The Ultimate Key West Bachelorette Party Itinerary: A Fun & Sun-Filled Weekend

Planning a Key West bachelorette party? Whether you’re looking for sun-soaked boat days, lively nightlife on Duval Street, or delicious seafood spots, this itinerary has everything you need for an unforgettable girls’ getaway. From tiki boats to beach bars, here’s how to plan the perfect bachelorette weekend in Key West!

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Day 1: Arriving & Kicking Off the Celebrations

🏨 Check-In at The Laureate Hotel & Airbnb Setup

Start your bachelorette weekend in Key West by checking into The Laureate Hotel—a chic, waterfront hotel perfect for relaxing between the festivities. If you’re staying in an Airbnb, set up some bachelorette decorations to make it extra festive! Caitlyn’s Bachelorette was Love Island themed — specifically Casa Caitlyn which was adorable.

Love Island Theme

🍹 Sunset Drinks & Live Music at Sunset Pier

First stop: Sunset Pier for tropical cocktails, stunning ocean views, and live music. It’s the perfect way to soak in the Key West sunset and kick off the weekend.

🍽️ Dinner at Two Friends

After drinks, we enjoyed a laid-back dinner at Two Friends, a Key West staple known for its seafood, key lime pie, and welcoming atmosphere.

Day 2: Brunch, Poolside Drinks & A Special Surprise

🍳 Early Morning Brunch at Blue Heaven

No Key West bachelorette itinerary is complete without brunch at Blue Heaven! Known for their banana pancakes and mimosas, this is a must-visit. Arrive early to avoid long waits! They open at 8AM.

🍹 Pool Party at Dante’s Pool Bar

Head to Dante’s at 11 AM to snag a poolside table. This is the ultimate daytime party spot, with DJ sets, frozen drinks, and a fun, laid-back vibe.

☀️ Relax at the Airbnb Pool

After a high-energy morning, chill out at your Airbnb’s pool and recharge for the night ahead.

🎤 Surprise PowerPoint Night & Lingerie Shower

A bachelorette must—PowerPoint Night! Each friend made a funny presentation about the bride, and we also threw a lingerie shower to surprise her with cute bridal pieces.

Day 3: Boat Day & The Ultimate Key West Nightlife Tour

🏝️ Pontoon Tiki Boat Adventure (11 AM – 3 PM)

We booked a Pontoon Tiki Boat and spent the day cruising, sipping cocktails, and relaxing on a secluded island. This was by far one of the best parts of the trip!

🍸 Happy Hour at George’s (Spritz Bar in a Historic Hotel)

After freshening up, we made it to George’s, a beautiful spritz bar with an elegant atmosphere—a must for Instagram-worthy cocktails!

🐶 Drinks at Hank’s (The Golden Retriever Bar!)

If you love dogs, Hank’s Hair of the Dog Saloon is the place to be. Golden retrievers everywhere, plus great drinks and live music!

🍽️ Dinner at Bagatelle

A charming restaurant perfect for a pre-game dinner before hitting the town. This was our most upscale dinner and it was delish. Highly recommend Bagatelle!

🎶 The Ultimate Key West Bar Crawl on Duval Street

No bachelorette party in Key West is complete without a Duval Street bar crawl. Here’s where we went:
✔ Rick’s & Durty Harry’s – Great for dancing & fun crowds
✔ Irish Kevin’s – High-energy live music & hilarious crowd engagement
✔ Sloppy Joe’s – A Key West classic for drinks & dancing

We danced the night away and had the best time exploring Key West nightlife!

Day 4: Heading Home

✈️ Easy Departure with Silver Airways

After an incredible weekend, we took an easy Silver Airways flight home—quick, convenient, and stress-free.

Key Takeaways for the Perfect Key West Bachelorette Party

✔ Book reservations early where you can – Popular spots like Blue Heaven & Dante’s fill up fast but many don’t take reservations. Arrive early to avoid long waits.
✔ Pack for the heat – Lightweight outfits, sunscreen, and comfortable shoes for bar-hopping.
✔ Plan a mix of activities – Balance boat days with poolside lounging and plenty of nightlife fun.
✔ Stay hydrated – With all the cocktails and Key West sun, make sure you’re drinking water too!

If you’re planning a bachelorette party in Key West, this itinerary will give you the perfect mix of relaxation, adventure, and unforgettable memories. Cheers to the bride-to-be and the best girls’ trip ever! 🥂☀️💃

Cait and I are college besties from our Zeta days. So fun being engaged at the same time!

What to Wear

PSA: Everything I’m wearing is from Fashion Pass. It’s kinda ideal for bachelorette weekends or weddings when you’re only wearing items once. It’s been a fun challenge to pick clothing items a little out of my comfort zone to shoot with too! If you’re interested in Fashion Pass, you can use my code HELLOEMILYERIN for $$$ off your first month.

Goodie Bags

Make your bachelorette party an affair to remember with specially curated bachelorette party favor bags for your girls! These thoughtfully designed bags are the perfect way to show appreciation to your closest friends and make them feel extra special during this celebratory occasion. Each bag is filled with carefully selected goodies and surprises that will make your bridesmaids feel pampered and loved.

I’d recommend goings with items you know your girls will use on the trip. Below are some of the essentials that your bridesmaids will actually use, versus another silly little “bridesmaid” embroidered item that they’ll just stuff in a drawer or donate.

📌 Save This Itinerary for Your Key West Bachelorette Party!

Are you planning a Key West bachelorette trip? Drop your must-do recommendations in the comments! ⬇️

The Ultimate Key West Bachelorette Party Itinerary: A Fun & Sun-Filled Weekend

Day 1: Arriving & Kicking Off the Celebrations