Key West is more than just the end of U.S. 1—it’s a pocket-sized island crammed with more history, literary legends, and iconic bars than almost anywhere else in the country. Planning a full three-day escape (plus 2 travel days) here requires a good strategy, balancing the must-see historical tours with the necessary Key West traditions, like finding the best sunset and, of course, a slice of key lime pie.
After a recent trip that included everything from bike mishaps and presidential history to overpriced burgers and amazing scenery, I’ve broken down our experience into a comprehensive, practical guide. This is how we navigated three intense days, what was absolutely worth the time and money, and the few things we definitely would have done differently.
Ready to trade your stress for sunshine? Let’s dive into the details of our most recent long weekend to Key West.
In This Post:
🗺️ The Complete Key West Itinerary: Day by Day
Key West is incredibly walkable and bikeable, so be sure to wear comfortable shoes and plan to cover a lot of ground!
Day 0: The Overseas Highway and Island Arrival
The journey itself was part of the destination for us on this trip. Driving the entire stretch of the Overseas Highway (U.S. 1) is a breathtaking experience, especially that final section across the famous bridges. We recorded the trip and will post it soon.
Once we got there, we unpacked, found our rental bikes and went to dinner at Mac’s where we sat outside with a view of the water and enjoyed the fresh warm air. We were exhausted from the 7 hour journey, so we headed back to the hotel to unwind and get a good night’s sleep.
Day 1: Literary Legends, Maritime Views, and Pie Perfection
Day one was dedicated to exploring the island’s most famous historic sites, all easily accessible in the downtown area. We opted for road bikes to cover the distance quickly, which proved both brilliant and a little eventful!
- The Southernmost Point Start: We rode downtown straight to the Southernmost Point Buoy, the famous marker that sits just 90 miles from Cuba. The line was manageable, so we queued up for the essential photo. It was right here, as someone was taking our picture, that Justin realized he’d dropped his phone!
- Lesson Learned: We rely on Life360, and I was thankfully able to track the phone a few blocks away where we quickly recovered it. But in the rush of the moment, I didn’t check the photo, and only later realized I had blocked the “SO” in “Southernmost” in the frame. We never got back for a retake. Check your photo before you leave the buoy!
- Ernest Hemingway Home & Museum: This stop was a highlight for Justin, as Hemingway is a favorite author of his. The guided tour was fascinating, not only for learning about the author’s life and work on the island but also for meeting the famous descendants of his six-toed cats. The house and grounds are well maintained.
- The Key West Lighthouse: Right across the street from the Hemingway Home, we paid for admission and headed to the Key West Lighthouse. I was curious why this classic lighthouse was landlocked, but the tour information quickly explained it: the Army continually made the island bigger over the years.
- Climb Comparison: The climb up was much easier than others we’ve done (like the Pensacola Lighthouse). It’s shorter, and the staircase doesn’t hug the interior wall quite as tightly, though maneuvering past people going the other way was still a challenge. The view from the top is great, offering a perfect perspective on the island. However, the museum was a bit small, and the overall experience felt a bit overpriced for the admission cost.
- Mile 0: After descending, we walked toward Duval Street and found the iconic U.S. 1 Mile 0 Marker. A quintessential photo opportunity marking the end of the line.
- Southernmost Point Brewery: We stopped in here, initially thinking of it for lunch since they offer a variety of vegetarian options (and boast a full gluten-free kitchen and beer menu—a major plus for anyone with dietary needs). We decided against a meal but had a lovely time talking with the lady working there. The atmosphere was fun, with 80s music on, making it hard not to sway around a little!
- Key Lime Pie Tour vs. Tasting: It was officially Key Lime Pie Time! We considered doing the popular Key Lime Pie Tour, but at $70 per person for three hours, we figured we could buy a lot of pie for that price and didn’t want another 1.5 hour tour. While we missed the cool historical background the tour would have provided, we opted to buy and taste slices from three different famous spots. Read about that here.
- Rest and Recharge: After a jam-packed day full of history, sun, and pie, it was time for Justin to take a nap while I sat outside by the pool. A mandatory break to recharge before the evening.
- Dinner & Trivia: We went to an Irish place for dinner because they were hosting trivia. It was a format we hadn’t encountered before, and while we enjoyed trying, we didn’t do too well (8 out of 11). Dinner was a mixed bag: the pizza was unfortunately quite gross, but Justin’s meatloaf was excellent. A full, fun, and very diverse day!
Day 2: Deep Sea Escape and Sunset Rituals
Day two was anchored by one of Key West’s most famous excursions: the journey to Fort Jefferson.
