Weekend in Key West Itinerary: Maximizing Your 2-3 Days (+ Tips!)

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Are you looking for the best way to maximize your time during a weekend in Key West? Keep reading – our Key West itinerary has you covered!

Are you planning your trip to Key West last minute?

Be sure to book yourself a hotel and tours well ahead of time in Key West! It can get difficult the longer you wait!

🇺🇸  Top recommendations for tours/activities in Key West:

  1. Key West snorkeling trip (top-rated!)
  2. Sunset Champagne cruise around Key West (my fave chilled-out tour)
  3. Dolphin-watching and snorkeling excursion

🛌  Top recommendations for accommodation in Key West:

  1. Opal Key Resort & Marina (Luxury)
  2. Silver Palms Inn (Mid-range)
  3. Southwinds Motel (Budget)

🚗  Looking for the best way to get around the Florida Keys? Click here to check rental car rates for Florida!

This guide dives into how to plan 2 days in Key West – it is broken down day by day so that you can see where to go and what to do!

And… if you have more than two days in Key West, we give some add-ons that will help you plan 3 days or more down in the Keys!

How to spend a weekend in Key West itinerary
How to spend a weekend in Key West itinerary

Whether you’re planning a casual weekend in Key West with family, an all-out Key West Bachelorette Party with friends, or simply a solo trip this itinerary has you covered.

So, if we missed anything in this guide of one of the coolest places in the US, let us know in the comments! Thanks!

How to Get to (and Around) Key West

Once you determine that Key West is worth visiting, you then have several options for arriving to and getting around this island city.

Getting to Key West 

Key West is part of the Florida Keys and is the southernmost point of Florida (and of the continental US!).

There are several different ways that you can reach Key West — by plane, by boat, and by car. 

Road to Key West
Road to Key West

The closest airport to Key West to fly into is Key West International Airport (EYW) itself.

Alternatively, you could fly into Miami or Ft. Lauderdale and from there you could rent a car to drive over to Key West. From Miami, the drive is 3 hours, and from Ft. Lauderdale, it’s closer to 4 hours long. 

One additional route to Key West involves taking a 4-hour ferry ride from Ft. Myers. 

Getting Around Key West 

Once you’re in Key West, you have several fun options for how to get around.

One option, if you’re staying in the Old Town, is to mostly walk around and use the free “Duval Loop” bus. You might also consider renting a bike to get around Key West. 

If you’re staying in New Town, renting a car might be useful for getting around.

Tourist buses on Key West
Tourist buses on Key West

However, you could also use local taxis or rideshare services like Uber and Lyft. A fun way to get around Key West is to rent an electric car.

You could also rent a moped, but if you’re not already experienced in how to drive one, then it isn’t the safest option. 

Whatever you choose, you’ll find that getting around Key West is easy and enjoyable. 

Weekend Key West Itinerary Overview 

Day 1 Overview 

  • Take a Historic Conch Train Tour
  • Stroll Through Popular Duval Street 
  • Visit the Ernest Hemingway Home & Museum
  • Explore the Lighthouse and Keepers Quarters Museum 
  • Join the Sunset Celebration in Mallory Square

Day 2 Overview 

  • Snap Photos at the Southernmost Point 
  • Relax at the Fort Zachary Taylor Historic Beach
  • Learn a Bit at the San Carlos Institute
  • Unwind With an Evening Boat Cruise 

Day 1 in Key West 

Take a Historic Conch Train Tour

One of the best ways to kick off your visit to Key West and to get oriented to the city is by taking a famous conch (pronounced ‘conk’) train tour.

Started by Michigan natives who moved to Key West, the conch train tours have been running since 1958. 

The tour passes by all the top attractions and is a great way to maximize your trip to see more if you’re short on time.

Conch Train Tour - Chuck Wagner - Shutterstock
Conch Train Tour – Chuck Wagner – Shutterstock

The 75-minute tour provides the narrated history of the island and makes three stops along the way. Tours depart every 30 minutes between 9:15 a.m. and 4:15 p.m.

The conch train tour is also handicap accessible, and it is advised to give the tour company advance notice so they can ensure space for all guests. 

This is a relaxing, fun, and informative way to begin your weekend in Key West. 

