Key West Best Activities For A Weekend Getaway

If you are looking for a quick and fun getaway with lots of options on things to do, Key West is the place for you. Located in the most southern point in Florida, Key West is famous for its beaches, nightlife, architecture, museums and of course water-sports. 

How To Get To Key West:

There are a few ways you can get to Key West. You can flight straight to the Key West International Airport which is couple of miles of the downtown area or you can flight to Fort Lauderdale or Miami, rent a car and take the scenic drive down to the keys, it’s an adventure in itself, it takes roughly ~4 hours.

You get to drive by some beautiful small islands like Key Largo, Marathon, Islamorada among some others. And, if you have time, there is plenty of beautiful beaches with some awesome pictures opportunities on the way. 

For us, it was a kid free extended weekend so we stoped at Islamorada and had couple of appetizers and I got to enjoy a cocktail.

Tasty cocktail in Islamorada
Fried Calamari

The views you experience driving down are majestic, especially when you are going over the 7 mile bridge. Also, you get to check the Henry Flagler Overseas Railroad

Now if you are concerned that you are going to be driving when you get there, don’t worry my friends, once you park you car you can rent a bicycle or a moped and you are set for your stay regardless of the length of it.

We parked our car at the hotel, we were staying at the Casa Marina Resort and did not have to move the car until it was time to leave. Everything can be done by bicycle. And is so much fun.

Things To Do While in Key West:

There are an array of thinks to do in Key West but when you are on a time constrain you have to pick and choose what makes you happy and what is going to make your vacation unforgettable.

Dry Tortuga National Park

Dry Tortuga National Park

Our number one activity and I’d say, one that you should not skip is the Dry Tortuga National Park (Fort Jefferson). Rich in history this unbelievable site brings you back in time. It has some of the most beautiful view that you’ll ever experience. 

Fort Jefferson
Picture from the ground at Dry Tortuga
Light House at Dry Tortuga

There are a few ways you can get to the Park. You can take the ferry, you can charter a boat or you can get there by seaplane.

We chose to take the Yankee Freedom III ferry. The fare is $180.00 per person (children and senior are a little cheaper) and you get a continental breakfast and light lunch included, you also get complimentary snorkeling equipment.

Ferry ride to the Dry Tortuga National Park

You check in at the ferry terminal at 7:00 am, the ferry departs at 8:00 am and return back to Key West around 5:15 depending on weather.  

Just a FYI, June is jelly fish season. Therefore, if you decide to snorkel, swim or any water activities, be aware of them.

June is Jelly Fish Month

While there, you can take advantage of the narrated 45 minute tour of the fort, you can take walks on the beach, snorkel, swim, take some pictures or just sunbathe. You can also overnight camp at the Dry Tortuga National Park.

Inside Fort Jefferson – Dry Tortuga
Inside Fort Jefferson – Dry Tortuga National Park

Mallory Square

Mallory Square

It was a hit with us also. At this amusing location you get to experience some of the most beautiful sunsets in your life. However, get there early to find a good spot to watch the sunset, it gets very crowded. 

Sunset from Mallory Square

If you get there early enough or hang out after dark, you are going to hear some local artists performing, as well as some acrobats, they are very talented and know how to play the crowd. 

Sunset Sail Cruise

When visiting Mallory Scare, you can also grab a bite to eat at some of the amazing restaurants located around the square. Lots of local artisan shops there too where you can find unique knick knack to remember your vacation.

Ernest Hemingway Home

You can’t come to Key West and dismiss the history behind the great author and his love for this small town.

I forgot to take pictures inside.

While inside, you can take a guided tour or just wonder through the beautiful manicured landscaped gardens. Doing so, you are bound to encounter one of the cats (more than 40 cats are rumored to live there). Don’t forget to look for his last penny pressed on the pool’s cement.

This museum is located in Old Town Key West.

Harry Truman Little White House

Harry Truman Little White House

This interesting museum has a lot of history attached to it. The building served as the naval station headquarters during a few battles like WWI and WWII among others. And later as the winter house for President Truman, inside you’ll find lots of artifacts related to America’s history.

Harry Truman Museum
Harry Truman Museum
The Little White House

You can also take a 15 to 20 minutes tour at this museum or just explore at your leisure.

Fort Zachary Taylor Historic State Park

Fort Zachary Taylor Historic State Park
Fort Zachary Cells

Not only can you visit the fort at this state park, but you can also enjoy the beach, One of Key West’s favorite. You can swim, do some bird watch, picnic, snorkel and all water related activities that your little heart desires. There are some great picture opportunities in this National Historic Monument.

Fort Zachary Taylor canyons
Checking the weight of the cannon balls

Southern Most Point

Because you are in the most southern point in the United States, of course you are going to want to visit the Southern Most Point. Just remember that you, plus hundreds of people are trying to do the same thing, so be patient and courteous. 

The southernmost point of USA

Since this activity doesn’t take too long we visited twice to see if we could take a better picture. I don’t think it helped but it doesn’t cost to try.

Duval Street

When you are traveling without kids this is a fun activity, to find a nice restaurant patio and people watch, this city can attract some unusual characters. But I would to do this while the sun is out.

Key West is a diverse town with array of foods for you to choose from. 

We love seafood, and shellfish is my favorite so I had to try this soft shell crab and I have to tell you that it is the best that I have tasted so far. It was a lot of fun to walk around to the different bars and restaurants.

Fried soft-shell blue crab

If Key lime pie is what rocks your boat, you are in luck. You can try this delicious goodness all around town, another local favorite are the conch fritters. You need to make sure you try both of them. Besides, you’ll be burning calories riding your bike around.

Mile Marker 0

Located in the intersection of Fleming St. and Whitehead St. this is the end of US1. Hundreds of people stop by to get their picture taken. Therefore, depending on the time of year visit Key West, you might have to wait to take your picture under the sign.

Mile Marker 0

We did not have to wait at all, we went early in the morning, I guess people were still asleep.

Higgs Beach Park

This park is located right next door to the Waldorf Astoria. Its beautiful waters, the white sandy beaches and, gorgeous landscape makes Higgs beach one of the most popular beach parks in Florida. Also, the only shore accessible underwater park in America.

Sand Castle Sculpture at the Waldorf Astoria

There are a multitude of activities available at this park, there is a children’s playground, a beach stand for you to rent chairs, umbrellas and, water sports related activities. 

Roaming Chickens

Do you know the joke “Why the chicken crossed the road”? Well, I think it’s because they lived in Key West.

Rooster Roaming around
Having a conversation with the rooster

They are every where and there are a lot of them roaming around that is very fascinating and definitely worth a mention. Sit on a restaurant/bar patio on Duval Street, have a cocktail and watch them for a while. It’ll make you giggle.

Rooster Crossing the Street

Conclusion

The fun part about visiting this place, besides all the activities, is that we did all the activities while riding bikes. As far as weather goes, it was perfect almost 100% of the time, you are in Florida after all. On our Dry Tortuga National Park excursion we were graced with some rain on our way back, but that did not altered our experience. 

We Loved riding our bikes everywhere

Key West is so diverse in terms of the people that live there and the visitors, also, in terms of food and activities. You can have a quick couple getaway. For instance, we were there for 3 nights. Or you can go all out as a family vacation. However, I wouldn’t take the kids out on Duval Street at night time. 

But, with so much history involved around this great piece of paradise you  and your family would have a great amount of activities to choose from and to keep you entertained while on the island. 

Light House

If you like the outdoors, you can snorkel, sunset cruises or just a cruise around the island, dive, fish, sightseeing, eco nature tour and the choices are endless.

Got a question? I would love to hear from you. Also, sign up for our email list so you don’t miss out on upcoming posts.

“To Travel Is To Live.” – Hans Christian Anderson

Visited in 2013

All the Best. Patricia M.

148 thoughts on “Key West Best Activities For A Weekend Getaway

    1. I would love to go to Key West one day I have never been. I have talked about this with my family a couple times so hopefully we are able to do this one day.

