8 Reasons To Love Whitehead Street

Experience the Wonders of Whitehead Steet

We all know that Duval Street in Key West gets all the fame, and deservedly so.  But neighboring Whitehead Street makes a solid case for one of the best streets on the island. Here are eight reasons to take a stroll down this captivating lane:

1. Southernmost Point Buoy

Start here, at the must-see marker.  No trip to Key West is complete without a photo at this famous monument! Stop and snap a selfie to prove to your friends you were most definitely here in the Southernmost city. 

2. The Lighthouse Museum

Continue northwest to the Lighthouse Museum at 938 Whitehead Street and climb the 88 steps up, up, UP! Get a pelican’s eye view of historic Old Town, plus learn all about this fascinating landmark, that opened with a woman Light Keeper in 1848 (unheard of at the time.)

3. Ernest Hemingway Home and Museum

Directly across the street from the lighthouse is the home and museum of Key West’s most famous former resident. The story goes that Mr. Hemingway intentionally bought a home close to the lighthouse so that no matter how much rum he drank at Sloppy Joe’s, he could always find his way home!

4. Green Parrot Bar & The Courthouse Deli

Time for a break after those museum tours! Duck into this famous Key West dive bar for a root beer barrel and outstanding live music, then head across the street for a thick Cuban Mix sandwich from the Courthouse Deli.

5. The Kapok and Banyan trees

Stop at the Monroe County Courthouse and gaze in wonder at the majestic Kapok tree.  The Mayans believed that spirits climbed these trees to heaven.  It’s enormous root system and trunk make for a great photo.

Not to be outdone, just down the street from the impressive Kapok tree are some of the most stunning Banyan trees you will ever see.  Known for their aerial prop roots that grow into thick trunks, these Banyan trees are located (fittingly) just in front of the Banyan Resort.

6. Mile Marker Zero

Starting right here and stretching to upper Maine, US 1, known locally as the Overseas Highway, is a 2,369-mile interstate that connects most major cities in the eastern U.S. 

A photograph here is proof that you have made it to the “end of the road” and escaped normal life on the mainland!

7. Audubon House & Gardens

Built in 1840 by Captain John Huling Geiger for his family, this stately home now is a museum dedicated to the work of John James Audubon, a famous painter of birds.

Mr. Audubon spent time at the home and painted some of the birds of Key West while there.

8. Mel Fisher Museum

End your time on Whitehead Street at the museum of Mel Fisher, a famous treasure hunter known for finding the 1622 wreck of the Nuestra Senora de Atocha, worth approximately $450 million dollars, just off the coast of Key West on July 12, 1985.

“Today’s the day!”

Six Tips for a Key West Trip on a Tight Budget

Enjoy Key West without Breaking the Bank

A luxury Key West vacation on a budget? Is that even possible?

With these six pro tips, it’s not only possible-  it’s as easy as Key Lime Pie. 

(Psst- there’s even FREE stuff!)

1.  Travel with a group of friends or family

Gather up a group of your old college buddies, a couple of your favorite co-workers, or consider a destination family reunion in Key West.  A group of about 8 to 10 people is the sweet spot for massive savings. More on this in a minute.

2.  Fly Direct… or Drive

A few airlines are now offering direct flights to Key West from major airports such as Chicago, Newark, Philadelphia, and Dallas.  

Flying direct means skipping the connection in Atlanta or Miami saving you $300- $600 depending on airline rates.  That’s a considerable amount of cash.

Or, if you’ve never driven the Overseas Highway, consider a road trip.  With bright sunshine and endless turquoise water on either side of you as you make your way over 140+ bridges, the journey itself is as dreamy as the destination.

3.  Skip the Hotel

On average, a tiny hotel room in Old Town Key West will cost you about $350-$650 per night in season.

Yikes.  

Consider renting one of our sprawling, luxurious vacation rental homes, like the Duval Square Penthouse.

At first glance, you think “Nah, there’s no way I could afford that.”  Here’s where your group of pals comes in handy!

Rent the Duval Square Penthouse with seven of your friends, and you’ll be paying about $140 per night per person in season.  

Travel in the off-season of August or September and you’ll be spending about $90 per night.  Cha-ching!

Plus, an over-priced, cramped hotel room can’t offer you a fully-equipped kitchen, several private outdoor spaces, laundry facilities, a huge living area with a 70-inch television and four gleaming, spa-like bathrooms.  Duval Square Penthouse has all that and more.

4.  Dine In

When you first arrive on the island, take a quick trip to the grocery store and stock up on supplies, then prepare and eat breakfast in your fully stocked kitchen.  Gather the crew together at the farmhouse dining table and linger over a casual, leisurely lunch.

Saunter back from the Duval Square rooftop pool for a quick snack or a homemade cocktail.

When you aren’t forced to eat and drink at a restaurant for breakfast, lunch, and dinner- like you would at a hotel- the savings stack up quick.

