Stella Overboard

Just an American and an Australian, sailing and surfing our way around the world. Inexperienced but determined, we sold everything we owned and bought a sailboat to chase waves across the globe. With little idea of what we are doing, just a dream and some grit, we set off to learn how to sail, explore untouched places, and live a life less ordinary. Follow along as we dive headfirst into an unch…

Kedah, Malaysia· Oct 2026

77 videos· 75 deeply analysed

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The BEST Dinghy on the Market?! | Unboxing & Setup (TRUE KIT)The True Kit inflatable tender features independent pontoon valves and a high-pressure 8 PSI air-mat floor.12 Oct 2026 · Kedah, Malaysia

Published12 Oct 2026

Duration13:54

Views17K

LocationKedah, Malaysia

I Took My Australian Boyfriend to America…The owners of the 39-foot sailboat Stella sourced marine electronics and gear in Annapolis, Maryland.4 Oct 2026 · Gunnison County, United States

Published4 Oct 2026

Duration17:35

Views15K

LocationGunnison County, United States

Our Life at Sea | Living OFF-GRID on a SailboatThe crew of the 39-foot sailboat Stella performs a chemical flush to troubleshoot a sluggish water maker.30 Sept 2026 · West Sumatra, Indonesia

Published30 Sept 2026

Duration26:16

Views10K

LocationWest Sumatra, Indonesia

Traveling to a New Country by SailboatThe 39-foot sailboat Stella navigates the Malacca Strait while dodging container ships and squalls during a passage.27 Sept 2026 · Gunnison County, United States

Published27 Sept 2026

Duration27:39

Views19K

LocationGunnison County, United States

American & Australian Couple Living on a Sailboat & Traveling the WorldCamille Milligan and Jesse cruise Indonesia aboard their 39-foot sailboat, Stella, while spearfishing and trading with locals.20 Sept 2026 · Great Falls, United States

Published20 Sept 2026

Duration19:08

Views33K

LocationGreat Falls, United States

INSANE Fishing From Our Sailboat! Mahi Mahi & WahooThe crew of the 39-foot sailboat Stella catches mahi-mahi and wahoo before encountering a 42-knot squall.12 Sept 2026 · Kapuas, Indonesia

Published12 Sept 2026

Duration18:56

Views77K

LocationKapuas, Indonesia

The Reality of Off-Grid Sailing: Trouble in ParadiseThe crew replaces a sheared boom pivot pin with a stainless steel bolt before a long passage.5 Sept 2026 · Marga, Indonesia

Published5 Sept 2026

Duration20:03

Views66K

LocationMarga, Indonesia

Crossing the Equator in Search of Waves & Fish | Sailing IndonesiaThe crew of Stella replaces a broken surfboard at Kandui Resort before crossing the equator toward Nias.29 Aug 2026 · Kapuas, Indonesia

Published29 Aug 2026

Duration20:52

Views38K

LocationKapuas, Indonesia

Living Off the Ocean: Fishing, Sailing & SurfingThe crew of Stella navigates the Mentawai Islands while managing fishing, surfing, and remote medical first aid.22 Aug 2026 · Kapuas, Indonesia

Published22 Aug 2026

Duration22:05

Views48K

LocationKapuas, Indonesia

WE SAILED TO THE MENTAWAIS FOR THIS WAVEA 36-foot catamaran anchors near the Mentawai Islands to access a significant surf swell in Indonesia.15 Aug 2026 · West Sumatra, Indonesia

Published15 Aug 2026

Duration23:25

Views12K

LocationWest Sumatra, Indonesia

3 Perfect Waves in One Day | Sailing the MentawaisA crew navigates the Mentawai Islands to hit three surf breaks in one day while managing deep anchorages.8 Aug 2026 · West Sumatra, Indonesia

Published8 Aug 2026

Duration25:30

Views36K

LocationWest Sumatra, Indonesia

Our OFF-GRID Life on a Sailboat in Indonesia1 Aug 2026

Published1 Aug 2026

Duration25:41

Views10K

Surfing the Mentawai Islands Off Our SailboatThe crew of *Stella* ends a four-month fishing drought by catching a yellowfin tuna while sailing.25 Jul 2026 · North Kuta, Indonesia

Published25 Jul 2026

Duration26:02

Views45K

LocationNorth Kuta, Indonesia

Hitchhiking on a Sailboat to Perfect Waves in IndonesiaThe 39-foot sailboat Stella transports surfers to remote breaks in the Tello Islands, Indonesia.18 Jul 2026 · North Kuta, Indonesia

Published18 Jul 2026

Duration22:12

Views14K

LocationNorth Kuta, Indonesia

2 Girls, One Sailboat & Our Biggest Milestone YetStella crosses the equator off Indonesia with a rum tribute and egg-cracking shellback ceremony.11 Jul 2026 · North Kuta, Indonesia

Published11 Jul 2026

Duration23:49

Views17K

LocationNorth Kuta, Indonesia

A Girl Asked to Join Our Sailboat... So We Said YesAn Instagram follower joins Stella in Indonesia for surfing, spearfishing, and an equator crossing ahead.4 Jul 2026 · North Kuta, Indonesia

