2 Day Itinerary for Key West, FL- How to Plan your Trip to Key West

This post is my 2 day itinerary for Key West, FL.

Key West, is a tropical island located at the southernmost point of the U.S. mainland, in the state of Florida. It is the most popular Key out of the 800 Florida Keys! The island is about 4 miles long and is known for its unique culture, stunning waters, and laid-back vibes.

I visited Key West and Key Largo during my trip and there is a noticeable difference between the 2 Keys. I felt Key West was popular amongst visitors, I saw lots of families visiting, a ton of bars and restaurants along the coast, and a lively downtown area. Key Largo on the other hand had lots of local businesses and seemed less touristy.

I enjoyed my trip to Key West and would love to see you go too! So keep on reading my post for all the travel tips I picked up during my trip to Key West.

THINGS TO KNOW- HOW DO I PLAN A 2 DAY TRIP TO KEY WEST

When is the best time to visit Key West?

December to April is considered peak season for visiting the Key West. This means larger crowds and higher prices. As someone who lives in Central Florida, I suggest visiting either in May or Novemberish, right before Thanksgiving break. This way you will avoid the crowds and hopefully get better deals. I went towards the end of April which is Spring break in some parts of the country and that means it was still crowded.

How to get around Key West?

I chose to drive from Orlando to Key West which would have been a 7ish hours long drive. I said “would have been” because I ended up spending a night in Key Largo which was about 2 hours away from Key West. I know a lot of folks like to spend a night or two in Miami too to break up the drive.

In case you didn’t know, Key West has it’s own international airport too. It might not be the biggest but is pretty convenient especially if you do not want to fly in to Miami Airport. Major airlines such as Delta, American Airlines, jetBlue, etc. offer non-stop flights from cities like New York, Boston, Atlanta, and more. Check out the airport details here.

What to pack for Key West?

I’d obviously start with some cute beachy outfits and then proceed to the other essentials. When visiting the beaches of Key West, I highly recommend bringing a pair of water shoes with you. The beach had a ton of rocks which made it difficult for me to walk on.

• You can also checkout my Amazon storefront for some inspiration. Click here.
• A travel plug adapter for your electronics. Click here.
• Portable phone battery charger. Click here.
• Portable fan to keep cook in the blazing heat. Click here.
• A beach bag to carry all your beach essentials such as a towel and beach hat.
• Makeup- mostly my essentials and whatever fits in this bag. I have it in brown. Click here.
• Skin care- travel size only, the Origins travel skincare set was perfect, I use most of their products at home too. Click here.
• Sunscreen- again travel size only, I like the Neutrogena stick version which works for face & body. Click here.
• Camera- I have the Canon EOS T7i, there is a great bundle deal on Amazon. Click here.
• Waterproof camera- under $50, loved it! The quality is pretty good for the price. Click here. I also purchased a wide angle lens. Click here.
• Tripod- solo traveler problems. Get something sturdy and lightweight, especially if you plan on taking pics when it is windy. Click here.
• Shoes- 2-3 sandals, a reliable pair of sneakers and some water shoes.
• Packing cubes- to keep things organized especially when you have limited space. Click here.
• Blister bandages because you never know how painful walking all day can be. Click here.

Where to stay in Key West?

This was a tough one! I found room rates in Key West extremely steep both for hotels as well as private rental properties on Airbnb and Vrbo. I am talking $600/night for a motel room. It was insane. Now having said that, I did go during peak season. My point is expect to pay high hotel prices during peak season as demand is high.

If budget is important then consider staying in one of the other Keys, such as Key Largo or Marathon. I spent one night in Key Largo which helped me save some $$$. Another option is to travel during off-season. Here are the 2 hotels I stayed at during my trip:

• Holiday Inn Key Largo– I spent one night here as room rates in Key West were extremely high plus I wanted to break up the drive from Miami to Key West. I’d say it’s an okayyy hotel, probably 2.5/5 rating, not as glamourous as the pics online.
• Oceans Edge Key West Resort– Loved this one. It’s a beautiful resort, I enjoyed the amenities especially the hourly shuttle service to Key West and customer service was really good.

What to do with Two Days in Key West?

DAY 1

I like to start my mornings with a hearty breakfast and some coffee. I opted for an iced coffee from Cuban Coffee Queen Downtown to wake me up and breakfast. I enjoyed the Sunrise Special for breakfast, the eggs and ham on the freshly baked Cuban bread were delicious.

Then I headed out for my first activity which was to lay at Smathers Beach. The crystal clear turquoise waters and white sand make the long drive to Key West worth it. I also noticed there was a lot of jet skiing and parasailing going on, you can definitely add those to your agenda. I opted for a lazy beach day.

For lunch, I stopped by Kennedy Cafe which was a Mediterranean restaurant. I had some Bruschetta Pomadoro and buffalo chicken wings. I heard the fried calamari and shrimp were also good options. After lunch, I headed to explore Key West for a bit. I went to the Southern Most Point of the U.S. and explore downtown Key West. Duval Street is known for it’s lively scene, boutique stores, and bars for those who would rather just grab a drink and relax.

Later on in the evening, I had dinner at Hot Tin Roof Restaurant which was highly recommended for as it had outdoor seating overlooking the sea as well as good food. I am glad I made reservations well in advance as the place was packed! Last stop for the night was Green Parrot Bar. They had some great live music going! It was the perfect way to the end the first night of my 2 day itinerary for Key West.

DAY 2

I had a late start to my morning and headed straight to brunch at The Breakfast Club, Too. I love starting my day with a good meal! Then I made my way to explore Key West for a bit. First stop was the Fort Zachary Taylor Historic State Park. It is the last stop in Florida before stepping off into the Gulf of Mexico! There is a beach and picnic tables too, so definitely plan on spending a few hours there.

Another historical landmark that I recommend is the Hemingway Home and Museum. It was the residence of the famous American writer, Ernest Hemingway. Very interesting to get a glimpse of his life.

One of my favorite activities of this trip was a sunset cruise. Key West is known for it’s stunning sunsets and there is no better way to experience one. My sunset cruise was perfect. The boat crew was fun and friendly, it wasn’t overcrowded, and the music and dancing made me forget my worries. Highly recommend you book one!

After my sunset said, I headed for some dinner and live music at Blue Heaven. The Jamaican Jerk chicken was delicious! Flavored and cooked to perfection. It was the perfect way to end my short trip to Key West. I loved the ambiance and how relaxed the crowd felt.

CONCLUSION

2 days in Key West is definitely not enough to soak in all the sunshine and beautiful waters. I am definitely planning to take another trip out there sometime next year. Key West is like a paradise right in my backyard. In addition to the beautiful beaches, I loved me some key lime dessert and several other dishes.

I hope you plan a vacation to Key West soon and as always feel free to ask any questions in the comments below.

I now offer a custom vacation planning service. Check it out here!

SAVE ME- 2 DAY ITINERARY FOR KEY WEST, FL