Weekend in Key West: The Perfect 2 or 3 Day Itinerary

Key West is one of the most vibrant and quirky cities in the US, and has the perk of being located in a tropical climate. Therefore, many people choose this island city as their vacation destination each year. There are plenty of fun experiences to be had, and this itinerary for 3 days in Key West will ensure you see the best of everything.

Although Key West is surrounded by water, it is connected to the mainland United States via a series of bridges through the Florida Keys called the Overseas Highway, or Highway 1. The endpoint of Highway 1 can be found at the corner of Fleming Street and Whitehead Street in downtown Key West.

Its unique location is just one thing that sets Key West apart from every other US city. Whether it’s bar hopping, foodie spots, sightseeing, or enjoying the great outdoors, there is something for everyone to enjoy in the “Conch Republic”. Without further ado, here is the perfect itinerary for an unforgettable 3 days in Key West.

3 Days in Key West – Itinerary for First Time Visitors

Weekend in Key West 2 or 3 Day Itinerary Travel Blog Disclaimer: This article contains affiliate links. This means that if you make a booking after clicking on these links, I may earn a small commission (at no additional cost to you) which helps pay for the running of this blog.

Day 1: Explore Classic Key West

Day one of this Key West itinerary focuses on getting an overview of the city and visiting some of its most famous landmarks.

Arrive into Key West & Rent Bikes

You will likely arrive in Key West by flying into Key West International Airport (EYW) or driving in via Highway 1. If you flew, the airport is only 11 minutes from Duval Street, which is Key West’s famous main drag. You can simply grab an Uber from the airport to your lodging if you don’t rent a car.

Your next step is to rent bikes for the duration of your stay from Key West Bicycles. With the island being only four miles long and two miles wide, a car is not necessary and a bike will be more economical for reaching destinations just outside of walking distance.

If you enjoy guided tours, this guided bike tour is a great introduction to the top attractions.

Southernmost Point Concrete Buoy

No Key West itinerary is complete without a stop at the Southernmost Point Concrete Buoy. Located at the corner of South Street and Whitehead Street, this large buoy marks the Southernmost Point of the Continental United States. While the accuracy of this claim is questionable, other points in the Keys that are further south are not nearly as accessible to the public.

Upon arrival to the big concrete buoy, you will most likely need to wait in line for your photos, unless you arrive first thing in the morning. However, the line moves fast and people are generally very cooperative in helping one another take pictures.

Hemingway Home & Museum

Front of Hemingway House

One of the most essential places to visit in Key West is the Ernest Hemingway Home & Museum. This is where Ernest Hemingway lived with his second wife, Pauline, from 1931 until their divorce in 1940. Hemingway wrote some of his most significant works in his studio above the carriage house.

While at the Hemingway House, you’ll likely see many cats roaming about.  If you look at their paws, you may notice that many of them have six toes!  Some of these cats are descendants of a 6-toed cat Hemingway received from a sea captain, who was departing Key West.

This house museum is open every day to walk-ins from 9am to 5pm, and the $16 ticket must be paid in cash. The price includes a 20 to 30-minute guided tour of the house.

Brunch at Blue Heaven

From the Hemingway House, walk four minutes to Blue Heaven, which is one of Key West’s most famous restaurants. Be sure to arrive by 2:00pm to make it in time for the breakfast & lunch menu. There is often a wait since they do not take brunch reservations, but it’s totally worth it.

Key Lime Pie at Blue Heaven Key West

Blue Heaven offers a variety of pancakes and benedicts, with some delicious options being the pineapple pancakes and Key West shrimp benedict. There is both indoor and outdoor seating, but outdoor allows you to eat in a garden-like setting with eclectic art, cats and chickens roaming about, and large tree canopies overhead. Save room for a slice of their signature key lime pie, which is piled high with merengue.

Key West Lighthouse

weekend getaways in Key West Lighthouse

Burn off some of your brunch with a short climb up the Key West Lighthouse, which is just a four-minute walk from Blue Heaven. The current structure was built in 1848 after the original was destroyed in a catastrophic hurricane. It reopened with a woman, Barbara Mabrity, as its Keeper – a highly unusual circumstance at that time.

After climbing 88 steps to the top, you will be rewarded with panoramic views over Key West and the surrounding waters of the Atlantic and Gulf of Mexico. Tickets cost $17 at the door or $15.40 online, and give you access to the lighthouse and Keeper’s Quarters Museum. Visitors are welcome daily from 10am to 4pm.

