Bermuda Bliss: My Immersive Sailing Adventure with Windstar Cruises

There’s a moment, just as the sun begins its descent, when the world softens. On the teak deck of a Windstar yacht, this moment is sacred. It’s not marked by the roar of a mega-ship’s engine, but by the whisper of the wind catching the sails and the gentle clinking of ice in a glass. It’s the moment you realize this isn’t just a cruise; it’s true sailing. And there is no destination more suited to this elegant, unhurried pace than the jewel of the Atlantic: Bermuda.

For years, I’ve traversed the globe on vessels of all shapes and sizes, but my recent voyage with Windstar Cruises to Bermuda was a profound reminder of what luxury travel should be—intimate, immersive, and utterly unforgettable. It’s a world away from the floating cities that dominate the seas, offering an experience that feels more like being a guest on a private yacht than a passenger on a cruise ship. If you’re seeking an escape that combines adventure with tranquility, history with modern luxury, then allow me to share why this journey is the one you’ve been dreaming of. As you read, feel free to explore available dates and pricing for this exact itinerary using the convenient Cruise Booking Toolbar at the top of this page.

180 Degrees from Ordinary: The Windstar Difference

Before we even cast our eyes on Bermuda’s legendary pink shores, it’s essential to understand what sets Windstar apart. Their motto, "180 Degrees from Ordinary," isn’t just clever marketing; it’s the foundational philosophy of everything they do. With a fleet of sleek sailing yachts and all-suite motor yachts carrying no more than 342 guests, the atmosphere is immediately different.

Gone are the crowds, the queues, and the impersonal service. In their place, you find genuine warmth and recognition. By the second day, the crew knows your name, your preferred morning coffee, and the perfect time to offer a cool towel after a day of exploration. This intuitive, anticipatory service is the hallmark of true luxury.

The Private Yacht Experience

Onboard, the ship itself is a destination. The design is a masterful blend of classic nautical charm and contemporary elegance. Think polished wood, brass fittings, and expansive, sun-drenched decks. My favorite moments were often the simplest:

• The Open Bridge Policy: A rarity in the cruise world, Windstar invites you to visit the bridge at almost any time. Chatting with the Captain and officers while they navigate the turquoise waters, with charts spread before you, creates a deep connection to the art of sailing.
• The Watersports Platform: Imagine this: the yacht anchors in a secluded, pristine cove, and a platform lowers directly into the sea. Within minutes, you have complimentary access to kayaks, paddleboards, and snorkeling gear. It’s your own private slice of ocean paradise.
• Unstructured Bliss: There are no rigid schedules or assigned dining times. The day is yours to shape. Whether you’re reading a book in a quiet nook, enjoying a cocktail at the Pool Bar, or indulging in a treatment at the World Spa by Windstar, you are on your own time.

Have a quick question about the ship’s dress code or a specific suite? The 'Chat with us' button in the lower right corner connects you instantly to a cruise expert who can provide immediate answers.

An Itinerary Woven into the Fabric of Bermuda

Windstar’s small ships have a distinct advantage: they can navigate into smaller, more character-filled harbors, bringing you closer to the heart of each destination. Our Bermuda itinerary was a perfect example, a graceful dance between the island’s most iconic and intimate ports of call.

Sailing into History: St. George's

Our arrival in St. George’s was nothing short of magical. As a UNESCO World Heritage site, this historic town is a time capsule of 17th-century British colonial life. We didn't dock in a sprawling industrial port; we glided right up to Ordnance Island, stepping off the yacht and directly onto cobblestone streets. We spent the day wandering through the narrow alleys, admiring the pastel-hued architecture of King’s Square, and visiting the sublime St. Peter’s Church, the oldest continuously used Anglican church in the Western Hemisphere.

A short, breezy walk led us to Tobacco Bay Beach, a stunning cove protected by limestone rock formations, offering some of the island's best and most accessible snorkeling. The water was impossibly clear, teeming with parrotfish and sergeant majors darting through the coral.

The Vibrant Heartbeat: Hamilton

From the old-world charm of St. George’s, we sailed to the sophisticated, bustling capital of Hamilton. The iconic view of Front Street, with its multi-colored Victorian buildings, is a sight to behold from the deck of the ship. Here, the island’s energy is palpable. We explored high-end boutiques, perused local art galleries, and, of course, paid a visit to the famous English Sports Shop to admire the kaleidoscope of authentic Bermuda shorts.

Hamilton is also the perfect launchpad for exploring the island's renowned South Shore beaches. A short taxi or bus ride delivered us to the breathtaking arc of pink sand at Horseshoe Bay. While the main beach is popular, a little exploring along the coastal trail reveals a series of smaller, more secluded coves like Peel Rock Cove and Butt's Beach, where you can find your own private paradise. Our travel specialists have deep knowledge of the best local guides and private tours to make your beach day truly exceptional. Give our dedicated line a call at 1 (888) 883‑0460 to discuss personalizing your shore excursions away from the crowds.

Maritime Majesty: The Royal Naval Dockyard

Our final port offered a fascinating glimpse into Bermuda’s strategic maritime past. The Royal Naval Dockyard, once the British Royal Navy's largest base outside the United Kingdom, is now a sprawling complex of culture, shopping, and adventure. We delved into 500 years of island history at the National Museum of Bermuda, housed within the formidable fortress, and even got to interact with dolphins at Dolphin Quest.

The Dockyard is also home to a vibrant community of local artisans. We spent hours at the Bermuda Craft Market and the Dockyard Glassworks, watching artists create stunning works and finding unique souvenirs that truly captured the spirit of the island. It was the perfect, culturally rich conclusion to our on-shore explorations.

Ready to feel the Bermudian breeze for yourself and create your own stories in these historic ports? Plan Your Bermuda Adventure with a no-obligation quote tailored to your travel style.

Life Onboard: Unpretentious Luxury and Culinary Delights

As captivating as Bermuda is, returning to the ship each evening felt like coming home. The onboard atmosphere strikes a perfect balance: it’s elegant without being stuffy, luxurious without being pretentious. Guests mingle easily, sharing stories of their day’s adventures over cocktails at sunset, but there’s always ample space for quiet reflection.

The culinary program, a partnership with the James Beard Foundation, is a highlight. Every meal is a celebration of fresh, locally sourced ingredients and culinary creativity.

• AmphorA: The main dining room offers a sophisticated, course-by-course menu that changes daily, with no reservations required.
• Veranda: For breakfast and lunch, this sun-lit venue offers a sumptuous buffet and à la carte options, with both indoor and outdoor seating.
• Candles: My personal favorite. Each evening, the Veranda’s outdoor deck is transformed into a romantic, al fresco steakhouse. Dining under the stars, with the gentle sea breeze and the sizzle of a perfectly cooked filet mignon, is an experience not to be missed.

Why Windstar and Bermuda are a Perfect Match

This journey solidified a belief I’ve long held: the vessel you choose is as important as the destination itself. Windstar and Bermuda are a symbiotic pairing, each enhancing the other. The grace and intimacy of a sailing yacht perfectly mirror the island's blend of British charm and relaxed island spirit. You don't just visit Bermuda; you experience it at a pace that allows you to absorb its beauty, connect with its culture, and rejuvenate your soul.

It’s about watching the full moon rise over a tranquil bay from your private balcony. It’s about the Captain pointing out a pod of dolphins playing in the bow wave. It’s about returning from a day of exploration to a genuine smile and your favorite drink waiting for you. This is the magic of small-ship cruising. To get started on crafting your perfect getaway, I highly recommend you Inquire About This Sailing. Our team can tailor it to your exact preferences, ensuring every detail is flawless.

Let us handle the details while you dream of pink sands and turquoise waters. Get a Custom Quote today and see what exclusive amenities and special insights we can add to your voyage.

Frequently Asked Questions about Windstar Cruises to Bermuda

What is the dress code on a Windstar cruise?

The dress code is "casual elegance." During the day, shorts, sundresses, and resort wear are appropriate. In the evening, slacks, polo shirts, or collared shirts are recommended for men, while women often wear casual dresses, slacks, or skirts. There are no formal nights or requirements for jackets or ties, reinforcing the relaxed, private yacht-style atmosphere.

Are shore excursions included with my Windstar cruise fare?

While the cruise fare is incredibly inclusive (covering all dining, non-alcoholic beverages, and more), shore excursions are typically an additional cost. This allows guests the flexibility to choose experiences that best suit their interests, from historical walking tours and snorkeling adventures to private island tours. Our travel experts can help you pre-book the best excursions.

What makes Windstar different from other luxury cruise lines?

The primary differentiator is the intimate, small-ship experience. With a maximum of 342 guests, the service is highly personalized. The Open Bridge Policy, the complimentary Watersports Platform, and the overall feeling of being on a private yacht rather than a cruise ship create a unique and memorable vacation that is "180 degrees from ordinary."

Is a Windstar cruise to Bermuda suitable for families?

Windstar's intimate and sophisticated atmosphere is generally best suited for adults, couples, and solo travelers. While children are welcome, there are no dedicated kids' clubs or programs. It is an excellent choice for families with mature teenagers who appreciate travel, history, and water sports.

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

Bermuda enjoys a beautiful, temperate climate. The peak season runs from May to October when the weather is warmest and ideal for swimming and water activities. The shoulder months of April and November can also be lovely, with fewer crowds and pleasant temperatures. Windstar schedules their sailings to take advantage of this prime weather window.