Is a Windstar Cruise to Bermuda Worth It? My Honest Review

There’s a moment on every truly exceptional voyage when the world seems to pause. For me, it was standing on the open-air deck of a Windstar yacht, a warm breeze carrying the scent of salt and cedar across the turquoise expanse of the Great Sound. The sun was setting, painting the pastel-hued houses of Bermuda in shades of apricot and rose. There were no crowds, no booming announcements, just the gentle hum of the ship and the clink of glasses. In that moment, I wasn't just a tourist visiting an island; I was a traveler experiencing a destination in a way that felt personal, privileged, and profoundly peaceful. This is the essence of Windstar, and it’s the heart of the answer to the question: Is it worth it?

For over two decades, I’ve sailed on everything from colossal mega-ships to intimate riverboats. I’ve seen the industry evolve, but my core belief remains: the right ship can transform a great destination into a life-changing journey. Bermuda, with its unique blend of British charm, island soul, and legendary pink-sand beaches, is a destination that begs to be savored, not just seen. A massive cruise ship can get you there, but a small, yacht-style vessel like those in the Windstar fleet allows you to truly connect with it.

So, let’s dive deep. This isn’t just a list of features; it’s an honest, firsthand account of the experience. We’ll explore the ship, the itinerary, the unique magic of Bermuda, and ultimately, help you decide if this is the dream vacation you’ve been searching for. If at any point you feel that spark of inspiration, remember you can explore current sailings and pricing using the Cruise Booking Toolbar at the top of this page.

The Windstar Difference: Why Small Ship Cruising Changes Everything

Before we even talk about Bermuda, we need to talk about Windstar. To compare a Windstar cruise to a conventional cruise is like comparing a private dinner party to a stadium concert. Both can be enjoyable, but the experience is fundamentally different. Windstar’s motto, "180 Degrees from Ordinary," isn’t just clever marketing; it’s a promise delivered.

With a guest count typically under 350, the atmosphere is immediately distinct. You’re not a cabin number; you’re a name, a face, and a fellow traveler. The crew learns your preferences, from how you take your morning coffee to your favorite cocktail at sunset. This isn't forced pleasantry; it's genuine, personalized service that makes you feel less like a passenger and more like a guest aboard a magnificent private yacht.

Onboard Ambiance & Amenities: Your Private Oasis at Sea

The ships themselves, whether the iconic sailing yachts like Wind Surf or the all-suite Star Plus Class yachts like Star Pride, are designed for relaxation and connection with the sea. Decks are clad in rich teak, public spaces are elegant yet comfortable, and you’ll never find yourself fighting for a lounge chair by the pool.

One of my favorite Windstar signatures is the Open Bridge Policy. You can literally walk onto the bridge at almost any time, chat with the captain and officers, and gaze at the nautical charts. It’s a level of access and transparency that demystifies the art of navigation and makes you feel like part of the journey.

Key features that define the experience include:

• All-Suite Accommodations: On the Star Plus yachts, every stateroom is a spacious, beautifully appointed suite with an ocean view. Many feature French balconies or full verandas, perfect for a private breakfast as you sail into a new port.
• The Watersports Platform: When the yacht is at anchor in a calm bay, a platform at the stern lowers directly into the sea. Suddenly, the ocean is your swimming pool. You can kayak, paddleboard, or simply float on a mat in the warm, clear water—all complimentary.
-
• World Spa by Windstar: The onboard spa is an intimate sanctuary offering a range of treatments, a sauna, and a well-equipped fitness center. It’s the perfect way to unwind after a day of exploration.
• Casual Elegance: Forget tuxedos and formal gowns. The dress code is "country club casual." Think linen trousers, sundresses, and collared shirts. The focus is on being comfortable and chic, not stuffy and formal.

This relaxed, unpretentious luxury is the soul of Windstar. If you have specific questions about suite layouts or onboard amenities, our travel specialists are a fantastic resource. Click the 'Chat with us' button in the lower-right corner to connect with an expert instantly.