Stroll Down Popular Duval Street

Next, stroll along popular Duval Street. This is the main heartbeat of Key West and you’ll find plenty to do here. You’ll even be surprised to find that the street isn’t even one mile long!

With that being said, Duval Street is sometimes referred to as the “longest street in the world” because it runs from the Gulf of Mexico to the Atlantic Ocean.

The street is lined with pubs, bars, cafes, galleries, shops, and restaurants, providing visitors with many options to choose from. 

Beautiful Duval Street
Beautiful Duval Street

There are plenty of opportunities to enjoy live music and people-watch on Duval Street. Note that it isn’t really a kid-friendly area since it’s also the main party street of Key West.

If you are traveling with kids, Duval Street is a fine option for a daytime visit. 

Visit the Ernest Hemingway Home & Museum

One iconic thing to do when in Key West is to visit the Ernest Hemingway Home & Museum.

The home was built in the Spanish colonial style in 1851, and was a real fixer-upper when the Hemingways bought it. 

Here, you can learn more about the legendary author and his life while strolling along the beautiful gardens, seeing his Keys home, and even going to the on-site shop to purchase some souvenirs.

Ernest Hemingway Home
Ernest Hemingway Home

Today, you can visit and tour the home and even see descendants of Hemingway’s 6-toed pet cat on the museum grounds. 

No reservations are needed in advance if you’d like to take a 30-minute guided tour, and you can walk in anytime daily between 9am-5pm.

Address: 907 Whitehead St, Key West, FL 33040

Explore the Lighthouse and Keepers Quarters Museum

Across the street from the Hemingway Home and Museum is another museum worthy of a visit.

The Florida lighthouse opened in 1848 and its first keeper was a woman, which was unheard of at the time. 

Lighthouse on Key West
Lighthouse on Key West

Today, you can visit this small museum and learn about the maritime history of the city. You can also climb the 88 steps up to the top to take in picturesque, panoramic views.

The museum is open daily from 10am-5pm, with final admission at 4:30pm. 

Address: 938 Whitehead St, Key West, FL 33040

Join the Sunset Celebration in Mallory Square

End your first day in Key West with a can’t-miss activity — participate in the city’s nightly sunset celebration in Mallory Square.

This arts festival draws in tourists and locals alike to enjoy street performances, food carts, and the stunning sun setting into the Gulf of Mexico. 

It’s essentially a large neighborhood block party and it takes place every night beginning approximately 2 hours before sunset. It’s the perfect cap for your first day in town.

Mallory Square at dusk
Mallory Square at dusk

If you plan to attend (which you absolutely should), have some cash on hand for food carts and to tip the street performers. 

Contributing in these ways is a great way to help keep the local arts scene alive, and presents an opportunity to be a responsible, supportive tourist. 

Day 2 in Key West 

Snap a Photo at the Southernmost Point of USA

Begin day 2 with a visit to the Southernmost Point of the Continental USA!

You won’t need long here, just long enough to get in line and have a friendly fellow tourist snap your photo with the buoy marking the point.

The concrete buoy stands at a height of 12 feet and was made to be able to withstand strong hurricane winds.

Southernmost Point of USA
Southernmost Point of USA

This is a great way to commemorate your weekend trip. 

Address: 1400 Whitehead St, Key West, FL 33040

Relax at Fort Zachary Taylor Historic Beach

Afterwards, spend your day at the beach. One of the calmest, most beautiful beaches to visit is Fort Zachary Taylor.

While you do have to pay a small entrance fee, it’s the perfect place to lounge around in the sun for a few hours.

At the beach, you will have the opportunity to participate in a variety of beachside activities, such as swimming, snorkeling, fishing, and paddling.

You can even enjoy a nice picnic along the beach while basking in the sun and taking in the beautiful views.

Fort Zachary Taylor Historic Beach
Fort Zachary Taylor Historic Beach

If you like, you can also visit Fort Zachary and learn about its role in the Civil War.

Fort Zachary is significant not only due to its location at the southernmost point in the continental United States, but also because it is home to the largest collection of Civil War armaments.

Learn a Bit at San Carlos Institute 

Founded by Cuban exiles in 1871, the San Carlos Institute is a library, museum, art gallery, theater, and school all in one.

It’s a beautiful building and a unique place to visit in Key West, where you can learn a bit about Cuba’s independence movement.

The museum is home to a variety of permanent and temporary exhibitions about Cuban culture and heritage.