Check out Duval Street

Duval Street in the evening

One of the most fun things to do in Key West is spending an evening on Duval Street, which is notorious for its party scene. There are plenty of spots to grab dinner, as well as make a night of it with drinks afterwards. Here are two casual and delicious dinner options:

    • D.J.’s Clam Shack: DJ’s Clam Shack was once featured on Diners, Drive-Ins and Dives and is famous for their “overstuffed” lobster rolls and conch fritters. Order at the small counter just off Duval Street, and enjoy their mouthwateringly good food on the small back patio.

Bowl at Poke in the Rear 2 or 3 days in Key West Florida itinerary

  • Poké in the Rear: Visit this open-air restaurant behind the Aqua Bar and Night Club for super fresh and delicious poké bowls.

Afterwards, you may want to continue your evening with drinks on Duval Street. The street is lined with bars, but start at Sloppy Joe’s, which is an old standby once frequented by Ernest Hemingway. The drinks are standard, but there is usually live music and always plenty of atmosphere.

Day 2: Cuban Coffee & Sunset Sail

The second of your three days in Key West introduces you to the city’s most spectacular feature: its sunrise and sunset views. You will also get a taste of Key West’s strong Cuban culture.

Sunrise at Higgs Beach

sunrise from pier at Higgs Beach

Sunrises in Key West are absolutely stunning, and the best viewing spot is the Edward B. Knight Pier at Higgs Beach. You will need to get up really early for this, but it’s totally worth it. The sun rises anytime between 6:37am and 7:37am over the course of the year.

This is where you’ll be thankful to have a bike, since you won’t need to rise as early. Higgs Beach is only a five-minute bike ride from Duval, but it’s more like twenty if you walk.

Drink Cuban Coffee

Exterior of Key West Cuban Coffee

Key West has a longstanding Cuban influence, being only 90 miles from Cuba.  Therefore, it’s imperative to try some Cuban coffee and cuisine while you’re in town.  Here are two great choices:

  • Key West Cuban Coffee: This restaurant is located in a tiny space on Duval Street. Behind a small counter will be three ladies working nonstop at the grill and espresso machine. Cuban and Mexican fare is served here, including breakfast burritos, empanadas, and light Cuban coffee.
  • Cuban Coffee Queen: Located in a shaded courtyard right off Duval Street, this outdoor restaurant is close to the action. You could keep things simple with a Cuban coffee or cortado paired with some pan Cubano. There are also more substantial items like Cuban sandwiches on the menu.

Butterfly Conservatory

Step away from Key West’s bustling scene for a moment without even leaving Duval Street. The Key West Butterfly & Nature Conservatory contains hundreds of living butterflies made up of over 50 different species.

In this glass enclosed space, you can wander past tropical plants with colorful blossoms, while the butterflies and over 20 species of exotic birds fly around you.  The conservatory is open every day from 9am to 5pm, and tickets cost $15.

Stop at Rum Bar

For some high-quality cocktails, stop in for a quick drink at the Rum Bar. This small bar is only a four-minute walk down Duval Street from the Butterfly Conservatory. The cocktails are a little pricey, but they are definitely among the best in all of Key West.

The Pusser’s Rum painkiller in particular is a must; especially when consumed while people watching on the bar’s front porch.

Sunset Sail

sailboat on the horizon during sunset

Rest up before heading back out for one of the best tours in Key West: a sunset sail. Like sunrises, sunsets in Key West are like no other, and they are especially spectacular to view from the water.

There are many different boat charter companies to choose from, and Danger Charters is among the best. Their sunset sail is two hours long and limited to twenty-five guests.

As the sun lowers onto the horizon and the sky turns brilliant shades of orange and pink, the crew serves wine and beer tastings paired with hors d’oeuvres. The atmosphere is relaxed and the views from the sailboat could not be any more magical.

Schooner Wharf Bar

If hors d’oeuvres during the sunset sail didn’t fill you up, a great next stop is Schooner Wharf Bar. This bar and grille is only a ten-minute walk or five-minute bike ride from Opal Key Resort & Marina, where the sailboat drops you off.

Schooner Wharf Bar sits waterside along the Key West Historic Seaport.  This restaurant isn’t fancy at all, with its simple wood structure and “patio seating” made up of tables and plastic chairs on top of gravel.  However, that’s part of its charm as you sip a cocktail and snack on some tuna nachos or fried shrimp.

Day 3: Last Day in Key West

Breakfast at Glazed Donuts

Glazed Donuts is a Key West favorite due to its drool-worthy donuts baked Wednesday through Sunday of each week. The donuts are by no means skimpy and the dough has just the right amount of chew. They come in fun flavors like Cuban coffee, blueberry cheesecake, key lime pie, and seasonal varieties.

