The Perfect Weekend in Key West - 3 Day Itinerary

If you’re planning a memorable weekend in Key West, you’re in the right place! In this guide, guest author Polly Clover shares the ultimate 3-day Key West itinerary for a fun-filled weekend alongside all of her top tips for visiting.

Key West, the southernmost point in the United States, is one of Florida’s most lively and beautiful vacation destinations. In fact, if you ask me, no Florida Itinerary is complete without visiting.

Known for its iconic watersports, historical landmarks, energetic nightlife scene, and picture-perfect scenery, Key West has it all.

It’s an excellent place to visit solo or with family or friends. From fun and laid-back beaches to delicious dining experiences and cool bars, there’s something for almost every traveller in Key West.

Below, I’ve compiled a detailed itinerary for the ultimate long weekend in Key West. I’ll also share some helpful tips and advice for making the best of your experience.

So with all that said, let’s get to it and check out how to spend a fantastic island getaway in Key West!

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Is 3 Days in Key West FL enough?

Three days is absolutely enough time to spend in Key West. The island is small and offers the perfect 3-day vacation experience.

With that said, there’s so much to enjoy that you can easily extend your trip and not get bored.

The 3-day Key West itinerary below takes you on a journey to experience the best of this fantastic island – nature, history, scenery, and food.

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Where to Stay for a Key West Weekend Getaway

Although Key West is a small island, running 4 miles long and about 2 miles wide, there are several distinct areas to stay.

The island comprises several small neighbourhoods, each unique in its own way.

I personally recommend staying in Old Town, also referred to as the Historic District or Downtown. This is where the popular Duval Street is, complete with shops and restaurants.

It’s also where the Historical Seaport is, which offers more entertainment and gorgeous views. Accommodations in Old Town are within walking distance to many of Key West’s best activities.

Beachside is also a great area to stay. Located along the island’s southern shore, it’s close to many of the popular beaches.

Beachside is the perfect spot to stay if you prefer a beach-only vacation away from the downtown area yet still close enough to get to and from there easily. You’ll find several hotels and vacation rentals here.

There are a few other residential neighbourhoods that are also lovely if you prefer staying outside of the city centre.

The following areas have a couple of hotels and/or vacation rentals: Truman Annex, Bahama Village, and The Meadows. These neighbourhoods are all located just outside of Old Town.

Key West Florida Hotels & Accommodation

Best Family Friendly Hotel in Key West: Margaritaville Beach House. If you’re spending a weekend in Key West with your family, the Margaritaville Beach House is an excellent place to stay. It offers a convenient location near the beach and other popular attractions. The hotel itself offers an on-site restaurant, an outdoor swimming pool, a fitness centre, and a bar.

Best Budget Hotel in Key West: Nyah. Nyah is a bed and breakfast that welcomes adults only. Guests appreciate a complimentary continental breakfast, three outdoor pools, and a hot tub at Nyah. It’s conveniently located in Old Town, within walking and a short driving distance to many fun things to do.

Best Mid-Range Hotel in Key West: The Cabana Inn. The Cabana Inn is another adult-only hotel in Key West. It’s the perfect place for travellers who want to enjoy relaxing at their accommodation and exploring Key West. The Cabana Inn has a swimming pool, hot tub, a continental breakfast, and a daily happy hour with cheese and wine. It’s also located just a minute’s walk from the historic Duval Street.

Best Luxury Hotel in Key West: Ocean Key Resort & Spa. If you’re planning a luxury Key West weekend getaway, the Ocean Key Resort & Spa is ideal. This stunning hotel overlooks the Gulf of Mexico with amazing views from the outdoor pool and private balconies. Guests can enjoy massage therapies, nail treatments, facials, and more at the on-site spa.

You can also check out many other accommodation options in Key West here. Or use the Map below to see all your options:

Booking.com

Tips for a Long Weekend in Key West, FL

With so much to see and do and Key West’s breathtaking scenery, it’s almost impossible not to have an incredible trip. However, the tips below can help you make the best of your Key West weekend getaway.

3 Days in Key West Budget

Your weekend Key West budget will vary depending on your travel experience, but most travellers can plan to spend between $380 and $500 per day. This includes accommodation, transportation, meals, and activities.

Key West is considered a paradise vacation, and with that comes high prices, so it’s easy to splurge. However, there are ways to visit on a budget.

Here are some affordable ways to enjoy 3 days in Key West:

$ – Go during the off-season: June through November.

$ – Book accommodation outside of the city centre.

$ – Enjoy picnics at local parks.

$ – Check out free activities, including a self-guided tour, Key West Wildlife Center, watching the beautiful sunsets, and hanging out on Higgs Beach.

$ – Save on transportation and stay in Old Town, the walkable, lively area of Key West.

Getting Around Key West

One of the best parts about a vacation in Key West is how easy it is to get around. Keep in mind that the island is only 8-square miles, so just about everything is close together.

