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Key West Specifically

Updated: May 7

If you are planning a trip to the Florida Keys that focuses on time in Key West, this itinerary is for you! Key West Specifically is written considering that many visits will focus on a group of Upper, Lower, or Middle Keys. This is itinerary specific to quality time in Key West. I have other blogs for all the Keys, for more, click here.


At the Key West Bouey, a family has fun at night
The Southernmost point, on the south side of Key West

Key West is full of life no matter when you are there. Day or night, January 1 - December 31, around the clock this is a is a fabulous vacation destination for so many reasons. As Floridians we have enjoyed the Key West experience several times. The majority of the time I find myself more on the water and less on the land. As I'm leaving, I make a list of all the activities I want to come back and do. In talking with the locals, I gain insights for future trip ideas and even gain ideas from fellow travelers in hotel elevators. All of this to say: I never run out new fun ideas and look forward to returning for the next ideas to get tried!

Baby in Key West
My sweet girl having a blast

Recently, as the grandma, I opted to do more low-key activities to stay with the baby while my crew ran around. I greatly enjoyed this! Here are some of our favorites for anyone else planning a trip to Key West. The vibe in the farthest South Island of the US is definitely less planning, more lounging and living. This will help you navigate and be intentional with your time, we all know vacations go waaaay too fast. I am happy to share itinerary ideas to make your trip all you envision.


This is NOT something I say everywhere you go:

This is where you go to RELAX.

The colors of the water which surround you at every turn can only be described as “tranquility”. If these varied shades were a crayon, it would be every color of blue and turquoise, changing with the sky all day long, a living rotation of aquamarine.

 

How you relax is entirely up to you. We all run on different fumes, and these are all suggestions. You may work in plenty of down time by the pool or on a boat and this may be a mirage of possibilities for your exploration.


Watching the sun set in Key West
Sunset at Mallory Square

Bolded underlined test will link to the matching website for your convenience. These is no affiliate marketing or sharing of my subscribers. This is a work of my own experience shared to make traveling easier. I do appreciate your likes, shares, and reviews. Feel free to leave a comment below with your own suggestions as well.

 

Accommodations:

Where should we stay?

On this most recent April 2024 trip to Key West, we stayed at the Double Tree Resort by Hilton Hotel Grand Key - Key West.

Why the Double Tree? They accept AAA, AARP, and Government rates. They have a free shuttle to the airport AND to downtown areas like Mallory Square. They have an onsite restaurant which is affordable and delicious. Great pool, hot tub, and rooms with a balcony. Are they the fanciest or most luxurious? No, but they are a solid choice. Cons of this site include: No microwave in the room and no free breakfast. However, the pleasantness of the staff, and great atmosphere outweigh this in my opinion.



Details below on the following:

A few things that seem top of everyone’s list: The Hemmingway House, Butterfly Conservatory and Mallory Square at Sunset.

A few things to know: Beaches here are NOT your regular beaches. They are rocky and narrow strips along the coast. There are four beaches in Key West, however and each offer a different vibe and are worth a visit. If you are planning to explore, don’t forget your water shoes!

A few hidden FREE treasures: The Key West Garden Club, the Historic Key West app for self-guided tours, and free rum tasting at the First Legal Rum Distillery.

Photo Ops Must stops (ALL FREE):

The Southern Most Bouey

Mile Marker 0

Best Sunsets

Directional Markers

You haven’t been to Key West if you didn’t get a photo of a rooster, iguana, and a six toed cat.

 


Recommended Itinerary: Spend 3 full days exploring the Island of Key West, divided by section.

Day 1: The South Side

1. You’ll want to start your day at Smathers Beach – paddle board or float in the water

2. Lunch: Margaritaville (across the street) for lunch. Cheaper option is a cooler and Publix subs

3. Higgs Beach and the White Street Pier

This area is packed with history. There is an African American Cemetery, also an AIDS Memorial.

Cool place to walk, roller blade or even ride a bike.

Playground across the street

4. The Key West Garden Club inside of Martello Tower (9:30 – 5pm)

5. Eat dinner at Salute! Great food and views.

6. Walk / ride down to the Southern Most buoy.

 

This day (not including food or rentals) is free – no fees for entry, we found free parking as well at the beaches. Eating will not be free and renting and beach chairs or extras will have a cost. To save: bring your towels and cooler and whatever else you might like! I REALLY enjoy Key West walking as the streets are safe and scenic.

