The Perfect Weekend in Key West: 3-Day Itinerary

I just got back from what I would consider a perfect weekend in Key West, Florida. It had a day of exploring downtown Key West, a day trip to Dry Tortugas National Park, and a day to relax. I had good food (with the exception of one bad meal), fun experiences, sunshine, and of course, lots of humidity!

I’ll share my exact 3-day weekend itinerary and provide a few alternatives, but this itinerary has it all from relaxed exploration to a bucket list day trip, and from good food to relaxing by the pool!

Key West Weekend Itinerary: Quick Reference

Day 1: Exploring Downtown Key West

• Morning: Breakfast at The Koffie House → Truman Little White House tour
• Afternoon: Drinks at Moondog Cafe → Key West Butterfly and Nature Conservatory → Southernmost Point photo → Lunch at Moondog Cafe → Key West Lighthouse climb
• Evening: Sunset and dinner at hotel (or explore Mallory Square/Duval Street)

Day 2: Dry Tortugas National Park

• 7:00 AM: Check-in for Yankee Freedom Ferry
• 8:00 AM: Depart Key West
• 10:00 AM-3:00 PM: Explore Dry Tortugas (Fort Jefferson tour, snorkeling, beach time)
• 5:30 PM: Return to Key West
• Evening: Dinner at Half Shell Raw Bar

Day 3: Relaxation Day at the Pool or Beach

• Morning: Sleep in, pack, pool time at Hotel
• Afternoon: More pool relaxation (or visit Smathers Beach/Bahia Honda State Park)
• Evening: Farewell

Arrival: Downtown Key West and Horrible Dinner

My friend and I chose to fly from Central Florida instead of driving 8 hours! We arrived on a Thursday afternoon, checked into our hotel (Havana Cabana), and then we enjoyed walking downtown Key West before having dinner that night.

The dinner on this night was the worst for me! My friend enjoyed her salad with shrimp, but I had the “fresh catch” and it was truly terrible. I’m not a major food critic, but I should have sent it back. However, I’m not great in these situations.

So if you find yourself eating at Viva Argentinian Steakhouse, I do NOT recommend the fish or really anything I had. The Caesar salad had too much dressing, the fries were meh and the fish had NO flavor, seemed rubbery, and it was probably not fresh in the least, making the sandwich completely not worth it.

Next time, I hope I will speak up, because it was that level of terrible. Anyway, since I mentioned one meal I had wasn’t good, I wanted to tell you where and what I had! If you try it, go with the steak.

The service was excellent and the atmosphere was fun, but my food was horrendous.

Day 1: Exploring Key West’s Top Attractions

My friend and I spent this day exploring downtown Key West. We visited several attractions and the day included history, nature, southern most point of the continental USA, a lighthouse climb, and good food!

We started at the west end, but you could easily flip this and it actually might be worth doing so! The southern most point and butterfly conservatory would probably have been less busy if we started there.

We also skipped The Hemingway Home and Museum since my friend had explored it on a previous day trip to Key West. However, there is plenty of room in this itinerary to add it to this day or you can trade out one of the stops for this one.

Morning

My friend and I took the free shuttle provided by Havana Cabana to downtown Key West. After walking around the night before, we had scouted a coffee place that looked promising and was close to where we were dropped off.

The Koffie House ended up being the perfect little breakfast spot. I was able to get a classic, unsweetened, iced matcha and an egg and turkey sandwich.

After breakfast we headed to the Truman Little White House and actually arrived just in time for the tour! There was a lady in a tent outside, so we purchased tickets and immediately joined the tour. However, you can purchase the tickets in advance.

The guide first gave us a brief overview with facts about the house, before he took us inside. The home is old but well preserved and overall the tour was quite interesting.

Purchase tickets in advance for Harry S Truman Little White House Admission

Afternoon

As we walked toward our next stop, we passed The Kapok Tree. It’s a gorgeous and very interesting looking tree! It was sacred to the Mayans and while it won’t be a long stop, it’s worth walking by.

We stopped near the Hemingway House to grab a drink at Moondog Cafe Key West. My friend and I each got a cucumber, watermelon and lime drink. It was delicious, genuinely fresh and much needed hydration!

Again, we chose to skip Hemingway House since my friend had been before. However, this is a great time to add it on to your Key West itinerary. Of course, The Hemingway Experience in Key West is a four-hour tour offering more than just a visit to the house and could be perfect for true fans or return visitors.

We made it to The Key West Butterfly and Nature Conservatory just as we finished our watermelon drink. I’m not sure what my friend and I expected, but we were immediately blown away by the amount of butterflies as well as the size of some of them!

