- Blog -

Best Things to Do in Key West: First-Time Visitor Guide

The best things to do in Key West go far beyond Duval Street, sunset bars, and key lime pie, although obviously those things are not exactly a problem.

For a first-time trip, Key West is best planned as a mix of historic sites, waterfront areas, beaches, food, sunset experiences, and a few quirky stops that make the island feel different from the rest of Florida.

What stood out to me most was how walkable Key West can be if you stay near Old Town, how much history is packed into a small area, and how many activities can be done without needing a full day. Some stops are quick photo stops. Some are longer tours. Some are mainly about eating, which is a very legitimate travel category in my opinion.

This guide includes the Key West attractions and experiences I would prioritize for a first visit, along with what surprised me, what I would plan around, and what I think is actually worth your time.

Best things to do in Key West on a Dry Tortugas National Park day trip

Best Things to Do in Key West for First-Time Visitors

These are the Key West attractions and experiences I would keep on a first-time itinerary, especially if you want a good mix of history, water views, food, and classic island stops.

Visit Fort East Martello Museum and Robert the Doll

If you are interested in local history, ghost stories, or slightly strange attractions, Fort East Martello Museum is one of the most unique places to visit in Key West.

The museum houses Robert the Doll, one of the most famous haunted dolls in the United States. It also has exhibits covering Key West history, military heritage, and local art.

This is a good option if you want something beyond the usual Old Town stops. It is especially helpful if you are visiting Key West for several days and want to see more than the same main attractions everyone talks about.

It is weird, historic, and very Key West.

Best things to do in Key West including the Southernmost Point buoy

Visit the Southernmost Point

The Southernmost Point is one of the most famous landmarks in Key West and one of the first places many visitors stop.

It is located on the southern end of the island and is a quick stop in theory, but the line can be longer than you might expect. When I visited, it took about 30 minutes just to get a photo with the buoy.

If getting a picture is important to you, go early in the morning before the crowds build. If you do not care about being in the photo, you can still walk by, see it, and move on pretty quickly.

This is not an activity that needs a huge amount of time, but it is a classic first-time Key West stop people usually want to see at least once.

Best things to do in Key West on Duval Street during a first-time visit

Spend Time on Duval Street

Duval Street is the center of Key West tourism.

This is where you will find shops, restaurants, bars, live music, souvenir stores, late-night crowds, and plenty of people-watching. Even if you are not planning to spend much money, I think it is useful to walk the length of Duval Street at least once so you understand the layout of the island a little better.

During the day, Duval feels more casual and easy to walk. At night, especially after 9:00 PM on a weekend, it gets much busier and more bar-focused.

I would not plan your entire Key West trip around Duval Street, but I also would not skip it on a first visit. It is a big part of the island’s personality, even if your favorite moments end up being somewhere quieter.

If you are planning to be out after dark, my Things to Do in Key West at Night guide will help you decide what actually makes sense once the daytime attractions close.

Best things to do in Key West at Mallory Square sunset

Watch Sunset at Mallory Square

Watching the sunset at Mallory Square is one of the most iconic things to do in Key West.

Each evening, street performers, artists, musicians, vendors, and visitors gather along the waterfront to watch the sun set over the Gulf of Mexico. It is touristy, but it is also a Key West tradition that makes sense once you are there.

I would arrive about an hour before sunset if you want time to walk around, see the performers, find a spot, and not feel rushed.

This is not the quiet, peaceful sunset option. It is crowded and very much a production. But for a first-time visitor, I do think Mallory Square is worth experiencing once because it captures the busy, quirky, waterfront side of Key West.

Best things to do in Key West including a sunset sail on the water

Take a Sunset Sail

If you want a classic Key West experience, a sunset sail should be high on your list.

You can choose from catamarans, schooners, and more polished sailing experiences, depending on your budget and travel style. Being out on the water at sunset gives you a completely different view of Key West than watching from land.

This is also a good option if you want sunset without standing in a crowd at Mallory Square.

