Watch Sailing & Boating Adventures Around the World tagged “Chesapeake bay” – Page 2 of 4
Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.
Showing 25-48 of 96 results
Off Season Cruising down the Chesapeake (Calico Skies Sailing, Ep 83)
Annapolis seems to have some sort of magnetic pull on us in the late fall 😂, this years challenge is to escape before the first snow falls..can we do it?! This town is a great stopover for us as we make our way up and down the east coast. We have lots...
Oops, ANOTHER tow?!!…. (Calico Skies Sailing, Ep 82)
They say bad things come in threes.... In this episode we once again find ourselves needing a tow from one of our buddies, SV Avalon. We are becalmed off Cape May NJ after a rough sail in near gale force winds and a malfunctioning engine. We attempt to s...
Sailing South – Chesapeake Bay to Florida (Take the Waters) S2:E8
With our season in the Chesapeake Bay now over, we begin our journey south down the coast from Maryland to Florida. We make our first ever passage around Cape Hatteras and visit some new coastal towns and pristine national parks along the way. Once in Flor...
Sailing Destinations of the Chesapeake Bay (Take the Waters) S2:E7
Our summer in the Chesapeake Bay was a busy one with unexpected work. But with our last two weeks in the bay we were determined to set sail and discover what have become our favorite destinations of the Chesapeake Bay. - - - - - - - - - - - - - - - - - -...
Stalking DELOS as they Enter the Chesapeake (MJ Sailing – Ep 170)
It's time for more friends to arrive in Annapolis, and when sv Delos enters these waters, we hop in a 17ft Boston Whaler to hunt them down. After we make another quick run out to Kentmorr marina to inspect the tent and the Viking a little closer, it's tim...
That Time Bobby Gave Me A Bikini… (MJ Sailing – Ep 169)
Thanks for the bikini Bobby! I know it's YOUR birthday, but funnily enough, I end up with the gift. During our time in Annapolis, in mid- October, we decide to get on a few more boats. Being invited out by a few of our Patrons, we go inspect one of the ...
Fall 2020 passage to FL
The Meri Crew sails offshore from VA to FL. We leave Hampton VA where the weather is getting downright cold and head south on the Atlantic ocean. After a four day passage we arrive in Florida where it is shorts and T-shirt weather. Along the way we have...
Adventures Sailing the ICW and Chesapeake Bay (Take the Waters) S2:E5
Our sail north continues towards the Chesapeake Bay as we navigate our way through the intracoastal waterway (ICW). We find our favorite and most beautiful spots of the ICW, experience a terrifying lightening storm, and have fun in our Carolina Beach ancho...
Sailing and Motor Woes – Flooded Engine & Fuel Starvation – Ep 9
If you’ve been following our journey since we left Canada, you may already know that we’ve been having some motor issues. A flooded engine and fuel starvation were on the list to repair while stopping in Chesapeake, Virginia. [Where We Dropped Ancho...
She’s Sailing Again! – S6:E03
Megan is back on Sailing doodles and sailing again! This time we sail up the chesapeake bay to the C&D canal. This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron http://www.patr...
Buddy Boating – S5:E71
We continue our sail up the Chesapeake bay with our buddy boat SV Westwind owned by our friends and patrons Jeff and Cameron. This channel is funded by viewers like you. Please help us keep this channel creating great content by becoming a patron http:...
COSTS to sail the ICW to Florida
If you are sailing from Norfolk, VA to Jacksonville, FL via the ICW this video is for you. We explain in detail How much does it costs to sail the ICW to Florida. If you like what you see don't forget to give us the thumbs up! To watch our entire budget ...
NEW YORK CITY to the Chesapeake Bay BUDGET
If you are sailing from the New York City to the Chesapeake Bay via the Delaware this video is for you. We explain in detail How much does it costs to sail from NYC to the Chesapeake Bay. If you like what you see don't forget to give us the thumbs up! To...
Chesapeake and R.I. 2020
The Meri Crew sails the Chesapeake Bay and Rhode Island - Summer 2020. We continue our summer adventures cruising up the Chesapeake Bay and then take an ocean passage to Rhode Island.
How We’re Celebrating 20k Subs! | Sailing Wisdom
http://Chesapeake.cbf.org/goto/sailingwisdom Music provided by Bensound https://www.bensound.com
E13 Under Way Sailing the Chesapeake, Lagoon 420 Good Life. Bahamas Express
We spent a few days in Georgetown, checking all of the fluids and filters, nav controls and instruments, helm and autohelm, electrical systems and the new anchor chain. The first leg was from our mooring at Sassafras Harbor marina near Galena on the Sas...![Top 10 Best Anchorages [Live] | Sailing Wisdom](https://i.ytimg.com/vi_webp/o5fhqeVDJwo/mqdefault.webp)
Top 10 Best Anchorages [Live] | Sailing Wisdom
After 8 years of living aboard and cruising, Herby and Maddie discuss their favorite anchorages and marinas! Harness Creek, Maryland: https://www.youtube.com/watch?v=k2VWcFznONs&list=PLlDgR504BxwmQKpzSKXSnLpJFqHfn5Kk1&index=9&t=0s Oxford, Ma...![Just keep going OVERNIGHT SAILING Chesapeake Bay | Norfolk Navy Base [Wildly Intrepid Ep 81]](https://i.ytimg.com/vi_webp/DBMwDk68GG4/mqdefault.webp)
Just keep going OVERNIGHT SAILING Chesapeake Bay | Norfolk Navy Base [Wildly Intrepid Ep 81]
We always say how plans constantly change when you are sailing. This time is no different as we start running out of daylight. So we decide to just keep going, overnight sailing on the Chesapeake Bay. At the time it seemed better than pulling into a crab p...![Sailing Chesapeake Bay & Exploring ANNAPOLIS [Wildly Intrepid Ep 80]](https://i.ytimg.com/vi_webp/9F6TMxCk53g/mqdefault.webp)
Sailing Chesapeake Bay & Exploring ANNAPOLIS [Wildly Intrepid Ep 80]
Early start on the C&D Canal to beat the current which also rewards us to a stunning pink sunrise. A perfect way to start sailing on the Chesapeake Bay. Even though the Boat Show is over we have so much fun exploring Annapolis and all its bricks buildi...
Chesapeake Sailing on a 2019 Hylas 48! – S4:E25
We sail a brand new 2019 Hylas 48 on the Chesapeake bay from Annapolis MD to St Michaels. Check out Hylas Yachts: https://www.hylasyachts.com/ This channel is funded by viewers like you. Please help us keep this channel creating great content by becomin...
Keeping it REAL Cruising on a Catalina 30
Cruising on our 30 foot sailboat. We have a little thanksgiving dinner to ourselves and get some things done in Annapolis to continue traveling down the Chesapeake on our sailboat. Vlog #126 Teresa and Ben - https://www.youtube.com/user/SailingSimplicity...
Annapolis and the Great Dismal Swamp! Barefoot Sail and Dive (Episode 4)
We have finally left Annapolis and are heading down the coast via The Great Dismal Swamp and the ICW! The Dismal Swamp (terrible name for such a beautiful place) is something we will never forget. It was incredibly beautiful and we are so happy we choose t...
Problem Solving! Barefoot Sail and Dive (Episode 3)
Living on a boat involves a lot of problem solving! It's a good thing Davy knows how to fix an engine! We had our engine on the galley floor for a week. We had to wait for the parts we wanted to arrive to Annapolis. Luckily Catalina Direct was able to help...
Seasons’ end, south to Deltaville
We are up at the crack of dawn to catch a fair wind for the 90-mile run from Annapolis to Deltaville. We have good luck with the winds--though some thunderstorms disrupt our pleasant overnight sailing--but then leave us drifting at the mercy of the tide j...
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.