Popular forms of transportation in Key West include cars, bicycles, and walking. There are also taxis, moped rentals, city buses, pedicabs, and hotel shuttles.

If you’re driving to Key West, it’s easy to get around by car or on foot. There are also local bicycle tours, which offer a fun and convenient experience.

If you’re flying in, I recommend staying in Old Town as this will allow you to walk to most activities. Or, for activities further away, you can use a taxi or your hotel’s shuttle.

Is Key West LGBTQ+ Friendly?

It is! Key West is known for its safe, relaxed, and welcoming vibe. Many travellers, including the LGBTQ+ community, love visiting this carefree Florida island.

The Key West Business Guild is dedicated to encouraging LGBT travel to Key West. They work to promote special events, support gay-owned, gay-managed, and gay-friendly businesses, and strengthen the gay community’s position within the local community.

Be sure to visit Duval Street between Angela and Petronia Streets for a fun time! This neighbourhood is home to some of Florida’s most lively gay bars and clubs.

When to Visit Key West

Key West is a paradise all year long. For affordability, fewer crowds and the best weather, visit in late spring or early summer.

Many snowbirds head to Key West during winter to escape the cold. Because of this, you’ll find more crowds and higher prices.

That said, winter offers amazing weather in Key West – sunny days with temperatures in the 70s.

From late spring through the end of summer, you’ll find that snowbirds have headed home, and spring breakers and summer vacationers are visiting Key West. Naturally, this brings a fun atmosphere but again higher prices.

Fall in Key West brings the rainy season, so you’ll find fewer crowds and lower costs. Although, the weather during this time is hit and miss.

If you can plan a last-minute trip depending on predicted weather, fall can be a great time to enjoy a long weekend in Key West for pleasant weather and fewer people.

Key West Tours

Sometimes, the best way to experience a new place is to take a guided tour.

Not only does it take all the stress out of planning, but you get to learn a lot more about the area than you would when exploring alone.

We always use Get Your Guide when we book tours. They have a diverse and unique selection of tours in locations all over the world, including Key West. Check them out!

Save Time and Book a Tour

For a more local experience, we recommend checking out the guided tours on Get Your Guide:

Best Things to See and Do on a Long Weekend in Key West

This weekend in Key West itinerary includes a wide range of experiences. There’s a fun mix of things to see and do, from popular attractions and hidden gems to relaxing activities and exciting adventures.

If you’re looking for an overview of what to do during your 3 days in Key West, here you go or keep reading for your detailed itinerary:

Hang out on the beach: Smathers Beach, Rest Beach, Higgs Memorial Beach, and Zachary Taylor State Park.
Go on a sunset boat cruise.
Hop on a ferry for a tour of Dry Tortugas National Park.
Bar hop on Duval Street.
Watch a live show at the Key West Theater.
Enjoy scenery, food, and drinks at Sunset Pier.
Explore the city (Old Town) and discover delicious food, historical sites, beautiful views, and a nightlife scene.

3-Day in Key West Weekend Itinerary

A long weekend in Key West is the perfect opportunity to enjoy nature, relax, and have a little adventure.

It’s easy for just about anyone to enjoy the itinerary below, but it can also be easily adjusted if you want to include anything else or switch some things around.

Here’s a quick rundown for each day in Key West:

Day 1: Hang out on the beach and take a sunset boat cruise.

Day 2: Visit Dry Tortugas National Park.

Day 3: Explore the city – shopping, historical sites, dining, and more.

Weekend in Key West, FL: Day 1

Hang out on the beach and take a sunset boat cruise.

During the day – A day at the beach is the perfect way to start your long weekend in Key West. There are so many gorgeous beaches to choose from, and you really can’t go wrong with any of them.

I would personally pick one beach and settle in for the day. You can also beach hop and visit two or three if you want to squeeze in a couple of beaches.

Here are a few of the best beaches in Key West:

Smathers Beach – offers a picture-perfect sunrise if you’re up for an early morning. It’s also one of the biggest and most popular beaches in Key West.

Smathers Beach is the perfect spot for families or beachgoers who enjoy activities. There are watersport rentals, including kayaks and jet skis. Beach volleyball is also popular here!

There’s plenty of sand space for relaxing and getting a tan, too, if that’s your activity of choice.

If you’re going to go with just one beach for the day, this one’s a great option. There are tons of amenities and food trucks, making it a comfortable spot to spend the day.

Rest Beach – If you prefer to kick back and appreciate a low-key beach day, Rest Beach is the place to go. It’s located at C.B. Harvey Park and boasts soft sand perfect for laying out and seacombing.

You can also find picnic tables at the park and lots of shade.

Higgs Memorial Beach – Just next to Rest Beach is Higgs Memorial Beach. This beautiful beach is filled with amenities and offers plenty of space for visitors to spread out.