Some of the permanent exhibits include The Life and Works of José Martí, The Pichs Collection, and Cuba’s Commercial Aviation History. Be sure to check out the website for more information on temporary exhibits during the time of your visit.

San Carlos Institute - Daniela Migliorisi - Shutterstock
San Carlos Institute – Daniela Migliorisi – Shutterstock

Visiting hours are Thursday through Sunday from noon to 6pm and admission is free. 

Address: 516 Duval St, Key West, FL 33040

Unwind With an Evening Boat Cruise 

End day 2 with another sunset viewing, this time aboard a boat cruise. It is something you can do in the winter or summer!

It’s the perfect option whether you want to go as a couple, with friends, alone, or with your family. 

You can choose from options that include a dinner with champagne for two, as well as private sightseeing tours of some of Key West’s most notable landmarks from the ocean.

Glass bottom boat in Keys - Chuck Wagner - Shutterstock
Glass bottom boat in Keys – Chuck Wagner – Shutterstock

Key West offers several different boat cruises and most serve food and drink on board. It makes for a wonderful evening and a way to say farewell to this special island city. 

Where to Eat During Your Trip 

There are more than 400 restaurants in Key West, so there’s no shortage of great food to be had.

Key West is best known for Key Lime Pie, of course. Another must-eat when you’re in Key West are conch fritters.

Key lime pie is a must in Key West
Key lime pie is a must in Key West

You’re likely to find both served at many different establishments across the town, so be sure to order as often as you like and compare to find the ones you like best. 

You won’t have much trouble finding a great meal in Key West, and here are some options to add to your weekend in Key West itinerary.

Blue Heaven

Blue Heaven is an authentic breakfast, lunch, and dinner restaurant with a chill atmosphere and delicious food.

The outdoor seating is also the perfect place for some chicken-watching. Enjoy Floridian-Caribbean food and live music at Blue Heaven.

Blue Heaven - Fotoluminate LLC - Shutterstock
Blue Heaven – Fotoluminate LLC – Shutterstock

Be sure to go early for a seat at breakfast and lunch, or prepare to wait. Limited reservations are available here for dinner, but they also accept walk-ins. 

Address: 729 Thomas St, Naval Air Station Key West, FL 33040


For a beachfront fine dining experience, head to Latitudes.

It’s located on a private island (Sunset Key) and part of the Sunset Key Cottages.

You’ll arrive in style, by boat which departs at your ‘reservation’ time. Latitudes is popular, so make your reservations as far in advance as possible. 

Here, you can enjoy fresh seafood, tropical fruits, exquisite wines, and so much more as part of the fine dining experience.

Address: 245 Front St, Key West, FL 33040

Kermit’s Key Lime Shoppe 

There are several different places to get Key Lime Pie in Key West.

One to add to your list for sure is Kermit’s Key Lime Shoppe. It’s part cafe, part bakery, and part shop complete with a tranquil koi pond out back.

Kermit's - LMspencer - Shutterstock.com
Kermit’s – LMspencer – Shutterstock.com

In addition to Key Lime Pie, you can visit for breakfast or Cuban sandwiches at lunch.

This is also the perfect place to buy gifts and souvenirs, choosing from a wide array of key lime-themed gifts. 

Address: 200 Elizabeth St, Key West, FL 33040

Seaside Cafe at the Mansion

Reviewers rave about the lobster pizza and street corn pizza at Seaside Cafe at the Mansion.

Located near the Southernmost Point Buoy, it’s the perfect place to stop for a bite before or after you snap your photo there.

In addition, be sure to enjoy customer favorites such as the Mansion Mojitos, wood-fired pizzas, and Honey-Butter lobster biscuits, all made with fresh ingredients on-site.

Plus, you’ll enjoy the ocean views at this outdoor cafe. 

Address: 1400 Duval St, Key West, FL 33040

Key West First Legal Rum Distillery 

Less of a food and more of a beverage recommendation, the Key West First Legal Rum Distillery offers free 15-minute tours throughout the week.

The tours run every 30 minutes from 12 PM to 5 PM every day.

You definitely must enjoy some rum in Key West
You definitely must enjoy some rum in Key West

On Fridays and Saturdays, they also teach a mojito class so you can learn how to make an excellent cocktail of your own. 