To splurge: Rent the paddle board or jet ski. The view in the water is just amazing.



Day 2: The North Side – Start early to squeeze in three (or four) local hot spots before 5 pm

1. Start your day at Zachary Taylor State Park – $7.00/car: bring your snorkels and go out to the little reef where you can see all of the marine life you wish! Rentals are available. Concession stand has unusually good beach food. Water shoes needed as the rocky coast here is rough on feet.

*Drive over to the Fort side of the park. There is a free tour daily at 11 am (fort closes at 5)

*Hike the Tropical Hammock Trail or Fort View Nature Trail and take in some of the native plants and ocean views

2. Head over to the Ernest Hemmingway Home and Museum (9:30 – 5, last entry 4:30) - $18.00/adult,  $7.00/ child (6 – 12),  Children 5 and under free:  take a tour or self-guided tour around the home and gardens (Apx. 2 hours)

3. Stop by the Key West Lighthouse & Museum (10:00 – 4:30 pm) -$15.50/ adult,  $11.50/ Senior/ local/ college,  $7.50 kids (7-18),  FREE 6 and under, Active Military: Walk up to the top, enjoy the views, and browse the history

4. Spend an hour at the Butterfly & Nature Conservatory (9:00 am – 5:30pm) Buy tickets online and save – $17.50/ adult, $12.50/ child,  Free /3 and under, $14.50/ military (Save up to $2.00 each adult by buying online). Walk through this scenic beautiful place and truly be surrounded by the butterflies with in!

5. Mallory Square for Sunset – AMAZING views and every night starting an hour before the sun sets is the nightly celebration!

6. Free Rum Tasting: (11:am – 6:00 pm) stop at the First Legal Rum Distillery and do some tasting!

7. Food: Today eat at Sloppy Joes, Alanzo’s Oyster Bar

 

This is a pricey kind of day. Maybe you make all of these stops and maybe not. For one person, entry fees alone will be over $50.00. With a family this can quickly multiply. My advice is add some of these quality additions into your plans and take advantage of the activities you can only find here. ** Note: The Butterfly Conservatory is closer to the Southside and Southern most buoy. If you swap out your afternoon Day 1 plans and can make it there before 4:30, go for it! If it's a bit rainy or you need a day out of the sun (lots of burned skin going around) these indoor hot spots can be a full day.



Day 3: Duval Street and some historical fun

1.Download one of the two apps: Explore Key West Historic App – call 305 – 507 – 0300 to tune in for the walking tour OR the shorter walking tour is Florida Stories which has 12 key locations and comes from the Florida Humanities Council. Walk around through history!

This will wind you through some of the old historical sites with lots of references to the culture and significance of what you are a part of here in this unique area.

2. Walk Duval Street: Eat. Drink. Wander. See art, souvenirs, and try key lime pie. Have all the delicious things and wander the area. About 1 mile long, there is a wealth of bars, restaurants, gift shops, boutiques, art galleries, cafes, even spa services. Rent a scooter, or a bike. At the north end of the street, you will run right into South Beach, which is the smallest (only 200 feet long) stretch of beach and has no restrooms. Backing up to the Southernmost Café, walk out on the Pier and take in those Atlantic colors!

3. The Eco-Discovery Center – 6000 square feet of interactive free exhibits with very interesting and educational information. Great indoor activity and can be done as slowly or quickly as you wish.

4. The Key West Aquarium (9:00 – 6:00 pm) is a local gem. If you want some good tours and to watch marine life feeding times, check the website to plan your times of visit. Adults $20.00  Children (4-12) $11.99. Prices are better online.  

 

This day is a bit of a wander and explore vibe. I always want this time to just take it all in. It can be kept as a free of cost day if you skip the Aquarium, but if you add some of the museums along the tour, it can also add up. I never get enough time to meander through the streets of Key West. Because most of the sites close at 5 pm, this is always a time where I am forced to make decisions.

Spoiler alert: It's all good!



While many people come here to fish, snorkel, boat, paddle, kayak or float, the water is the most exquisite experience. Typically warm and full of colorful fish, the reef 3 miles out in the Atlantic creates an ecosystem unique to this area. There is not an abundance of sandy beach. Key West itself is very rocky and beaches are narrow. This creates a limited space and that leads to making good beach a hot commodity.


One of my favorite family memories is riding through Key West on scooters! This made for an awesome Christmas time excursion! We also snorkeled out to Alligator Reef as well.