A Culinary Journey at Sea

On large ships, dining can often feel like a logistical challenge. On Windstar, it’s a highlight of each day. With a focus on fresh, locally sourced ingredients and creative menus, the culinary program is exceptional. You won't find massive buffets with mediocre food. Instead, you'll discover intimate dining venues with restaurant-quality cuisine.

Amphora, the main dining room, offers a sophisticated setting with multi-course menus that change daily. For a more casual al fresco experience, the Veranda serves breakfast and lunch with stunning ocean views. But the true star of the show for many is Candles. Each evening, a portion of the deck is transformed into a romantic, open-air steakhouse. Dining under the stars as the yacht gently sways is an unforgettable experience. And the best part? All dining venues are included in your cruise fare, with no assigned seating. You dine when, where, and with whom you wish.

Dropping Anchor in Paradise: The Bermuda Itinerary

Bermuda is an archipelago of 181 islands, and its intricate harbors and shallow sounds can be challenging for mega-ships. A smaller Windstar yacht has a distinct advantage, often able to dock in more desirable locations and offer a more immersive itinerary. A typical Bermuda cruise will give you ample time to explore the island's three main hubs: St. George's, Hamilton, and the Royal Naval Dockyard.

St. George's: A Walk Through Living History

Sailing into St. George's feels like sailing back in time. As the oldest continuously inhabited English town in the New World and a UNESCO World Heritage site, its narrow, cobblestone lanes and 17th-century architecture are impeccably preserved. You can almost hear the echoes of its 400-year history. I spent a day simply wandering, discovering hidden alleys, popping into the historic St. Peter's Church, and enjoying a pint at the White Horse Pub & Restaurant, a local institution. Because the ship is docked right in town, you have the freedom to explore at your own pace, returning to your floating oasis whenever you please.

Hamilton: The Vibrant Heart of Bermuda

The capital city of Hamilton is a symphony of color and sophistication. Front Street, which runs along the harbor, is lined with iconic pastel-colored buildings housing high-end boutiques, art galleries, and inviting restaurants. It’s the bustling commercial and cultural heart of the island. From here, you can easily arrange for a round of golf at one of Bermuda’s world-class courses, explore the lush Botanical Gardens, or simply find a balcony overlooking the harbor to sip on the island’s signature cocktail, the Dark 'n Stormy.

Royal Naval Dockyard: A Fortress of Fun

Located at the island's western tip, the Royal Naval Dockyard is a testament to Bermuda's strategic maritime importance. This former bastion of the British Royal Navy has been brilliantly repurposed into a hub of activity. You can delve into maritime history at the National Museum of Bermuda, watch artisans at work at the Bermuda Craft Market, or enjoy the family-friendly Snorkel Park Beach. The sheer scale of the historic stone fortifications is awe-inspiring and provides a fascinating contrast to the island's gentle, beachy vibe.

The beauty of a Windstar itinerary is the time it affords you in port. Often, you'll have overnight stays, allowing you to experience the island's nightlife and culture after the day-trippers from larger ships have departed. To see what a specific itinerary looks like, you can Inquire About This Sailing and receive a detailed, day-by-day plan from one of our cruise specialists.

Beyond the Ports: Embracing the Bermudian Vibe

A trip to Bermuda is about more than just its towns. It's about immersing yourself in a unique island culture and its breathtaking natural beauty.

The Legendary Pink Sand Beaches

Let’s be clear: the sand really is pink. It’s a subtle, rosy hue created by the crushed shells of tiny red foraminifera. The effect is magical. Horseshoe Bay Beach is the most famous, a perfect crescent of soft sand against impossibly turquoise water. While it can get busy, a short walk over the dunes reveals a series of smaller, more secluded coves like Port Royal Cove and Peel Rock Cove, which feel like private discoveries. A small ship experience means you’re not descending on these natural wonders with thousands of others at once, preserving their tranquility.

