Sombrero Vacation Rental

09/04/2026

Kilts in the Keys is @ Dockside @ Boot Key Harbor Sept 27 from 5:00-7:00! The Skallywagz are performing so grab your kilt and bring the craic!

09/02/2026

Today, Marathon is a bustling community along the Overseas Highway, but in 1911 it looked very different.

At the time, Marathon was home to workers building and operating Henry Flagler’s Florida East Coast Railway. FEC employee housing had electricity and wooden sidewalks, but there was little need for streets. Most travel was done by foot, boat, or train.

Look closely and you can even spot the outhouses behind the homes. A public water supply would not reach Marathon until 1942–43.

Courtesy: Jerry Wilkinson

08/31/2026

08/01/2026

07/29/2026

😎🙏 Living the Keys Life 🎯

---------

💰 One day, a successful business man went to Islamorada on vacation. He bellied up to the bar on a Tuesday afternoon and started talking to the man sitting beside him.🌴🌊

💻 No laptop.
📧 No emails.
📅 No meetings.

He asked, “What do you do down here for work?”

The guy responded that he did odd jobs when he needed money. His house was paid and he didn’t have any debts.

He explained that most days he spent time with his family, ❤️ fished, 🎣 cooked, 🍳 and sat right where he was sitting.

The wealthy man laughed.

“You could be doing so much more.”

He started telling him how he could build a business. 📈 Work harder. 💼 Make more money. 💵 Hire workers, and eventually build something big enough that he could retire and live off his hard work and investments.

The guy asked,

“And then what?"

“Whatever you want the man replied. Spend time with your family. ❤️ Go fishing. 🎣 Sit by the water. 🌊 You wouldn’t have to answer to anybody.”

The guy looked around for a second. 👀

Then said,

“Isn’t that what I’m doing now?”

🤔 Whenever you find yourself chasing more, come back to this story and remember what you’re chasing it for. 💙

07/04/2026