Beyond Beaches: Discover Bermuda's Hidden Gems on a Luxurious Windstar Cruise

Close your eyes and picture Bermuda. What comes to mind? Is it the impossible blush of pink sand sinking into a turquoise sea? Perhaps it’s the iconic image of businessmen in crisp Bermuda shorts, a charming nod to the island's British heritage. For decades, these postcard-perfect scenes have defined this mid-Atlantic jewel. But I’m here to tell you, as someone who has sailed the world’s most beautiful coastlines for over twenty years, that the true soul of Bermuda lies just beyond the frame of that postcard. It’s found in the quiet cobblestone lanes of a UNESCO World Heritage town, in the subterranean sparkle of a crystal cave, and in the genuine warmth of a local welcome—discoveries best made from the deck of a ship that values intimacy over immensity.

This is the Bermuda that reveals itself when you trade the floating cities of mass-market cruising for the refined elegance of a private yacht experience. This is the Bermuda you discover with Windstar Cruises. Forget the crowds, the queues, and the rigid schedules. Instead, imagine dropping anchor in a secluded bay, the ship’s Watersports Platform lowering to invite you for a spontaneous swim in the azure water. This isn’t just a vacation; it’s an immersion into a destination, a journey that is truly 180 degrees from ordinary.

The Windstar Difference: A Private Yacht Journey to Paradise

To sail with Windstar is to understand the profound difference between being a tourist and being a traveler. With a guest capacity of just 312 on their all-suite Star Plus Class yachts, the atmosphere is less like a cruise ship and more like your own private vessel. The crew knows your name, your preferred cocktail, and the way you take your coffee in the morning. The uncrowded decks offer a sense of freedom and space, where your most pressing decision is whether to lounge by the pool with a book or watch the island’s pastel-hued coastline glide by from a shaded daybed. This is casual elegance perfected—no formal nights, no assigned dining, just the liberty to enjoy your vacation, your way.

Your All-Suite Sanctuary at Sea

Aboard ships like the magnificent Star Pride, every stateroom is a suite, and every suite is an ocean-view sanctuary. These are not mere cabins; they are expansive, beautifully appointed living spaces designed for relaxation and rejuvenation. Picture waking to the gentle lapping of waves, drawing back the curtains to a panoramic ocean vista, and stepping out onto your French balcony to breathe in the fresh, salt-kissed air. The interiors are a study in understated luxury, featuring plush bedding, marble-finished baths, and ample space to unwind after a day of exploration. It’s your private haven, a comfortable and sophisticated base from which to launch your Bermuda adventures.

A Culinary Voyage to Match the Destination

Windstar’s commitment to excellence extends wholeheartedly to its culinary program. The dining experience is a journey in itself, celebrating fresh, locally sourced ingredients and creative, world-class cuisine. The main dining room, Amphora, offers a dynamic menu of gourmet dishes in an elegant setting, while still maintaining the line’s signature open-seating policy. For a more casual but equally delicious meal, you can dine al fresco under the stars at Candles, the ship’s beloved outdoor steak and seafood grill. And with the addition of the Star Grill by Steven Raichlen, a world-renowned grilling authority, the barbecue offerings are simply sublime. Every meal is an event, crafted to delight the senses and enhance your connection to the destination.

Unforgettable Onboard Experiences

What truly sets Windstar apart are the moments that simply can't be replicated on a larger vessel. The signature Open Bridge policy invites you to visit the Captain and officers, learn about navigation, and enjoy the best view on the ship. The iconic Watersports Platform, available when the yacht is at anchor, is your personal gateway to the ocean.

• Launch a kayak or a stand-up paddleboard directly from the ship’s stern.
• Enjoy complimentary use of snorkel gear and water trampolines.
• Take a refreshing dip in the sea from the safety of the yacht.

An Itinerary Crafted for Discovery: Beyond the Postcards

One of the greatest luxuries Windstar affords its guests in Bermuda is time. Unlike itineraries that offer a fleeting, eight-hour glimpse of the island, Windstar often docks for multiple days, allowing for a deep, unhurried exploration. This gives you the freedom to venture beyond the well-trodden tourist paths and connect with the island’s authentic rhythm. From the historic East End to the vibrant capital, you’ll have the time to truly see, taste, and feel what makes Bermuda so special.

St. George's: A Walk Through Living History

Your journey often begins in St. George’s, a UNESCO World Heritage site and one of the oldest English settlements in the New World. Stepping ashore here is like stepping back four centuries. The air is fragrant with hibiscus and frangipani as you wander the narrow, winding lanes with evocative names like "Featherbed Alley" and "Old Maid’s Lane." You’ll explore St. Peter’s Church, the oldest continuously used Anglican church in the Western Hemisphere, and marvel at the romantic ruins of the Unfinished Church. This is a place to be savored slowly, a living museum waiting to be discovered at your own pace.

Hamilton: The Vibrant Heart of Bermuda

The island’s capital, Hamilton, is a symphony of color and energy. Pastel-hued colonial buildings line the bustling Front Street, housing sophisticated boutiques, art galleries, and inviting pubs. This is the commercial and cultural heart of Bermuda. You can delve into maritime history at the Bermuda Underwater Exploration Institute, explore the lush gardens and impressive ramparts of Fort Hamilton, or simply find a waterfront patio to sip a perfectly mixed Dark 'n' Stormy, the island’s signature cocktail. Finding the perfect shore excursion in Hamilton can be overwhelming, with so many incredible options. Let us curate the ideal day for you. Get a Custom Quote, and we'll include personalized recommendations tailored to your interests.

