January 21, 2025

Home » Blog » YOUR VACATION GUIDE TO EXPLORING KEY WEST

When the chill of January blanketed much of the Continental United States, I found myself in the perfect placeKey West, the southernmost gem of the Florida Keys & Key archipelago. Known as the Conch Republic, this island paradise seamlessly blends natural beauty, vibrant culture, and historic charm, making it the best place to escape the winter blues. I am so excited to bring you information that I gathered on my first–but not last–visit to this amazing island in my vacation guide to exploring Key West.

ARRIVAL AND GETTING AROUND

My first trip to Key West began at Key West International Airport, where the tropical warmth embraced me the moment I stepped off the plane. We originally opted for a rental car to explore the 125-mile Florida Keys island chain. I longed to drive the iconic Overseas Highway from Fort Lauderdale to Key West. With breathtaking views of the Atlantic Ocean and Gulf of Mexico, this route was a great way to start the adventure. However, the forecast for the week was bleak with mostly overcast days. And, since we were one of four couples, we went straight to our condo to begin the adventure, instead.

Once in Old Town Key West, it was obvious that parking lots were sparse. Navigating the narrow streets was easiest with a golf cart. A lot of locals have their own golf carts to get around town. Renting a golf cart for the week, for eight people, would cost around $800 for the week. So, we quickly realized walking or biking was the best way to soak in the local charm.

Our condo was around four miles away from Duvall Street. So, we rented taxis to get into town and back, each day. The cost was $4.50 per person each way. In total, we spent around $430 in taxi fees as a group, not including tip ($108 per couple).

One thing that you will quickly notice is all of the hens and roosters running free throughout Key West. I am from a rural community, but even I was quite endeared to the sight of such beautiful chickens meandering about.

This excerpt was taken from Google AI:

HISTORIC SITES AND CULTURAL GEMS

Key West is a treasure trove of historic sites. My first stop was the Ernest Hemingway Home, where I admired the charming property and its famous six-toed cats. Just a short distance away, the Key West Lighthouse offered panoramic views of the historic district and beyond.

Nearby, the Tennessee Williams Museum paid homage to the legendary playwright who called Key West home. Walking through the art galleries scattered around Duval Street, I marveled at the island’s cultural diversity and vibrant artistic scene.

If you are sensitive to the smell of cat urine, beware! This property is worth seeing, but understand that it is inhabited by A LOT of cats!

And we visited during a cold spell; I cannot even imagine how the property smells on a hot humid day.

And, if you are allergic to cats, this may just be one of the sights that you opt out of visiting.

The cats definitely rule this roost!

FOOD, FUN, AND NIGHTLIFE

No Key West vacation is complete without indulging in its culinary delights. I savored indigenous Florida Keys cuisine like fresh fish, local seafood, and the iconic key lime pie. At waterfront restaurants and food trucks on Duval Street, conch fritters and chilled mojitos will become your go-to snacks.

Nightlife in Key West is electric! Sloppy Joe’s, once frequented by Hemingway, was brimming with energy and live music is everywhere. The sunset celebration at Mallory Square brought together street performers, delicious food stalls, and a front-row seat to the famed Florida Keys sunset.

No visit is complete without visiting the southernmost point iconic buoy! We walked to the point late at night. I regret not going back during the day to get an image with the beautiful blue water as a backdrop. So, my advice is to make sure to visit this spot during the daylight hours.

MALLORY SQUARE: SUNSET CELEBRATION

I didn’t engage much with the vendors or the street performers during my visit to Mallory Square. To get a front row seat to the sunset (a must if you intend to take the very purest photos) it is imperative to get there early and establish your spot out front of the crowd. But, there was definitely a lot going on! I would recommend attending the sunset celebration on more than one night so that you can enjoy it all.

WATER ADVENTURES AND NATURAL BEAUTY

Key West’s natural beauty is unparalleled. From the white sand of Smathers Beach to the sandy beaches of Fort Zachary Taylor Historic State Park, there’s no shortage of idyllic spots to unwind. For those seeking adventure, water sports like jet skiing and scuba diving in the vibrant coral reefs offer thrilling encounters with the teeming backbone of marine life.

FORT ZACHARY TAYLOR HISTORIC PARK

The park does require an entrance fee based on the number of people in your vehicle ($6.00 per car, up to eight people).

Luckily, we visited on the warmest day of the week; but, the water was still not warm enough for me to take a plunge! If you enjoy cold therapy, you would have been just fine.

Key West does not have natural sandy beaches. The Keys are built up on a limestone foundation. This prevents the formation of your traditional sandy beaches. Instead, most beaches consist of crunchy coral rock debris. The minimal soft sand that does exist was brought in from other locations. Therefore, it is highly recommended that you wear comfortable beach shoes that can get wet.

