Sailing Across The Bay

As the dawn breaks over The Bay, Captain Jack and Ja of ‘Sailing Adventures on Blackbird’ set off early from Drum Point in a race against time and the impending bad weather approaching their route.

An Early Morning Departure

The duo leaves the tranquility of Drum Point behind, heading towards Solomon’s Island with one mission in mind – to reach their destination of Onancock before the storm clouds roll in.

A Fleet of Sailing Enthusiasts

As they make their way across The Bay, other sailboats join them on the water. It seems that this batch of boating enthusiasts have caught wind of the same weather forecast and decided to make a dash for it. In this race against time, ‘Blackbird’ holds its own with the help of its well-tuned sails.

The Arrival in Onancock

In this sleepy little town, Jack and Ja take some time to explore the local sights. They anchor their boat, record their day’s log which shows they traveled 54.2 miles, covering almost nine hours at sea that day. But it doesn’t take long before Captain Jack is eager to set sail once again.

Facing Adverse Weather Conditions

Never one to shy away from a challenge, the ‘Blackbird’ crew pushes on against unfavorable winds and rainy conditions. The small, tucked-away spot in Onancock offers respite for a brief moment as they await calmer waters.

The Journey Continues

A day later, with winds picking up again, they set off towards Fishing Bay near Delville. Flash flood warnings add an extra layer of excitement to their sailing adventure.

Arrival at Fishing Bay

In Fishing Bay, they find the spot is already teeming with other sailboats sharing their sense of adventure. Jack and Ja decide to drop anchor in this new location before deciding on their next move.

The Race is On

In the midst of their sailing journey, Jack and Ja encounter a variety of interesting people. East Coast Diving’s owner offers to look at their boat’s propeller, while a friendly fellow sailor shows off some smooth dance moves as they all navigate the waterways together.

Making the Most of a Sailing Adventure

In true sailing spirit, they take advantage of every opportunity to make friends along their journey. Their shared dinner with Rick and Alyssa on ‘Coconut Moonshine’ features an added twist – oyster shucking.

The Sailing Life

The couple continues their voyage down the ICW (Intracoastal Waterway), facing new challenges and enjoying every moment of this unique lifestyle. The winds, weather, and people encountered along the way all contribute to their unforgettable adventure across The Bay.

Finding Shelter

To ensure they stay warm and out of the wind, Captain Jack ingeniously creates a makeshift enclosure for their boat using a shower curtain, strings, and fenders. As M watches on with amusement, ‘Blackbird’ remains snug despite the chilly breeze.

The End of an Adventure

In Hampton Roads, Jack and Ja find a welcoming slip for their vessel. They appreciate the respite as they reflect on their journey across The Bay, which was marked by early mornings, unexpected camaraderie, and overcoming nature’s challenges.

In typical fashion for seasoned sailors like Jack and Ja, each new day brings fresh opportunities to learn from their adventures and further appreciate the freedom of life on the water. Stay tuned for more tales in their continuing quest towards warmer weather down south.

This time we visit a new spot across the bay before returning to an old favorite. We hang out with some friends, enjoy some local seafood and start heading south to warmer weather.

Thanks for watching!!!

Sailing Across The Bay Locations

  • Drum Point is a beautiful coastal location located just outside Solomon's Island on the western side of the Chesapeake Bay. (38.2576,-76.5033)
  • Fishing Bay is a scenic harbor located near Deltaville in Mathews County, Virginia, with plenty of spots for boats to anchor or moor. (37.6687,-76.3778)
  • Hampton Roads is a natural harbor located at the mouth of the James River and the Hampton Roads Harbor. (36.9605,-76.3363)

Note of Recognition for Sailing Adventures on Blackbird

At WeBoating.com, we profoundly acknowledge the unwavering dedication that Sailing Adventures on Blackbird and other creators invests in crafting each and every video. Their passion for delivering exceptional content shines through every frame, and it's a labor of love that deserves your attention.

We invite you to watch their captivating videos and actively engage with their content, including their social media links above. Liking, commenting, and sharing their work goes a long way in fueling their creative fire.

