Sailing Into Oblivion

On October 3rd 2017, Jerome Rand set sail from Gloucester Mass aboard his Westsail 32 "Mighty Sparrow." 271 day later a bearded, skinny sailor came over the horizon after sailing 29,805 miles around the world. These videos are from the collection taken during the trip. This was one of the very few solo nonstop circumnavigations aboard a boat 32 feet or less. The adventure of a life time brough…

Lunenburg, Nova Scotia· May 2026

411 videos· 54 deeply analyzed

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Matt Rurtherford Returns to the Show, EP#429 with Atlantic Waves background LoopMatt Rutherford details his solo nonstop Arctic circumnavigation attempt, departing Lunenburg in July.May 30, 2026 · Lunenburg, Nova Scotia

PublishedMay 30, 2026

Duration1:16:06

Views809

LocationLunenburg, Nova Scotia

@Sailing With Phoenix | Oliver returns to the show!Jerome Rand and Oliver discuss refit logistics, Cape Horn timing, and sea trial strategies for a circumnavigation.May 25, 2026

PublishedMay 25, 2026

Duration1:09:29

Views2K

Sailing Into Oblivion Podcast EP#422 Offshore Recordings with Background Sailing View LoopA Westsail 32 navigates light winds and Gulf Stream rips during a coastal passage to Cape Fear.May 17, 2026 · off the coast of Florida, USA

PublishedMay 17, 2026

Duration54:16

Views424

Locationoff the coast of Florida, USA

Sailing Adventures with Brendan and Chanell, EP#421A tandem anchor setup using Dyneema provides increased holding security for cruising sailors in varied conditions.Apr 22, 2026 · Fort Pierce, Florida

PublishedApr 22, 2026

Duration1:24:19

Views463

LocationFort Pierce, Florida

Reality of a Refit with Colin Denker, EP#418Colin Denker's Westsail 32 refit in Beaufort, South Carolina tests motivation, procrastination, and liveaboard endurance.Apr 11, 2026

PublishedApr 11, 2026

Duration1:24:00

Views459

Exercise, Sailing to Charlston, and what's next, EP#417A delivery passage from Fort Pierce to Charleston highlights the risks of overconfidence after easy sailing conditions.Apr 5, 2026 · Charleston County, United States

PublishedApr 5, 2026

Duration53:50

Views448

LocationCharleston County, United States

The Engine Lives! EP#405A worn Perkins 4108 lift-pump lever caused two months of fuel-starvation problems aboard Into Oblivion.Mar 29, 2026

PublishedMar 29, 2026

Duration39:50

Views46

Living Life and Facing Fear with Shane Pollard, EP#406Jerome Rand and Shane Pollard discuss managing fear and anxiety during solo offshore sailing and adventure writing.Mar 29, 2026

PublishedMar 29, 2026

Duration1:25:35

Views71

Chartering a Yacht with Ian Pedersen, EP#407The Moorings operates 200-plus boats in the BVI across a tiered bareboat qualification system.Mar 29, 2026

PublishedMar 29, 2026

Duration1:02:55

Views9

Solo Show Updates, EP#408Jerome Rand discusses boat market trends, upcoming speaking engagements, and plans to move his Westsail 32 north.Mar 29, 2026

PublishedMar 29, 2026

Duration27:01

Views12

Self-Steering Systems, EP#409An Aries wind vane paired with a tiller pilot powers a Westsail 32 through offshore passages on minimal solar.Mar 29, 2026

PublishedMar 29, 2026

Duration1:24:02

Views52

Fireside Podcast from JeromesTown EP#410A solo sailor discusses using the moon and stars for night navigation and managing travel delays.Mar 29, 2026 · Boon Township, United States

PublishedMar 29, 2026

Duration46:42

Views15

LocationBoon Township, United States

Knocking Out the Checklist, Pre-departure, EP#412A solo sailor prepares a Westsail 32 for a two-week offshore passage using a comprehensive maintenance checklist.Mar 29, 2026 · West Palm Beach, United States

PublishedMar 29, 2026

Duration35:26

Views52

LocationWest Palm Beach, United States

Time for a Quick Trip in the Atlantic! EP#411A solo sailor prepares his Westsail 32 for an Atlantic passage, timing his departure around inlet conditions.Mar 29, 2026 · Saint Lucie County, United States

PublishedMar 29, 2026

Duration21:08

Views19

LocationSaint Lucie County, United States

Holding Fast on the Dock, EP#413A Westsail 32 owner delays an offshore departure to avoid thunderstorms, using the time for boat maintenance.Mar 29, 2026 · Fort Pierce, Florida

