Resort Style Florida Wedding

A Playful, Stylish Wedding With Resort Vibes at a Historic Cigar Factory

Okay, this wedding was FUN! As a Florida wedding photographer who lives for colorful, tropical resort-style weddings, and Hannah-Leigh & Ryan’s day checked every single box. Their wedding was in a historic cigar factory that had all the charm you’d want from an old building: original brick, huuuge windows, rooftop views and the whole day had this vibrant, laid-back vibe that felt like a vacation and a celebration!

Hannah-Leigh got ready in a beautiful old mansion from the early 1800’s, then did a first look with Ryan in the backyard garden. I always ask my couples if there was just one photo they could have from their wedding day, what would it be? HL + Ryan said it would be a black and white portrait of them that also showed off historic homes and palm trees – mission accomplished!

The bridesmaids wore mixmatch blue dresses that looked so good together, and HL wore a gorgeous gown with a floral embellished veil that was just… next level. I’m obsessed.

Their ceremony was in the same historic church where Hannah-Leigh’s parents and grandparents were married, which was such a sweet full-circle moment for them. 

Some of my favorite things from their tropical resort style wedding day:

• Hannah-Leigh’s look. The gown, the veil, the earrings. And then she changed into her mom’s pearl-covered shift dress for dancing which was SO cool and made it feel even more personal!

• Their custom made wedding invitations! A sailboat dyecut?! Watercolor monogram?! Swoon

• Their “tropical resort” theme actually worked so well in the historic cigar factory. Their planner designed a space that used palm fronds, colorful flowers, custom bar decals with puffer fish & sand hill cranes, and lush greenery creeping up the wooden columns, and guests leaned into the theme and dressed like they were heading to a welcome party in Tulum!

• Ryan’s personality in literally every photo. He was throwing thumbs-ups and cracking jokes all day. 

• The sunset rooftop portraits with sunglasses (iconic)

• Espresso martinis + ice cream sandwiches as a late night snack? A power move.

• Flower leis handed out on the dance floor along with glow sticks

• A pedicab exit (!!)

It was such a good balance of thoughtful and fun. Stylish without being overdone. Personal in all the right ways. You could tell that everyone felt comfortable, relaxed, and ready to celebrate!

If you’re planning a Florida wedding with tropical or resort-inspired details, and especially if you’re considering a historic venue like one of the cigar factories in Tampa’s Ybor City, scroll through this one for inspo. There’s so much to love.

 

10 Wedding Venues That Work for a Tropical Resort Vibe

Florida

• Cheeca Lodge & Spa – Islamorada
  Right on the water with actual palm trees and beachy energy. Perfect for a welcome party-to-wedding weekend that feels like a mini vacation.
• Gasparilla Inn – Boca Grande
  Old Florida charm in the best way—banyan trees, wraparound porches, and that timeless private club feel. You’ll want to stay all week.
• Casa Marina Key West – Key West
  Historic meets breezy resort. Ceremonies under the palms, string lights by the ocean, and everything just steps from the sand.
• Hotel Faena – Miami
  This place is basically tropical resort energy wrapped in red velvet and gold leaf. With palm-lined terraces, ocean views, and bold, art-forward interiors, it’s perfect for couples who want their wedding to feel like a vacation and a fashion editorial.
  
• The Breakers Palm Beach – Palm Beach
  Over-the-top in all the right ways. Think seaside arches, palm-draped courtyards, and full iconic glam. Big energy, zero ballroom vibes.

Outside Florida

• La Casa Que Canta – Zihuatanejo, Mexico
  Cut into a cliff with infinity pools and warm terracotta walls. Feels like a secret resort takeover with every view straight out of a movie.
• Hotel San Cristóbal – Todos Santos, Mexico
  Bright, bold, and design-forward. It’s got personality for days—and yes, the beachfront ceremony + poolside cocktail hour combo hits hard.
• Andaz Maui at Wailea – Maui, Hawaii
  Tropical, minimal, and modern. Palms, soft light, ocean air, and tons of open space to play with. Resort energy but cooler.
• The Ocean Club, A Four Seasons Resort – Bahamas
  Picture bougainvillea, breeze-block walls, and a Versailles-style garden… on an island. Somehow lush and architectural.
• Villa Balbiano – Lake Como, Italy
  Okay, hear me out, I know its Europe—but with palms, gardens, and private lake views, it fits the vibe. Think tropical luxury with an Italian passport.

FAQ’s because if you’re planning a tropical wedding, you’ve probably got at least 87 tabs open

Can I pull off a resort-style wedding in Florida without it feeling cheesy?
Yes! Hannah-Leigh & Ryan wanted to stay indoors because they knew it’d be too hot to be outdoors for 12 hours, so they nailed it by using vibrant flowers, palm fronds, personal details, and a venue with charm. You don’t need tiki torches or flamingos to make it feel like a party in paradise (but hey…I love flamingos lean into that kitch if you like it!)

What kind of venues work best for tropical-inspired weddings?
Look for historic spaces with character (like cigar factories in Tampa’s Ybor City), private estates with lots of greenery, or blank-slate venues where you can bring in the vibe yourself. It’s less about location, more about how it feels. But of course, the easiest way to actually host your wedding at an upscale tropical resort!

I’m not into traditional decor—can the design still feel elevated?
Totally. This wedding had custom illustration bar decals with fish and cranes, colorful flower leis on the dance floor, and a pearl shift dress from the 80s—and it still felt stylish and pulled-together. It’s all about intention!

Planning a resort-style Florida wedding with colorful tropical details?
I’m a Florida wedding photographer who loves documenting celebrations that feel fun, stylish, and full of personality—whether you’re getting married at a historic cigar factory or an actual resort on the water.
If that sounds like the kind of day you’re planning, get in touch here I’d love to hear all about it.