The Royal Naval Dockyard: A Bastion of Maritime Legacy

At the island's West End lies the historic Royal Naval Dockyard, a former stronghold of the British Royal Navy. This sprawling complex of stone fortifications and historic buildings has been masterfully repurposed into a hub of activity. Here you can explore the National Museum of Bermuda, which houses the impressive Commissioner’s House, or interact with marine life at Dolphin Quest. The Dockyard is also a haven for local artisans, with the Bermuda Craft Market and Clocktower Mall offering unique, handmade souvenirs. It’s a fascinating blend of history, culture, and entertainment.

Curated Experiences: Your Bermuda, Your Way

The beauty of a Windstar cruise is the freedom it gives you to craft your own perfect day. Whether you are an intrepid adventurer, a cultural connoisseur, or someone simply seeking serenity, Bermuda offers a wealth of experiences that go far beyond its famous beaches.

For the Adventurer: Caves, Trails, and Shipwrecks

Beneath Bermuda’s serene surface lies a world of adventure. Descend into the breathtaking Crystal and Fantasy Caves to witness a subterranean wonderland of crystal-clear pools and stunning calcite formations. Hike or bike a section of the Bermuda Railway Trail, a scenic 18-mile path that winds through lush landscapes and offers spectacular coastal views. As the "Shipwreck Capital of the Atlantic," Bermuda is also a world-class diving destination, with over 300 wrecks scattered across its protective coral reefs, each with a story to tell.

For the Connoisseur: Golf, Gastronomy, and Gombeys

Bermuda boasts more golf courses per square mile than anywhere else in the world, including several championship-level tracks with staggering ocean views. Beyond the ship's exquisite dining, the island’s culinary scene is a vibrant fusion of British, Caribbean, and Portuguese influences. Be sure to try a classic Bermuda fish chowder seasoned with sherry peppers and black rum. For a truly unique cultural experience, seek out a performance by the Gombey dancers, whose vibrant, rhythmic folk art is a mesmerizing spectacle of island history and pride.

For the Relaxationist: Secluded Coves and Sunset Sails

While Horseshoe Bay is stunning, the true magic lies in discovering your own secluded slice of pink-sand paradise. With a little exploration, you can find quiet coves like Jobson’s Cove or Warwick Long Bay, where the crowds thin and the sound of the surf is all that fills the air. Ready to design your perfect blend of adventure and relaxation? Our experts are waiting to craft your itinerary. Give us a call at 1 (888) 883‑0460 to speak with a Bermuda specialist today. They can help you find those hidden gems that will make your trip unforgettable.

Why Book Your Windstar Bermuda Cruise With Us?

In a world of endless online options, the value of human expertise has never been greater. We are more than just a booking engine; we are passionate travel professionals and specialists in luxury cruising. We have sailed on Windstar ships, we have walked the lanes of St. George's, and we understand the nuances that elevate a great trip into a journey of a lifetime. When you work with us, you gain a dedicated advocate who will handle every detail, from securing the best suite to arranging personalized shore excursions and ensuring you receive every available perk and amenity. You can browse available dates and suites right now using the Cruise Booking Toolbar at the top of this page. When you're ready for our expert touch, we're here. The first step to your private yacht experience is a simple inquiry. Plan Your Bermuda Adventure and let us handle every detail.

Frequently Asked Questions about Cruising to Bermuda on Windstar

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 water sports. However, the "shoulder seasons" of April and November can also be lovely, with pleasant temperatures and fewer crowds.

What is the dress code on a Windstar cruise?

Windstar features a "casual elegance" dress code. During the day, shorts, sundresses, and casual wear are appropriate. In the evening, slacks, polo shirts, and casual dresses are the norm. There are no formal nights, so you can leave the tuxedos and gowns at home.

Are shore excursions included with my Windstar cruise?

While the cruise fare covers your accommodation, all onboard dining, and select beverages, shore excursions are typically an additional cost. This allows you the flexibility to choose the activities that most interest you. We can help you pre-book excursions to ensure you get your first choice.

What makes Windstar different from larger cruise lines?

The primary difference is scale and philosophy. With fewer than 350 guests, Windstar offers a highly personalized, intimate experience. The smaller ships can visit ports and anchor in bays inaccessible to larger vessels, and the onboard atmosphere is relaxed and unstructured, feeling more like a private yacht than a cruise ship.

How do I get the best deal on a Windstar Bermuda cruise?

The best way to ensure you receive the maximum value is to book through an experienced travel advisor. We have access to the latest promotions, exclusive offers, and potential amenities like onboard credit or suite upgrades that you won't find online. Contacting us is the first step to a perfectly planned and value-packed vacation.

The turquoise waters and hidden lanes of Bermuda are waiting. This isn't just an opportunity to see a beautiful island; it's a chance to experience it in a way that is intimate, authentic, and 180 degrees from ordinary. Don't just dream about it. Inquire About This Sailing today and let's begin crafting your unforgettable journey.