Watch Sailing & Boating Adventures Around the World tagged “Chesapeake bay”

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 1-24 of 96 results
Sailing the C & D Canal, Chesapeake City, and Plans for Delaware Bay (Ep.197) ⛵ The Foster Journey
The Foster Journey

Sailing the C & D Canal, Chesapeake City, and Plans for Delaware Bay (Ep.197) ⛵ The Foster Journey

Join The Foster Journey as they sail through the C & D Canal, explore Chesapeake City, and plan their route for the Delaware Bay. Get tips on navigating currents, timing, and preparing for a successful voyage!
sailing with FRIENDS away from DANGER
sailorama

sailing with FRIENDS away from DANGER

Discover how Robbie navigates a sailing adventure with friends up to Chesapeake Bay, showcasing challenges they face on this unforgettable trip, including locks, bridges, fish, and more.
Taking advantage of a front, 20 Knots in the Chesapeake Bay  #chesapeakebay #sailboats #sailing
The Foster Journey

Taking advantage of a front, 20 Knots in the Chesapeake Bay #chesapeakebay #sailboats #sailing

Experience an unforgettable sailing adventure in the beautiful Chesapeake Bay, as The Foster Journey embraces a refreshing chill and harnesses a 20-knot wind for a remarkable outing on the water.
8 Months Cruising Chesapeake Bay on a Sailboat (Ep.192)   |  ⛵ The Foster Journey
The Foster Journey

8 Months Cruising Chesapeake Bay on a Sailboat (Ep.192) | ⛵ The Foster Journey

Part cruising guide and part sailing vlog, this episode takes you into the last 8 months of sailboat live cruising the Chesapeake Bay. Cheers, Matt SV Cadence Sign Up Here https://thefosterjourney.blog/subscribe/ 00:00 Overview Cruising the Chesapeake Ba...
8 Months Cruising Chesapeake Bay TRAILER 2
The Foster Journey

8 Months Cruising Chesapeake Bay TRAILER 2

From Norfolk to Deltavile - up to Annapolis and back down the East Coast of Chesapeake Bay. We're taking you to towns, anchorages, rivers, and bays - sailing the Chesapeake for 8 Months. The episode releases 4/28/2024. #chesapeakebay #sailing #sailboat
Cruising the Chesapeake  #sailboats #chesapeakebay
The Foster Journey

Cruising the Chesapeake #sailboats #chesapeakebay

Embark on an unforgettable sailing adventure through the magnificent Chesapeake Bay, stopping at picturesque ports and thriving cities as you make your way from Norfolk to Annapolis with The Foster Journey.
Ep 35: Sailing single-handed from the Azores to Brasil
M Jambo

Ep 35: Sailing single-handed from the Azores to Brasil

I sail from the Azores to Brazil. This sailing cruise is very challenging in terms of weather navigation as I am sailing near Cape Verde in September. This is the birthplace of hurricanes at this time. Good weather information is crucial to avoid strong wi...
Ep 35: Einhand von den Azoren nach Brasilien
M Jambo

Ep 35: Einhand von den Azoren nach Brasilien

Von den Azoren segle ich nach Brasilien. Die Fahrt ist bezüglich der Wetternavigation anspruchsvoll, da ich im September an den Kapverden vorbeisegle. Hier ist die Geburtsstätte der Hurrikans zu dieser Zeit. Gute Wetterinformationen sind hier entscheiden...
Cruising the Chesapeake Bay in a Sailboat for 6 Months #sailboats #chesapeakebay
The Foster Journey

Cruising the Chesapeake Bay in a Sailboat for 6 Months #sailboats #chesapeakebay

Cruising the Chesapeake Bay for 6 Months on a Sailboat. Enjoy this episode preview!
Ep 34: Single-handed from New York to the Azores
M Jambo

Ep 34: Single-handed from New York to the Azores

From New York I set off single-handed towards South Africa. My first stop are the Azores and after 21 days and 2368 nm I reach Horta. This sailing cruise is affected by the Gulf Stream, but is also characterized by strong winds and calms. As always, I give...
Ep 34: Einhand von New York zu den Azoren
M Jambo

Ep 34: Einhand von New York zu den Azoren

Von New York aus starte ich einhand Richtung Südafrika. Meinen ersten Stopp mache ich auf den Azoren und nach 21 Tagen und 2368 sm erreiche ich Horta. Die Fahrt steht unter dem Einfluss des Golfstroms, ist aber auch von Starkwind und Flauten geprägt. Wie...
Ep 33: New York, New York
M Jambo

Ep 33: New York, New York

Meine Tochter Alex kommt in Baltimore an Bord und gemeinsam segeln wir nach New York. Für uns wird ein Traum wahr, der einige Jahre zuvor in New York geboren wurde, auf eigenem Kiel nach New York zu segeln. Es ist ein unvergessliches Erlebnis. Viel Spaß...
Ep 32: Chesapeake Bay from Norfolk to Baltimore
M Jambo