5.  Free Stuff!

All completely free- all totally fun.

6.  Eat Cuban Food

Key West is just 90 miles from the city of Havana, Cuba.  Just for reference- the nearest Walmart is 140 miles away. Yup, Key West is closer to Cuba than it is to a Walmart.

Embracing the Cuban culture of Key West will not only add flavor and authenticity to your trip-  it can also save you big bucks on meals.

Cuban food is delicious and affordable- think juicy rotisserie chicken, spicy pulled pork, savory picadillo, sweet plantains, and the ever-present black beans and rice.  Get hooked on Cafe Con Leche ($2.75) and Cuban Cheese Toast ($3.50)- yummy, cheap, and a local favorite.

Try the Cuban Coffee Queen, Sandy’s Cafe, or El Siboney for some outrageously tasty and inexpensive authentic Cuban fare.

With these six pro tips, your Key West dream vacation is a lot closer than you think.  

A Tropical Holiday on Key West

In other parts of the United States, fall means a large change in the weather. The leaves change color and the temperature drops. Air conditioners get turned off and heaters come back to life. People swap their flip flops and tank tops in for socks and sweaters. The first snowfall is just around the corner…

Key West has a few of these changes though they aren’t as extreme. The temperature doesn’t go down much but the humidity in the air declines.

Our air conditioners get turned down or off and we rarely rely on heaters. Locals never trade in their flip flops or our tank tops; we just pair them with jeans instead of shorts.

The winter holidays are very unique in Key West. Since a good percentage of the locals work in the tourism industry, we stay put during the holidays. A number of people have very tiny kitchens making it difficult to cook a large spread or host a table of guests. Luckily, many restaurants take this stress off our backs and host their own festive meals.

Pirates and Paradise brings swarms of seafaring adventure to the shores of Cayo Hueso. We also make our own festive island traditions. The City of Key West’s Holiday Parade (305-809-3881) on December 7th welcomes Santa and Mrs. Claus as they float down Truman Ave. In mid-December the Schooner Wharf Bar hosts the 23rd annual Schooner Wharf Bar/Cruzan Rums Lighted Boat Parade also known as the Bight before Christmas. Watch lighted boats parade in the Historic Seaport in competition for the best decorated vessel!

Get into the holiday spirit by taking a self-guided tour of beautifully decorated inns and houses. The Holiday Historic Inn Tours take place in the evenings in December. Your ticket includes light appetizers and holiday refreshments; not to mention the many dazzling lights and displays! The Old Island Restoration Foundation hosts their Annual House Tours. The much anticipated tours run once a month December – March. The tour features lovely homes and gardens of 5 private homes.      

The Mermaid and the Alligator house and gardens are decorated every holiday season with thousands of lights.

Key West’s music scene is eventful and exciting; the holidays are no exception. Tune in to a variety of concerts and performances around the city. The Keys Chorale Holiday Concert on December 6th is a musical event you can’t miss. 

Before you know it the New Year will be here. Key West celebrates in a number of different ways on December 31st. Ring in the New Year with Sushi as she drops from a giant red high heel at Bourbon Street Pub (305-296-2388). The Liberty Clipper drops a pirate wench at the Historic Seaport (305-292-3302). Perhaps you’d enjoy Sloppy Joe’s (305-296-2388) conch shell drop! No matter where you choose to indulge you’re sure to enjoy the celebration. Come back year after year and create a holiday tradition you will never forget!

Top 7 Things to Do in Key West in December 2019

Enjoy 7 Unique Holiday Activities on Key West

Escape the winter chill and hop down to Key West for a multitude of magical ways to celebrate the holiday season on the island. The inclusive and warm nature of Key West lends itself to be a perfect setting for getting into a holiday spirit.

Here are some of our favorite festivities this December:

Schooner Wharf Tree Trimming and Toys for Tots and Angels Just 4 Kids Drive

Kick off the holiday season with the locals at  Schooner Wharf Bar… craft your own nautical ornament to add to their tree (and maybe win a prize), enjoy live island music, peruse the craft fair, and bring an unwrapped toy for their toy drive! Trimmers and gifters receive a complimentary holiday libation! 

When:

Sunday, December 1, 2019, 5 pm

Details

Key West Lighted Bike Parade

Whether you want to hop on a bike and join the parade, or simply watch the sparkling fun go by, this is a wonderful way for the whole family to get the season rolling! A benefit Wesley House Family Services, this neighborhood parade features lighted and decorated bicycles. Registration is free with a toy drive donation. The fun begins at 7pm (check-in, 6pm) at Bayview Park, and ends at locals’ favorite hangout, Mary Ellen’s for a Block Party (free for riders)!

When:

Wednesday, December 4, 2019, 6 pm 

Visit Wesleyhouse.org or registration, the new route, and other details. 

