Planning a destination wedding means more than just saying “I do” under the palm trees — it’s about creating an experience your guests will never forget. And when your celebration is set in paradise, you want your loved ones to soak up every minute of it.

As a Key West wedding planner, I’ve helped countless couples craft unforgettable wedding weekends that feel like a getaway, not just an event. Whether your guests are flying in for the first time or they’re seasoned island hoppers, here’s my go-to key west wedding weekend guide to make their trip effortless and extraordinary.

Key West Wedding Weekend Guide

Getting Here — Travel Tips for a Smooth Arrival

Key West is the southernmost point in the continental U.S., which means it’s both magical and a little tucked away — and that’s part of its charm.

Fly in with ease: The closest airport is Key West International Airport, just minutes from Old Town. Guests can also fly into Miami International Airport or Fort Lauderdale-Hollywood International Airport and enjoy a scenic drive down the Overseas Highway.

Make it a road trip: The drive from Miami is about 3.5–4 hours — with turquoise water views and iconic pit stops along the way.

Once here, go car-free: Key West is a walkable island, and most guests love getting around by bike, scooter, or golf cart. Parking can be limited, so skipping the car is often the best move.

Planner Tip: If many guests are flying into Miami, consider arranging group shuttles to make the journey smooth and stress-free.

Where to Stay — Island Hotels, Inns & Rentals

One of the best parts of hosting a wedding in Key West is the variety of accommodations — from charming historic inns to oceanfront resorts. Whether your guests want a romantic hideaway or a poolside resort, there’s something for everyone.

Here are a few guest favorites to recommend:

Historic Charm: Old Town Manor — a beautiful, lush oasis in Old Town, perfect for couples who love boutique elegance.

Luxury Resort: Casa Marina Key West — a classic beachfront resort with stunning views and excellent amenities.

Chic & Cozy: Kimpton Winslow’s Bungalows Key West — colorful, charming, and great for groups who want to be near everything.

Group-Friendly Rentals: Vacation homes and cottages near Old Town are ideal for bridal parties or families who want a “home base” for the weekend.

Planner Tip: Encourage guests to book early. Key West is a small island, and hotels can fill up fast during peak wedding season. A room block or list of suggested hotels at different price points makes travel planning easy for everyone.

What to Wear — Island Style Meets Wedding Chic

Key West has its own effortlessly elegant vibe — think breezy, tropical, and timeless. Guests will be most comfortable in outfits that are stylish yet weather-appropriate.

For the Welcome Party: Sundresses, linen shirts, sandals, and light fabrics set the tone for laid-back fun. Think coastal chic, not corporate cocktail.

For the Wedding: Lightweight fabrics, chic resort wear, and sensible heels or flats are perfect for garden or beach ceremonies. Guests should also plan for warm temperatures and humidity.

For Exploring: Pack swimsuits, hats, comfy shoes, and something dressy for a night on Duval Street.

Planner Tip: Add a quick “What to Pack” section on your wedding website. Include sunscreen, sunglasses, and bug spray — these little reminders go a long way.

Things to Do — Your Guests’ Mini Vacation

Your wedding weekend isn’t just a day — it’s a whole experience. I love helping couples plan itineraries that give guests plenty of ways to enjoy the island before and after the wedding.

Here are a few can’t-miss favorites:

Sunset Sail: A catamaran cruise with Fury Water Adventures or Danger Charters is a magical way to welcome guests.

Snorkel or Paddleboard: Explore the coral reef or paddle through mangroves. The water here is postcard-perfect.

Duval Street Crawl: For the party crowd, this legendary strip is full of energy, live music, and local cocktails.

Beach Day: Fort Zachary Taylor Historic State Park is a local favorite for clear water and ocean breezes.

Sightseeing: From the Southernmost Point buoy to historic landmarks like The Ernest Hemingway Home & Museum, the photo ops are endless.

Island Eats: Suggest a few crowd-pleasers like Blue Heaven for brunch, Latitudes Key West for sunset dinners, or Santiago’s Bodega for a cozy group meal.

Planner Tip: A printed or digital itinerary included in a welcome bag makes guests feel instantly oriented and excited to explore.

Itinerary Ideas — How to Structure the Weekend

For destination weddings, a little structure goes a long way. I always recommend offering a few optional activities alongside your wedding events so guests can enjoy the island at their own pace.

Sample Weekend Timeline:

Thursday: Guests arrive. Optional welcome happy hour or casual dinner.

Friday: Morning beach time or sightseeing → Welcome party at sunset.

Saturday: Wedding day celebrations.

Sunday: Farewell brunch before everyone heads home.

This simple structure gives guests a mix of planned moments and free time to explore on their own — the perfect balance of celebration and vacation.

Thoughtful Touches — Elevating the Guest Experience

The best Key West wedding weekends are full of personal touches. A few simple details can make a huge difference in how welcomed your guests feel:

Welcome Bags: Include sunscreen, water, snacks, bug spray, and a handwritten note.

Mini Map & Recommendations: Share your favorite cafes, beaches, and cocktail bars.

Transportation Tips: Include golf cart rental info or walking directions from hotels to your venue.

Signature Moments: A casual welcome party, sunset sail, or farewell brunch adds that extra sparkle.

Planner Tip: Think of your guests’ weekend the way you’d plan a mini vacation — because that’s exactly what it is for them.

Final Thoughts — Making Your Wedding Weekend Unforgettable

When you host a destination wedding, your celebration becomes a shared adventure — and Key West is the perfect backdrop for that magic.

With the right travel tips, hotel recommendations, outfit inspiration, and a dash of island fun, your guests will leave with memories that last far beyond your wedding day.

As a Key West wedding planner, I’ve seen how thoughtful planning turns a weekend getaway into a once-in-a-lifetime experience. So go ahead — give your guests the ultimate tropical escape. They’ll thank you for it.

Let’s Plan Your Key West Wedding Weekend

This is your chance to create a celebration that feels like a vacation. Bookmark this Key West wedding weekend guide and start dreaming up your own unforgettable celebration.

If you’re dreaming of a destination wedding that feels effortless and unforgettable, we’d love to help make it happen.

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Ready to start planning? Reach out to us — we’ll help you bring your Key West wedding weekend to life.