Arrive as early as possible, or be prepared to wait in a line that sometimes extends down the sidewalk. The shop is open until 1pm unless it sells out, and you won’t want to miss out on the best flavors.

Fort Zachary Taylor State Park

beach at Fort Zachary Taylor State Park key west weekend getaway

Spend some time outdoors at Fort Zachary Taylor State Park, which is located in downtown Key West, covers 54 acres, and has a beach and fort worth exploring. The fee to enter the park is $2.50 for walkers and bikers and $6 if you are parking a car.

While Key West is not a huge beach destination, this one is definitely worth a visit.  It offers beautiful scenery with its white sand and turquoise water that is popular for swimming.  There are chair and umbrella rentals available, or you can simply grab a picnic table and enjoy the view for a bit.

If you’d like to do some more exploring, check out Fort Taylor, which was built before the Civil War to defend the nation’s southeastern coast.  The fort was used in the Civil War, Spanish American War, WWI, WWII and the Cuban Missile Crisis, though it was never fired upon.

This state park also has the continental US’s southernmost hiking trails, including the Tropical Hammock Trail and Fort View nature trail.

Truman Little White House

Truman Little White House

The Truman Little White House is just a three-minute bike ride from Fort Zachary Taylor State Park, so it’s the perfect next stop on this Key West itinerary. While this house was used intermittently by six American presidents, its most significant usage was during Harry Truman’s presidency. He used the Little White House as his winter home, and spent about 175 days of his presidency here.

Tickets do not come cheap at $22.52 ($20.27 online), but a tour here allows you to see why Truman saw this as a retreat.  In this setting, he also would have contemplated issues surrounding post WWII foreign policy and the beginnings of the Civil Rights movement.

Kermit’s Key Lime Pie

Bike or walk .3 miles from the Truman Little White House to Kermit’s Key West Key Lime Shoppe on Front Street. This local establishment makes many lists for having one of the best key lime pies in Key West.

In addition to traditional pie, this little shop has an assortment of key lime treats that celebrate this flavor. A popular choice is chocolate covered key lime pie on a stick that you can nibble while walking around town. Just remember napkins for when the chocolate starts to melt in the tropical heat and humidity.

Mallory Square

Sunset Celebration at Mallory Square

In case you couldn’t already tell, the sunset is a big deal in Key West; so much so that there is a nightly Sunset Celebration in Mallory Square.  This is something you should experience at least once during your stay, and it’s just a two-minute walk from Kermit’s.

The celebration begins about two hours before sunset when local vendors and street performers gather for a large party in the square. There are magicians, psychics, and food stalls to name just a few, and they build anticipation for the orange glow of the sun to lower over Sunset Key.

Dinner at Latitudes

Water view from Latitudes

Top off your last night in Key West with an incredibly romantic and memorable experience: dinner at Latitudes. As this fine dining restaurant is located on Sunset Key, you will need to head back to the Opal Key Resort and Marina to catch the ferry. This is free to anyone with a reservation at Latitudes.

Be sure to make reservations at least one month in advance, if not more, as dinner here is very popular. However, it’s worth the hype to eat right on the water with your toes in the sand. Plus, they offer a sophisticated menu with plenty of fresh seafood dishes, as well as an excellent wine list. Dinner at Latitudes is guaranteed to end your Key West itinerary on a high note.

Key West Travel Tips

  • Weather: Key West generally has pleasant weather year-round. High season is between December and February, and brings crowds and high prices; September through November is hurricane season, making this the least ideal time to travel. April is ideal, as the crowds have tapered off and the sweltering summer heat hasn’t set in yet.
  • Where to Stay in Key West: If it’s your first time visiting Key West, your itinerary will likely center around Duval Street. Therefore, it’s best to stay in close vicinity of that main stretch. Old Town Garden Villas is just one block from Duval, and has an adorable courtyard with a small dipping pool.

. . .

You are now all set with the perfect 2 or 3 days in Key West itinerary. Be prepared for the best sunsets you’ve ever seen in this eternally festive, yet laid back atmosphere. Just remember to pace yourself and keep an open mind to all the quirks this city has to offer.

Theresa’s Bio: Theresa is the creator of Fueled By Wanderlust, a travel blog. Although she did not start traveling until her mid-twenties due to some pesky student loan debt, with careful budgeting, she was able to pay that off and start planning trips. Since then, she has traveled more and more each year to various places in the U.S., Europe, and the Caribbean. You can follow along with Theresa’s adventures on Instagram, Twitter, and Facebook.

weekend in Key West Florida 2 or 3 days itinerary


Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.