I would book this in advance, especially if you are visiting on a weekend, holiday, or during a busier travel season. Sunset is one of the most popular times to be on the water in Key West, for obvious reasons.

You can compare Key West sunset cruises and boat tours through Viator or Get Your Guide. If you would rather stay on land, my Best Sunset Dinner Spots in Key West (And the Best Places to Watch Sunset) guide will help with that decision too.

Best things to do in Key West at the Hemingway House with tropical landscaping

Visit the Hemingway House

The Hemingway House is one of the most famous attractions in Key West, even if you are not a huge history person.

You can tour the historic home where Ernest Hemingway lived and wrote, learn more about his time on the island, and see the famous six-toed cats that still live on the property.

This is a good activity to pair with other Old Town stops because it does not require leaving the main historic area. It is also a nice break from walking around in the direct sun because parts of the tour move through the house and shaded areas.

For a first-time Key West itinerary, this is one of the main historic sites I would keep on the list. I also have a full Visiting the Hemingway House in Key West guide if you want more details before you go.

Visit the Harry S. Truman Little White House

The Harry S. Truman Little White House is another worthwhile historic stop in Key West.

The home served as President Truman’s winter White House and is one of the most significant historic sites on the island. Visitors can tour the home, learn about Truman’s time in Key West, and see where important presidential decisions were made.

The guided tours do a good job of making the history feel more interesting, even if you are not usually someone who seeks out historic homes on vacation.

If you are interested in Key West history, this is one of the most worthwhile tours on the island.

Best things to do in Key West near the Historic Seaport waterfront

Explore the Historic Seaport

The Historic Seaport was one of my favorite areas to wander in Key West.

A lot of visitors stop for a drink or pass through quickly, but I think this area is worth spending more time in. You can watch fishing boats, charter boats, sunset cruises, and everyday waterfront activity, which gives you a different view of Key West than Duval Street.

It is still busy, but it feels more connected to the water and the working side of the island.

This is also an easy area to combine with lunch, drinks, a walk along the marina, or a sunset cruise departure. If you like waterfront views without committing to a full beach day, the Historic Seaport is a great place to add to your itinerary.

Save this for later on Pinterest so you don’t forget it.

Best things to do in Key West at First Legal Rum Distillery

Take a Tour of First Legal Rum Distillery

One of the most underrated attractions in Key West is First Legal Rum Distillery.

The distillery offers free tours every hour, and it was actually really interesting. If you are looking for something to do in Key West that is indoors, quick, and different from the usual beach-and-bar itinerary, this is a good stop.

The tour explains the distilling process and how different barrel-aging methods affect the final flavor. I thought it was fascinating to see how dramatically the barrel-aging process changes the flavor of each rum even though they are all produced by the same distillery.

Their Raw & Unfiltered Rum is aged in American oak barrels cured with Key West saltwater and develops notes of dark chocolate, vanilla, maple, and a slightly salty finish.

Their best-selling Bad Bitch Rum is aged for seven years in French oak barrels that previously held pinot noir wine, which gives it softer caramel notes and added complexity from the wine-soaked wood.

The lighter Bad Bitch Blonde Rum is aged in French Chardonnay barrels and develops buttery, toasted flavors often compared to macadamia nuts, almonds, cashews, and other roasted nuts.

Our tour guide told us her favorite was the Bad Bitch Rum, which was one of the more unique spirits we learned about during the tour.

We also tried the piña colada, and it was incredibly smooth. You could barely taste the alcohol, even though they told us it was surprisingly strong. They joked that if you order a small, you will definitely feel it.

Even if you are not a huge rum person, this is a fun and easy Key West attraction to add between bigger plans.

Wander Through West Martello Tower and the Key West Garden Club

West Martello Tower and the Key West Garden Club feel completely different from busy Duval Street.

The garden is set inside a historic Civil War-era fort and is filled with tropical plants, orchids, winding pathways, and quiet corners. It was one of the calmest places I found anywhere in Key West.