- Dry Tortugas National Park: We took the boat out to Dry Tortugas (a monumental day trip that absolutely requires its own detailed post to cover the history of Fort Jefferson, the snorkeling, and the logistics which you can read here). We barely made it back in time, but…
- Mallory Square Sunset: It is essential to make the time for the Mallory Square Sunset Celebration. Despite our return time from Dry Tortugas, we rushed over and made it just in time to view the incredible sunset. The atmosphere was radiating with excitement and happiness with performers, food, and drink vendors makes the sunset a true island ritual.
- The Waterfront Brewery: Dinner was at a local brewery right on the water. We managed to snag a table right by the open windows and doors—a truly great experience with the marina views and sea breeze.
- Nightcap: We walked around the marina area for a bit and had a final drink while listening to live music before calling it a night.
Day 3: Presidents, Forts, and Tourist Traps
With rain in the forecast, we decided to pack our final day with mostly indoor / covered activities and the super tourist ‘must do’s’, utilizing the free hotel shuttle to head downtown one last time.
- The Breakfast Club, Too: Instead of the boring hotel breakfast, we went to The Breakfast Club. Justin got the traditional breakfast, and I opted for the hefty breakfast burrito—knowing it was going to be a long day of walking, I wanted to make sure I was full!
- Harry S. Truman Little White House: We walked over to the Little White House and took the guided tour. While waiting for the tour to start, we were given adorable gingerbread cookies! (They were also holding a gingerbread house activity, which I thought would be fun, but that simply isn’t Justin’s thing.) The house itself was interesting enough, detailing its history as a presidential retreat, but I expected slightly more depth.
- First Flight Restaurant & Brewery: We headed across the street to First Flight, the home of Pan American World Airways. It’s often cited as the southernmost brewery in the continental US, giving it great historical bragging rights. Beer Verdict: Unfortunately, we didn’t like the beers we selected. Justin couldn’t even drink his choice, and that says a lot since he is usually my beer garbage disposal. We didn’t stay for more and didn’t bother eating there.
- Fort Zachary Taylor: We then decided to walk all the way to Fort Zachary Taylor Historic State Park. This was an important stop for historical context. Fort Taylor (built pre-Civil War) served as a vital coastal defense, actively blocking Confederate supply ships during the Civil War. It’s an interesting comparison to Fort Jefferson (Dry Tortugas), which is known more for its massive isolation and scale, whereas Fort Taylor is known for its strategic, active role in the war.
- Duval Street: The weather was holding out, so we decided to walk the full length of Duval Street. We didn’t go into any shops, but there are quite a few local artists and unique boutiques that a shopper would appreciate.
- Margaritaville: We decided to have a drink at Margaritaville because, well, that’s what you do! Even though it’s touristy and we’ve been to others, this is the original location. The drinks were super yummy. I ordered the Ruby Red Renegade (which was surprisingly green!), and Justin’s choice, Tranquil Waters was even better—we both loved it.
- “The Smallest Bar”: Next up was a check-in at The Smallest Bar, which was a little bit of a letdown. It’s essentially just a walk-up bar with no stools, and since getting your drink to go is common downtown, it didn’t feel particularly unique or special.
- Sloppy Joe’s Bar: Keeping up with the typical tourist things, we went next to the legendary Sloppy Joe’s Bar. A guy was singing, which was nice, but it made it hard to hear each other talk. We were hungry, so Justin got the Sloppy Joe (which, they claim, originated here), and I got the fish tacos. Changing one thing about the day would have been our lunch—the food here was very overpriced and not very good. It really just came to timing, it was time to eat and this is where we happened to be.
- Final Pie: We had one more key lime pie place left on our list, so we quickly did that. It started to rain, so we found our hotel shuttle and headed back for some downtime before packing for the morning departure.
If I had to do this day over again, I would have opted to take the bikes. The rain came a few hours after the expected and would have been easy enough to manage getting back to hotel on the wet streets. Going out to Fort Zachary Taylor was a long walk and the bikes would have been a more fun and efficient way to cover that ground. BUT, if it did rain as much as they expected when they expected it – I would have been miserable on a bike….I guess the lesson is weather can change quickly, and we did pick the better choice with the information we had at the time.
Day 4: Departure
We enjoyed a final hotel breakfast and headed out by 8:30 AM to head up to the Everglades National Park before heading home.
🔑 Key Logistics and Lessons Learned
A trip to Key West is often defined by how well you handle the small logistical challenges. Here are the things we learned the hard way that should help you plan better:
Bikes: Convenience vs. Cost
- Rental Service: We used a local company that dropped the bikes off and picked them up at our hotel, which was incredibly convenient. It was only $10 per day per bike and they came with a basket and a lock. They were easy to work with and the bikes worked out great. We don’t regret renting them.
- Usage Assessment: Having the bikes was great for getting around areas a little faster than walking, but not restricted on time schedules like the shuttle or having to pay for car parking.
