The Ultimate Bermuda Cruise Packing List: What to Wear on Your Windstar Escape

Imagine the moment. You’re standing on the teak deck of an elegant motor yacht, a chilled glass of champagne in hand. The sun, a perfect orb of liquid gold, dips below the horizon, casting a warm glow on the pastel-hued houses of St. George’s Harbour. A gentle sea breeze whispers past, carrying the scent of salt and hibiscus. This isn’t just any cruise; this is the Windstar experience. And this isn’t just any destination; this is the sublime, sophisticated island of Bermuda.

The anticipation of such a journey is a thrill in itself, but it often comes with a nagging question: What on earth do I pack? Packing for a cruise can be daunting, but packing for a Windstar cruise to Bermuda is an art form—a delightful exercise in curating a wardrobe that mirrors the destination's unique blend of British charm and island ease, and the ship's ethos of relaxed, private yacht-style luxury.

Forget everything you think you know about cruise ship packing. We’re not talking about cavernous dining halls requiring tuxedos and ball gowns. We’re talking about intimate, open-seating restaurants, spontaneous dips from the Watersports Platform, and shoreside explorations that feel less like a tour and more like a personal discovery. This guide is more than a list; it’s your key to unlocking an effortlessly chic and perfectly prepared Bermudian escape.

Understanding the Windstar Vibe: 180 Degrees from Ordinary

Before a single item goes into your suitcase, it’s essential to understand the world you’re about to enter. Windstar Cruises prides itself on being “180 Degrees from Ordinary,” and this philosophy permeates every aspect of life on board, especially the dress code. The key phrase to remember is Casual Elegance.

This isn’t a suggestion; it’s an invitation. It’s an invitation to leave the stiff formalities of traditional cruising behind. On a Windstar all-suite motor yacht like the Star Pride or Star Legend, the atmosphere is akin to being a guest on a magnificent private yacht. The passenger count is intimate, the service is personal, and the feeling is one of belonging to an exclusive club. There are no formal nights, no assigned dining times, and no pressure to be anything but your most relaxed, sophisticated self.

What "Casual Elegance" Really Means

• By Day: Think resort wear. Swimsuits, stylish cover-ups, shorts, linen shirts, and sundresses are perfectly appropriate for lounging on deck, enjoying a casual lunch at the Star Grill by Steven Raichlen, or reading a book in a quiet corner.
• By Night: As the sun sets, the style elevates slightly, but comfort remains key. For dinner in the main dining room, Amphora, or the romantic outdoor Candles grill, the guideline is simple: no shorts, t-shirts, or jeans. It’s about showing respect for the beautiful setting and your fellow travelers.

The beauty of this approach is its freedom. It allows you to pack lighter and more thoughtfully, focusing on versatile pieces that make you feel good. If you're picturing the perfect ensemble but want to confirm it fits the Windstar style, our cruise specialists are here to help. Many have sailed on these very ships and can offer firsthand advice. Just click the 'Chat with us' bubble in the lower right corner to start a conversation.

Decoding Bermuda's Climate and Culture

Your wardrobe must also pay homage to your destination. Bermuda is not the Caribbean. It’s a semi-tropical island in the Atlantic with a distinct character—a refined, British-influenced jewel box of an island. The weather is balmy and can be humid, especially from May to October, making breathable fabrics your best friend. Think cotton, linen, and rayon blends.

Culturally, Bermuda is a touch more conservative than its southern neighbors. While beachwear is expected at stunning pink-sand beaches like Horseshoe Bay, it’s considered polite to cover up when walking through towns like Hamilton or the UNESCO World Heritage site of St. George's. This is the island, after all, where the famous "Bermuda shorts" are considered acceptable business and formal attire for men when paired with a blazer and knee-high socks. Embracing this local sensibility will make your experience all the more authentic.

Your Essential Windstar Bermuda Packing List: From Ship to Shore

Let’s open that suitcase. We’ll build your wardrobe layer by layer, from sun-drenched sea days to enchanting evenings ashore.

Onboard Daywear: Relaxed Sophistication at Sea

Picture yourself on a sea day, gliding across the turquoise expanse. Your time will be spent between the sun-drenched pool deck, the breezy open-air lounges, and perhaps a treatment at the World Spa by Windstar. Comfort is paramount.

• Swimwear (at least two suits): One to wear while the other dries. A classic one-piece and a stylish bikini will cover all your bases.
• Elegant Cover-Ups: A chic caftan, a linen tunic, or a sarong is essential for walking from your suite to the pool or grabbing a drink at the bar.
• Sun Protection Trio: A wide-brimmed hat, high-quality UV-blocking sunglasses, and reef-safe, high-SPF sunscreen are non-negotiable.
• Footwear: Rubber-soled sandals or espadrilles for the pool deck. Boat shoes are also a stylish and practical option.
• A Light Layer: A pashmina, cashmere wrap, or light cardigan is perfect for the air-conditioned interior spaces or for when the sea breeze picks up in the evening.

Onboard Evening Attire: The Art of Casual Elegance

As dusk settles, the ship transforms. The lights twinkle, cocktails are poured, and the anticipation of a gourmet meal builds. This is where "Casual Elegance" truly shines.

• For Women:
  • Dresses: Pack a few versatile options like a floral maxi dress, a classic sundress, or a simple slip dress.
  • Separates: Elegant tops paired with wide-leg linen trousers, silk pants, or a stylish skirt offer multiple outfit combinations.
  • Footwear: Dressy sandals, wedges, or low heels are perfect. Comfort is still key, as you might enjoy a post-dinner stroll on the deck.
  • Accessories: A few pieces of statement jewelry and a simple clutch can elevate any outfit.
• For Men:
  • Shirts: Collared shirts are the standard. Pack a mix of high-quality polos and long-sleeve button-down shirts in linen or cotton.
  • Trousers: Chinos, khakis, or smart linen trousers are ideal.
  • Footwear: Loafers, deck shoes, or smart leather sandals (no flip-flops in the dining rooms, please).
  • Optional Layer: A lightweight navy or linen sport coat is not required but is a fantastic way to add a touch of polish, especially for a special meal at Candles.