Flavors of the Island

Bermuda's cuisine is a delicious fusion of British, Caribbean, and Portuguese influences. You must try the Bermuda Fish Chowder, a rich, savory soup traditionally seasoned at the table with a splash of black rum and sherry peppers sauce. It’s the national dish for a reason. And, of course, no visit is complete without a proper Dark 'n Stormy, made with local Gosling's Black Seal Rum and ginger beer. It’s the taste of the island in a glass.

The Verdict: So, Is a Windstar Cruise to Bermuda *Really* Worth It?

After experiencing it firsthand, my answer is an unequivocal and resounding yes, but with a crucial caveat: it’s worth it if you are the right kind of traveler.

If your idea of a perfect cruise involves Broadway-style shows, rock-climbing walls, and a dizzying array of specialty restaurants, Windstar is not for you. There are no casinos, no kids' clubs, and no grand atriums. The entertainment is more refined: a live duo in the lounge, a local performance brought on board in port, and, most importantly, engaging conversation with fellow passengers who share a passion for authentic travel.

A Windstar cruise to Bermuda is worth it if you value:

• Intimacy and Personalization: You prefer a yacht with 300 guests to a city-at-sea with 3,000.
• Relaxed Luxury: You appreciate fine dining and attentive service without the need for formal wear and rigid schedules.
• Destination Immersion: You want to spend more time exploring the culture, history, and natural beauty of Bermuda and less time waiting in lines.
• Authentic Experiences: You find joy in simple, perfect moments—a sunset sail, a conversation with an officer on the bridge, a swim in the open ocean from the back of your ship.

This is not a budget vacation; it is an investment in a superior travel experience. It’s for the traveler who understands that value isn’t just about the price tag, but about the quality of the memories you create. It’s about returning home not just rested, but enriched.

Planning Your Windstar Bermuda Escape

Feeling that pull towards the pink sands and turquoise waters? Turning this dream into a reality is easier than you think, and our expertise can make all the difference. We can help you select the perfect suite, arrange pre- or post-cruise stays, and provide insights that you won't find online.

There are several ways we can help you start planning:

• The Cruise Booking Toolbar at the very top of this page is a great tool for browsing available dates and initial pricing.
• For a one-on-one conversation, our dedicated line at 1 (888) 883‑0460 connects you directly with a specialist who lives and breathes luxury cruising.
• For a detailed, no-obligation proposal tailored specifically to your travel style, dates, and preferences, the best first step is to request a custom quote. Let us craft the perfect itinerary for you. Get a Custom Quote today and let the journey begin.

Frequently Asked Questions

What is the dress code on a Windstar cruise?

The dress code is "Casual Elegance." During the day, shorts, sundresses, and casual wear are appropriate. In the evening, men typically wear collared shirts and trousers, while women opt for slacks, skirts, or casual dresses. No formal nights, jackets, or ties are required.

What is included in a Windstar cruise fare?

Your fare includes all dining in all venues (including the specialty restaurants), non-alcoholic beverages like soda, coffee, and tea, access to the Watersports Platform (weather permitting), and all onboard entertainment. Gratuities, alcohol, and shore excursions are typically extra, though all-inclusive packages are often available.

What is the best time of year to cruise to Bermuda?

The peak season for Bermuda is from May to October when the weather is warmest and ideal for swimming and beach activities. The shoulder months of April and November can also be pleasant with fewer crowds. Hurricane season officially runs from June to November, with the highest risk in late August and September.

Are shore excursions included with Windstar?

Shore excursions are not typically included in the base cruise fare. Windstar offers a curated selection of tours in each port that you can purchase. However, the small-ship experience and convenient docking locations also make it very easy to explore independently.

Is Windstar a good choice for solo travelers?

Absolutely. The intimate, friendly atmosphere on board makes it very easy for solo travelers to meet and mingle with other guests. The crew is exceptionally welcoming, and the open-seating dining allows for flexibility in joining others for meals if you wish.