Bachelorette in Key West, FL

Bachelorette in Key West, FL

Hamilton
If you're looking for a fun-filled bachelorette weekend, Key West, FL is the perfect destination! Here's a suggested itinerary for your 3-day trip. Included are daytime activities, places to explore, and great food and drinks
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Day One: Beach by Day and Bars by Night

Today is the day to get settled and enjoy the island life. Depending on what time you arrive you can switch up the timeline or cut things out based on your preference. 

Spend the day exploring the island and its beaches. 

Some suggested beaches are:

South Beach - 🌊

Southernmost Point of the Continental U.S.A.
@hamiltoncheatham
this is a small beach that can get very crowded. It is also the southern-most point in the continental US! It is definitely the place tourist go but has chair and umbrella rentals for those sunny days. Do keep in mind there are no public restrooms and coolers are not allowed!
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Smathers Beach - 🐚

Smathers Beach
@hamiltoncheatham
This is the most popular beach on the island so expect to see plenty of people! There are plenty of things to do and food vendors here. There are also water sport rentals if you're feeling adventurous!
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Higgs Beach/Rest Beach - 🏖️

Clarence S.Higgs Memorial Beach
@hamiltoncheatham
This beach can also get crowded depending on the time of year but is one of the best beaches. You can take a walk along White Street Fishing Pier while you're here. Parking is free here!
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In the evening, its time to explore the famous ...

Duval Street

There are plenty of places to eat along this strip so you can grab some food before its time to begin your bar-hopping adventure!

If you would rather not plan your own bar crawl, there are guided tours like the Duval Crawl

Day Two: Take to the Sea

Today is the day for hitting the water and enjoying the beautiful Gulf of Mexico.

Start by renting a boat or joining a day cruise 🛥️

Key West Boat Rentals

At Key West Boat Rentals you will have your pick of boat which is great for small or large parties. You can also rent a boat captain for an additional fee

Laggerhead's Rum Runner Boat Rentals

If you're looking for a booze cruise this ones for you! Laggerhead's Rum Runner Boat Rentals offers private, captained boats that you can bring your own drinks or select one of their drink packages!

There are also plenty of public cruises with varying options. Some include drinks or food, some include music. No matter what you want you can find the perfect rental for you!

Dinner: First Flight ✈️

First Flight Island Restaurant & Brewery
@hamiltoncheatham
For dinner, check out First Flight. This was the birthplace of Pan American World Airways, Pan-Am’s first tickets were sold out of this very building in 1927 this location is now home to brewery and restaurant
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Then, if you're feeling up to it, here are some more bar suggestions: The Rum Bar, The Porch, The Bull and Whistle

Day Three: Pool Bar

This day will include a fun party location at Dante’s and a fun place to explore and watch the sunset.

Dante's 🪩

For your last day in Key West we suggest visiting Dante's. The self proclaimed "alcoholics paradise" offers seating, a beautiful pool with a waterfall, and food and drink service. You could spend all day here or just a few hours and the best part: its free to enter!

If you are looking for a lounger or pool side table we suggest getting there when they open at 11 as they are first come first serve. Otherwise, there is plenty of seating al around.

Mallory Square ☀️

We also suggest spending time along Mallory Square. The best time to go is during sunset where you can watch along the water. This view is so spectacular they have a Sunset Celebration every night with  magicians, jugglers and clowns, local musicians, artists, and food vendors!

Where to Stay

House Rentals 🏠

If you're looking for something a little more eclectic: 

If you're looking for a big beautiful back deck and pool:

Hotels 🏢

If you're looking for more of a resort-vibe:

Key West Marriott Beachside Hotel
@hamiltoncheatham
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Or more of the Old Town feel that is close to the city hotel:

The Saint Hotel Key West, Autograph Collection
@hamiltoncheatham
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Where to Eat:

Stoned Crab: 🦀

The Stoned Crab
@hamiltoncheatham
here you can find fresh seafood and outdoor seating with a beautiful view of the water.
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Louie's Backyard: 🐟

Louie's Backyard
@hamiltoncheatham
this is a Caribbean American restaurant with multi-level deck seating
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Fogarty's & the Flying Monkey Saloon:

Fogarty's
@hamiltoncheatham
This restaurant is perfect for any Duval Street adventures and has an amazing frozen drink menu.
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Summary of Places to Go

Capt Tony’s Saloon
@hamiltoncheatham
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Sloppy Joe's
@hamiltoncheatham
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Fogarty's
@hamiltoncheatham
This restaurant is perfect for any Duval Street adventures and has an amazing frozen drink menu.
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Key West First Legal Rum Distillery
@hamiltoncheatham
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First Flight Island Restaurant & Brewery
@hamiltoncheatham
For dinner, check out First Flight. This was the birthplace of Pan American World Airways, Pan-Am’s first tickets were sold out of this very building in 1927 this location is now home to brewery and restaurant
Add to
Details
Southernmost Point of the Continental U.S.A.
@hamiltoncheatham
this is a small beach that can get very crowded. It is also the southern-most point in the continental US! It is definitely the place tourist go but has chair and umbrella rentals for those sunny days. Do keep in mind there are no public restrooms and coolers are not allowed!
Add to
Details
Clarence S.Higgs Memorial Beach
@hamiltoncheatham
This beach can also get crowded depending on the time of year but is one of the best beaches. You can take a walk along White Street Fishing Pier while you're here. Parking is free here!
Add to
Details
Smathers Beach
@hamiltoncheatham
This is the most popular beach on the island so expect to see plenty of people! There are plenty of things to do and food vendors here. There are also water sport rentals if you're feeling adventurous!
Add to
Details
Mallory Square
@hamiltoncheatham
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Dante's Key West Pool Bar & Restaurant
@hamiltoncheatham
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Key West Boat Rentals
@hamiltoncheatham
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Lagerheads Beach Bar & Watersports
@hamiltoncheatham
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ABOUT THE AUTHOR
Hamilton
I am known to friends and family for making travel plans and detailed itineraries. Here, I can share what I love to do, where I love to go, and where I want to go with everyone! I love good food and even better cocktails which will be found on almost all of my plans! My guides will typically include one to two things per day that need to be scheduled with optional things as well. For a more personalized or detailed plan, or the things I want to gatekeep, reach out to purchase my specialty items.
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