Key West Holiday Parade  

A Key West tradition, this family-friendly parade rivals the famous Fantasy Fest parade… full of floats, marching bands, and merriment marching through Old Town! Starting at White Street and Truman Ave, there are plenty of places to watch along Truman Ave and Duval, and plenty of candy raining down for one and all! 

When:

Saturday, December 7, 2019, 7 pm

I Heart Stock Island Festival

Celebrate the ever-growing “Brooklyn” of Key West! Stock Island, our closest neighbor, has become the newest spot to experience “island living.” Explore three days of free and ticketed events featuring food, art, and entertainment, including Food Truck Finds, the 1st Annual Stock Island Lighted Boat Parade and Christmas at the Sheriff’s Animal Farm.

When:

TBD

Details

Nutcracker Key West  

If you think you’ve seen the Nutcracker one too many times, think again! This magical production at the Tennessee Williams Theater is a unique reflection of everything there is to love about Key West… tiny chickens, lively shrimp, and graceful snowy egrets. The magic of Key West is alive in this production, which is simply not to be missed.

When:

Returning December 2020

Details

Music at Martello presents Perpetual Groove w/ The Happy Dog Band

Thursday, December 12, 2019, 5-10pm Perpetual Groove creates a unique music experience for each live show. Experience the new chapter for Perpetual Groove that showcases the evolution of their music andlive performances. 

When:

Thursday, December 12, 2019, 5-10pm 

New Year’s Eve in Key West

Monday, December 31 There is something for everyone when ringing in the New Year in Key West. You can march with the weiner dogs at the 14th Annual Key West Dachshund Walk during the day, and then you can countdown to midnight with the unique “ball drops” around the island. Who needs Times Square, when you can celebrate with a drag queen in a glittering high heel, a conch shell at the famous Sloppy Joe’s or a pirate wench down a ship mast at the seaport? There is no better way to welcome 2019 than here in Key West!

When:

Monday, December 31

Thanks for checking out our Key West vacation tips. We look forward to celebrating the holidays with you!

Stay with Us

Four Places Where the Locals Eat in Key West

Discover Our Favorite Key West Restaurants

These incredible eateries may not be found on a “Famous Key West Restaurants” list, like Blue Heaven or Margaritaville.  BUT they are packed year ‘round with hard-to-please locals, a testament to the fact that you should add them to your Key West must list!

The Café- 509 Southard Street- www.thecafekw.com

Healthy yet sumptuous, The Café is a local go-to when we want to indulge without feeling like a total glutton afterward.  Their menu is mainly vegetarian and vegan, but they serve some seafood dishes as well.

Our all-time favorite menu items include the Fig and Gorgonzola Pizza ($18) and the Cold Soba Peanut Noodles ($9.75), perfect when you don’t want something hot but also aren’t in a salad mood. Try their homemade Kombucha on tap ($6.25) or an ice-cold chai tea latte ($6).  Top it all off with the absolute miracle that is their vegan carrot cake.

Mary Ellen’s- 420 Applerouth Lane- www.maryellensbar.com

A fairly new spot, Mary Ellen’s is located on quaint Applerouth Lane, next to (ahem) Leather Masters. It has a classic dive bar atmosphere, but don’t let the appearance fool you. 

Make your way around the bar to the little Dutch door in the corner and order a “Mabel” grilled cheese sandwich ($9): white bread, brie, peach preserves and crushed cashews grilled to a light golden brown perfection. We like to order the lemony and cheesy Kale Salad ($7) too. Go out on a limb and order the heavenly Avocado Toast ($8).

The place is dark and cave-like, the air conditioning is always on full-blast and the Moscow Mule on tap is delicious. Combine all that with a simple, delectable menu and it’s the perfect spot to cool off and refuel on a hot Duval day.

Southernmost Beach Café- 1405 Duval Street- www.southernmostbeachcafe.com

If it’s your first time visiting Key West, make this your very first stop. The location simply cannot be beat. It sits right on the beach, so close in fact that the floor is always covered with a light dust of sugary sand.

Every time we bring someone new to Key West here, they say “this is exactly how I pictured Key West.” Their menu is basic but good.  Try the Beach Café Caesar ($11) with the tangy Key Lime dressing and the Ahi Tuna Stuffed Avocado ($12) with cream cheese and sriracha aioli. 

If you want a spot to Instagram your enviable view with a Mango Mojito ($10) in hand, this is the place.

El Siboney- 900 Catherine Street- www.elsiboneyrestaurant.com

We feel like this unassuming Cuban restaurant doesn’t really need the extra hype, but this is the place a majority of locals eat at with the most regularity. It already has a rabid cult following and is usually packed, and for good reason.

The food is outrageous.

We especially love the Half Roast Chicken Dinner ($11.25) with yellow rice, black beans, and plantains. We don’t know what they do to this chicken, but it literally falls right off the bone and melts in your mouth.

Don’t think. Just go. Trust us!

Book one of our vacation rentals in the Old Town area and you’ll be within strolling distance of all of these spots!

-Wendy Bixby