Crafting the perfect evening look is part of the fun. If you'd like to see sample itineraries and get a feel for the daily flow, our team can provide all the details. We invite you to Get a Custom Quote, and we’ll help you plan every aspect of your voyage, right down to the dress code.

Shore Excursion Essentials: Adventure-Ready Attire

Bermuda is an island of discovery, from its subterranean caves to its historic forts. Your packing should reflect the activities you have planned.

• For Beach Days (Horseshoe Bay, Tobacco Bay): Pack your swimwear, a cover-up, water shoes for rocky areas, and a waterproof bag for your essentials. Remember that famous pink sand can get everywhere!
• For Exploring Towns (Hamilton, St. George's): This is where you’ll do the most walking.
  • Comfortable Walking Shoes: This is the single most important item. Stylish sneakers, supportive sandals, or broken-in loafers are a must.
  • Breathable Clothing: A lightweight dress, shorts (of a respectable length), or linen trousers paired with a cotton top will keep you cool.
  • A Tote or Daypack: To carry your water bottle, camera, sunscreen, and any souvenirs you pick up from the local shops.
• For Active Adventures (Biking the Railway Trail, Exploring Crystal Caves):
  • Athletic Wear: Moisture-wicking tops and comfortable shorts or leggings are ideal.
  • Sturdy, Closed-Toe Shoes: Essential for safety and comfort on uneven terrain.
  • Insect Repellent: A good idea for any explorations in more verdant, natural areas.

The right shore excursions can make your trip unforgettable. Do you dream of snorkeling over shipwrecks or sipping a Dark 'n Stormy at a famous local pub? When you book with us, our experts help you curate the perfect activities to match your interests. Let us help you Plan Your Bermuda Adventure from start to finish.

Beyond the Basics: The Little Luxuries You Won't Want to Forget

These are the items that move a trip from great to exceptional. Don’t leave home without them.

• Electronics: A portable power bank for long days ashore, a waterproof phone case for beach photos, your camera, and a pair of compact binoculars to spot marine life from your suite’s balcony.
• Health & Toiletries: While your suite is well-appointed, bring your personal favorites. Also pack any necessary prescription medications, a simple first-aid kit, and seasickness medication if you’re prone (though Windstar’s smaller ships handle the waves beautifully).
• Documents & Money: Your passport, cruise e-tickets, and a copy of all important documents. US dollars are accepted everywhere on a 1:1 basis with the Bermudian dollar.
• A Reusable Water Bottle: Stay hydrated and be environmentally conscious.
• A Good Book: There’s no better luxury than losing yourself in a story while at sea.

What NOT to Pack for Your Windstar Cruise

Just as important as what to bring is what to leave behind. Free up that precious luggage space!

• Formal Wear: No tuxedos, gowns, or cocktail dresses needed.
• An Iron or Steamer: These are prohibited as fire hazards. The ship offers excellent laundry and pressing services for a fee.
• Heavy Fabrics: Leave the heavy wool and denim at home in favor of lighter, more versatile materials.
• Too Many Shoes: The eternal packing challenge! Aim for 4-5 versatile pairs: one for walking, one for the beach/pool, one for evenings, and perhaps a stylish sneaker.

The beauty of a Windstar cruise is its elegant simplicity. Let us simplify your planning process, too. If you have any questions at all, from cabin selection to flight arrangements, our team is standing by on our dedicated line at 1 (888) 883-0460. A quick call can provide the clarity and confidence you need.

Your Effortless Bermuda Escape Awaits

Packing for your Windstar Bermuda cruise shouldn’t be a source of stress. It should be an exciting part of the journey—a chance to dream of the days ahead and curate a collection of items that will make you feel comfortable, confident, and completely at home on your private yacht. This is travel as it was meant to be: personal, liberating, and utterly unforgettable.

Are you ready to feel the pink sand between your toes and the gentle sway of your yacht as it sails toward the horizon? The first step is a simple conversation. Use the Cruise Booking Toolbar at the top of this page to explore available dates and itineraries. For a truly personalized experience tailored to your exact preferences, we encourage you to Inquire About This Sailing through our custom quote form. Our experts will craft a proposal just for you. Your extraordinary Bermudian adventure is closer than you think.

Frequently Asked Questions about Windstar Bermuda Cruises

Does Windstar have a formal night?

No. Windstar Cruises does not have formal nights. The evening dress code is "Casual Elegance," which means items like collared shirts and slacks for men, and sundresses, skirts, or slacks with elegant tops for women. Shorts, jeans, and t-shirts are not permitted in the main dining venues in the evening.

What is the currency in Bermuda?

The official currency is the Bermudian Dollar (BMD), which is pegged to the US Dollar at a 1:1 ratio. US dollars are accepted everywhere, so there is no need to exchange currency.

Do I need a special power adapter for the ship?

Windstar's all-suite yachts are equipped with both standard 110-volt North American and 220-volt European outlets in each suite, so special adapters are typically not necessary for most travelers.

Can I do laundry on board?

Yes, a full range of laundry and pressing services are available on board for a fee. This makes it easy to pack light and refresh your wardrobe throughout the voyage.

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

The prime season for a Bermuda cruise is from April through October. This period offers the warmest weather, ideal for swimming and beach activities. May and June are particularly lovely, with pleasant temperatures and lush, blooming flora across the island.