3 Days in Key West: The Perfect Long Weekend Itinerary

Traveling around a full-time job and limited PTO doesn’t mean you have to skip the destinations that need more than a weekend. If you’re wondering whether you can actually see and do enough in just 3 days in Key West, the answer is yes — and I’d know, because I almost talked myself out of this exact trip.

I’d found myself in a rut of planning trips and then immediately talking myself out of them, convinced I “didn’t have enough time.” Then a few friends invited me to join their yearly RV trip to Key West, and even though I wasn’t sure I could fit in everything I wanted to do, I wanted to catch up with them — so I planned the trip anyway.

I was pleasantly surprised by just how much we fit into just 3 days in Key West, and it’s re-inspired to take more long weekend trips close-ish to home.

If you’re planning your own long weekend in Key West, rest assured: you can do a lot in a short amount of time, and this island is worth the trip even if you are working with limited PTO.

How to Spend a Long Weekend in Key West

Below I’ve broken down how to spend 3 full days in Key West.

Each day has 1-2 main activities, which lets you to make the most of your long weekend on the island while still having time to enjoy some rest and relaxation — because let’s be honest, that’s an important part of an island vacation too. 😉

I’ve laid this out day-by-day, but you don’t have to follow it in this exact order — for example, you could decide you want to do the Day 3 activities on your first day instead. Since you’ll likely be based at one hotel for all 3 days, it’s easy to rearrange if needed!

A quick note on how this itinerary is built: this is an activity-based itinerary — it’s built around the tours and experiences that mad tour trip what it was, not an exhaustive checklist of every landmark on the island.

Day 1: Explore the World’s 3rd Largest Barrier Reef

After my trip to Key West, there is one thing I couldn’t stop talking about: my two snorkel tours out to the barrier reef. In my opinion, it’s an absolute must for a Key West itinerary.

We joined Fury’s Double Dip Snorkel Tour two days in a row. It was so fun cruising along the turquoise water, swimming with all the colorful fish, and even spotting a couple of reef sharks!

But I’m getting ahead of myself.

You’re on an island, so start your day off with a slow, relaxing morning — maybe grabbing a nice brunch? Since I was staying with my friends in their RV, we cooked most of our meals, but I’ve heard great things about Breakfast Club Too and Bagatelle.

Then I suggest planning for an early afternoon snorkel tour. We booked ours for 12pm each day, which gave us plenty of time for a slow morning while also helping us beat the afternoon storms that are common in the summer.

Even outside of summer, the water stays fairly comfortable year-round for snorkeling, so I’d recommend joining a tour any time of year — just bring a change of clothes, since the wind can feel a bit chilly after snorkeling in winter

📌 BOOK AHEAD TIP: Our snorkel tour was sold out both times we went — and later on Day 3 we learned the hard way that booking a jet ski tour online is cheaper than booking in person. If there’s one thing to take from this itinerary, it’s this: book your must-do tours in advance.

Read more: My full review of the Double Dip Snorkel Tour.

If you book the 12pm tour, you should be back in Key West around 3pm — grab some Key Lime pie and ice cream from Kermit’s across the street, and in the evening head to Mallory Square in the evening.

Yes, it’s a touristy spot, but it really does have such a lively atmosphere, and the sunset we watched here was spectacular!

Day 2: Visit the National Park Only Accessible by Boat or Plane

Because my friends and I were only in Key West for a few days over the 4th of July, we decided to do two snorkel tours closer to Key West so we wouldn’t miss out on the fireworks.

If my long weekend had fallen at any other time of year, though, I would have planned to visit Dry Tortugas National Park instead.

The only way to reach Dry Tortugas is by boat or plane, so this one takes some advance planning. But it’s worth it: a scenic boat ride out, swimming and snorkeling once you arrive, and onboard guides sharing the park’s nature and history along the way.

This catamaran tour has phenomenal reviews and is the tour I plan to book next time I visit the island.

Since this is a full day tour, breakfast and lunch are included, but you’ll want to plan a nice dinner once you’re back. My friends and I tried the pizzas and seafood pasta at Roostica on our recent trip, and we loved the food!

Day 3: Zip Along the Island and Wander the Iconic Streets

For your final day in Key West, I suggest booking a jet ski tour around the island.

