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Published: 10/26/24
How To Spend One Week in Key West
Despite its small size, you can easily spend an entire week, or longer, in Key West, Florida.
In fact, I did just that in December 2024. Although our 7 days in Key West were very rainy, we found that Key West offers a wide-range of activities. From historic homes, plentiful museums, rum tastings, key lime pie, shopping, and a happening live music scene, Key West packs a lot into an 8-square mile island.
Beyond the busy island itself, Key West makes a perfect vacation base for other Florida Keys adventures. You can easily day trip to Dry Tortugas National Park or head north on the Overseas Highways to check out the 40+ islands of the Florida Keys.
Located at the far reaches of the Florida Keys in between the Gulf of Mexico and Straits of Florida, Key West visitors enjoy a Caribbean style vacation without (technically) leaving the contiguous United States. Only the U.S. Virgin Islands and Puerto Rico offer a similarly convenient beachy escape for U.S. citizens.
In this post, I’m sharing exactly what we got up to during our 7 days in Key West. Since we had less than ideal weather for our mid-December visit, I’m also sharing lots of itinerary suggestions of what I would have done if it hadn’t been raining incessantly. But rain or shine, it’s not hard to make the most out of your time on Key West.
Read on to start planning your own perfect 7-Day Key West itinerary!
7-Day Key West Itinerary
Day One: Arrive Key West
Multiple flight delays and hiccups pushed our arrival to Key West back by more than 15 hours. High winds threatened to divert us to Miami. Happily, when we finally touched down on the Key West tarmac, beautiful blue skies and balmy weather greeted us.
A quick rideshare ride delivered us to our rental house located in the heart of Key West’s Old Town. After a quick grocery run, our first order of business was to catch up on sleep. By late afternoon, we were ready to venture out on foot to explore this very walkable little city.
Waypoints: We started our Key West adventures on Duval Street. (From our rental, located just north of Truman Avenue, we accessed Duval Street via the iconic rainbow-colored crosswalks.) We took the obligatory photos at the Southernmost Point buoy, skirted around the edge of Zachary Taylor State Park, and strolled through Truman Waterfront Park.
Eats: We stocked up on groceries at Fausto’s Food Palace in the heart of Old Town. For dinner, we started off our Key West dining experiences with a true island icon: Blue Heaven. The al fresco dining experience in a grove of kapok trees with live music is truly not to be missed. Of course, their key lime pie with a signature mile-high mound of meringue is also a must.
Day Two: Dry Tortugas National Park Day Trip
Despite seas so rough that we had an option to cancel for a full refund, we decided to test our seaworthiness. At the break of dawn, we set out on a 70-mile boat ride to the Dry Tortugas in the middle of the Gulf of Mexico. I’m so glad we did. This day was the highlight of our time in the Florida Keys and I think it deserves a spot on any Key West itinerary.
Waypoints: I have a whole post devoted to our day trip to Dry Tortugas National Park on the Yankee Freedom III ferry.
Eats: Both breakfast and lunch were provided by the Dry Tortugas ferry. We grabbed a light dinner Garbo’s Grill. I continued my “best key lime pie in Key West” research by picking up a slice of pie from the Duval Street location of Kermit’s Key Lime Pie.
Day Three: Key West Highlights
While this was our third day in town, it kind of felt like our first! Between our delayed arrival and then spending our first full day in town actually out of town at the Dry Tortugas, we still needed to get the lay of the land.
We filled this day with some true Key West highlights that I think should be included in any Key West visit, whether you’re staying for a day or week.
Waypoints: We spent our morning at the number one Key West tourist attraction: Hemingway House. The celebrated American author lived here for about a decade and wrote many of his novels in the writing studio here. If you’re not prone to following Hemingway around the globe like I am, I still recommend coming just for the small herd of cats who live on the property.
In the afternoon, we headed over to Stock Island to Lazy Dogs Adventures for their Ecotour Kayak tour through the mangroves. Despite threats, the rain held off during our time on the water. By the time we headed to Mallory Square for the famous Sunset Celebration, the sun had disappeared prematurely behind a thick bank of clouds.