If you need a break from crowds, shops, bars, and constant activity, this is a good place to take a breather for a little while.

It is also a nice stop to pair with Higgs Beach since they are located close to each other.

Best things to do in Key West at Key West Cemetery

Walk Through the Key West Cemetery

I know recommending a cemetery sounds strange, but the Key West Cemetery was one of the most interesting historical stops on the island.

The cemetery is filled with unusual graves, local history, famous epitaphs, and stories that help explain Key West beyond the beaches and bars.

This is not necessarily a stop everyone will want to prioritize, but if you like local history, old cemeteries, unusual details, or self-guided wandering, I think it is one of the more interesting things to do in Key West.

Best things to do in Key West Banyan Tree

Find the Shel Silverstein Banyan Tree

Many visitors do not realize that the famous banyan tree connected to Shel Silverstein is located right on Whitehead Street.

This is a quick stop, not a full activity, but it is a fun one for book lovers or anyone interested in the smaller details around Key West.

I would not go far out of your way just for this, but if you are already walking near Whitehead Street, it is an easy thing to add to your route.

Relax at Higgs Beach

If you are visiting Key West with kids, Higgs Beach is one of the better family-friendly beaches on the island.

The beach has a playground, shallow areas, picnic tables, restrooms, and open space, which makes it easier for families than some of the smaller or more limited beach areas.

It is also close to West Martello Tower and the Key West Garden Club, so you can easily pair those stops together.

Key West is not always the easiest Florida beach destination if your main goal is wide, soft sand and resort-style beach days, but Higgs Beach is a practical option if you want beach time with useful amenities nearby.

For beach days in Key West, I would bring good sun protection, a quick-dry towel, and a dry bag if you are carrying your phone, wallet, or camera gear near the water.

Walk Smathers Beach

Smathers Beach is the longest public beach in Key West and one of the best places on the island for a morning walk.

The long stretch of sand makes it a good spot for walking, jogging, or watching the sunrise. If you want a beach that feels more open and spacious, this is one of the better options in Key West.

I would especially consider Smathers Beach in the morning before the day gets too hot. It is less about a hidden beach experience and more about having room to walk, move, and enjoy the water views.

If you are planning to be out walking a lot, I would also bring a lightweight bag like the Nano Bag and a good water bottle. Key West is not the place where I want to realize I forgot water.

Best things to do in Key West while snorkeling in the Florida Keys

Go Snorkeling

Snorkeling is one of the best things to do in Key West if you want to spend time on the water.

Many visitors do not realize the Florida Keys are home to the Florida Reef Tract, the third-largest barrier reef system in the world and the only living coral barrier reef in the continental United States.

If you are serious about snorkeling, Looe Key Reef is consistently ranked among the top snorkeling and diving locations in the Florida Keys because of its healthy coral formations, abundant marine life, and typically excellent visibility.

For most visitors, snorkeling trips from Key West are easiest to book as a half-day boat excursion. If snorkeling is a major priority for your trip, I would plan it earlier in your itinerary instead of saving it for the last day. Weather, wind, and water conditions can affect boat trips, so it is nice to have a little flexibility.

If you prefer having your own gear, a snorkel mask is a good thing to pack, especially if you are picky about fit. I would also bring water shoes for rocky beach areas, boat days, or anywhere you do not fully trust what your feet are about to touch.

Best things to do in Key West Local Shopping

Shop Local at Ashli Tillett Designs

If you happen to be in Key West Thursday through Sunday, look for Ashli Tillett Designs across the street from Blue Heaven.

Ashli Tillett Designs is a local Key West business creating sustainable fashion while teaching sewing and creative skills to students. In addition to her weekend pop-up shop, Ashli hosts sewing classes and private group events throughout the week at locations around Key West.

This is a fun way to support a local artist while finding something unique to take home that is not just another souvenir shop item.

For upcoming pop-up locations, classes, and events, visit AshliTillettDesigns.com before your trip.