THE DRY TORTUGAS NATIONAL PARK

On a day trip to Dry Tortugas National Park, I explored the historic fort and longed to snorkel in the local waters (it was too cold on our trip). This was my favorite part of our entire vacation. So, I can not recommend visiting the Dry Tortugas enough.

The island is 70 miles west of Key West. The only way to access the island is by ferry, sea plane or private boat. We took the ferry to the island, which is about a two and a half hour trip each way. The ferry is a more economical way to visit the island, for sure.

We reserved our ferry months in advance; and, I recommend that you do, as well, to ensure that you are able to make it to the island during your time in The Keys. You can purchase your tickets at the link: Dry Tortugas Ferry.

FERRY VS SEA PLANE:

Another more expensive option is to take a sea plane to the island. The trip runs about 40 minutes in length, each way. You can reserve tickets at Key West Sea Plane Adventures. You can book a half day or full day excursion.

If you choose to take the ferry to the island, you will depart at around 7:30 am and return to Key West around 5:15 pm. You will be on the ferry a total of five of those hours. I am of the opinion that if you visit during a warm day and are able to swim and snorkel, the four hours that you are on the island may not be long enough to do all that you hope to do.

If you take the sea plane, you have a much longer day on the island, but you will have to pay about $600 more dollars per person.

If you have no intentions of getting in the water, the ferry excursion is more than sufficient!

Please note that we were all very cold while at The Dry Tortugas. The weather was in the low 60’s, overcast and the wind was very strong. The wind was so strong that I covered my ears at times just for a little break from the sound beating my ears. I wore shorts, but wished that I had worn lights pants. Everyone who had a sweatshirt or hoodie had it on that day!

Useful items to bring along are:

  • Beach towel
  • Packable beach blanket
  • Sunscreen
  • Hat (wide brimmed)
  • Long sleeves or Sweatshirt
  • Phone in waterproof case
  • Snacks
  • Earbuds
  • Camera
  • Dry sack
  • Lip balm
  • Snorkel gear

For more information about The Dry Tortugas, go to my blog post: YOUR BEST GUIDE TO THE DRY TORTUGAS

TIPS FOR THE PERFECT VISIT

  • Best time to visit? 

January is ideal. With fewer crowds, pleasant weather, and no threat of hurricane season, it’s the right place at the best time. Keep in mind that the temperatures can drop in the low 60’s during this time, though.

  •  Getting around: 

While renting a car is convenient for exploring the Florida Keys, a golf cart or bike is better for navigating Key West’s narrow streets.

  •  Where to stay?

For an upscale experience, consider Sunset Key, a private island just a ferry ride away. If that is not in your budget, I highly recommend getting an AirBnB or Bed n Breakfast or resort as close to Duval Street as you can.

  •  Don’t miss: 

A guided tour of Fort Zachary Taylor, snorkeling at coral reefs, and the unforgettable Key West sunset. Another important tip to avoid missing out on locations and events is to book your reservations in advance! Check out what is available in Key West at Get Your Guide.

  • Budget tips:

You can find coupon books with savings at the following coupon links: Key West Vacation Pass and Keys Cash Saver.

WHAT TO WEAR GUIDE FOR EXPLORING KEY WEST

SPRING WEAR

As the temperatures are starting to inch their way back up, you can start taking more off! Comfortable items for the spring heat are:

  • Bottoms: Shorts (denim cut-offs, white, tan), lightweight linen pants
  • Tops: T-shirts, tank tops, flowy blouses, tropical print shirts
  • Outerwear: Light cardigan or jacket for cooler evenings
  • Footwear: Sandals, flip-flops
  • Swimwear: Colorful bathing suit, board shorts 
  • Casual attire is the norm: Key West has a relaxed dress code, so most places are fine with shorts and t-shirts. 
  • Breathable fabrics: Opt for cotton, linen, and other lightweight materials to stay cool in the heat. 
  • Tropical prints: Embrace the island vibe with colorful floral or palm tree patterns. 
  • Sun protection: Pack a good quality sunscreen and sunglasses 

SUMMER WEAR

Plan on it being very hot. Smart items for the summer heat and humidity are:

  • Bathing suits: Essential for beach days. 
  • Lightweight shorts: A staple for everyday wear. 
  • Flowy sundresses: Perfect for women looking for a slightly dressier option. 
  • Cotton t-shirts and tank tops: Opt for light colors to stay cool. 
  • Flip flops or sandals: Comfortable footwear for walking around town. 
  • Cover-up: A light wrap or beach shirt to throw on over your swimsuit. 
  • Wide-brimmed hat: To protect your face from the sun 
  • Sun protection: Pack high SPF sunscreen and reapply often. 
  • Breathable fabrics: Choose natural fibers like cotton and linen to stay cool. 
  • Casual attire: Key West is a very casual place, so you don’t need to dress up much. 
  • Rainy day gear: Though the rain is usually short, a light rain jacket can be helpful. 