    1. This is awesome. The ancient walls in key West look historical. It reminds me of the walls of Intramuros of Manila. Historical places are truly remarkable

  1. Beautiful pictures. I would choose to flight to Miami, rent a car and take the scenic drive down to the keys. Seems like 4 hours of awesome adventure by driving by small islands. l would also spend some time at the beaches on my way to Key West.

    1. This looks so exciting for a family picnic. I would love to go. I love museums and national parks. The food looks awesome too.

  2. Such a beautiful destination. Your photos are amazing! I wanna visit Orlando and Miami, maybe I can add Key West if I got the chance to visit Florida

  3. What an amazing place, pictures just stole my heart! We have been planning Key West for sometime now. Hopefully, we go soon.

  4. Seems like an amazing place to visit . It has a beautiful sunset. Im sure the whole family will enjoy.

  5. Key West is such an interesting place. I’ve never been, but I have family there and some of the things they share crack me up…like the chicken crossing the road ;-). Anyway, looks like you had a great time!

  6. I have visited Florida many times but never to the Keys. Based on your description I am eager to go.

  7. I’ve never been to Florida yet!! I would love to go one day and visit Key West, looks like an amazing place to spend a few days at.

  8. All of those places out there really do look amazing. Key West has been on my bucket list for such a long time. It’s such an exotic and beautiful locale. And all the amazing history to go with it as well.

  9. Wow, this place looks incredible. There’s so much to do and see there! Looks like a brilliant place to take the whole family

  10. Key West is simply amazing! The sunset, the local artist performing and some acrobats too? I love it! Also, I would definitely go on the boat ride and the bike ride too!

  11. I once tried soft shell crab and I thought it was interesting! I love shrimp so id love to visit and see the quality difference.

  12. I would like to visit Key West for its rich history. I am a fan of road trips and would prefer the 4-hour drive. The beaches would amaze me a lot. Hope to visit the place come June next year.

    1. Key west sounds like a fantastic place..! Their tasty cocktail and fried calamares looks so great..! I hope to visit soon..!

  13. I’ve never been to Key West, but it looks like a wonderful place for a short weekend trip! I’m placing it on my bucket list! Can’t wait to pay it a visit ! 🙂

  14. So nice! If budget wasn’t so tight and we don’t have to work some weekend, we’d love to keep bringing the kids to weekend road trips, too. We have one coming up in two days though, and I am really excited. 🙂

  15. This looks like a great place to visit! We are actually planning to spend some time down in Florida next year and I am excited to explore a new place. The sand sculptures look amazing, my kids would love to see that!

  16. Key West seems amazing! There are so many fun things to do in this place. That sand castle sculpture at the Waldorf Astoria looks awesome, and it’s interesting to know that there are a lot of chickens roaming around. Would love to explore Key West some day. ~ Ola @ WanderWithOla

  17. I have never been to Key West but as I can see here it was a great and historical place to visit. It looks like a lot of fun to be there and the food looks really delicious!

  18. This is right up my street. Historical while also visiting relaxing places such as the beach. I’d kill for a chill holiday like this right now!

  19. I’ve been seeing so many pics lately on Key West so that is a sign. This place looks incredible. There’s so much to do and see there! I need to take my family here.

    1. This place is so rich in history. There are so many activities to try in Key West. I love the skillfully made sand art. It is so awesome.

  20. My husband wants to take me to FL and convince me we should move there. So I am going to refer to this list when it finally comes time to him doing that, ha!

  21. Looks like you had fun taking in the local scenery and having some exercise while your at it. I never knew that the place hold so much history.

  22. This place reminds me of sri lanka, the fried calamari and the light house in particular. I bet those fried calamaris were brilliant. The place looks lovely and love the photos you have clicked.

  23. The place is very impressive and lovely. The sunset view is breathtaking, no wonder you enjoyed your vacation.

  24. I normally like to explore exotic countries for my holidays, but this looks good for someone who likes small weekend trips away.

  25. This place is so rich in history. There are so many activities to try in Key West. I love the skillfully made sand art. It is so awesome.

  26. This getaway looks like it was absolutely wonderful. I am going to have to visit Key West soon and I’ll have to remember to try the soft shell crab.

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