Best things to do in Key West near the waterfront

Grab Lunch at Loggerheads Beach Bar

Loggerheads Beach Bar is located at Simonton Beach and is one of the more laid-back waterfront spots in Key West.

This is a good stop if you want casual food, cold drinks, and a beachfront view. They are known for casual food, Cuban sandwiches, affordable beachfront dining, and people often recommend ordering the cheeseburger.

One thing I found interesting is that the owner purchased the property when the beach area was in rough shape and helped transform it into what it is today. She and her best friend from Key West High School created a really solid place to grab lunch with one of the best waterfront views in Key West.

I had the Cuban sandwich here, and this is exactly the type of easy waterfront lunch that makes sense in Key West. Nothing fussy. Just beach, food, and a view.

Best things to do in Key West at Christmas Tree Island

See “Christmas Tree Island”

Across from Simonton Beach is an area locals often refer to as Christmas Tree Island.

It is home to an off-grid community where people have built small structures and use things like solar panels to live independently on the water. The community is constantly changing, but there are often dozens of people living there at any given time.

One resident, known locally as Cliff, is said to cook dinner for the community each night.

From a distance, the island has a surprisingly charming look, especially with the small structures scattered throughout the mangroves.

The island also hosts occasional concerts and community gatherings. Twice a year, local high school students kayak over to help clean up trash around the island and surrounding waters. Some students even camp there during these cleanup events, which makes it a really unique part of Key West’s local culture.

This is not a formal attraction, but it is a small local detail that makes Key West more interesting once you know what you are looking at.

Best things to do in Key West at Food at Key Lime Pie

Eat Your Way Through Key West

One of my favorite things to do in Key West was simply eat.

Food deserves its own category here because Key West has some genuinely memorable restaurants, casual spots, bakeries, coffee shops, seafood stops, and key lime pie situations.

You can build a lot of your itinerary around meals without it feeling like you wasted the day. Grab tacos from Garbo’s Grill, try key lime pie around town, have a waterfront dinner at Hot Tin Roof, splurge on Café Marquesa, or keep things casual with Cuban sandwiches, conch fritters, and beach bar lunches.

Café Marquesa was my favorite dinner of the trip, and the food scene in general was one of the biggest reasons I enjoyed Key West as much as I did. My Best Restaurants in Key West guide goes deeper into the meals I would plan around.

If you are planning your first visit, I would not treat meals as an afterthought. Dinner reservations, breakfast timing, and lunch locations can make the day flow much better, especially if you are walking around Old Town in the heat and suddenly everyone’s mood depends on food immediately.

If you want to combine food with a guided activity, Secret Food Tours is a good option to compare while planning.

Best things to do in Key West on a Dry Tortugas National Park day trip

Take a Day Trip to Dry Tortugas National Park

If you have enough time, Dry Tortugas National Park should be high on your Key West itinerary.

Dry Tortugas was one of the highlights of my entire trip. The combination of history, snorkeling, beaches, and Fort Jefferson makes it one of the most unique national parks in the United States and one of the most memorable experiences in the Florida Keys.

You can visit by ferry or seaplane, and both options require planning ahead. The ferry takes longer but gives you more time on the island and includes a structured day. The seaplane is faster and gives you incredible views from above, but it is more expensive.

This is not something I would try to squeeze into a short Key West trip unless you have enough time. But if you are spending several days in Key West and want one bigger adventure, Dry Tortugas is the day trip I would prioritize.

If Dry Tortugas is on your list, read How to Visit Dry Tortugas National Park: Everything You Need to Know before booking anything.

Best things to do in Key West on Key West Activities

If you are driving through the Florida Keys before or after Key West, I would compare rental car prices through Discover Cars. I would not rent a car just for Old Town, but it can make sense for a longer Florida Keys road trip.

Final Thoughts on the Best Things to Do in Key West

The best things to do in Key West are a mix of classic attractions, local history, waterfront views, food, and slightly unusual stops that make the island feel different from other Florida beach destinations.

