Leading the Escapade

Hey everyone!

The official YouTube booth schedule for the Annapolis Boat Show is here!

If you want to stop by and say hi, here’s when we’ll be around:

Thursday, October 9th: 2:00 PM – 3:00 PM

Friday, October 10th: 3:00 PM – 4:00 PM

Sunday, October 12th: 11:00 AM – 12:30 PM

We'll also be hosting a Woodwind Schooner Sailing Meet & Greet with ‪@ExpeditionDrenched‬ & ‪@SailingYaba‬ on Saturday, October 11th: 2:45 PM – 4:15 PM (This is a ticketed event, read our previous post for more details)

We’d love to catch up with as many of you as possible! 

We'll also have some LTE merch available to purchase at the booth

Hope to see you there!

2 weeks ago (edited) | [YT] | 25

Leading the Escapade

Annapolis Boat Show – Meet & Greet Aboard the Woodwind! ⛵️

Hey friends! We’re so excited to host our very first Annapolis Boat Show event 🌊

⚓ Limited Spots: Only 30 people, so grab yours fast!

📅 Date & Time: Saturday, October 11 | 2:45 – 4:15 pm

📍 Location: Departing from Dock F2, Annapolis Sailboat Show

✨ What to Expect
-Meet us, Expedition Drenched, & Sailing Yaba aboard the iconic 74-foot Woodwind

-Help hoist all 4 sails or even take the wheel

-Kick back and enjoy the boat show atmosphere from the water

-Beer, wine, local craft brews, sparkling wine, soda & water available onboard

🎟 Tickets Info:
-US Sailboat Show ticket required
-Combo ticket available with discounted show entry
-Tickets purchased by Oct 6 → Boat Show tickets emailed Oct 7
-Tickets purchased after Oct 6 → emailed morning of sail

⛵ Don’t miss it! Click the link to purchase your tickets!

schoonerwoodwind.starboardsuite.com/e/sailing-meet…

2 weeks ago | [YT] | 43

Leading the Escapade

🚨 Exciting Update! 🚨

We’re officially heading to the Annapolis Sailboat Show (Oct 9–12)! ⚓️

Stay tuned here for details on meet-ups, our YouTube booth schedule, and other fun events happening during the show — we can’t wait to meet some of you in person! 🙌

👉 Patreon Plug: Our patrons always get first access to event announcements and limited spots (like meet-ups and sailing events). If you’d like to be the first in the loop, you can join our Patreon crew here: www.patreon.com/Leadingtheescapade 💙

💡 On another note — we’re also looking for some help closer to home. If anyone in the Stuart, Florida area (or willing to travel here) would be interested in boat/pet sitting our two cats 🐾 aboard our 40ft sailboat from October 8–13, please reach out!
• Preferably someone to stay aboard so the girls are in their usual space, but we’re open if you’d prefer to host them at your own home if you’re nearby the Stuart/Palm beach area
• Boat will remain at anchor, with dinghy provided for shore access
• Happy to pay for the help
• Ideally someone with boating experience who’s comfortable onboard

If that sounds like you (or you know someone who’d love the experience), let us know! 💙

3 weeks ago | [YT] | 28

Leading the Escapade

🚨 LAST CHANCE! 🚨

Just a quick reminder — July 31st is the FINAL day to enter the sailboat giveaway from our mates over at ​⁠@SpearItAnimal!

⛵️ They’re actually giving away their real sailboat in a raffle to help someone new jump straight into the cruising life — while raising funds to rebuild their hurricane-damaged catamaran. It’s the kind of full-circle generosity that makes this community so special 💙

🎟 This is a paid raffle — you buy a ticket to enter, and one lucky winner gets the boat!

If you’ve ever dreamed of living on a sailboat — or know someone who has — this could be that moment. It’s being drawn very soon, so don’t miss out.

👉 Enter here before it closes:
www.spearitanimals.com/giveaway?ref=6749

Let’s get someone new out there, living the dream 😍🌴

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2 months ago (edited) | [YT] | 73

Leading the Escapade

This week's episode just dropped! Enjoy 😉

Stuck in the remote Exumas with outboard engine trouble, we discover our dinghy is leaking oil—and we don’t have the right boat part to fix it. With limited options, we jury-rig a solution to keep cruising, wish us luck 🤞🏼

Along the way, we explore the stunning White Cay, a hidden gem in the southern Bahamas, and unwind at the laid-back Coconut Beach Club. From boat life challenges to tropical escapes, this episode has it all.

2 months ago | [YT] | 13

Leading the Escapade

Like Sailing Through a Giant Swimming Pool – Bahamas Magic!

Sailing the Bahamas in the clearest, bluest water we've ever seen—like a swimming pool! We explore sinkholes, swing off the boat, and soak it all in.

This episode is packed with classic Bahamas magic—turquoise water, underwater adventures, and a few unexpected moments (including one accidental boat bump during a swing!). Join us as we cruise through this surreal part of the Exumas, dive into crystal-clear sinkholes, and live our best barefoot sailing life.

2 months ago | [YT] | 24

Leading the Escapade

⛵️ Our mates over at ‪@SpearItAnimal‬ are giving away their actual sailboat — yep, their real boat — to help someone new jump straight into the cruising life!⁠
⁠
They’ve launched a sailboat giveaway to pass on their beloved boat to an aspiring cruiser, and the funds raised will go toward rebuilding their hurricane-damaged catamaran. It’s the kind of full-circle generosity that makes this community so special.⁠
⁠
If you’ve ever dreamed of getting out on the water — or know someone who has — this could be the chance to make that dream happen right now!!
⁠
💙 Check out all the details and enter here:
👉 www.spearitanimals.com/giveaway?ref=6749]
⁠
Let’s get someone new out there living the dream 😍🌴

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2 months ago (edited) | [YT] | 127

Leading the Escapade

Hey friends 👋

We know it’s been a few weeks without a new episode… we hope you miss us just a little 😅
Don’t worry — we’ll be back next week with a fresh adventure!

In the meantime, if you want to show your support (or just need a sailing fix), this is the perfect time to catch up on any episodes you might’ve missed. Or, go back to the very beginning and binge your way through the chaos — our Mediterranean series is still our favorite we’ve ever filmed. Everything was new, wild, and very… us (even if our filming wasn’t exactly polished back then 😅).

Thanks for sticking with us 💛 we can’t wait to share what’s next!

2 months ago | [YT] | 91

Leading the Escapade

The scary side of sailing you don’t often see…
In this episode from ‪@CutterboveSailing‬ , the captain experiences a medical emergency offshore, forcing them to turn the boat around in worsening weather—70 nautical miles back to seek help in the remote Bahamas.

It’s a stark reminder of the realities of sailing: when things go wrong, you’re often completely on your own, with no one else to rely on but yourselves.

Our friends handled the situation with incredible strength and shared the experience so openly. Head over and watch the episode—it’s raw, real, and deeply moving. And while you’re there, hit that subscribe button! They pour their hearts into this channel and truly deserve more eyes on their journey ❤️

2 months ago | [YT] | 18

Leading the Escapade

Just watched this incredible documentary! 🥹 as ocean lovers ourselves this was so inspiring and eye opening! If you have Netflix make sure you check it out 🦈🩵 ​‪@OCEANRAMSEYSHARKS‬ ‪@juansharks‬

2 months ago | [YT] | 9