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Key West Time
October 16th
11:05pm · 81°F

A Key West Vacation Rental Story: 'No Routine, No Plans, No Worries'

unspecified Favorite Place On Earth

Ben Ambler admits he turned down tickets to Super Bowl 41 in Miami, because he preferred watching his Indianapolis Colts take the championship at Fat Tuesday’s in Key West – his “favorite place on earth.”

508 Bahama 003 Central and serene

Like so many others, Ben and his wife, Mary, loved Key West on first sight. Since their first spontaneous weekend visit in 2004, the Indianapolis-based couple has returned many times to revel in the bars, live music, cuisine and people that make Key West unlike any place in the world. “We just cannot stand to be away for very long,” Ben insists.

508-207 Down Island Diggs

On their second trip down in June 2016, Ben and Mary added yet another favorite to their long list: Down Island Digs. Hidden by mature tropical gardens sprawling across two full lots, the two-bedroom cottage rental is just a half-block off Duval Street in Old Town Key West. High fences convert the backyard garden into a very private outdoor living area with a hammock, stone dining table and a pool surrounded by a wooden deck.

508-209 Poolside

“The pool was wonderful,” Ben says. “A good size, in the shade and the perfect temperature. What also really impressed us was that, even though even though the back of Down Island Digs bumps up to Jack Flats on Duval and is a stone’s throw from Willy T’s … no noise! You just wouldn’t know that you are in the heart of all that makes Key West famous if you didn’t see it on a map. Incredible.”


Sweet serendipity

Being in the the heart of the action, makes it easy to surrender to the sweet serendipity that wide-open vacation days invite.

“We never make plans that go beyond the 15 minutes in front of us – and even those are subject to change as a shiny object may distract us,” Ben explains. “I have been wanting to go to Hogfish Bar & Grill on Stock Island for as long as I can remember, but then we see another restaurant and end up there instead. It is just another one of the things we love about our Key West vacations. There is no routine – no plans, no worries and no disappointments.”

IMG_2641 Key West Sunset

Over the years, Ben and Mary have spent time kayaking, biking, sightseeing and hanging out at local bars, including Jack Flats, Conch Republic Seafood, and 2 Cents. But, in the end, it is the people they meet – Key West residents, fellow tourists from around the world, bartenders, and especially that colorful character on the next bar stool, that delight them most.

“All of the things that seem to polarize and separate people on the mainland are merely a part of what makes people interesting in Key West,” Ben says.


Key West state of mind

DSC_0117 The Green Parrot

He remembers buying Trinidad Joe a beer one night at the Green Parrot Bar.

“I asked, ‘Well, what do you do Trinidad?’ and he answers, ‘I rob banks and write books,’” Ben recalls. “I’m thinking, ‘Sure you do buddy. But it’s Key West, why not?’”   He didn’t think of the conversation again until Mary returned from the airport gift shop with a book authored by….Trinidad Joe. Ben laughs, “Not sure about the bank robbing portion of his tale, but he wasn’t bs-ing me about being a writer.”

Ben acknowledges how time in Key West has changed him and Mary. It is reflected in the décor of their home, his affinity for good cigars and their more accepting attitude towards others. Swearing to return, “as long as I draw breath.” Ben adds, “The real question for us is when we will stop leaving Key West.”

DSC_0285 Until Next Time Key West

Friendly Advice

Take Time to Shoot the Breeze

“Talk to every stranger you sit next to in a bar. I cannot remember names of people in my own family, but I rarely forget the name of a particularly good bartender. They have become a part of our Key West experience and are just another reason we feel like we are coming home whenever we return.”


Don’t Pinch Pennies

“It is expensive in Key West, so leave the ‘I’m going to watch my money’ mentality behind once you cross the bridge from Stock Island. Accept it, and just know that you are going to have one of the best times of your life if you leave those kinds of worries behind. You will not regret it.”


Venture Off the Beaten Path

“I think you have to do the traditional bars like Sloppy Joe’s, Hog’s Breath Saloon and a dozen others, but also go off the beaten path and explore some of the lesser known establishments. Rent a scooter for a day. Take a boat ride. By all means do a ghost tour.”


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