For a first-time visitor, I would not skip the big sights like the Southernmost Point, Duval Street, Mallory Square, the Hemingway House, and the Historic Seaport. But I also think Key West gets better when you add in quieter places like the cemetery, West Martello Tower, local shops, casual waterfront lunches, and a few details you would not notice if you only stayed on the main tourist path.

I would absolutely go back to Key West, but I would plan it the same way again: walk a lot, eat well, book the important things ahead, and leave room for the small stops that make the trip feel more personal.

Planning Resources for Key West

If you end up booking anything for your trip, using my affiliate links helps support my blog at no extra cost to you. I spend a lot of time researching and writing these guides, so I really appreciate the support.

Travel Planning

For flights, compare prices on Skyscanner. If you are staying several days and want a full plan, read my Key West 3 Day Itinerary for First Time Visitors.

For first-time planning questions, my Key West FAQs: 25 Questions First-Time Visitors Always Ask covers the practical things people usually wonder before booking.

Hotels + Where to Stay

For hotels, compare options on Booking.com and Hotels.com. Staying near Old Town makes the main things to do in Key West much easier to reach without a car.

Tours + Activities

For tours, sunset cruises, snorkeling trips, and day trips, compare options through Viator and Get Your Guide.

What to Pack

For beach days, snorkeling, and boat trips, I would pack a snorkel mask, dry bag, quick-dry towel, water shoes, and face sunscreen.

For a more detailed packing list, see my What to Pack for Key West in May (What I Actually Used and What I Didn't).

I planned to spend maybe an hour at a cheese farm outside Amsterdam and left several hours later with an engraved clog birdhouse, way too much cheese, and a strong opinion on 1.5-year aged Gouda.

Clara Maria Cheese Farm near Amstelveen does a free cheese and clog demonstration that was genuinely one of my favorite things from the entire Netherlands trip. The farm is over 160 years old, the people running it are wonderful, and the tour guide Delo was hilarious in a way I was not prepared for.

A few things that surprised me: Dutch cheese gets its golden color naturally from beta carotene in cow’s milk. The entire cheese-making process is still done largely by hand pressed, flipped, salt-soaked, and hand-waxed before aging even starts. And Americans (myself included) have been pronouncing Gouda wrong our whole lives. It’s closer to “HOW-da.” I understand this now and will still panic and say it wrong anyway.

We tried about ten cheeses ranging from fresh to 20 years aged. The 20-year was aggressively pungent, think concentrated smelly feet... but the 1.5-year was perfect. We also met the cows. Honestly the whole thing was a lot more personal than I expected from a tourist stop.

Full review with what to know before you go, link in bio. 🧀
The tulip fields in the Netherlands look exactly like the photos, except the photos don’t capture how massive the color blocks actually are stretching across the countryside. Or the windmills. Or the sheep randomly standing in the middle of everything like they don’t know they’re in the most photogenic country on earth.

The honest caveat: tulip season moves fast, the fields rotate every year, and peak bloom is not a guarantee, it depends on the weather, the harvest schedule, and a little bit of luck. But that’s also part of what makes it feel less like a tourist attraction and more like something you actually found.

Full driving route with towns, parking tips, and what to expect | linked in bio. 🌷

#netherlands #travelling #tulipfields #exploreeurope
Amsterdam has a way of making you feel like you need to see everything, and then rewarding you most when you slow down anyway. The museums and canal cruises are worth it, but so is just wandering neighborhoods, eating whatever looks good, and sitting along the canals with a grilled cheese and nowhere to be.

First-time visitor guide is on the blog. Link in bio. 🌷

#travelling #travel #amsterdam #visitamsterdam #traveleurope

Follow Me @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.

My Exact Packing List

I use this packing list for every trip — grab it and make packing way easier.

Embark. Explore. Eat.

Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.

© Travel with Wendy
Site Credit // SouthMade

The Exact Packing List I Use Every Trip

Insider travel system from someone who travels constantly.