a very key west bachelorette.

a very key west bachelorette.

So this post is a long, and I mean long, time coming (it’s also very long πŸ™‚ ).

Last August we went down to Key West for my best friend’s Bachelorette party (she, Ashley of Lifestyle blog NeverBeenSo, is now married, you can read her wedding story here). I was honored to have been her MOH and had the opportunity to plan this entire celebration. We had seventeen (YES… 17) girls gather from around the east coast and meet down in Florida to celebrate. It turned out to be the BEST weekend ever. Great food, great drinks, great expereinces. So great that I decided I had to share it with you.

Whether you’re going for a Bachelortte party or are just #cravingcurrently a quick weekend away in Key West here’s your go-to guide to everything you need to know in Key West.


Since there were so many of us I utilized HomeAway to find us a place that could accommodate 17 guests. The site is super easy to use and you have the ability to ask questions, see availability and total pricing all before even requesting to book.

We ultimately stayed at Old Town Garden Villas which is managed by Key West Vacation Rentals. You have the ability to book just one or as many Villas as you need up to the total five. Again, since we had 17 people we booked all five Villas.

PROs: The best part about this rental is that it’s close to Duval street – pretty far up but we definitely walked to the bars a couple times. Also cabs know where this property is so it’s easily navigated to and from.

CONs: The down side to this rental is that the Property Manager (not Key West Vacation Rentals but actual owner) lives in one of the Villas. If you plan on hanging out in the courtyard beware of the Property Manager. We had drinks out there one evening and we were told we were “too loud”. Bottom line – don’t rent this property if you are thinking to “stay in” – this is more a great place to house multiple people for a decent price.

Another accomodation that I found in researching:

La Concha Hotel & Spa


Blue Heaven 

While known for their Brunch with the Roosters – They have some fabulous lunch options. I went with the Chicken Salad on a roll but the Bachelorette went with this Sharp Cheddar, Arugala, Tomato & Avocado sandwhich.

Location: 729 Thomas St Key West, FL 33040 Hours: 8AM – 10:30 PM Daily

  • Good for? Breakfast served until 2PM, a live band + outdoor seating w. plentiful shade
  • Most recommended menu item? Shrimp & Grits, Mimosas, Key Lime Pie


Image via Instagram @NeverBeenSo

Cuban Coffee Queen 

You’ll likely need a morning or afternoon boost and this place should 100% be on your list. Their coffee is strong and will give you the kick in the pants you need to continue on your Key West binge. They also have some delicious looking sandwiches!

Location: 284 Margaret St. Key West, FL 33040 Hours: 6:30 AM – 7PM Daily

  • Good for? Funky take-out spot for Cuban fare
  • Most recommended menu item? Iced coffee with Coffee ice cubes

Glazed Donuts

Location: 420 Eaton St. Key West, FL 33040 Hours: 7AM – 3PM Daily

  • Good for?  DONUTS
  • Most recommended menu item? Maple Bourbon Candied Bacon Donut

Image from GlazedDonuts.com

Garbo’s Grill

Location: 409 Caroline St. Key West, FL 33040 Hours: 11AM – 3PM & 5PM – 9PM Thurs-Sat

  • Good for? Quick lunch (Food Truck)
  • Most recommended menu item? Yum Yum Shrimp Taco + being featured on Diner’s Drive-ins & Dives for their Koren Bulgogi Taco

Image via Instagram @KeyWestFoodTours

DJ’s Clam Shack

Location: 629 Duval St. Key West, FL 33040 Hours: 11:30 AM – 10 PM

  • Good for? A Quick bite
  • Most recommended menu item? Lobster rolls & Conch Fritters + being featured on Diner’s Drive-ins & Dives for their Clam Chowder

D R I N K + D O

Now there are PLENTY of bars in Key West so be sure to hit up more than just these – but our top favorites for a group of our size are below.

World’s Smallest Bar

Honestly – when in Key West you HAVE to have atleast one drink out of a pineapple. While it will run you $18 you can reuse the pineapple at other bars when you’re crawling along Duval Street. Bonus: It’s an arm workout..

Sloppy Joe’s 

Now I know this seems pretty ‘typical tourist’ but it became one of our favorite bars/”home base” if you will. First – because it always had enough room for all seventeen of us, second – they had some pretty delicious french fries and third – their live music was always on point.

Dante’s Key West

When you think of Florida I’m sure you assume that means you’ll be spending a lot of time on the beach – BUT in Key West there really isn’t a walking distance beach.

Enter… DANTE’s Pool Bar!

We spent one morning there and it was perfect – quick bar service, plenty of space, amazing music. I think it’s safe to say we all enjoyed ourselves and were able to get a nice break from the heat in the pool

Flamingo drink float via Amazon.


Yes I’m recommending you check out a Drag Queen show.

It’s fun, hilarious + just flat out amazing. If you’ve never been to one this is a great first experience. That’s all I’m going to say – buy tickets in advance and just enjoy the show. πŸ™‚


With all the drinking and barely any sleep you typically get on a bachelorette party I decided to organize a mid-morning yoga session for all the girls who wanted to participate.

Key West Yoga Sanctuary  was amazing and affordable. Gretchen came to the Villas and even brought mats for all of us. If you’re looking to hop in and take a class at their studio they are also flexible!


I cannot recommend Sebago Watersports more – since we had enough girls we were able to get a Private Charter, 41′ Maine yacht catamaran, (JUST US) from 10AM to 4PM for less than $150/person.

The private charter included breakfast (quiche, fresh fruit, pastry and juices) buffet lunch (peel & eat shrimp, sandwiches, fried chicken, various side salads and chocolate chip cookies) and cocktails, premium beers, boutique wines, sangria, soft drinks & water.

We were able to snorkel, see dolphins, and just anchor out in backcountry shallow water drinking and enjoying each others company. I think this day was everyone’s favorite  f o r   s u r e. If you have time in Key West this should 100% be on your list.


The best way to wrap this post up is to mention all the amazing things that helped to make this Bachelorette weekend a true success – the extras you need for a Bachelorette theme OF COURSE!

Since we were in Key West I went with the “Let’s Flamingle While Ashley’s Still Single” aka Flamingo theme (hence the Flamingo drink float shared above).

Welcome Bag Designed by me printed via Zazzle

Above image via Instagram @NeverBeenSo

Groom Tattoos via Dunkirk Designs


Custom Sunglasses via TheGlassHeartCo (Etsy)

So tell me – are you planning a Bachelorette trip or a weekend getaway anytime soon? Maybe considering Key West after this post?

Let me know in the comments below!




Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Stay Up to Date on Posts

Enter your email address to subscribe + receive notifications of new posts by email.