2 Day Key West Itinerary

2 Days to See Key West?

Whether you've never Been or it's your first time in Key West, There is a lot to do and see on this tiny little island at the end of the Florida Keys. Key West is basically a 2 by 4-mile island which at one time boasted of being the largest city in Florida and is steeped in history involving the U.S. military, treasure and wreckage salvaging, and pirate lore, Cuban affairs, famous authors, artists, and architecture, with some of the most diverse fishing anywhere.

The historic west side of town referred to as “Old Town”, encompasses Henry Flagler’s Casa Marina Resort to Fort Zachary Taylor on the South. “Old town” also runs along the channel on the West that leads to the northern harbors. Its more recent military bases are now filled with fishing charters and yachts. “New town” on the eastern side of Key West is comprised of many smaller concrete homes built in the 50s and 60s’, with shopping centers, schools, the airport, and where most of the local population affords to live.

The most enjoyable, relaxing, and secluded beach of Key West resides within Fort Zachary Taylor state park. A small fee to get into the park is worth the privacy of the island’s South-West corner. Here you can watch the sailboats leaving and entering the Key West harbor while the sun sets straight West behind them! Don’t forget a snorkel & mask and a picnic basket when visiting the park. There is not much out here but nature, so pack-in, pack-out with everything. If you’re the adventurous type, I have grilled a few Mahi sandwiches out here with only lettuce, tomatoes, Cuban bread, Mahi, a lemon, and charcoal. Enjoy the grills while you are there. View Beach & Park

Regardless of where your accommodations are located, I would begin with a 90-minute historical tour. It is the quickest way to orient yourself with the island demographics, history, and attractions, giving you a chance to go back and explore on your own. The Conch Tour Train is an open-air, wheeled train that is always fun for the family and is Key West’s original historical tour, and I would recommend this first, being one of the original Key West attractions.

The Old Town Trolley is also a wonderful tour that offers a Hop-on & Hop-off tour allowing you to see attractions at 13 different locations and maybe a better option if there’s a chance of rain.

Old Town for breakfast in Key West only brings a few selections to mind that are original Key West well-established local favorites that have stood the test of time.

The first is the oldest eatery in the Keys with great history, Pepe’s Cafe & Steakhouse. Established in 1909 by a Cuban fisherman, Pepe’s is an older, rustic-looking, and fairly small place located on 806 Caroline Street near the Key West Historic Seaport. Open at 7:30, graciously serving a cafe-style breakfast until noon and lunch until 5 every day. Menu!

Don’t miss out on a chance to be refreshed with a visit to Croissant De France located at 806 Duval Street. A bakery & a bistro cafe with seating in the back to relax. Aromas of fresh loaves of bread and fragrant pastries rolling out the front door as you enter the small storefront. Make your way to the quaint, tropical back deck, as the scents stoke your hunger. This French restaurant offers a savory display of dishes such as a galette, quiche, brie & fruit, seafood egg’s Benedict, and more, as well as an array of pastries & loaves of bread great to take with for a later picnic lunch on the go or save for a later hotel snack. Great selections! Menu

A little farther south, you can find Banana Cafe & Creperie located at 1215 Duval, serving up more than just your average breakfast, omelets, crepes for breakfast, lunch, and dessert. Don’t miss out on one of their seafood crepes if you get the opportunity. You can also find a good variety of salads, sandwiches, wines, and beer here. Check out the menu loved by locals for the great fresh food and the friendliest staff in a super relaxed atmosphere. Menu

You can’t go wrong with these three breakfast choices, always check out their menus and locations to determine what best suits you.

If you are rushed for time, you can always stop in the window at Sandy’s Cafe for a coffee & breakfast or lunch sandwiches to go. Great for boating or the beginning of a beach day! Sandy’s Cafe is located on White street located beside M&M Laundry. It is a traditional Cuban window-service cafe; you can expect an authentic experience that hasn’t changed in the last 30 yrs. Friendly service & Quality food with a refreshing pick me up on a friendly street corner.

If you can work any two of these breakfast selections into your scheduled plans you will be delighted and satisfied by their delectable food, drinks, and ambiance. Enjoy your morning ensconced within one of these awesome little tropical-styled, unique cafes. Get charged up for a couple of opportunistic sightseeing days!

In planning a trip down to Key West, to have the best time, one should plan to adapt, the same as a vessel at sea, avoiding a few thunderheads passing by the side. My first goal would be to get out on the spectacular waters of the Florida keys.

