We Quit Work to Sail! ⛵ Retiring Early, Living on a Sailboat & Sailing the Caribbean

Sat, 22 Aug 2026 18:00:19 +0000

What happens when you quit working, retire early, and decide to live on a sailboat? ⛵🌴

Come aboard Sailing Peregrine as we build, upgrade, and prepare our sailboat for a completely different kind of life — one centered around sailing, adventure, and living on the water.

This isn't just a boat tour.

It's the beginning of a plan to retire early, leave the traditional work life behind, and go sailing.

We'll take you aboard for a sailboat tour, show you the projects and upgrades that are turning our boat into a comfortable cruising home, and share what we're learning along the way.

The ultimate goal?

🌴 Sailing the Caribbean.
⛵ Living on a sailboat.
🌊 Exploring the Chesapeake Bay.
🏝️ Cruising from island to island.
⚓ Building a life around the water instead of a desk.

But getting there takes work.

In this episode, we're tackling sailboat projects, upgrades, maintenance, organization, and improvements that will make the boat safer, more comfortable, and better prepared for extended cruising.

You'll get a look inside our sailboat and see what we're doing to prepare for the next chapter — including the realities of turning a sailboat into a home.

⛵ IN THIS VIDEO:

• Complete sailboat tour
• Sailboat projects and upgrades
• Preparing a boat for long-distance cruising
• Retiring early to sail
• Quitting work and changing our lifestyle
• Living aboard a sailboat
• Preparing for Caribbean sailing
• Chesapeake Bay sailing
• Cruising and sailboat life
• What it takes to make a sailboat your home
• Plans for sailing the Caribbean
• The good, the bad, and the work behind the dream

We're not just dreaming about sailing away. We're preparing for it.

The Chesapeake Bay is where we're learning, experimenting, upgrading the boat, and building our cruising skills.

The Caribbean is where we ultimately want to go.

And between the two are thousands of miles of water, countless anchorages, boat projects, unexpected problems, incredible sunsets, and adventures waiting to happen.

🌴 The dream is simple:

Wake up on the boat.

Look outside.

See the water.

Decide where we're going next.

That's the goal.

If you've ever wondered what it would be like to quit your job, retire early, live on a sailboat, and sail the Caribbean, follow along as we turn that dream into reality.

⚓ WELCOME ABOARD SAILING PEREGRINE.

Subscribe and join us for the journey from Chesapeake Bay sailing to Caribbean cruising and life aboard a sailboat.

**We're working toward a life where the boat isn't just where we go on vacation...

It's home.** 🌊⛵🌴

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