My friends and I actually hadn’t planned to include this — we’d originally hoped to visit the butterfly house (which I’ve heard is really lovely) — but after seeing so many people riding around on jet skis, we decided to see if there was any last-minute availability instead, and swapped our plans.

We managed to grab some of the last spots on a 90-minute jet ski tour, so if you’re one the fence, you could probably still find something last-minute.

That said, I found out afterward that we’d overpaid by booking in person — so if you think you’ll want to do a jet ski tour, make sure to book it online ahead of time instead!

Since these tours run are pretty quick, you’ll likely have some time left before you need to head out. If you have more time than we did, wander down the iconic Duval Street or visit the Hemingway House to learn some of the island’s history — I didn’t get to do either of these on this trip, but they’re high on my list for next time.

I have stood at the Southernmost Point marker on a quick cruise stop years ago — it’s a hectic, crowded little photo spot, elbow-to-elbow with people waiting for their turn at the sign… but it’s a classic, fun piece of the Key West experience if you can carve out 10 minutes for it.

It’s pretty incredible just how much can be packed into just three days in Key West!

Planning Your Trip to Key West

How to Get to Key West

The most efficient way to get to Key West is to fly directly into Key West International (airport code: EYW). This is a very small airport with year-round direct flights from a handful of east coast airports, plus seasonal routes from about 20 airports across the east and central United States.

Because EYW is a smaller airport, with limited daily flights, it can be pricey to fly directly into the island.

The alternative is to fly into Miami International (airport code: MIA), rent a car, and then drive about 3.5 hours along the Overseas Highway, which ends in Key West. You could also fly into Fort Lauderdale (FLL) if you don’t mind adding another 30 minutes to the drive.

A long drive at the start and end of a trip might not sound exciting, but the Overseas Highway takes you through the Florida Keys and is genuinely scenic, with turquoise water and coral surroundings the whole way down. Plus, flying into EYW usually means a connection for most travelers, so your total travel time often ends up similar either way.

Where to Stay for a Long Weekend in Key West

Key West is a small island — just 4 miles long and 2 miles wide — so the real question with where to stay is how walkable you want your visit to be.

If you fly into EYW and stay in Old Town, you can walk almost your entire visit without needing for a car…but you’ll pay a premium for that location.

On the other hand, if you’re renting a car anyway and want something more budget-friendly, staying just outside Old Town and driving in for activities and exploring may be the better fit.

Read next: Where to Stay in Key West for a Long Weekend (coming soon)

I had a bit of a unique setup, since my friends invited me to stay in their RV at a campground in Stock Island (about 15-20 minutes from Old Town Key West). Had done this trip without the RV option, I’d look for a hotel more centralized in Key West, so I wouldn’t have to worry about parking on the small island.

For a more budget-friendly option in the Old Town, I’d suggest Heron House, just a block off Duval Street.

For more of a resort feel in Old Town, H2O Suites is close to the Hemingway House and the beach.

When to Visit Key West

Key West is a great island to visit throughout most of the year:

• November through April is “snowbird” season, with visitors escaping cold winter and spring weather up north for some sunshine.
• May through July brings warm water temperatures and great visibility for water activities. I took my own trip in July and while the humidity was hard to handle, my time in and around the water was incredible!
• August and September are peak hurricane season, so weather can be more unpredictable — but these are also some of the quieter months on the island. Temperatures are still great for water activities, and prices tend to be cheaper during this low season.

I go into a lot more detail on what a July trip is actually like — heat, crowds, and all — in my full guide to visiting Key West in July.

Is 3 days Really Enough Time in Key West?

Three days is enough to have a genuinely great trip to Key West — but it’s worth being upfront that this itinerary is built around a handful of standout activities, not a checklist of every landmark on the island.

On our trip, that meant we didn’t make it to Duval Street, the Hemingway House, or the butterfly house — all things I’d still like to do next time. If wandering historic streets or spending an afternoon learning local history matters more to you than water activities, you may want to either swap a few things our or stretch your trip to 4-5 days so you can fit in both.

But if you’re after an activity-packed long weekend — reef snorkeling, a national park boat trip, and jet skiing around the island — 3 days is genuinely enough to make it feel like a full, memorable trip. That’s exactly what convinced me to stop talking myself out of short getaways.

Figuring out where to stay for your trip? Check out my full guide to Where to Stay in Key West (coming soon).

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