PublishedMar 29, 2026

Duration33:56

Views44

LocationFort Pierce, Florida

The Westsail has Sold with Marc EP#414Marc's Westsail 32 sold in under six months after showing to just three parties.Mar 29, 2026

PublishedMar 29, 2026

Duration1:13:01

Views180

Offshore Recordings March 2026, EP#415A Westsail 32 owner reports erratic windvane performance requiring a full bearing and bushing overhaul.Mar 29, 2026

PublishedMar 29, 2026

Duration30:06

Views48

Glad to be on the Dock, Gale Warning in Effect EP#415A Westsail 32 remains docked in Florida during a gale, highlighting the stability of heavy-displacement cruising sailboats.Mar 29, 2026 · Saint Lucie County, United States

PublishedMar 29, 2026

Duration44:14

Views107

LocationSaint Lucie County, United States

The Devil WaveDec 24, 2025

PublishedDec 24, 2025

Duration1:07

Views199K

High Seas Adventure in the North Atlantic 2022, Westsail 32 Mighty SparrowA near-knockdown to 180 degrees strips Mighty Sparrow's solar panels and ends a 14,000-mile Atlantic figure-eight attempt.Dec 15, 2025 · Gulf of Maine

PublishedDec 15, 2025

Duration1:00:03

Views27K

LocationGulf of Maine

EP#393 From the Sea, to a Plane, to a CarJerome Rand discusses offshore passage planning, crew vetting, and upcoming sea anchor experiments for heavy weather.Dec 8, 2025

PublishedDec 8, 2025

Duration39:44

Views310

Cape Cod to Florida, North Atlantic in November 2025 Westsail, 32 Mighty SparrowA Westsail 32 rides out a 982 hPa low 70 miles north of the Gulf Stream in November.Dec 5, 2025 · North Atlantic, 70 miles north of the Gulf Stream

PublishedDec 5, 2025

Duration9:31

Views5K

LocationNorth Atlantic, 70 miles north of the Gulf Stream

Sailing In a Gale, Westsail 32, North Atlantic OceanThe video contains no relevant sailing information.Dec 1, 2025 · North Atlantic Ocean

PublishedDec 1, 2025

Duration6:21

Views24K

LocationNorth Atlantic Ocean

EP#392 Dry Land is not a Myth!Jerome Rand hand-pumps a failing diesel injector every two minutes to navigate Fort Pierce Inlet solo.Nov 30, 2025 · South Andros, Bahamas

PublishedNov 30, 2025

Duration1:03:10

Views311

LocationSouth Andros, Bahamas

EP#391 Welcome to Squall CountrySinglehanded Westsail 32 navigates squalls and AIS ship traffic approaching the Abacos on day 12.Nov 26, 2025 · South Abaco, Bahamas

PublishedNov 26, 2025

Duration43:53

Views228

LocationSouth Abaco, Bahamas

EP#390 Low Input Mode AchievedA Westsail 32 sailor manages battery drain, light-wind sail selection, and weather routing during a Florida passage.Nov 23, 2025

PublishedNov 23, 2025

Duration59:25

Views218

EP#389 A Quiet Day at SeaA rising oil level in the engine suggests a potential diesel leak into the crankcase on *Sparrow*.Nov 21, 2025 · Bermuda Triangle

PublishedNov 21, 2025

Duration32:13

Views164

LocationBermuda Triangle

EP#388 Becalmed and then SailingSolo on a Westsail 32, 700 miles from Florida, Rand weighs Gulf Stream timing after a two-day gale.Nov 19, 2025 · North Atlantic Ocean

PublishedNov 19, 2025

Duration36:55

Views130

LocationNorth Atlantic Ocean

EP#387 The GaleSolo sailor rides a Force 9 gale on a Westsail 32 after a 25-millibar pressure drop in 24 hours.Nov 18, 2025

PublishedNov 18, 2025

Duration44:42

Views247

EP#386 Going for it!Jerome Rand navigates a Westsail 32 through a Gulf Stream crossing while managing shifting weather and connectivity.Nov 16, 2025 · off the coast of the Gulf Stream

PublishedNov 16, 2025

Duration34:16

Views161

Locationoff the coast of the Gulf Stream

EP#385 Day 1 Escape From the CapeJerome Rand sails his Westsail 32, Into Oblivion, south from Cape Cod to avoid an incoming gale.Nov 15, 2025 · off the coast of Massachusetts, south of Martha's Vineyard

