impressed by so many things during this cruise, starting with the staff. They were truly so friendly, fun and gracious, and don’t ask me how but they seemed to have miraculously memorized every single passenger’s name by day two.

The service was also top notch with 192 crew on board for just 204 passengers, so nearly a 1:1 ratio.

The Star Pride’s crew

Windstar’s itineraries are excellent, not only with the unique ports they pick but also how much time you get to explore them. The yachts are beautiful, rooms are spacious, the food is incredible and the pool area never seemed too busy.

I also liked that there was a bit of an age range among passengers: while most were retirees, there were some middle-age groups of friends, a few younger couples and even families.

I also appreciated that Windstar avoids those frequent annoying on-board announcements over the loudspeaker that are so common on other ships. We’re all adults who can tell time and don’t need someone nagging us that dinner is about to be served, thank you very much.

Terre-de-Haut, Guadelopue

In terms of improvements, while the spa itself is beautiful I wasn’t too impressed with my body wrap spa treatment, especially considering the price tag. From what I’ve heard from fellow travellers, this unfortunately seems to be a pretty common issue with most cruise lines.

Things to do in St Maarten
Mullet Bay Beach in St Maarten

It would have been helpful to have more in-depth write-ups on Windstar’s website about each port while planning our trip; while there’s great information and briefings onboard, that isn’t shared until the night before each stop which makes it hard to plan or book a tour if all of the spots are full.

On some islands like Terre-de-Haut I wish we hadn’t done a tour at all, as it would have been better to rent a golf cart for the day and explore on our own but by the time we realized that they were all booked up.

Terre-de-Haut, Guadeloupe is fun to explore by golf cart

A few guests expressed disappointment that we never got to use the water sports platform, even though it was scheduled to be out during two of our stops that week.

I believe the reason was due to wind and wave conditions, but we actually had pretty great weather so it’s unclear what the criteria is for using the platform.

Terre-de-Haut, Guadeloupe

My review of Windstar Cruises: Smooth sailing

There were quite a few people on the cruise I chatted with who mentioned that was the first one they’ve done, and I was sure to let them know they picked well and will probably want to stick with Windstar in the future so they’re not disappointed by a different cruise line.

It really does make such a difference to sail with only a couple hundred passengers, versus thousands.

In terms of comparisons, the Windstar experience is similar to the also highly-regarded Viking Cruises, but while Viking focuses on larger ocean cruises and European rivers, Windstar excels at the small ship experience–especially in the South Pacific.

All in all our week with Windstar Cruises absolutely exceeded even my loftiest expectations, and I would absolutely recommend it to everyone and hope to sail with them again.

Windstar Cruises Star Pride



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