Key West Beaches:

Fort Zachary Taylor Historic State Park: Just wow. As far as State Parks go this one is jaw dropping gorgeous.



South Beach: The smallest of the choices on the island, it’s also a lively spot to experience! Close to Duval Street, this is a local favorite, I


The North side of Duval Street, South Beach
Beautiful South Beach view, Key West

Higgs Memorial Beach Park - which is right next to White Street Pier. There is also the African American Cemetary and AIDS Memorial all in one row.



Smathers Beach is the biggest beach of Key West and starts at mile marker 0, which is the end (or beginning based on which way you are going) of A1A. Approximately a half mile long, this strip of Ocean is a tropical paradise. This is a popular beach for water sports, they rent umbrella chairs, as well as jet skis, and paddle boards. They have shower facilities and volleyball courts. I see lots of people set up shop for the day bringing all the beach toys they would need for digging to China (lol).



 

Key West is the best tropical experience in the US and a fabulous vacation destination. I live in Florida, I visit here often for family vacations. This particular trip was for business, and I was able to experience a different side of Key West (literally). I greatly enjoy the culture here and Island time.

 More Details

Let's talk food...

** Lobster Shack - amazing lobster rolls.

** Sloppy Joes - typical bar food but a really good time! Live music and loud crowd.

** Salute! - Right besides Higgs each and this was my favorite grouper of this trip.

** Fogarty's - Great for groups, outside environment, excellent service and fun.

**Alonzo's Oyster Bay - Delicious food with a seaport view.

The culture of the Keys is built on excellent service. There are no bad restaurants! Seafood is especially fresh and delicious.


Driving in:

The road trip to Key West will take you through a chain of small islands known as "the Keys" and if you like the beautiful Ocean, this drive is for you. If you like stopping off along the way and enjoying the scenic route, this is definitely for you! My favorite way to get here is driving, as the windows down and fresh sea salt air immediately lift the mood and set the pace for the trip. Do NOT speed - the police here are serious about those speed limits.


Flying in:

The Key West airport had gained momentum! Airlines that fly in: Delta, American, Silver, United, JetBlue and Allegiant. While flights are limited and sometimes more moderately priced, many fly into Miami or even Fort Lauderdale, to rent a car and drive through the Keys. Honestly, this is the way most still visit. The car rental locations in Key West do not keep a high enough inventory in my experience.


Packing: When luggage is weighed paid, I am as conservative as possible. A few bathing suits, something nice to wear for dinner, casual shorts and yoga pants, tee shirt, tank tops.

You still need some beach towels as many of the Hotels don't provide good beach towels. I suggest a soft sided cooler and the items listed below if possible.


Must Haves:

Bring - Snorkel, underwater camera or go pro, sun hat, sunscreen, after sun lotion, beach bag, beach towels, small bag for valuables, waterproof phone case, consider a floatation option - if you do drop a phone or camera in the water it will sink pretty fast!

I like the essential oil "passed tense" which is good for spot treatment of bug bites or irritations from any environmental type skin issues. allergy pills/ essential oils, dinner clothes.

*Anything that you forget to bring can be found locally. It's actually a fun place to shop and there are plenty of sandal shops, and beach hats everywhere.


Walking on the rocks
Walking the jetty at Fort Zachary State Park

🐓🐟🐠🐬🐬🐠🐟🐓

~~Stay positive and enjoy the road you are traveling.

~~Be flexible. Don't forget to breathe deeply.

~~I love a good list and plan, but just as much I love being in the moment and just pulling over to see something! I will say on this trip I slept a little longer than usual, probably because of some really comfy beds mixed with the need to recuperate from a stressful school semester ending. Teacher fatigue is a real thing! That's why we need to plan these beautiful breaks!

~~Put the people above the things. People remember details, stuff does not.

~~Create amazing memories to look back on joyfully!

~~If driving, bring a good variety of clothing for the seasons. If flying, one sweater or hoodie and a few options for summer attire will be best. Layers are helpful!

~~It's usually 10 degrees warmer in the Keys than in Central Florida. But warm does not mean sunny, dry, or windless.

~~Bring the sneakers too. You'll be glad.

~~Sunhats and snorkels are definitely the vibe here.


I'd love to hear of your experience in the Florida Keys! Feel free to leave feedback and share your tips as well.

Mz. Savvy


The Key West Garden Club is really like a free Botanical Garden. They have open air yoga, art, and plants for sale. If you want to go to the butterfly conservatory and don't have the $$, this is a great alternative.

 

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