We're also inviting you to explore any sponsorships and partnerships highlighted in the video description of "Sailing Across The Bay", or directly on YouTube. By considering their offerings or purchasing services and items, you not only support Sailing Adventures on Blackbird but also the brands and collaborators they're associated with.

If you have any feedback, corrections, or additional information about Sailing Adventures on Blackbird or their videos, please use the comment form below to share your thoughts with us.

Thank you for being a part of our community and supporting the creators we cherish. Your time and support truly matter!

Sailing Adventures on Blackbird Lastest Videos

Showing 1-24 of 44 results
This kind of water never gets old no matter how many times you see it
Sailing Adventures on Blackbird

This kind of water never gets old no matter how many times you see it

This kind of water resets everything. No filters, no noise, just time slowing down as the boat cuts straight through it. You think you’d get used to it… you don’t.
Sunsets making us all look bad
Sailing Adventures on Blackbird

Sunsets making us all look bad

Sunsets like this have a way of putting everything into perspective. All the noise, the stress, the rushing around… it fades for a minute. Out here, the sky slows you down whether you’re ready or not. Bright oranges, soft pinks, and a quiet reminder th...
Everything slows down when you stop looking for “perfect” and start noticing what’s already there.
Sailing Adventures on Blackbird

Everything slows down when you stop looking for “perfect” and start noticing what’s already there.

Everything slows down when you stop looking for “perfect” and start noticing what’s already there. The wind through dry grass. Salt on the air. Kids disappearing into the wild like it’s their backyard. Light finding its way through leaves. Water so...
We Let Our Kids Lead on a Cursed Island
Sailing Adventures on Blackbird

We Let Our Kids Lead on a Cursed Island

Coffin Island: abandoned, overgrown, and a little questionable. Two kids, zero plan, and a full day of exploring anyway. These are the days I know they’ll remember and so will I.
5 year old makes the decisions – part 2
Sailing Adventures on Blackbird

5 year old makes the decisions – part 2

I gave my 5 year old full control of the day… and somehow we ended up hiking through cactus, searching for pirate treasure, and heading toward a haunted cave. Worth it, but I was not prepared for the cardio.
Boat Life: Shakedown Cruise from Salinas to Coffin Island (Before Breakfast)
Sailing Adventures on Blackbird

Boat Life: Shakedown Cruise from Salinas to Coffin Island (Before Breakfast)

Boat life shakedown cruise from Salinas to Coffin Island. Testing systems, anchoring, troubleshooting problems, and morning sailing with kids.
This will do for a while 😎
Sailing Adventures on Blackbird
I let my 5-year-old make every decision…We ended up at a haunted pirate island.
Sailing Adventures on Blackbird

I let my 5-year-old make every decision…We ended up at a haunted pirate island.

Boat life needed more chaos, so I handed control to my 5-year-old. He picked the route, the plan… and a haunted pirate island. Probably not my best decision.
Boat life problems 😎
Sailing Adventures on Blackbird
Trade your Monday?
Sailing Adventures on Blackbird

Trade your Monday?

Monday and we didn’t go anywhere. No rush. No schedule. Still building a life just not the one most people expect. Some days it is chaos some days it looks like this. Either way I would not trade boat life for anything.
Sailing Across The Bay
Sailing Adventures on Blackbird

Sailing Across The Bay

Join the crew of 'Sailing Adventures on Blackbird' as they set off early one morning from Drum Point and head towards Onancock, all while attempting to outpace a batch of inclement weather moving into the region. Will their efforts pay off?
Annapolis and The Boat Show
Sailing Adventures on Blackbird

Annapolis and The Boat Show

Episode 19 - Baltimore to the Boat Show Thanks for watching, please like and subscribe if you enjoy this episode. We’re starting to make our way south. The first stop is Annapolis where I have a job. I get paid to work the boat show and get to meet some...
Chesapeake Bay – Urbanna to Baltimore
Sailing Adventures on Blackbird

Chesapeake Bay – Urbanna to Baltimore

Episode 18 - Urbanna to Baltimore Thanks for watching, please like and subscribe if you enjoy this episode. We make a final push to get to our northernmost stop this season. Enjoy some sailing with family and the many beautiful anchorages. Again we hope ...
Sailing Around The Chesapeake Bay – Ep 18
Sailing Adventures on Blackbird