We also saw flamingoes, birds, a turtle and hundreds of butterflies! It was far more magical than we thought it would be, though we were sweating a lot by the time we left. It was actually more humid in there than outside!

The southernmost point has moved and is now conveniently on the east end of Duval Street. It’s very close to the observatory, so we headed there for a quick photo.

We decided to head back to Moondog Cafe Key West for lunch and this was definitely the right move! We both LOVED our meals. Mine was light, healthy, and delicious. And of course, I had to try their key lime pie!

After lunch, I headed to the Key West Lighthouse. I had recently made the climb up the Ponce Inlet Lighthouse, which is the tallest in Florida, so I knew this climb would be easier. It was indeed, but the 360 degree views were still lovely.

Evening

We ended up heading back to our hotel early. However, visiting Mallory Square for sunset is a great option as well or you can enjoy the shops on Duval Street more!

We had dinner at the lounge at Havana Cabana, where we were staying and watched the sunset from there. Since we were heading to Dry Tortugas the next day, we wanted an early night.

Of course, downtown Key West has plenty to offer to fill your weekend! While we aren’t big partiers, there is plenty of options if you are!

Want a detailed breakdown of exploring Key West? Read my full 1 Day in Key West Itinerary (coming soon) for more details and options.

Day 2: Dry Tortugas National Park Day Trip

Dry Tortugas National Park has to be one of the coolest, yet least visited parks. It sits about 70 miles off the coast of Key West, but is one of the largest forts. I had been wanting to visit for a while, and the planning finally came together!

I booked the Yankee Freedom Ferry about three months in advance! The dates sellout fast, so book early if you have specific dates in mind.

The Dry Tortugas ferry requires a 7AM checkin and you don’t return until 5:30PM, so it’s a very full day! After two and half hours on the ferry, we finally arrived. My friend and I enjoyed the guided tour, then lunch, before exploring and snorkeling on our own.

The snorkeling was good, but not as amazing as Fiji. However, it was fun and felt similar to snorkeling in Key Largo, just without the underwater Jesus statue. Of course, if you don’t want to snorkel, you can enjoy some time on one of the beaches.

Is Dry Tortugas Worth Visiting?

Visiting Dry Tortugas is absolutely worth it, but you should definitely go prepared. It’s a long day with five hours of total time on the ferry. There are no facilities at the island (we only had restrooms on the boat), so if you decide to use a different method to the ferry, girl to girl, I’d ask about the bathroom situation.

Overall, I absolutely loved this Dry Tortugas day trip, so be sure to plan ahead and add it to your weekend in Key West.

Breakfast and Dinner

While the ferry does offer breakfast, it’s all carb heavy or sweet. So even though it was raining a little, we grabbed food near the port at Cuban Coffee Queen Waterfront. It was a delicious egg sandwich and I got some Cuban coffee as well!

Originally, my friend and I planned to go back to the hotel and then return for dinner after we got cleaned up from the long day. However, we walked by a seafood restaurant and just decided to try it!

I’m not always the most decisive person, so this was impressive, and even more impressive that we loved our dinner! Half Shell Raw Bar was delicious and we sat by the water and ended up enjoying the sound of rain while we ate.

Day 3: Relaxation Day

On our last day in Key West, my friend and I decided relaxing was in order! We considered hitting a beach in Key West, but in the end elected to relax by the hotel pool.

Since Key West isn’t known for beaches and we live in Florida near miles upon miles of beaches, it wasn’t something we were desperate to experience.

After breakfast, we packed and then found some lounge chairs by the pool. We ate lunch by the pool as well, and had to fend off three iguanas! And we stayed by the pool until it was time to leave for the airport.

This was the perfect way to end our weekend in Key West, especially after a full day at Dry Tortugas.

Beach Options

Of course, I do love the beach, so I did some research before my trip and asked while in Key West.

The employee at my hotel said the only beach club he knew was Salute! On the Beach, which I had bookmarked as well. It’s on Higgs Beach and on the area of Key West with several other beach options nearby.

Smathers Beach is probably one of the best options on Key West. It’s a long stretch of beach, which is rare for the Keys in general and there are rentals available. Additionally, some reviewers mentioned food trucks are around, which is perfect if you want to spend a full day at the beach.

If you want a small beach that’s near the action, consider Ponce de León Beach that sits at the end of Duval Street. I personally wouldn’t like being in a crowded area, but if you’re okay with that, there is a restaurant (Southernmost Beach Café) on the beach, or it’s a short walk along Duval Street for food.

