Your Guide to Planning the Perfect Key West Wedding Weekend

One of the perks of planning a Key West wedding is that it doesn’t have to be just one day. It can be a full weekend of memories. With guests flying in from all over, couples often want to maximize their time together and make the most of everything paradise has to offer. As Key West wedding planners, we often help couples design multi-day celebrations that blend wedding traditions with tropical island fun.

Here’s how to host an unforgettable multi-day Key West wedding weekend, from welcome parties to farewell brunches.

Photo By: Sand and Sea Studios

Start Your Key West Wedding Weekend with a Welcome Party

Guests are often arriving from long flights or drives, so a welcome event is the perfect way to greet them and set the tone for the weekend. This doesn’t have to be overly formal—it could be as simple as a poolside cocktail hour, a casual dinner at a local Key West favorite, or even a sunset cruise around the island.

Ideas: Rum punch and island-inspired hors d’oeuvres, live acoustic music, or a tropical-themed evening.

Planner Tip: Include a welcome bag with local goodies. Think key lime cookies, flip flops, sunscreen, and bottled water so guests instantly feel at home in paradise.

Photo By: Sand and Sea Studios

Add Flavor with a Rehearsal Dinner in Paradise

The rehearsal dinner is traditionally the night before the wedding, but in Key West, couples often use it as another opportunity to showcase the island’s personality. From garden courtyards to waterfront restaurants, the setting can match your vibe—intimate and relaxed or bold and festive.

Ideas: Host a Cuban-inspired dinner with mojitos and live music, or a seafood feast highlighting Key West’s local catch.

Planner Tip: If your wedding guest list is on the smaller side, consider inviting everyone to the rehearsal dinner—it sets the tone for a more connected celebration.

Photo By: Iris Moore Photography

The Wedding Celebration

The wedding day itself is, of course, the centerpiece of the weekend. Whether it’s a tropical garden ceremony, a waterfront exchange of vows, or a beachfront soirée, Key West offers the perfect backdrop. With so many venues to choose from, your wedding can truly reflect your personal style.

Planner Tip: Keep the timeline smooth by arranging shuttles or trolleys for guests—especially important if venues are spread across Old Town or the beachside resorts.

Ideas: Start the morning with mimosas while getting ready, plan golden-hour portraits, and end the night with a lively dance floor under the stars.

Photo By: Meagan Puett Photography

End the Weekend with a Relaxed Farewell Brunch

Wrap up the weekend with a relaxed farewell brunch. This gives you one last chance to connect with your guests and say thank you before everyone heads home. Many couples choose an outdoor café, hotel terrace, or even a casual beachside spot for this sendoff.

Ideas: Key lime pancakes, Bloody Mary and mimosa bars, or light island fare like fresh fruit and pastries.

Planner Tip: Keep it casual—this is the day for sundresses, flip-flops, and lots of hugs goodbye.

Photo By: Macy Ryan Photography

Optional Add-Ons for Your Key West Wedding Weekend

Want to take your wedding weekend to the next level? Consider weaving in island activities for guests to enjoy:

-Snorkeling or sailing excursions

-A group visit to the local attractions or museums

-Sunset sails with champagne

-A bar crawl down famous Duval Street

-Guided bike tours of Old Town Key West

Photo By: Iris Moore Photography

A Key West wedding weekend isn’t just about the wedding day—it’s about creating a full experience for your guests and making memories that stretch far beyond the ceremony. From welcome parties to farewell brunches, every moment is a chance to celebrate love, laughter, and a little bit of island magic.

As Key West wedding planners, we love helping couples map out their entire weekend so that each day flows beautifully. Whether you want laid-back beach vibes, glamorous soirées, or a mix of both, paradise has everything you need to turn your wedding into the ultimate getaway.

Ready to plan your Key West wedding weekend? Our team of experienced Key West wedding planners will help you design a full celebration, from welcome cocktails to farewell brunches. Contact us today to start planning your dream wedding in paradise.