When it comes to destination weddings, Key West offers couples a unique blend of romance, history, and vibrant nightlife. If you’re like many couples planning to get away to the Southernmost City for your nuptials, you might be wondering how to entertain your small group of guests after your short ceremony. Enter “The Duval Crawl”, the perfect way to extend an otherwise-intimate ceremony at a favored local attraction like the Ernest Hemingway Home and Museum, and keep the celebration going as you hit the hotspots all along this iconic stretch of paradise.

To give your guests a true taste of Key West, the Duval Crawl combines much-loved locations, unforgettable moments, and, of course, countless opportunities for stunning photographs. Here’s how you can turn your intimate or non-traditional wedding day into an epic adventure your guests will talk about for years.

But First, Let’s Do the Details

Just because the majority of the day will not follow the traditional trajectory of a typical Key West wedding doesn’t mean we don’t need to capture those little details that make up the in-between moments of your special day. We will start by getting together your shoes, attire, and other accessories to create unique vignettes of all the carefully-considered accoutrements.

Next Stop, Ceremony Site

Once everyone was ready, it was time to head over to the Hemingway House, where close friends and family were gathering under the lush greenery beside the historic home of the late famed author. By scheduling a tour of the home, you can provide your guests with a little entertainment and enjoyment of the literary arts throughout the visit, while also taking in the views from the veranda in your wedding photography.

Start the Night at Green Parrot Bar

With the formalities done, it’s time to kick off your Duval Crawl at the Green Parrot, a beloved local haunt known for its laid-back vibe and quirky decor. Underneath the signature parachute ceiling, we captured stunning shots of the guests and snuck in candids of the laughs and revelry as patrons gathered around the bar for their preferred imbibement. For a peek into classic Key West charm, we also snagged some playful photos framed by the Parrot’s wide-open windows, letting in the golden island light.

Leave Your Mark at Willie T’s

Next, we stopped at Willie T’s, where the walls are famously covered in dollar bills. One of the best traditions here is to have a guest write a special message on a bill and staple it to the wall—a fun way to commemorate your wedding day and leave a piece of your love story in Key West forever. Strike a pose with a “just married” dollar, surrounded by the rich, layered history of past visitors.

For a bit of humor throughout the day, and to give guests a bit of an ice-breaker who don’t know one another, consider setting up a scavenger hunt, or as this one guest initiated, a Wedding Day Adlib notebook. No doubt the family will enjoy a hearty chuckle at the mismatched plot lines filled in with random nouns, colors, and terms of endearment as they read back the story at the end of the day.

A Toast to Jimmy Buffett at Margaritaville

As you stroll down Duval, make sure to pause under the Margaritaville sign, a tribute to the late, great Jimmy Buffett. The neon glow makes for a vibrant backdrop as we capture candid photos of your group basking in the fun, carefree island vibe. It’s a quintessential Key West moment, perfect for music lovers and fans of Buffett’s legendary lifestyle.

Dancing AMID History at Irish Kevin’s

For live music and hearty laughs, Irish Kevin’s is a must-visit. The handcrafted wooden cabinetry, quirky artwork, and iconic Jameson bottle chandelier create an intimate yet energetic atmosphere. Here, you can take to the dance floor while Irish Kevin himself plays a tune. In a space like this, we can capture every joyful moment, from the energetic sway of an impromptu air guitar move, to the nom-nom of a scrumptious chicken wing by a hungry nephew, to the laughter over a shared toast with family and friends.

GET SILLY at Sloppy Joe’s

No Key West experience is complete without a stop at Sloppy Joe’s, a favorite hangout of Ernest Hemingway. We seized the chance to take striking photos in the middle of the road, with the Sloppy Joe’s facade standing in the background. The group’s energy, paired with the historic charm of this bar, created unforgettable moments that embodied the spirit of the island.

Tossing Pennies and Playing Pool at Captain Tony’s

At Captain Tony’s, it’s time to embrace playful traditions, tossing coins into the fish statue overhead for good luck. Inside, the atmosphere turns competitive as you’re able to challenge guests to a friendly game of pool. This venue offered some of the night’s most candid shots, capturing laughter, camaraderie, and those fleeting in-between moments that make your wedding day truly special.

Shot Ski at Smallest Bar

As the night wound down and the group got a little smaller, we hit the appropriately sized Smallest Bar, a quirky stop perfect for a quick beverage, courtesy of the “shot ski”. This Key West tradition involves lining up shots on a wooden ski and downing them in unison—a guaranteed crowd-pleaser. Guests enjoyed the camaraderie while we captured photos of their synchronized toasts and infectious smiles.

Capturing Musical Moments at Schooner Wharf Bar

Finally, we landed at Schooner Wharf Bar, nestled in the heart of Key West’s marina district. With live music filling the air and the sea breeze carrying laughter and conversation, it was the perfect place to end the night. As the couple and their guests danced and dined, we captured the relaxed yet lively atmosphere, highlighting the joy of celebrating love in one of the island’s most visited venues.

Why Choose a Duval Crawl for Your Wedding Day?

Planning a Duval Crawl after your Key West wedding isn’t just about the fun—it’s about creating a memorable experience for your guests and capturing those moments in a way that lasts a lifetime.

We know that no two weddings are alike, which is why we always emphasize that no matter how your big day is structured, we will be there to capture elevated images at every angle, documenting not only your ceremony but also the spontaneous, joyful adventures that follow. From iconic landmarks to hidden gems, we’ll make sure every part of your celebration is beautifully preserved.

For couples planning a destination wedding in Key West, the Duval Crawl is a perfect way to keep the party going, introduce your guests to the island’s rich culture, and capture unforgettable memories. One minute you’re sipping cocktails at Green Parrot or dancing under the stars at Schooner Wharf, the next you’re making friends with the people down the bar from you, taking photos in the 30 seconds before the next traffic light turns green, and whisking away your loved ones through a tropical island oasis that only Key West can deliver.

May your wedding day, no matter how non-traditional it may be, be filled with laughter, love, and plenty of photo-worthy moments.

Ready to turn your Key West wedding into an unforgettable adventure? Contact us today to learn more about our wedding photography services and how we can help you with your Key West wedding vision.

Special thank you to the other vendors who made this event a success:

Planner: WCO Events

Getting Ready Venue: The Galleon resort

First Look Spot: Truman Annex

Ceremony Venue: Hemingway House

Bar Crawl Stops: Green Parrot, Willie T’s, Irish Kevin’s, Sloppy Joe’s, Captain Tony’s, Smallest Bar, Schooner Wharf

Flowers and Decor: Karro Events

Beauty: Casa Salon

Groom’s Attire: Tommy Bahama

Officiant: Ralph at Hemingway

Videographer: Joanna Cooper | Soundwave Productions

Photographers: Karrie Porter and Mark Funkhouser

Host a Duval Crawl During Your Intimate Key West Wedding