- The Cost Mistake: We ended up paying for the bikes the full five days but probably only used about 40% of the time we paid for. Be honest with yourself about your schedule. If you are doing a full-day excursion (like Dry Tortugas) or spending a day entirely walking Duval, you may not need the bike that day, We also thought the delivery date before was not part of the price, and we changed our plans to go to Everglades and cut Key West short a day; our errors. Be aware of your rental duration to maximize your spend.
The Value of the Hotel Shuttle
- Especially when the rain was looming, using the hotel shuttle was a huge win. It saved us time, money, and hassle dealing with parking or navigating the island in bad weather. Honestly we didn’t remember until after we got there that the hotel had this service, which is why we rented bikes, but if we did know, we may have just relied on the free shuttle If your hotel offers this service, utilize it strategically.
Eating on Duval: The Cost of Convenience
When eating at the most famous, highest-traffic places on Duval, you are paying for the atmosphere and location, not the culinary quality. Save your money for the smaller, local spots or the breweries that focus on craft.
💰 Honest Breakdown: Food, Drink, and Admissions Costs
This budget is based on two adults traveling for three full days plus a travel day in each direction and includes the necessary costs for historical immersion and Key West traditions. Prices are estimated average admission/tour costs and can be subject to seasonal changes.
Admissions and Logistics
| Item | Cost Per Person – estimate | Total Cost for Two – Actual | Notes/Specifics |
| Ernest Hemingway Home & Museum | $18.00 | $36.00 + 3.05 tax = $39.05 | Admission for a guided tour of the house and grounds. |
| Key West Lighthouse & Museum | $17.00 | $34.00 | Overpriced for the experience. |
| Little White House Guided Tour | $25.00 | $50.00 | Guided tour of the historic Presidential retreat. A bit pricey for the short tour. |
| Fort Zachary Taylor Admission | $2.50 | $5.00 | Fee per person entering the State Park by walking (or bike). |
| Dry Tortugas Ferry | $210.00 | $420.00 (+20 tip at end) | Full-day excursion to Fort Jefferson |
| Bike Rental (5 Days) | $50.00 | $100.00 + $7.50 tax + $20 tip | Lesson: We should have only paid for 3 days of rental. |
| Key Lime Pie Tastings | $65 if done via tour | $7.48 Kermit’s $6.95 The Original Key Lime Pie $5.86 Key West Key Lime Pie $14.37 Limes & Pies Subtotal $34.66 DIY | For 4 tastings. We split 3 of them on the first day, and then each got one on the last day. |
| TOTAL ADMISSIONS/LOGISTICS | $422.50 | $730.00 | This total excludes all food and drink. |
Food & Drink Costs
| Item | Food & Drink Budget | Food & Drink – Actual | My Actual Experience |
| Breakfast/Coffee | $60.00 | $44.45 – The Breakfast Club Too | Breakfast was free at hotel – changed it up one morning, but breakfast is getting expensive! |
| Lunch/Mid-Day Snack | $120.00 | $61.13 Sloppy Joe’s $29.70 – Pepe’s Subtotal $90.83 | |
| Dinner | $220.00 | $76.31 – Irish Place for Trivia $103.85 – Waterfront Brewing Subtotal $180.16 | We try to pick at least one nicer restaurant every trip. This trip didn’t have a ‘fancy’ place. |
| Drinks/Bars (Non-Meal) | $160.00 | $25.99 – Southernmost Pint Brewing $28.00 + tip- Hotel Bar $14.00 – Schooner Warf Bar $14.00 – First Flight $30.52 – Margaritaville $14.21 – Smallest Bar $17.51 drinks on ferry Subtotal $144.23 | We knew the drinks would be a fairly large budget item |
| TOTAL FOOD & DRINK (Estimate) | $560.00 | $459.67 (we also paid cash a few places, so this is probably closer to $510). | Dining quality is variable; spend wisely away from Duval Street. |
Grand Total Estimated Trip Cost (Excluding Lodging/Gas): $1,189.67 plus Lodging $1,338.51 = $2,528.18 plus gas.
Key West delivers on its promise of a unique, sun-drenched escape. By focusing on the historical sites in the morning, taking an essential day trip in the middle, and saving the tourist-heavy Duval spots for the afternoon, you can experience the best of the island efficiently.
Of course you can fly there too, ensuring you’d have more activity time and not travel time. And the nightlife is vibrant if you are into going out dancing, listening to music, or drinking later in the evening/night there are lots of places to go. Instead of bike rentals, a lot of people chose to rent golf carts.
It was an incredible and busy three days, full of learning, sunshine, and a few lessons learned on logistics and dining value. We wouldn’t trade the experience for anything—not even for a flawlessly framed photo at the Southernmost Point!