The snorkelling is great here, and it’s an excellent beach for relaxing and enjoying the scenery.

You can also find beach rentals if you want to participate in watersports.

Zachary Taylor State Park – The best beach for those looking to get off the beaten path and enjoy nature. It’s home to a pristine beach with breathtaking clear waters that are perfect for snorkelling.

It’s also an incredible place to take underwater photos with a go pro!

For the Evening: A Sunset Cruise – Finish your beach day with a sunset cruise and enjoy panoramic views of the Gulf of Mexico. From a live music sunset sail to a buffet boat dinner with an open bar, there are many options for enjoying a Key West sunset from the water.

Weekend in Key West, FL: Day 2

Visit Dry Tortugas National Park.

During the day – Just west of Key West is Dry Tortugas National Park. While it’s not directly in Key West, I recommend a day trip to this stunning 100-square-mile park.

This natural wonder is made up of 7 small islands and offers endless outdoor attractions and activities, including historical sites, snorkelling opportunities, and secluded beaches.

To visit Dry Tortugas National Park, you can take the Yankee Freedom Ferry from Key West first thing in the morning, with a check-in time at 7 AM. The ferry arrives back in Key West at 5:15 PM.

The ferry trip and tour will take you on a full-day adventure, with a tour of the fascinating Fort Jefferson and a snorkel adventure in some of the world’s most pristine waters.

The cost for this visit to Dry Tortugas National Park is $190. This includes activities and meals. There are discounts for children, students, active military, and seniors.

For the evening – If you’re looking for nighttime activities when you arrive back in Key West, here are some noteworthy things to do in the evening:

Sunset Pier: a laid-back seafood spot on the water with drinks and live music.
Key West Theater: an award-winning performing art theatre.
Duval Street: a lively area in Key West with a vibrant nightlife scene.

Weekend in Key West, FL: Day 3

Explore the city – shopping, historical sites, dining, and more.

While Key West is mostly about the ocean and gorgeous views, the city itself is also well worth exploring.

In fact, the Old Town area has enough to offer that it’s easy to spend the entire final day of your weekend in Key West here.

Old Town is walkable, and bicycle rentals are also available.

During the day – Start the morning at Key West Historic Seaport, where you can discover picturesque views and charming cafes. The Cuban Coffee Queen has excellent coffee and serves breakfast all day.

After exploring Key West Historic Seaport, you can make your way to Duval Street. This is the centre of Old Town, or downtown, and Key West’s most lively area.

I suggest spending your entire day here. There are countless shops, restaurants, bars, and historical sites worth visiting, along with nighttime activities.

For a start on what to see and do around Duval Street, check out these places:

Truman Little White House: a museum that was once President Truman’s winter home; entry is $22.20 with a discount for children.
Ernest Hemingway Home and Museum: the stunning historical home of the famous writer Ernest Hemingway; entry is $17 with a discount for children.
The Tennessee Williams Museum: a fascinating museum for the literary playwright who once called Key West home Tennesee Williams; entry is $7 with discounts for children, students, and active military.
The Key West Butterfly and Nature Conservatory: a charming butterfly park and garden; entry is $15 with discounts for children, active military, and seniors.
Mallory Square: a waterfront area that boasts terrific sunset views, delicious restaurants, and a vibrant nightlife scene.

Tip – A free shuttle takes you around the city if you stay at the Dunhill Hotel.

Other Key West Activities

While the 3-day Key West itinerary above offers a top-notch experience filled with the best local activities, here are some additional noteworthy things to do:

Join a local bicycle tour.
Go on a dolphin tour.
Dive the Vandenberg, a massive artificial reef and iconic wreck.
Visit the Key West Lighthouse.
Take a picture in front of the famous anchored concrete buoy, “Southernmost Point of the Continental U.S.A.”

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Where to Eat and Drink in Key West Florida

Foodies are in luck on a weekend trip to Key West. There are endless places to enjoy delicious food and drinks during your weekend getaway to the beach.

The restaurants and bars below are all located in the popular Old Town area, Key West’s city centre.

Breakfast: the breakfast club, too ($$)
Seafood: Lagerheads Beach Bar & Watersports ($)
Pub & bar food: Lucy’s Retired Surfers Bar & Restaurant ($$)
Caribbean-American: Louie’s Backyard ($$$)
Tapas: Santiago’s Bodega ($$)
Cocktail bar: General Horseplay ($$)
Dessert: Better Than Sex – A Dessert Restaurant ($$)

Enjoy Your Long Weekend in Key West!

I hope this 3-day weekend in Key West itinerary has you excited for an unforgettable vacation to this beachside paradise!

If you’ve visited Key West and have something to add to the list, feel free to share in the comments below. We love to hear from you!

Stay adventurous and Happy travels.

Planning a trip along the East Coast? Check out our East Coast USA series to help with inspiration.

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