Ep 32: Chesapeake Bay from Norfolk to Baltimore

We sail up the Chesapeake Bay and experience the beauty of this sailing area with many creeks and anchorages. We drive to St. Michaels via Hampton, Deltaville and Reedville. The city is well worth seeing and a popular destination not only for sailors. Afte...
EP 32: Chesapeake Bay von Norfolk bis Baltimore
M Jambo

EP 32: Chesapeake Bay von Norfolk bis Baltimore

Wir segeln die Chesapeake Bay hinauf und erleben die Schönheit dieses Segelreviers mit vielen verschlafenen Creeks und Ankerplätzen. Über Hampton, Deltaville und Reedville fahren wir nach St. Michaels. Die Stadt ist sehr sehenswert und ein beliebtes Zie...
Unpredictable Winter Sailing in the Chesapeake Bay | Sailing Sunday Ep  231
Sailing Sunday

Unpredictable Winter Sailing in the Chesapeake Bay | Sailing Sunday Ep 231

This week on Sailing Sunday we head south in the Chesapeake Bay in what was meant to be a beautiful calm peaceful sail turned into chaos making us abort mission in the middle of the night. Follow our travel vlog with myself Ryan, Brittni and our rescue p...
Sailing Vlog 17 – Sailing Choptank River, Chesapeake Bay and the Ladies Abandon Me in the Cold!
The Foster Journey

Sailing Vlog 17 – Sailing Choptank River, Chesapeake Bay and the Ladies Abandon Me in the Cold!

Can you believe they abandoned me? Oh well, it's a great day sailing the Chesapeake Bay down the Choptank River.
Sailing Vlog 16 FOUR Things we LOVE about Annapolis – Close Reaching in Chesapeake Bay
The Foster Journey

Sailing Vlog 16 FOUR Things we LOVE about Annapolis – Close Reaching in Chesapeake Bay

Join us for this gentle close reach as we cruise the Chesapeake Bay in the Fall and reflect on what we love about Annapolis. Thanks for watching.
Sailing Vlog 9 – Provisioning for Cruising the Chesapeake Bay (FAIL) Living on a Sailboat
The Foster Journey

Sailing Vlog 9 – Provisioning for Cruising the Chesapeake Bay (FAIL) Living on a Sailboat

Talking tool box organization, follow-up on the dinghy rub rail repair using G-Flex Epoxy, notes about Chesapeake remote anchorages, and provisioning failure due to a Zoom call. Thanks for watching! See you at the Annapolis sailboat show. Come say hi out...
Sailing Vlog 2. Sailors Warned Us About This! Chesapeake Summers – Living on a Sailboat
The Foster Journey

Sailing Vlog 2. Sailors Warned Us About This! Chesapeake Summers – Living on a Sailboat

Sailing Vlog 2 from Deltaville VA - Multiple sailors warned us about our timing heading to the Chesapeake Bay in the summer. "It's going to be hot and miserable there!" "Are you sure you want to do that?" As if they knew better. ...But they remained stuck...
Learning the Weakness of Tanbark Sails | Sailing Wisdom [S5 Ep54]
Rigging Doctor

Learning the Weakness of Tanbark Sails | Sailing Wisdom [S5 Ep54]

▸ MATERIALS NEEDED FOR OUR NEXT PROJECT: https://a.co/6y07tiz ▸ MERCHANDISE: https://rigging-doctor.creator-spring.com ▸ SUBSCRIBE DIRECTLY with us so you never miss an episode: https://www.riggingdoctor.com/subscribe ▸ PAINTING COMMISIONS: artisti...
Dreamy DOWNWIND SAILING + the Power of the CHESAPEAKE BAY Oyster | Harbors Unknown Ep. 49
Harbors Unknown

Dreamy DOWNWIND SAILING + the Power of the CHESAPEAKE BAY Oyster | Harbors Unknown Ep. 49

Dreamy DOWNWIND SAILING + the Power of the CHESAPEAKE BAY Oyster | Harbors Unknown Ep. 49 This week we’re casting the lines from Liberty Marina and the Sail Away Catamaran fam to begin our journey south to Florida. We enjoyed some amazing downwind saili...
CATAMARAN BUILD – Can 4 People Lift A Transom Into Place? (MJ Sailing – Ep 211)
MJ Sailing

CATAMARAN BUILD – Can 4 People Lift A Transom Into Place? (MJ Sailing – Ep 211)

With only 4 people, we manage to lift our 25 ft, 300 pound transom into place. In this week's episode, we focus on not only lifting the transom to get it up to the bridge deck, but find what's necessary to get it to, more or less, fit like a glove. We ha...
Go Sailing NOW with what you’ve got
The O'Kelly's

Go Sailing NOW with what you’ve got

Go now with what you got, we always say. The right boat to go cruising on always depends on where you want to go, how many people are going, and how much you have to spend. But....who's to say that the real adventure involves crossing oceans? After encoun...
This is How to Know if a Storm is Coming – No Computer is Needed
The O'Kelly's

This is How to Know if a Storm is Coming – No Computer is Needed

Our onboard meteorologist keeps a weather eye to the sky and makes a prediction based on the clouds. Plus, it looks like Hurricane season is almost over, but that means the first cold fronts are arriving. There are so many anchorages in the Chesapeake to s...
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