PublishedNov 15, 2025

Duration36:27

Views197

Locationoff the coast of Massachusetts, south of Martha's Vineyard

Weather Planning for the coming PassageJerome Rand delays a passage on his Westsail 32 to avoid hazardous wind-against-current conditions in the Gulf Stream.Nov 13, 2025 · Yarmouth, United States

PublishedNov 13, 2025

Duration5:58

Views1K

LocationYarmouth, United States

EP#384 Getting Ready for the High Seas Once Again!Jerome Rand delays his solo passage on *Sparrow* to avoid gale-force winds in the North Atlantic.Nov 13, 2025 · Brunswick County, United States

PublishedNov 13, 2025

Duration24:35

Views150

LocationBrunswick County, United States

EP#383 Waylaid by the WeatherJerome Rand manages weather delays and maintenance on his Westsail 32, *Into Oblivion*, while planning a southern transit.Nov 2, 2025 · Yarmouth, United States

PublishedNov 2, 2025

Duration38:26

Views143

LocationYarmouth, United States

EP#382 Sailing with a 14-month-old, the Vanabond TalesEddie and Kelly sail the Mediterranean with a 14-month-old aboard their 29-foot boat, adding netting, tethers, and a life raft.Oct 30, 2025 · Municipal Unit of Fournas, Greece

PublishedOct 30, 2025

Duration54:56

Views142

LocationMunicipal Unit of Fournas, Greece

EP#381 Maine-Cape Cod, Part 2A navigation system failure forced a manual approach into Nantucket Sound using pre-captured chart photographs on Into Oblivion.Oct 27, 2025 · Gulf of Maine

PublishedOct 27, 2025

Duration22:05

Views132

LocationGulf of Maine

EP#380 Maine-Cape Cod, Day 1Jerome Rand sails his Westsail 32 from Rockland to Cape Cod, navigating the Gulf of Maine via Starlink.Oct 25, 2025 · Rockland, United States

PublishedOct 25, 2025

Duration37:52

Views176

LocationRockland, United States

EP#379 Last Night on Land! Sparrow is going back to SeaJerome Rand prepares his Westsail 32 for a passage from Maine to Cape Cod during autumn gales.Oct 23, 2025

PublishedOct 23, 2025

Duration28:45

Views146

EP#378 Murf-Cast Special EditionThomas Murphy details his arrest for trespassing at the Boss Hog 150 race in Wiscasset, Maine.Oct 23, 2025 · Monson, United States

PublishedOct 23, 2025

Duration23:14

Views86

LocationMonson, United States

EP#377 Back on Sparrow, Pre-Launch ProjectsJerome Rand prepares the Westsail 32 *Sparrow* for a fall offshore passage from the Northeast to Florida.Oct 21, 2025

PublishedOct 21, 2025

Duration53:40

Views177

EP#375 @Sailing_With_Phoenix to sail Around the WorldJerome Rand coaches Oliver (Sailing With Phoenix) toward a solo nonstop 30,000-mile circumnavigation departing late September.Oct 15, 2025

PublishedOct 15, 2025

Duration49:43

Views3K

EP#373 Life on the RoadJerome Rand plans offshore training on a Hallberg-Rassy to navigate the hazards of Cape Hatteras safely.Oct 6, 2025 · Dodge County, United States

PublishedOct 6, 2025

Duration42:35

Views138

LocationDodge County, United States

EP#372 Coaching Trip to NYCJerome Rand conducts sail training and system refinement aboard a Tazwell 43 near Sandy Hook, New Jersey.Sep 30, 2025 · Middletown Township, United States

PublishedSep 30, 2025

Duration38:09

Views117

LocationMiddletown Township, United States

EP#371 Off to New York for some SailingSep 26, 2025

PublishedSep 26, 2025

Duration26:05

Views94

EP#370 Buying and Selling Boats with ChelleEffective boat sales require decluttering and high-quality photography to stand out in a cooling post-pandemic market.Sep 22, 2025

PublishedSep 22, 2025

Duration1:09:08

Views152

EP#369 Camping Trip Wrap-up, the Brutality on Mother NatureJerome Rand inspects and re-beds the chain plates on Into Oblivion before a planned offshore passage to Florida.Sep 9, 2025

PublishedSep 9, 2025

Duration42:00

Views116

EP#368 Guest Appearance on the Really Riveting Podcast with LexyJerome Rand explains how the team-building mantra "juicing" improves service quality and personal engagement on sailing charters.Sep 6, 2025

PublishedSep 6, 2025

Duration44:24

Views95

EP#367 Colin Denker Returns to the ShowJerome Rand and Colin Denker discuss Yanmar engine maintenance, inspecting whisker stay anchor points, and offshore passage planning.Sep 1, 2025