There were a couple ladies at our hotel who recognized us from the Dry Tortugas ferry. They told us about Bahia Honda State Park, which they claimed was about 30 minutes away, though it’s showing up on the map closer to 45 minutes by car.

It’s a state park, so there is an entry fee, but they mentioned they swam in the gulf and the Atlantic at the park! If you’re okay with a drive, this could be a great option.

Additional Ideas for a Weekend in Key West

While my itinerary covered exploring downtown, a day trip to Dry Tortugas, and relaxing by the pool, there are plenty of other ways to fill your weekend in Key West depending on your interests!

Water Activities

Key West is surrounded by water, so there are tons of options if you want to get out on (or in) the ocean. Snorkeling and diving trips are popular, especially to the coral reefs. You can also rent kayaks or paddleboards or book a tour to explore the mangroves at your own pace.

Heading out to a sandbar can be a fun experience and a good way to spend an afternoon on a hot day. I have enjoyed sandbar tours in the San Blas Islands and Fiji, so maybe on my next weekend in Key West, I’ll try it here!

Jet skis are super fun and if the water is calmer can be a great way to spend a few hours. Rent and go out on your own or book a tour like this Key West Island Adventure Jet Ski Tour: Bring a Partner for Free.

I love chasing a sunset when I travel and in Key West sunset cruises are very popular! Mix it up during your Key West weekend and enjoy the sunset from the land and sea!

Check availability for All-Inclusive Sandbar Safari with Dolphin Playground Encounter or Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

Museums and Historic Sites

I mentioned we skipped the Hemingway House, but it’s one of Key West’s most popular attractions. You can tour Ernest Hemingway’s former home and meet the famous six-toed cats that still live there!

If you’ve visited before or you’re very interested in Hemingway, there is a whole Hemingway Experience in Key West that you may love!

There’s also the Key West Shipwreck Museum, the Audubon House, and the Custom House Museum if you want to dive deeper into the island’s history. The Fort Zachary Taylor Historic State Park combines history with a beach, so you could knock out two things at once.

Duval Street and Nightlife

We didn’t spend much time on Duval Street at night, but it’s the main hub for bars, live music, and general chaos! Sloppy Joe’s is probably the most famous bar (Hemingway supposedly drank there), and there are plenty of other spots for drinks and dancing.

If you’re into the party scene, this is where you’ll want to be. Just know it gets crowded and loud, especially on weekends!

Food and Drinks

Key West has way more food options than what I covered in my itinerary. Cuban food is popular (hence all the Cuban coffee spots), and obviously fresh seafood is everywhere.

For drinks, I’d recommend trying a key lime pie martini or frozen mojito at one of the many bars. And if you’re a foodie, there are some higher-end restaurants on the island that I didn’t get to try but looked amazing.

Day Trips Beyond Dry Tortugas

If you’ve already done Dry Tortugas or it’s sold out, you could also consider a day trip to other parts of the Florida Keys. Bahia Honda State Park (mentioned earlier for beaches) is gorgeous, and you could easily spend a day exploring Islamorada or Marathon on your way back to mainland Florida.

Some people also do fishing charters or eco-tours to see dolphins and other wildlife. We didn’t prioritize this, but it’s definitely an option if that’s your thing!

Check availability for Key West Half-Day Fishing Charter

Explore in a Golf Cart or Bicycle

We didn’t end up doing this, but my friend on a previous trip rented a golf cart and rode around Key West. This is a great way to explore this small island.

Renting a bike or booking a bike tour could also be fun and would be a cooler experience to walking around on a hot day!

Check availability for Key West Golf Cart Rentals Explore at Your Own Pace or Guided Bike Tour of Old Town Key West

Slower-Paced Options

Not everyone wants to pack their weekend full of activities, and that’s totally fine! Key West has plenty of spots to just sit, relax, and people-watch.

Grab a book and post up at one of the waterfront bars or cafes. Rent bikes and cruise around at your own pace. Browse the art galleries and quirky shops. Sometimes the best travel experiences are the unplanned ones!

Planning Your Key West Weekend

Here are some quick tips for planning and booking your weekend in Key West.

When to Visit Key West

The best time to visit Key West is during the winter months! It’s dry season and hurricanes are no longer a threat. Of course, it’s also the best weather for being outside in general.

I just went in April and the weather wasn’t too bad. Yes, it was hot, but not nearly as hot as it will get come summer. There were plenty of people around, but a good amount of the tourists seemed to be Floridians like myself.

So after winter from November to March, I’d suggest those shoulder months of April, May, September and October.

Just know that September and October are still in hurricane season and it will still be very hot. However, you should get better prices as everyone has returned to school and work and those months tend to be slower for travel in general.