FALL WEAR

During the fall, all of your spring and summer attire is appropriate, just throw in a light jacket or cardigan for when the sun goes down!

WINTER WEAR

It dipped into the low sixties when we visited. Too, it was overcast most of the days, as well. So, I found the weather to be very chilly. Out of six days, we only had one day that I was comfortable enough to get into a swimsuit. I took loose drawstring pants, jeans, light sweaters and sweatshirts for those cooler nights.

The guys seemed comfortable enough even in their summer clothes. The guys wore golf attire, t-shirts and shorts the entire six days. The only exception was at The Dry Tortugas where we were all very cold because of the brisk wind and low temperatures.

REFLECTIONS ON EXPLORING KEY WEST

Key West’s unique charm is impossible to capture in a single visit. Whether you’re exploring the tranquil Lower Keys, indulging in the indigenous cuisine, or immersing yourself in the island’s vibrant history, it’s clear this destination is a great place for all. As I departed back to the mainland via the Key West International Airport (yes, the island has it’s own airport!), I knew this wouldn’t be my last time here—it would simply be the beginning of many more visits to come.

Enjoy this Guide to Exploring Key West. If you have any questions or suggestions, please add them in the comment section below!

Please follow and like us:
error80
fb-share-icon228
Tweet 20
fb-share-icon146

Winter 2025: YOUR VACATION GUIDE TO EXPLORING KEY WEST

If you love water sports–or ever wanted to be your own captain–and you’re looking for an adventure-filled family vacation, look no further than a house boat trip on Dale Hollow Lake in Tennessee! Our house boat adventure was an all time favorite for everyone. This man-made lake is perfect for house boating, and my family […]

HOUSEBOAT GUIDE: Our House Boat Trip On Dale Hollow Lake (Tennessee)

KIDS INFRONT OF A HOUSEBOAT

July 10, 2024

We recently took an RV road trip to Colorado and it was such a great experience! I wanted to share our Colorado itinerary in case anyone else is planning a similar trip. This itinerary includes both national parks and smaller towns, so there’s something for everyone. We traveled the last week of July, taking an […]

The Best 7 Day Itinerary: Our Colorado RV Road Trip (updated)

KIDS IN FRONT OF AN RV

June 24, 2022

Anyone with a camera phone can take a picture, but not everyone can take a good picture. Learning the basics of photography will help you take better pictures, whether you’re using your phone or a more advanced camera. In this post, we’ll go over the three main elements of photography; These are: aperture, shutter speed, […]

Beginners: The Basics of Photography

Table top covered with images

January 30, 2022

PROJECT BRIEF The Webb Project brief was that this couple wanted to remodel their outdated kitchen to allow more room and accessibility for family get-togethers and to allow room for more family activities with their sons. This Webb Kitchen Refresh was a very satisfying smaller project. Take a look! My first challenge was that if […]

The Webb Kitchen Remodel

October 12, 2021

It is a very unseasonably warm November night and I am laying in a hotel that overlooks the river. I can see and hear barge horns from the patio door as the barges are slowly pushed down the river by pusher boats. They are illuminated with blue and green lights against the dark night sky. […]

When My Stepson Completed Suicide

mEN HUGGING IN FRONT OF CASKET

November 27, 2020

Leave a Reply

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

Comments



I have big plans for things around here...

Please, subscribe

CONTACT ME

SHOP

ABOUT ME

LIVING A LIFE FULLY AND TRUTHFULLY WITH YOU

MY STORY

WORK WITH ME

MY FAVORITE THINGS

BOOKS BY ME!

PRESETS

JBTOLSINFO@GMAIL.COM

jbtolsinfo@gmail.com 

  ©Jennie Davis-Cambridge 2025 ALL RIGHTS RESERVED

THIS WEBSITE IS A PARTICIPANT IN THE AMAZON SERVICES LLC ASSOCIATES PROGRAM, AN AFFILIATE ADVERTISING PROGRAM DESIGNED TO PROVIDE A MEANS FOR SITES TO EARN ADVERTISING FEES BY ADVERTISING AND LINKING TO AMAZON.COM.

Pinterest146
Follow by Email80
Instagram
YouTube20
YouTube
Facebook228