PublishedSep 1, 2025

Duration1:05:36

Views779

EP#366 Coaching and Training with Author Francesca FilippiniJerome Rand and Francesca Filippini compare sailing instruction to retail coaching using the "skill or will" framework.Aug 29, 2025

PublishedAug 29, 2025

Duration1:28:11

Views98

EP#365 Conversation with Murf, Rockland MaineJerome Rand and Rockland lobsterman Thomas Murphy drink White Claws and trade stories at the shack in Maine.Aug 23, 2025 · Rockland, United States

PublishedAug 23, 2025

Duration1:07:42

Views139

LocationRockland, United States

EP#364 Yard Period Done, Back to JeromesTownJerome Rand maintains the teak cap rail and bowsprit of *Into Oblivion* during a Maine yard period.Aug 21, 2025 · Boon Township, United States

PublishedAug 21, 2025

Duration35:04

Views124

LocationBoon Township, United States

Relaxing Harbor View with Mighty Sparrow Westsail 32The video contains no actionable information regarding the Westsail 32 named Mighty Sparrow.Aug 20, 2025

PublishedAug 20, 2025

Duration1:02:53

Views544

EP#363 Cape Cod to Rockland Maine Coastal RecordingsJerome Rand sails Into Oblivion from Cape Cod to Rockland, Maine, for a scheduled boatyard haul-out.Aug 18, 2025 · Rockland, United States

PublishedAug 18, 2025

Duration1:06:27

Views124

LocationRockland, United States

Calm Ocean Sunrise View 40 MinA 40-minute recording captures calm ocean conditions and a sunrise at sea.Aug 15, 2025

PublishedAug 15, 2025

Duration46:10

Views376

Light Wind Trip Cape Fear to Cape Cod Westsail 32 August 2025Tightening fuel line hose clamps resolves intermittent engine surging caused by air leaks on a Perkins 4-108.Aug 14, 2025 · Edgartown, United States

PublishedAug 14, 2025

Duration12:07

Views813

LocationEdgartown, United States

EP#362 Offshore Recordings NC to Cape Cod Part ThreeJerome Rand heaves to *Into Oblivion* to weather 30-knot gusts and steep seas off the Massachusetts coast.Aug 14, 2025 · Harwich, United States

PublishedAug 14, 2025

Duration1:12:03

Views123

LocationHarwich, United States

EP#361 Offshore Recordings Part 2 NC-CapeJerome Rand troubleshoots engine performance and fuel filtration on the Westsail *Into Oblivion* during a coastal passage.Aug 11, 2025 · Harwich, United States

PublishedAug 11, 2025

Duration1:05:01

Views105

LocationHarwich, United States

EP#360 Offshore Recordings Part One, NC-Cape CodJerome Rand navigates the *Mighty Sparrow* from the Carolinas to Cape Cod while managing extreme offshore heat.Aug 7, 2025 · Yarmouth, United States

PublishedAug 7, 2025

Duration1:11:04

Views167

LocationYarmouth, United States

EP#359 It Was A Long NightJerome Rand navigates Mighty Sparrow through Nantucket Sound shoals and docks in Cape Cod after an overnight passage.Aug 5, 2025 · Yarmouth, United States

PublishedAug 5, 2025

Duration31:40

Views166

LocationYarmouth, United States

Long Night AheadJerome Rand navigates the wind farms south of Nantucket while sailing his Westsail 32, *Mighty Sparrow*.Aug 3, 2025 · south of Nantucket and Martha's Vineyard

PublishedAug 3, 2025

Duration12:43

Views148

Locationsouth of Nantucket and Martha's Vineyard

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Bermuda Triangle1Boon Township, United States2Brunswick County, United States1Charleston County, United States1Chestonia Township, United States1Dodge County, United States1Duplin County, United States1Edgartown, United States1Fort Pierce, Florida2Gulf of Maine2Harwich, United States2Lexington County, United States1Lunenburg, Nova Scotia1Luperón, Dominican Republic1Michigan, United States1Middletown Township, United States1Monson, United States1Municipal Unit of Fournas, Greece1North Atlantic Ocean2North Atlantic, 70 miles north of the Gulf Stream1off the coast of Florida, USA1off the coast of Massachusetts, south of Martha's Vineyard1off the coast of the Gulf Stream1Pamlico County, United States1Rockland, United States3Saint Lucie County, United States2Sermersooq, Greenland1South Abaco, Bahamas1South Andros, Bahamas1south of Nantucket and Martha's Vineyard1Southport, United States1West Palm Beach, United States1Yarmouth, United States4