How to Get to Key West

The best way to get to Key West is to fly! If I had driven from Central Florida, it would have taken about 8 hours! From Miami, Key West is 4 hours by car!

I flew Allegiant into Key West (EYW) and the flight was nice and short. We also didn’t need a car for our weekend in Key West, so that was a non-issue.

However, if you do need a car for your trip, or you plan to explore all of the Florida Keys, then flying into Miami or Fort Lauderdale could be an option. Just know you’ll have a long drive on the Overseas Highway until you get to Key West, but you can add more of the Keys to your trip.

Where to Stay in Key West

When deciding where to stay in Key West, you will not be short on options, but you will be short on affordable ones.

If you don’t have a car, you’ll want to choose a hotel within walking distance of Duval Street, or a hotel with a free shuttle.

If you have a car and want a budget friendly stay, consider staying on Stock Island or another island further north. The closer to Duval Street you get, the more expensive it will be.

We opted for a place with a free shuttle and stayed at Havana Cabana. The shuttle was super easy to use and extremely punctual. Soon I will be writing a full review of Havana Cabana and my experience staying there, but overall I recommend it.

Getting Around Key West

The best way to get around Key West is to walk! Duval Street and the surrounding area is very walkable. In addition, you can rent golf carts, bikes or scooters which can be a fun way to explore.

My friend rented a golf cart on a previous trip and she loved utilizing that method for exploring. It can be especially useful when it’s super hot and you don’t want to do a lot of walking.

Uber is plentiful in Key West and a lot of hotels offer a free shuttle to downtown. My friend and I used the hotel shuttle or uber to go long distances and then we walked a lot for our weekend in Key West!

Trolley tours can be perfect for your sightseeing day or days, but it’s so walkable you don’t have to go that route unless you really want that experience.

Check availability for Key West Hop-On Hop-Off Trolley Tour

Practical Tips for Your Key West Weekend

Key West is an easy destination to visit. If you forget something, it’s easy enough to find a store you’ll need. It’s a hot climate, so you won’t need bulky clothing either, which makes packing in a carry-on super easy!

What to Pack

Key West offers a super hot climate, so think casual and light layers. I love a summer dress, and that is what I mostly wore on my trip. You’ll also want your swimsuit, reef-safe sunscreen, a hat and sunglasses. Oh and comfortable walking shoes are a must.

Consider mosquito repellent, especially in the summer months! If you have snorkel gear you can bring it, but if you plan to do a tour most will offer it.

If you are planning a visit to Dry Tortugas, consider bringing a portable charger for your phone. Both my friend and I consumed all our battery and there’s no service for most of the trip! It won’t be necessary for your weekend in Key West as a whole, but could definitely come in handy for long day tours.

Money-Saving Tips

I’ve had the privilege of traveling to many countries all over the world, and travel in the USA is just expensive. There’s really no way around it. My dollar can go so much further, even on a Greek island!

If you really want to save money, avoid the weekend and try to travel during the week. That’s not very practical of course, but hotel prices can be much better during the week. Also, try and avoid the high season which is winter and into spring break.

For Dry Tortugas you have to book early, because it will sell out fast. However, if you are visiting during a less busy time, consider booking other Key West tours after you arrive as there may be last-minute deals as companies try to fill boats. Of course, if you have a tour your heart is set on doing, don’t wait to book it!

I’m not into drinking, but happy hour can save you some money. The restaurants are not exorbitant, but they are not budget friendly either. Consider grabbing some meals away from Duval Street or at the grocery store to save some money.

Lastly, beach and sunset are free activities! Walking Duval Street and window shopping is also free.

Things to Know Before You Go

Key West has random events throughout the year, so check their calendar to join or avoid, whatever your goal may be.

Hurricane season in Florida is June to November, so keep that in mind. As someone who lives in Central Florida, it’s not a yearly occurrence, but it’s worth keeping in mind.

While Key West does have a few beaches, the Florida Keys are not really a beach destination in general. For that type of vacation, you’ll want to visit the main land of Florida and its hundreds of miles of beaches. Key West is more about boating tours or exploring near and around Duval Street.

Final Thoughts on a Weekend in Key West Itinerary

I really enjoyed my 3 days in Key West, so even if you’re not a drinker like me, there’s something for you! From history to butterflies and from lighthouse views to a bucket list national park, my weekend in Key West was more full and fun than I expected!

Even if you don’t visit Dry Tortugas, Key West has plenty to offer for a weekend itinerary. It’s quirky, tropical, full of good restaurants, and a perfect little getaway!

Enjoy your time in Key West and if you want more inspiration for your trip, check out my Florida guide!