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· 116 deeply analysed

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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.30 May 2026 · Lunenburg, Nova Scotia

Published30 May 2026

Duration1:16:06

Views912

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.25 May 2026

Published25 May 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.17 May 2026 · off the coast of Florida, USA

Published17 May 2026

Duration54:16

Views448

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.22 Apr 2026 · Fort Pierce, Florida

Published22 Apr 2026

Duration1:24:19

Views508

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.11 Apr 2026

Published11 Apr 2026

Duration1:24:00

Views485

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.5 Apr 2026 · Charleston County, United States

Published5 Apr 2026

Duration53:50

Views459

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.29 Mar 2026

Published29 Mar 2026

Duration39:50

Views49

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.29 Mar 2026

Published29 Mar 2026

Duration1:25:35

Views75

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

Published29 Mar 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.29 Mar 2026

Published29 Mar 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.29 Mar 2026

Published29 Mar 2026

Duration1:24:02

Views55

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

Published29 Mar 2026

Duration46:42

Views18

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.29 Mar 2026 · West Palm Beach, United States

Published29 Mar 2026

Duration35:26

Views55

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.29 Mar 2026 · Saint Lucie County, United States

Published29 Mar 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.29 Mar 2026 · Fort Pierce, Florida

Published29 Mar 2026

Duration33:56

Views48

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.29 Mar 2026

Published29 Mar 2026

Duration1:13:01

Views200

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

Published29 Mar 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.29 Mar 2026 · Saint Lucie County, United States

Published29 Mar 2026

Duration44:14

Views108

LocationSaint Lucie County, United States

The Devil Wave24 Dec 2025

Published24 Dec 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.15 Dec 2025 · Gulf of Maine

Published15 Dec 2025

Duration1:00:03

Views28K

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.8 Dec 2025

Published8 Dec 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.5 Dec 2025 · North Atlantic, 70 miles north of the Gulf Stream

Published5 Dec 2025

Duration9:31

Views6K

LocationNorth Atlantic, 70 miles north of the Gulf Stream

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

Published1 Dec 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.30 Nov 2025 · South Andros, Bahamas

Published30 Nov 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 12.26 Nov 2025 · South Abaco, Bahamas

Published26 Nov 2025

Duration43:53

Views229

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.23 Nov 2025

Published23 Nov 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*.21 Nov 2025 · Bermuda Triangle

Published21 Nov 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.19 Nov 2025 · North Atlantic Ocean

Published19 Nov 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.18 Nov 2025

Published18 Nov 2025

Duration44:42

Views250

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

Published16 Nov 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.15 Nov 2025 · off the coast of Massachusetts, south of Martha's Vineyard

Published15 Nov 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.13 Nov 2025 · Yarmouth, United States

Published13 Nov 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.13 Nov 2025 · Brunswick County, United States

Published13 Nov 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.2 Nov 2025 · Yarmouth, United States

Published2 Nov 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.30 Oct 2025 · Municipal Unit of Fournas, Greece

Published30 Oct 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.27 Oct 2025 · Gulf of Maine

Published27 Oct 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.25 Oct 2025 · Rockland, United States

Published25 Oct 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.23 Oct 2025

Published23 Oct 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.23 Oct 2025 · Monson, United States

Published23 Oct 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.21 Oct 2025

Published21 Oct 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.15 Oct 2025

Published15 Oct 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.6 Oct 2025 · Dodge County, United States

Published6 Oct 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.30 Sept 2025 · Middletown Township, United States

Published30 Sept 2025

Duration38:09

Views117

LocationMiddletown Township, United States

EP#371 Off to New York for some Sailing26 Sept 2025

Published26 Sept 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.22 Sept 2025

Published22 Sept 2025

Duration1:09:08

Views153

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.9 Sept 2025

Published9 Sept 2025

Duration42:00

Views117

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.6 Sept 2025

Published6 Sept 2025

Duration44:24

Views98

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.1 Sept 2025

Published1 Sept 2025

Duration1:05:36

Views787

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.29 Aug 2025

Published29 Aug 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.23 Aug 2025 · Rockland, United States

Published23 Aug 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.21 Aug 2025 · Boon Township, United States

Published21 Aug 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.20 Aug 2025

Published20 Aug 2025

Duration1:02:53

Views548

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.18 Aug 2025 · Rockland, United States

Published18 Aug 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.15 Aug 2025

Published15 Aug 2025

Duration46:10

Views378

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 4-108.14 Aug 2025 · Edgartown, United States

Published14 Aug 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.14 Aug 2025 · Harwich, United States

Published14 Aug 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.11 Aug 2025 · Harwich, United States

Published11 Aug 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.7 Aug 2025 · Yarmouth, United States

Published7 Aug 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.5 Aug 2025 · Yarmouth, United States

Published5 Aug 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*.3 Aug 2025 · south of Nantucket and Martha's Vineyard

Published3 Aug 2025

Duration12:43

Views148

Locationsouth of Nantucket and Martha's Vineyard

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400 miles northeast of the Bahamas1Atlantic Ocean1Bermuda Triangle1Boon Township, United States2Brunswick County, United States2Charleston County, United States1Chestonia Township, United States3Dodge County, United States1Doldrums, Pacific Ocean1Duplin County, United States1East Grand Bahama, Bahamas1East Honolulu, United States1Edgartown, United States1Fort Pierce, Florida2Fort Pierce, United States1Gulf of Maine3Harwich, United States2Lexington County, United States2Lunenburg, Nova Scotia1Luperón, Dominican Republic1Michigan, United States1mid-Pacific Ocean1Middletown Township, United States1Monson, United States1Municipal Unit of Fournas, Greece1New Orleans, United States1North Atlantic Ocean3North 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 States4Saint Lucie County, United States4San Diego, United States2San Francisco, United States1Sermersooq, Greenland1South Abaco, Bahamas1South Andros, Bahamas1south of Nantucket and Martha's Vineyard1Southern Ocean1Southport, United States1West Palm Beach, United States1West Sulawesi, Indonesia1Yarmouth, United States4