You can also purchase the rums online if you wish to take a memory home with you!

Address: 105 Simonton St, Key West, FL 33040

Garbo’s Grill 

For a small brush with fame, visit Garbo’s Grill. Garbo’s Grill was featured on Diners, Drive-ins, and Dives when Guy Fieri visited the food truck.

Try the Korean barbecue tacos, kimchi hot dogs, and more. The menu also features favorites such as tacos, burritos, poke bowls, lobster bowls, burgers, and fabulous Key West desserts.

All meals are prepared with the freshest ingredients, and the menu changes from season to season to ensure that everything is fresh.

The grill is open every day from 11 AM to midnight.

Address: 409 Caroline St, Key West, FL 33040

More Than 2 Days in Key West? 

Planning to spend more than a weekend in Key West? If you have 3 days in Key West or more, here are some additional suggestions for things to do.

Catch a Flick at Tropic Cinema

This retro theater plays both mainstream and indie films, as well as plays host to a variety of cultural events and lectures.

Tickets and snacks at the Tropic Cinema are reasonably priced and the onsite cafe also serves beer and wine.

Tropic Cinema - Danita Delimont - Shutterstock
Tropic Cinema – Danita Delimont – Shutterstock

The small theater is volunteer-run and even offers memberships for those interested. Don’t miss out on the popcorn toppings bar.

Be sure to check out the website to see what movies and events the theater will host at the time of your visit.

Address: 416 Eaton St, Key West, FL 33040

Take a Day Trip to Dry Tortugas National Park

Located 70 miles away from Key West by boat is Dry Tortugas National Park, one of the least-visited national parks in the US.

If you’re spending extended time in the area, dedicate time to this day trip from Key West!

The park is 100 square miles and mostly covered by water, although it is home to seven islands.

Dry Tortugas National Park
Dry Tortugas National Park

You can snorkel, swim, or simply sit out under the sun for a relaxing mini-trip within a trip.  

While there, be sure to check out the renowned Fort Jefferson, as well as the stunning coral reefs and marine life.

If you want to plan a trip to Dry Tortugas, be sure to have sunscreen, a bathing suit, change of clothes, towels, and a National Park Pass. Depending on how you book the boat ride, you will also have access to free snorkeling equipment.

Nancy Forrester’s Secret Garden 

A unique and fun thing to do in Key West, especially with kids, is visiting Nancy Forrester’s Secret Garden.

Here, you can play with colorful parrots! The parrots were orphaned and then rescued by Nancy over the last 35 years.

It is the smallest parrot sanctuary in the USA and home to eight species of macaws, along with two hybrid breeds. The sanctuary’s main mission is to put an end to parrot abuse.

Support the conservancy and delight in the colorful, beautiful birds when you visit this unique gem in Key West. 

The garden is open from 10 AM to 3 PM every day. Tickets are $10 for adults and $5 for children between 5 and 11 years old. 

Address: 518 Elizabeth St, Key West, FL 33040

Key West Butterfly and Nature Conservatory 

Immerse yourself in the colorful, fluttering wings of hundreds of butterflies at the Key West Butterfly and Nature Conservatory.

De-stress in this tropical sanctuary, which offers a magical experience as visitors are surrounded by colorful plants, birds, and butterflies.

Key West Butterfly and Nature Sanctuary
Key West Butterfly and Nature Conservatory

This attraction was voted one of the best in Key West and one of the best places to bring kids to.

When you arrive, you’ll watch a 15-minute introductory video about the life cycle of butterflies.

Then, you’ll be able to walk through the glass-enclosed habitat to explore more than 50 species of butterflies, as well as birds and even flamingoes!

They even have an event space that is rented out for weddings. If you have time while in Key West, consider adding this experience to your itinerary. 

The conservatory is open every day from 9 AM to 4:30 PM. Ticket prices vary based on the package deal you choose.

Address: 1316 Duval St, Key West, FL 33040

Where to Stay in Key West

Looking for a few great options for where to stay in Key West? Here are some of our top picks – covering all budgets!

  1. Opal Key Resort & Marina (Luxury)
  2. Silver Palms Inn (Mid-range)
  3. Southwinds Motel (Budget)

There you have it, a complete weekend itinerary for Key West! What recommendations would you add to this guide? 

Let us know your tips and suggestions for a weekend in Key West in the comments.

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