Agenda: 5 Days in Key West

Something about Key West just keeps calling me back.  It could be the “come as you are” casual attitude.  It could be the eclectic, funky, quirky vibe.  Perhaps it’s the charming, colorful homes surrounded by tropical gardens.  There is an ineffable feeling the moment you glimpse the colorful buildings from your window seat.

Since most everyone who has had more than two conversations with me is aware of my obsession with The Conch Republic, people heading down on vacation inevitably ask for recommendations on what to do and where to go. Here is my perfect agenda for a first weekend trip to Key West:

Day 1:  1pm

Check into an Oceanfront Room at the Casa Marina Key West Resort. If you have some time before your room is ready, grab a Corona and a blue-cheese burger at the Sun Sun bar overlooking the water.

Casa Marina


Sun Sun Bar at Casa Marina Resort

If this is your first trip to Key West, we must first manage your expectations regarding the island’s beaches. This is not the place to go if you require beautiful beaches on which to lounge for hour upon hour with rolling waves lulling you to sleep.  Key West is a water town, but it is not a beach town. You’ll simply be happier knowing this from the start.

That being said, the Casa Marina Key West has much to offer in the way of beach resort like amenities:  A lovely water view,  lovely pools with the mandatory poolside food and beverage service.  While it does have a beach of sorts, it is the pool, upscale rooms, and the resort’s historic past that have made the Casa our go-to place to stay.

Pool View Casa Marina

2pm:  Go wandering

One of the most enjoyable activities in Key West is simply strolling about the streets of key west, soaking up the tropical breezes, eclectic surroundings, and picture perfect little houses.  Stretch your legs after the flight, make your way through the Casa Marina district, and head across the island to Key West Bight waterfront.

 The bight

4pm:  Live music and cocktails on the waterfront

At the end of Elizabeth Street you’ll find Conch Republic Seafood Company, an open air bar and restaurant perfect for your first happy hour.  If you can tear yourself away, saunter back to the hotel (or catch a pedi-cab if you must) to get ready for dinner.

Conch Republic

7pm:  Dinner at Louie’s Backyard

A very short walk from the Casa you’ll find the charming Louie’s Backyard. Louie’s has two separate dining areas, the downstairs with a more formal environment (yet you’ll still be right at home in a tee shirt and shorts), and the upstairs a tapas style, both with amazing views.  Louie’s isn’t particularly known for super friendly service, so be prepared to ignore that to concentrate on the delicious food and tropical breezes. The afterdeck bar is one of the best places for a drink in Key West, so plan to hang out there before heading back for an evening beach stroll or swim at the Casa.

The Upper Deck at Louie's Backyard

Day 2:  History and Food

10am…ish. Breakfast with the chickens

Roll out of bed, grab some coffee and head down to brunch at Blue Heaven, which needs to be on your “absolutely cannot miss” list.  There will be a huge wait for breakfast. Do not be dismayed. Grab a seat near in the bar with your feet in the sand floor, order a mimosa or Bloody Mary, settle in and enjoy the live music and freely wandering cats and chickens. Once you are seated (wait on an outdoor table, whatever you do) order a lobster omelet or benedict.  Ask them to add bacon. Also, for the love of all that is good in this world, order the homemade banana bread.

Breakfast at Blue Heaven with the Chickens

Noonish: Get your history fix

After breakfast, head to the nearby Hemingway Home for an always entertaining tour, followed by a climb up the Key West Lighthouse for nice island views and Keepers Quarters just across the street.  If you have an interest in American History,  visit Truman’s Little White House, where Harry Truman ran the country during the winters of his presidency. This man was no dummy.

When you grow weary of touring, and hunger or thirst returns, stop for a snack and a Corona at B.O.’s Fishwagon, a counter service, eclectic hangout where even more roaming chickens and cats will inevitably stop by in the hopes of sampling your fish sandwich.


3pm Take an afternoon dip
Head back to the hotel for a rejuvenating afternoon dip in one of the Casa’s two pools. If you time it right, you may be offered a complimentary popsicle or “drink of the day” sample.

6pm: Do the Mallory Square thing

If this is truly your first trip to Key West, you’re practically obligated to head down for the sunset spectacle that is Mallory Square: Hoop jumping cats, conch fritters, magicians and acrobats, etc… The whole bit. If there isn’t a cruise ship blocking your view, you just may even see the very lovely sunset. Once is enough. I promise.

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7:30pm Dinner at Flaming Buoy Filet Company

If you don’t mind a walk back towards the eastern end of old town, you will be rewarded with the charming Flaming Buoy Filet Co., an intimate neighborhood restaurant housed in a charming clapboard building.  The almost wrap-around porch along with their bar seating, offer an appealing alternative to the limited dining tables if they happen to be full.  You’ll likely be tempted to order the lobster mac and cheese, as I always am, but be warned: their entrees are not small, so plan accordingly.

Day 3:  Get out on the water

10am Another big breakfast

After a lazy morning at the hotel, take a leisurly walk down to Pepe’s Cafe for a late breakfast.  Just as with Blue Heaven, expect a wait and plan on grabbing a mimosa and chilling out for awhile.  Ask for a seat in the outdoor garden or sit at the bar if the opportunity arises.  I recommend the eggs benedict or whatever kind of spectacular french toast they are offering.  This time, it is the coconut bread you’ll not want to forget to order.

2pm Danger Charters half-day cruise

Key West is a water town and you can’t come here without spending some time out on on the water.  For those unfortunate souls like me who have no boat of their own, Danger Charters offers a fun half-day excursion.  Their kayak and snorkel tours offer the best of both worlds with some yummy snacks and adult beverages to share after all your hard work.

 Danger Charters


7pm Dinner on Duval

Although it is on Duval Street, which I typically avoid as much as possible, Blackfin Bistro is a tasty, centrally-located spot to grab dinner not far from the Marina.  Clean yourself up after your sailing trip (we change in the Westin’s restrooms) and ask for a seat in Blackfin’s garden.  They have a to-die-for burger if you are in a burger-sort-of -mood.

blackfin bistro

Eating at Blackfin situates you for some evening bar hopping along Upper Duval if you are up for it.  Try the bar at Nine One Five (also a lovely place for dinner) or the tiny Rum Bar at The Speakeasy Inn.  Alternatively, make your way back towards the Casa Marina district and hit the Afterdeck at Louie’s Backyard which is always a great way to end a night.

Day 4  Adventures in the middle of nowhere…

Spend the day with Key West Seaplane Charters and venture out to the Dry Tortugas National Park.  It’s a splurge that I highly recommend (although you can also take the cheaper but longer ferry). The flight over perfect turquoise water, isolated islands, sea turtles, and sharks is an adventure in and of itself.  After 70 miles of sea, you’ll see Fort Jefferson arise out of the blue.  The four-hour half-day option is the way to go with 2.5 hours on the island to tour the fascinating fort and do some awesome snorkeling along the fort’s historic brick walls.  There is no running water on the island, but the tour includes water, soft drinks, and snorkeling equipment, too.


Book the morning seaplane trip and then spend the rest of the day recuperating from your adventure with an early poolside dinner at the Casa. If you can muster the energy to go out, a great nearby super casual option is El Siboney for some of the best Cuban food and Homemade Sangria on the island.  Another option for dinner, if you fancy a chic, off-the-beaten-path spot, is the super tiny Seven Fish on Olivia Street.

Day 5  Do absolutely nothing.

On your last day, sleep in, linger at Blue Heaven for breakfast, stroll the lovely neighborhoods, drop in on art galleries, grab a bite at any of the garden restaurants you happen to be walk by, relax at the pool…  Have a relaxing, spontaneous kind of day.




  1. Great article. I am ready to go!

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