Road Trippin’ to Key West
Writer’s Update | We traveled back to Key West in July 2023 for Hemingway Days. According to locals - and to us - it was one of the hottest seasons ever in the Keys. Not only was the water registering 100 degrees, but people wore little clothing and always had a cold beverage in their hands. Fighting the heat was as hard as grabbing a seat at the bar at Sloppy Joes. This simply confirmed what we’ve known for so long: traveling during off-season or shoulder season provides the best experience. Not only are airline and hotel rates better, but things (like the heat) which you have no control over doesn’t factor in the fun. Read our new post on Key West here. We stayed at El Patio; we ate the Glazed Donuts. And we did it all sweating profusely. For us, it will always be January in the Key.
Original Post | January 2014
There’s not much that trumps a warm weather getaway in the depth of winter. Load the convertible with a weekend’s worth of clothes, a cooler full of snacks and hit the road just in time to revive the spirit. Our first winter escape happened in 2014, and these are the gems we discovered. Come along and experience the unexpected in Key West.
We usually stay at best western hibiscus (simonton), and yes, it's a convenient place that serves breakfast daily. But with such a great deal at El Patio (Washington), we couldn't pass up the chance to stay at a 'motel' and actually have a studio apartment for almost 30% less (than the Best Western) per night. If you're lucky enough to be attending the literary seminar in January, you get an extra 20% discount. You can't beat this in a town where everything is off-the-charts expensive. For example, we lunched at Jimmy buffet's Margaritaville and walked out with a $90 lunch tab. Nothing is ever as it seems, so look around.
Why it's a WINNER
large studio apartment with own entrance and courtyard; privacy
quiet neighborhood yet only about 3 blocks from duval
roof top patio
price - a studio sleeps 4 comfortably AND it has old world character! the cleaning service isn't always dependable, but there are always clean towels and a made bed. perfection.
It's been there since the late 1800s, and at times, it feels like it and smells like it. This dive serves live music and cold beer, no food with the exception of a help-yourself-popcorn kettle in the back. Go on a Sunday and you'll enjoy live jazz, complete with harmonicas. Their signature cocktail: a Bloody Mary. Located on Whitehead street, just down the street from the Hemingway house.
Thank heaven for holes in the wall. named as one of the top 10 donut holes in the United States by USA Today, glazed over-sized homemade/handmade donuts takes the classic glaze and makes you forget about wanting a napkin. When they need a little more 'uhmp' for flavor, they add fresh fruit. They even have key lime! Heaven with a hole! You might want to get lots, but I recommend getting only one (or whatever you plan to inhale this instant) and then returning for fresh ones each morning. On Eaton street, beside Tropic Cinema. closes at 3 p.m. "everything in moderation, including moderation."
Located on Grinnell Street, near the ferry, it's got the usual Irish fare of bangers & mash and my favorite, Dublin Chicken Pot Pie. You must drop in during happy hour - every day from 4 p.m. to 7 p.m. and 12-2 a.m. with no exceptions - for half price beer. There's live music, and it's obvious there's a mix of locals and tourists, and anytime there's locals, you know you've hit the jackpot! Celebrate in true Irish style. arguably one of the best values in Key West.
5. Fort Jefferson / Dry Tortugas
Fort Jefferson sits about 70 miles from Key West in the middle of the Gulf of Mexico. Garden Key, as the land is known. The fort was built in 1846 to defend this strategic harbor (the dry tortugas) against a naval assault. It was used during the Civil War as a union fort. Although it saw no combat, it did serve as a federal prison and housed those whose crimes did not bring the death penalty. The most notorious prisoner was Dr. Samuel Mudd, the doctor who set booth's leg after the assassination of president lincoln. He was later pardoned by President Andrew Johnson and released.
Tortugas is Spanish for turtles. Ponce de Leon found an amazing number on the islands, and dry was added to inform mariners of no fresh water on the island.
There are few options on getting there: by private boat, ferry or sea plane. The Yankee Freedom provides day trips which includes 2 meals, beverages, and a guided tour, as well as snorkeling equipment. You can easily make reservations online, and do so far in advance of intended travel. Coming and going is 2 1/2 hours each. Be aware that trips are not cancelled due to inclement weather. Cost is $170 per person. from 7:10 a.m. until 6:00 p.m. Key West Sea Plane Adventures provides two options - half day ($295 each) / full day ($515 each) trips. It's a 40 minute flight to and from the island. It's definitely a pricey adventure, but you figure, it's probably a once in a lifetime opportunity.
When You Arrive
Birdwatching - the 7 islands are layovers for birds traveling from south to north america. Over 300 species have been spotted.
Snorkeling - some of the most beautiful coral reefs in the gulf. Look, but don't touch. (that's the rule on the entire island)
Camping - with limited sites, make reservations early. what you bring in, you take out. There is nothing available on island
There's all types of inspiration to be had in Key West. It's the writer in me that is drawn to places like Duncan Street where Tennessee Williams lived and to Whitehead Street, where the public can visit the home of Pauline and Ernest Hemingway who lived here from 1931 until 1940. You'll see the famous-named six-toed cats (direct descendants) and just across the street, the lighthouse that Hemingway used as his guide toward home each night. Surrounding the estate is a brick wall, bricks that Hemingway 'found' on the streets of Key West. Behind the main residence is a pool, Key West's first fresh water pool, and then there's his writer's studio. The home is the largest residential property on the island. open daily, From 9 a.m. until 5 p.m. Tour rates include a 30-minute guided tour, from $13 adults to $6 for children 6 and older.
2023 Pricing | Open daily; no reservations required; adults, $18
Definitely one of the most spirited places in key west. Its 19 acres are cramped quarters, and now its new residents will be resting up. More people are buried here than currently live on the island. St the entrance, there are brochures for self-guided walking tours which will take you to some of the most notable inhabitants. There's soldiers, millionaires, paupers, Cuban cigar makers and Joe Russell, aka Sloppy Joe. the tombstone of B.P.. Roberts with its epitaph of 'I told you I was sick' should put a smile on your face.
7 a.m. until 6 p.m. Free. Corner of Angela and Margaret streets.