The waters surrounding the Keys and Key West have so many unique adventures to offer you could spend months and still be awed by the ever-changing blue-green colors.

Always plan to go early on your first morning; the Sunlight is important to the visibility in the water (10 am-3 pm. is the best time). Then, try to schedule a snorkeling trip to the reefs or a wreck site for a better chance of sea life activity. Snorkeling is the best way to fully immerse yourself into a completely different environment of tranquility and peace here. You can get away from it all to relax or be a little bolder and adventurous exploring sea life with a friend, you will experience the thrills of the sea by varying timed snorkel trips aboard one of the Fury catamarans or boarding a Sebago catamaran. Either of these two companies will have a crew that is always ready for a great time!

If your sunny day doesn’t look so sunny by chance, but you have your heart set on a boat trip, you can always look for a backup ½ day fishing trip to save the day. Fish don’t mind a little rain! One should realize the vast beauty of these waters and do your best to take advantage of such an opportunity to go boating in some form.

You may have gotten preoccupied with some of the historical sites and/or breakfast; maybe just a late start. Just try to plan and catch a couple of sunsets, preferably one from Mallory Square and one from a sunset sail. The Fury and Sebago offer sunset cruises and several schooner-type vessels(usually winter-seasonal), and other smaller charter sailboats that can be arranged for a more personalized experience.

With any luck, we’ll be out there with you, listening for the sizzle and spying a green flash as the sun goes down!

After sunset is a great time to regroup and make sure all plans for the evening are in place. Not everyone is used to a long day of activities in the sun and the water, which may be exhausting. I always recommend an hour or so to rest if you plan a late night out for music and dancing with a few cocktails.

The Key West nightlife weekend will be highly active between 8 pm, and 2 am. I suggest you choose to eat on the later side of the evening dining spectrum 7-9 pm and plan enough time for an appetizer or dessert. This provides you a better, more relaxed service after the rush, allowing more time to regenerate for a later evening.

Every dining experience I recommend comes with a reasonably priced ideal with considerations of freshness, quality, and experience that you will receive!

A reservation at Louie’s Backyard is a must; if you have the opportunity to do so, make it happen. Doug Shook has been creating dishes since the mid 80’s as the executive chef, offering up artistically prepared, regionally crafted island dishes of locally harvested seafood that are perfectly paired with choice wines.

If you can’t get a reservation, you can always visit the after-deck bar for happy hour to enjoy the ambiance for an hour or two, usually open (11:30 am-1 am).

An evening at Alonzo’s Oyster Bar located at the Key West Historic Seaport has the best variety of Seafood.

Happy hour from 4 pm-6:30 pm offers drinks under $5, $2 oysters, and most appetizers under $10. An amazing variety with epic service and incredible views around the Key West Bight!

An after-dinner stroll along the boardwalk to the Schooner Wharf bar is always a good idea before doubling back, passing by the shops on Lazy Way to Duval’s liveliness and entertainment.

The Ocean Grill & Bar will exceed your expectations for dinner, breakfast, or brunch! Highest quality, freshest kinds of seafood designed and crafted into some of the most tasteful worldly delights you can find served upon this island! “Teamplay” best describes what comes to mind with this extraordinary group with family quality service led by their creatively gifted chef Lea for over 2 decades.

Also offering daily brunch from 10 am-3 pm with bottomless mimosas & bloody marys.

I truly hope you get to enjoy some of the island-cultured culinary adventures during your stay. Unique Dining experiences can provide the basis for good conversations and lasting memories; the rest of the evening is filled in with characters we meet in the spontaneity of the night!

If you’ve never been on the corners of Duval & Green streets around 9 pm on a Friday or Saturday night in Key West. It is the epicenter of fun for live music, dancing, and a little drinking downtown. Go to the world’s famous Sloppy Joe’s bar and enjoy a beer where Ernest Hemingway once frequented, and don’t miss Rick’s Bar & complex across the street.

Take a stroll down Duval street, letting your ears guide you to your favorite live music or dancehall; spontaneity is everything in Key West. I always say have an outline, not a plan. A safe bet is that a lot of fun will begin around 10 pm, and it’s good to know everyone is safe with plans by 2 am.

There are late-night food spots to regroup and recharge with your party near this location, so always make plans to rendevous and ensure everyone gets safely home for the night. Enjoy your stay your way for the best of Key West!