Sailing Around The Chesapeake Bay – Ep 18

Episode 18 - Urbanna to Baltimore Thanks for watching, please like and subscribe if you enjoy this episode. We make a final push to get to our northernmost stop this season. Enjoy some sailing with family and the many beautiful anchorages. Again we hope ...
Exploring the Chesapeake Bay – Ep 17 Sailing Summer Rules
Sailing Adventures on Blackbird

Exploring the Chesapeake Bay – Ep 17 Sailing Summer Rules

Episode 17 - Yorktown to Urbanna - Sailing Summer Rules Thanks for watching, please like and subscribe if you enjoy this episode. We’ve been blown away by all the history that’s on display up the east coast. Yorktown played an important role in Americ...
Chesapeake Bay in our sights – Ep 16
Sailing Adventures on Blackbird

Chesapeake Bay in our sights – Ep 16

Episode 16 - Manteo to the Chesapeake Bay Thanks for watching, please like and subscribe if you enjoy this episode. We negotiated bridges, shallow cuts, barges and locks but we finally made it to the Chesapeake Bay. Today we changed the engine oil, traver...
Sailing to the Outer Banks – Ep 15
Sailing Adventures on Blackbird

Sailing to the Outer Banks – Ep 15

Episode 15 - Beaufort to Manteo Thanks for watching, please like and subscribe if you enjoy this episode. After our muddy adventure to see the horses, they mock us as we leave by standing on the beach. We motor to New Bern to see what it has to offer and ...
Sailing Summer Rules in Beaufort NC with Wild Horses – Ep 14
Sailing Adventures on Blackbird

Sailing Summer Rules in Beaufort NC with Wild Horses – Ep 14

Episode 14 - Mile Hammock to Beaufort NC Thanks for watching, please like and subscribe if you enjoy this episode. In this installment we get up close to the military, see more pirates and visit some wild horses. Again I hope you enjoyed watching and if y...
Sailing Summer Rules Encounters Pirates Northbound ICW – Ep 13
Sailing Adventures on Blackbird

Sailing Summer Rules Encounters Pirates Northbound ICW – Ep 13

Episode 13 - Osprey Marina to North Carolina Thanks for watching, please like and subscribe if you enjoy this episode. This time we enjoy some of Jocelyn’s commentary as we continue on the ICW. It also seems to rain a lot while we’re trying to navigat...
Summer Rules in Autumn Weather – Ep 12 ICW
Sailing Adventures on Blackbird

Summer Rules in Autumn Weather – Ep 12 ICW

Episode 12 - Charleston to Osprey Marina, Myrtle Beach Thanks for watching, please like and subscribe if you enjoy this episode. We leave Charleston and continue making our way north. Charleston was a fun stop but we like to keep moving so we threw off th...
Sailboat on the ICW, Beaufort to Charleston South Carolina
Sailing Adventures on Blackbird

Sailboat on the ICW, Beaufort to Charleston South Carolina

Episode 11 - Beaufort to Charleston Thanks for watching, please like and subscribe if you enjoy this episode. Today we start off in Beaufort and take you for a walk around while we look for a grocery store. We then head further up the ICW to Charleston an...
Sailing the ICW Georgia to South Carolina
Sailing Adventures on Blackbird

Sailing the ICW Georgia to South Carolina

Episode 10 - Savannah and Beaufort Thanks for watching, please like and subscribe if you enjoy this episode. We’re still heading north this time. We take you for a walk in Savannah before continuing on the Beaufort South Carolina. State number 3 on our ...
Making It Out Of Florida
Sailing Adventures on Blackbird

Making It Out Of Florida

Episode 9 - St Augustine to Georgia Thanks for watching, please like and subscribe if you enjoy this episode.This episode we spend a little more time in St Augustine before casting off again. We continue making progress to the north. We stop for a night i...
Sailing, Storms And St Augustine.
Sailing Adventures on Blackbird

Sailing, Storms And St Augustine.

Episode 8 - Sailing the Intracoastal Peck Lake to St Augustine Thanks for watching, please like and subscribe if you enjoy this episode.In this episode we pick up from last time in Peck Lake and start making our way north. Anchor at one spot before makin...
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart