I arrive in the Florida Keys. Warm waters, sunshine, carefree ... um, no, not carefree, not in the winter. Cold fronts come sweeping across the Keys typically once a week during the winter months. The low islands offer little wind protection, and the holding is not always great. So one has to keep a constant weather eye out, and know where to go anchor in case of a severe frontal passage. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: The Temple -- Kevin Boothby VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS R6 Mk II with RF 70-200mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

I arrive in Biscayne Bay in the middle of the night (naturally), nearly fourteen days out of Poquoson, Virginia. After re-provisioning and making some repairs, I am promptly off to the Florida Keys. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Ripples -- Kevin Boothby VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS R6 Mk II with RF 70-200mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

Following that screaming gale I spend a week inching along toward Biscayne Bay in little or no wind. Entering into the Bahamas the seas become flat as a lake, and the sunsets are spectacular. Still I wish I was progressing a little faster, especially when the fresh food runs out. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Loose Ends -- Kevin Boothby VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS R6 Mk II with RF 70-200mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

After a screaming gale I get light airs. Not complaining, although the slow progress does get frustrating after a while. An old Gordon Lightfoot song brings back memories of when I lived in a tiny apartment in Evanston, IL, worked at Arthur Andersen in Chicago, and constantly dreamed of blue water sailing. Now that dream is my life. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS R6 Mk II with RF 70-200mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

I am unable to get far enough south to avoid gale conditions ushered in by a passing cold front. No option remains but to reef down and ride it out. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS R6 Mk II with RF 70-200mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

The usual late fall offshore passage scenario. You depart the US east coast on the tail of a cold front, which supplies you with favorable northerly winds. But there's always another front moving through in a few days' time. The typical strategy is to sail south as fast as you can, by which you hope to avoid the worst of it. That's the hope. It's a race against the weather clock. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Is This Love (Whitesnake) -- Kevin's No-Copyright Covers VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS R6 Mk II with RF 70-200mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

No offshore weather window will be perfect. So long as the forecast calls for mostly fair winds and no severe weather, that's a window. And so it is. Well almost. I have to move south fast in order to avoid a rather strong frontal passage four days out. Other than that, looks like a decent run to the Bahamas, and then on to Florida. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Is This Love (Whitesnake) -- Kevin's No-Copyright Covers VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS R6 Mk II with RF 70-200mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

Despite the light and fickle winds I work my way up the Corrotoman River to a place called Sandy Point, where I am detained for several days on account of inclement weather. It is October after all. With the standard southbound departure date of November 1 only days away, I am now paying attention to the offshore weather maps. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS R6 Mk II with RF 70-200mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

A forecasted gale obliges me to put in to Put-in-Creek, on the East River of Mobjack Bay. It is still too early to head south, and October is a great month for cruising the Chesapeake, so the choice is clear. Owing to light winds I don't make Jackson Creek until just after dark. A tricky entrance to negotiate in the daytime--and which requires a fair wind if under sail--at night is quite the adrenaline rush. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Just Now -- Kevin Boothby VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

In this episode we pick up where we last left off--in the middle of the ocean, approximately halfway between Buzzards Bay and the Chesapeake Bay, drifting with no wind. Light conditions persist for the next 36 hours until some solid southerlies finally show up ahead of a strong cold front. But before then we are met with all sorts of wonders, from a giant Fin Whale to a (yellowish) green flash! SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: The Temple -- Kevin Boothby VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

After a swift departure from Buzzards Bay, MA, I am beset with several days of light and variable winds. I sometimes play the catspaws for a few miles, otherwise get back to my book. Or guitar. Or video editing. I'm rarely bored at sea, regardless of the conditions. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Freedom -- Atch VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

Approaching inclement weather sends me into the sheltered waters of Cuttyhunk Pond. The narrow dredged channel, however, presents a challenge to the engineless boat, for tacking is not possible hence a fair wind is a must. Meanwhile, two major hurricanes are churning up the North Atlantic, but are forecast to move on soon, opening up a southbound sailing window. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Feel Better -- Kevin Boothby VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

After negotiating some terrifying currents while entering Nantucket Sound, I am treated with some fine sailing days on Buzzards Bay. Approaching inclement weather, however, obliges me to seek shelter inside the Cuttyhunk lagoon. The easterly winds preceding the low should blow me right in through the narrow, dredged channel--in theory. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Just Now -- Kevin Boothby VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

It's time to head south if I want to avoid the worst of winter's wrath. I have to tack all the way out from Quahog Bay against the standard southwest wind, but once past Round Rock, I'm off toward Cape Cod. Except that the latest GRIB's are showing serious thunderstorm activity down south, so I delay my departure one day. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Freedom -- Atch VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

Time has come to pay the piper for the pleasant shelter of Ebenecook over pressing on to Quahog Bay when I had a fair, though brisk wind. Upwind, up-current. All day, all the way to Cape Small. Then the wind goes light. Decision time: do I try to make an anchorage for the night, or heave-to offshore? SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Freedom -- Atch VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

Well I can't just wander the coast of Maine in perpetuity because, firstly, summer will end and then comes winter, and that really changes things. Plus there's mundane things like doctor's appointments. I have an eye appointment back in Brunswick, but here I am in Bar Harbor, more than 100 miles away. I have ten days, but no engine, so best to get a move on. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

Well the prevailing afternoon seabreeze means I have to tack back out of Somes Sound. Also, I have to wait until 14:30 hours for the current to turn fair at the entrance. This means that I don't make Bar Harbor until early evening. And the wind continues to play hide-and-seek with me, finally obliging me to drop anchor in Hull Bay for the night. That wasn't the original plan, but it will do. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Time Out -- Atch VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

I continue my peregrinations down east along the Maine coast, to Southwest Harbor and Somes Sound. Wonderful summer sailing--except for the ever changing, ever challenging sailing conditions. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: The Temple -- Kevin Boothby VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

Ruth Avery goes romping down Eggemoggin Reach in classic fashion: reaching in a brisk afternoon southwester. This is literally a storied part of Maine, as the Brooklin Boatyard's late in-house architect, Joel White, was the son of the famous author E.B. White. This inspires me to re-read Charlotte's Web, a story I remember quite vividly from my childhood. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Fields of Gold (Sting) -- Kevin's No-Copyright Covers VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs

In this week's episode I sail from Pulpit Harbor to Northwest Harbor, a distance of scarcely ten miles. But this is the Penobscot Bay and I am under sail alone. Flukey winds, tidal currents, a maze of island and rocks can turn a mere day sail into a memorable adventure. SUPPORT HOW TO SAIL OCEANS ON PATREON: https://patreon.com/user?u=12372934 HOW TO SAIL OCEANS ON RUMBLE: https://rumble.com/c/c-1981134 HOW TO SAIL OCEANS TEE SHIRT: https://maritimetees.net/search?q=how+to+sail+oceans DONATE: https://www.paypal.me/KevinBoothby WEBSITE: https://www.kevinboothbysailing.com MUSIC: Echoes --- Atch Just Now --- Kevin Boothby Journey -- Atch VIDEO SOUNDTRACKS: https://soundcloud.com/user-177118317 CAMERAS: Canon EOS 60D with EF 24-105mm L IS zoom lens Go Pro Hero 9 Black Go Pro Hero 12 Black Go Pro Hero 13 Black DRONE: DJI Phantom 3 Professional THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs