Watch Sailing & Boating Adventures Around the World
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The Haulout “Third Quarter” | Ep. 356
Working through the middle stretch of a boatyard haulout, Kevin Boothby refits the wooden spars and hull of the Gilmer 31 Ruth Avery, applying epoxy barrier coats, servicing rigging, and stepping the rig.
We Went Through All Kinds of Weather on the Way Down the East Coast!!
Steve and Madison sail Arabella from Rockport, Maine south toward Savannah, weathering gusty winds, canal currents, a dragging anchor at Sandy Hook, and an engine fuel blockage.
Much to do With Wooden Spars | Ep. 355
Kevin Boothby repairs rotted timber on the mast of Ruth Avery using a bi-directional scarf joint and shapes a new yard and jackyard for a larger gaff topsail.
We Rounded America’s Most Dangerous Cape! | Cape Hatteras
Bobby White navigates an offshore passage from Cape Charles around Cape Hatteras to Beaufort, North Carolina, tackling pre-departure fuel line repairs, calm seas, and 230 miles of motoring over 33 hours.
Driving My Boat from NY to Annapolis
After spending a month building a custom Bimini structure, Daniel hauls his MacGregor power sailboat over 400 miles from Albany, New York to Annapolis, Maryland for a solo launch on the Chesapeake Bay.
Annapolis Sailboat Show 2026 FULL Tour
Adventureman Dan explores the 2026 Annapolis Sailboat Show at City Dock on the Chesapeake Bay, inspecting world-cruising monohulls, luxury catamarans, cutting-edge ground tackle, and innovative offshore sailing hardware.
2.5 Years Boat Build Update in 25 minutes – LIVE Quantum Sails Annapolis 2026
Brian and Karin of Sailing SV Delos deliver a 2.5-year retrospective on Delos 2.0 at Quantum Sails in Annapolis, breaking down aluminum naval architecture, electrical systems, and ocean sails.
I’m Buying a POWER YACHT?! Touring the Annapolis Boat Show 2026
Bobby White of Sailing Doodles tours the Annapolis Powerboat Show, evaluating aluminum expedition motor yachts, power catamarans, and vessel refit projects in Maryland.
Where to find us at the Sailboat Show
Ryan and Sophie of Rigging Doctor announce their appearance at the Annapolis Sailboat Show and Cruisers University, presenting standing rigging masterclasses.
Our Final Week of Pregnancy & Annapolis Boat show Announcement!
Ryan and Shaunella of Sailing Sunday prepare their cruising sailboat for infant safety while Ryan heads to the Annapolis Sailboat Show to source offshore gear.
Props // Rerun
Andy Schell and the 59° North Sailing team examine cruising sailboat propellers, weighing the hydrodynamic drag and efficiency of fixed, folding, and feathering designs.
The Realities of Living at Anchor | Solving Everyday Boat Problems Ep. 75 #boatlife
Life at anchor isn't always about sailing. Sometimes it's about solving the everyday challenges that come with living aboard full-time. In this episode, we've settled into one of our favorite anchorages in Spa Creek, Annapolis, and we're tackling three very different problems—ea...
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
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.
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 00:00 Overview Cruising the Chesapeake Bay 01:18 Starting in Norfolk VA, Anchorages 02:36 Sailing the James River 03:37 Delta...
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 winds and storms. After that I'm in the I...
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 entscheidend, um Starkwind und Sturm aus dem Weg zu gehen...
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 a good insight into my weather navigation. ...
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 immer gebe ich einen guten Einblick in meine ...
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! Mein 1. Buch ist bei Amazon erhältlich: Bis...
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. Afterwards we sail to Annapolis. A thunderstorm ...
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 Ziel nicht nur für Segler. Danach segeln wir nach ...
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 pup Jackson as we travel the world on our sai...