Eats: I procured my first Cuban coffee of the trip at Key West Cuban Coffee, a friendly neighborhood shop on Truman Avenue just a block from our house. For dinner, we stopped at Kaya’s Islands Eats off of Duval Street.
Day Four: Museums and Beaches
We continued exploring Key West on foot today, hitting up some of the island’s best museums, beaches, and restaurants.
Waypoints: Our first stop of the day was Truman Little White House, a small naval officer home that President Truman used as a vacation home during his presidency. We also toured the USCGC Ingham museum ship docked next to Truman Waterfront Park. While the forecast promised rain, we managed to sneak in a very sunny visit to Fort Zachary Taylor State Park.
Other Itinerary Options: If these museums don’t speak to you, I recommend checking out the Mel Fisher Maritime Museum, the Key West Museum of Art and History, or the Key West Butterfly and Nature Conservancy.
Like all beaches on Key West, the beach at Fort Zachary Taylor State Park is manmade. However, it’s generally considered the best beach on the island, so definitely include the state park in your Key West plans.
Eats: We returned to Key West Cuban Coffee for lunch to try their Cubano sandwich and mojo pork. Not wanting to squander a rainy afternoon, we popped into The Roast, a little hole in the wall speakeasy just off Duval Street, for one of their signature cocktails. Dinner was fish baskets from Eaton Street Seafood Market and a slice of key lime pie from Limes and Pies.
Day Five: Overseas Highway Exploration
Since parking in Key West is a major hassle, we spent the first half of our trip without a car. This morning we headed back to the airport to pick up a car for the remainder of our visit. Since this was the start of a very rainy 48 hours, it was extra nice to have the shelter of the car while exploring the great Florida Keys.
Waypoints: Our first stop was Big Pine Key to visit the National Key Deer Refuge. We did a couple short hikes, but the steady drizzle kept the wildlife tucked away. We did spy the two resident alligators at the Blue Hole Observation Platform. We continued on to Islamorada Bass Pro Shop, because guess who has two thumbs and forgot to pack a rain jacket.
Other Itinerary Options: If you want to save a little money, you could certainly rent a car for a single day and return it to the airport at the end of today. In that case, I’d plan to pack this day full of the best stops along the Overseas Highway including the Turtle Hospital, Bahia Honda State Park, and Porky’s for fried key lime pie!
Eats: We ducked into the atmospheric No Name Pub for lunch on No Name Key. It’s fairly common to see key deer in this honky-tonk’s parking lot, but with the rain, these little deer were all bedded down. Upon our return to Key West in the evening, we enjoyed dinner at Sarabeth’s, although the meal ended with the second power outage of the trip!
Day Six: Rain Day
This is the day it rained and rained and rained in Key West. We really enjoyed our spacious rental which allowed us to spread out and work on various projects while we waited out the weather. I’m pretty sure I spent most of this day editing my 11 Things to do in Richmond, VA post!
Waypoints: We briefly flirted with the idea of driving up to the Turtle Hospital in Marathon, but quickly changed plans when we realized how bad visibility was on the Overseas Highway.
Other Itinerary Options: If the weather isn’t dictating a zero day for you, I’d recommend doing a snorkeling trip to the Key West coral reef. I actually had this scheduled, but rough seas kept me on land. Another great option would be a food walking tour around town or heading to Key West First Legal Rum Distillery for a mojito class.
Eats: We grabbed coffee and breakfast from Key West’s most popular breakfast spot: Cuban Coffee Queen. For dinner, we headed over to Moondog Café on Whitehead Street. With Moondog a whopping 4 minute walk from our rental, we kind of wondered why we hadn’t eaten every meal of the trip here . . .
Day Seven: Florida Keys Highlights
For our last day in the Keys, we drove up the Overseas Highway again as far as Marathon so we could visit some Florida Keys highlights in the first truly good weather of the trip.
Waypoints: Small, but beautiful Bahia Honda State Park was our first stop. At the Turtle Hospital in Marathon, we learned a lot about sea turtles and the rehab work done in the hospital. The 7 Mile Bridge on the Florida Overseas Heritage Trail was a great place to stretch our legs and watch folks fishing. We also swung into the National Key Deer Refuge on Big Pine Key.
Once we were back in Key West, we enjoyed a lovely stroll through the marina. I finally got my photo taken next to the famous “Greetings from Key West” mural on the Cuban Coffee Queen!
Eats: Since it was our last day on the island, we hit up our favorite restaurants a second (or third) time. Breakfast called for more takeout from Key West Cuban Coffee. In the evening, we were happy to enjoy patio weather at Moondog Café.
Helpful Key West Trip Planning Information
Other Fun Things To Do in Key West
When To Visit Key West
While our mid-December visit was characterized by high winds, cooler than average temps, and a fair amount of precipitation, I don’t not recommend a trip to Key West this time of year. As a huge tourist destination with about 9000 non-residents on the island on any given day, there’s really no perfect time to visit.
We visited right as tourism was starting to pick up for the winter season. Key West’s a fairly popular Christmas destination, so expect to find some over the top Christmas decor if you visit during December. In general, visitors taper off during hurricane season, from late August into October. Tourists reach their peak in March and April over spring break.
But not even the hot summer temps – when it’s rare for the mercury to drop below 80 – keep visitors at bay. Since Key West attracts visitors of all ages and walks of life, it’s a pretty popular summer break destination. If you can, I recommend booking your lodging and any “must see” tours, like a ferry to the Dry Tortugas, as soon as possible, no matter when you plan to visit.
Where To Stay In Key West
Our lodging plays a big role in Andy and my vacations, so I spent a lot of time analyzing all of Key West’s hotels, resorts, and vacation rentals. There’s a dizzying number of accommodations and it took some time to sift through it and find the right spot for us.
In the end, we stayed in a VRBO, Sailor House, on Center Street, in between Truman Avenue and Duval Street. This ended up absolutely being the right choice for us. We loved having a full kitchen and tons of living space as well as four different patios and verandas. The Old Town location was also great for roaming the city on foot.
Ultimately, I chose Sailer House over a small conch style cottage. Key West Hideaways offers three little conch cottage rentals, located south of Truman Avenue in Old Town. I’m glad I opted for more space and a more central location, but I think the conch cottages would have been a great, more budget friendly option.
Other places I considered included the Southernmost Beach Resort on the far south end of Duval Street. Winslow’s Bungalows with its tempting free parking was another serious contender. I looked into several B&Bs like Duval House, but ultimately decided I wanted the ability to cook some of our meals ourselves.
Conclusion: Our Week in Key West, Florida
We certainly didn’t struggle to fill a week in Key West. However, if you’d prefer not to do out and back trips up and down the Overseas Highway, you might prefer to turn 7 days in the Florida Keys into a road trip. A popular vacation option is to book a multi-city flight into Miami, rent a car to drive the length of the Keys, then fly out of Key West.
I’m not sad to have missed out on Miami traffic and between our cozy rental house and the plethora of dining choices, it was really lovely to “come home” to Key West every night. Just note that flying in and out of Key West isn’t always straightforward. Between high winds and the short runway, this airport is a recipe for flight delays.
I found a week in Key West to be the perfect amount of time to settle into island life and see the best of the Florida Keys. Even though we stayed pretty busy during our 7 days, we still missed plenty of Key West highlights including Tennessee Williams’ house, First Flight Brewery, snorkeling at the nearby coral reef, and taking a sunset sail.
I hope this post inspired you to create your own week to remember in Key West. Be sure to include plenty of Cuban coffee, historic homes, and time on the water, whether you opt for a 70-mile day trip to the Dry Tortugas or a sunset sail around the Key West harbor.
Key West has a relaxed vacation vibe all its own. The best way to experience it is to stay a while!
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