Published4 Jul 2026

Duration22:31

Views170K

LocationNorth Kuta, Indonesia

Sailing to Paradise for Perfect WavesA windlass fails mid-retrieval during a 42-knot squall, forcing manual chain hauling to avoid grounding.27 Jun 2026 · Kuta Selatan, Indonesia

Published27 Jun 2026

Duration25:18

Views18K

LocationKuta Selatan, Indonesia

Sailing Into the Jungle to Find the Perfect WaveCruisers in Nias, Indonesia, trek through jungle and coastline to access a remote surf break.20 Jun 2026 · North Kuta, Indonesia

Published20 Jun 2026

Duration20:01

Views10K

LocationNorth Kuta, Indonesia

The Most Remote Wave We've Found YetThe crew performs engine maintenance and replaces a worn anchor roller while searching for remote surf breaks.13 Jun 2026 · South Jakarta, Indonesia

Published13 Jun 2026

Duration22:40

Views18K

LocationSouth Jakarta, Indonesia

90 Days Sailing Indonesia… Here's What It's LikeSailing Nias's northern coast in wet season: squalls, a leaking diesel can, and 8-to-10-foot reef breaks.6 Jun 2026 · North Kuta, Indonesia

Published6 Jun 2026

Duration25:00

Views151K

LocationNorth Kuta, Indonesia

Crocodiles, Malaria & Surf | Sailing IndonesiaA drone spots a crocodile below Matt and Grace seconds before they jump in at the Banyaks, Indonesia.31 May 2026 · Kuta Selatan, Indonesia

Published31 May 2026

Duration27:29

Views38K

LocationKuta Selatan, Indonesia

2 Australians and an American sail to a secret surf spot in IndonesiaA stopover anchorage in remote Indonesia unexpectedly delivers barreling reef waves with no other surfers in sight.23 May 2026 · Kuta Selatan, Indonesia

Published23 May 2026

Duration20:03

Views22K

LocationKuta Selatan, Indonesia

How Two 20-Year-Olds Afforded to Buy a Sailboat & Sail AwayWorking fly-in, fly-out mining jobs in Australia provided the capital to purchase and maintain a sailboat.16 May 2026 · Ban Nong Chaeng, Thailand

Published16 May 2026

Duration20:16

Views33K

LocationBan Nong Chaeng, Thailand

1 Year Living on a Sailboat… The Good, The Bad & Was It Worth It?Two sailors with no prior experience bought a boat in Malaysia and reached Indonesia in one year.9 May 2026 · Kapuas, Indonesia

Published9 May 2026

Duration21:15

Views25K

LocationKapuas, Indonesia

Getting to This Surf Spot Wasn’t Easy (Sailboat Life)A drone-spotted wave in Indonesia required a jungle hike across a local family's island to reach.2 May 2026 · Marga, Indonesia

Published2 May 2026

Duration15:54

Views63K

LocationMarga, Indonesia

Lightning Everywhere… We Sailed Into a Storm We Never Saw ComingA 130-mile overnight crossing turns into 48 hours of continuous lightning and squalls with two reefs in.25 Apr 2026 · Kapuas, Indonesia

Published25 Apr 2026

Duration14:43

Views8K

LocationKapuas, Indonesia

Spend the Day With Us in Indonesia (Surfing, Fishing & Boat Life)Sailing the northern Sumatra coast: reef early, troll a line, and catch aku for sashimi.18 Apr 2026 · Marga, Indonesia

Published18 Apr 2026

Duration26:02

Views18K

LocationMarga, Indonesia

We Just Arrived in Indonesia… Now the Adventure Begins (Ep 1)Sabang's five-group boat check-in requires ferrying officials by tender before Indonesia entry is complete.11 Apr 2026 · Sabang, Indonesia

Published11 Apr 2026

Duration20:22

Views17K

LocationSabang, Indonesia

Our FIRST Crossing Was WAY More Intense Than ExpectedFirst-time offshore sailors navigate the Malacca Strait's 250-daily-ship traffic and unlit fishing boats at night.4 Apr 2026 · Sabang, Indonesia

Published4 Apr 2026

Duration24:57

Views19K

LocationSabang, Indonesia

How We Sanded, Antifouled & Painted Our Sailboat (No Experience)First-timers apply five coats of Micron 99 antifoul to a sailboat hull before sailing to remote Indonesia.28 Mar 2026 · Cenang Beach, Malaysia

Published28 Mar 2026

Duration13:30

Views11K

LocationCenang Beach, Malaysia

From Boatyard Chaos to Back in the Water (Full Transformation)Five coats of Micron 99 and a new cutlass bearing recovered nearly two knots of engine speed on Stella.21 Mar 2026 · Kedah, Malaysia

Published21 Mar 2026

Duration16:18

Views21K

LocationKedah, Malaysia

The Worst Part of Owning a Sailboat (Boatyard Chaos Begins)A seized propeller hub and an incorrectly sized cutlass bearing force a major delay during haul-out maintenance.14 Mar 2026 · Cenang Beach, Malaysia

Published14 Mar 2026

Duration12:18

Views17K

LocationCenang Beach, Malaysia

Replacing Every Thru Hull on Our Sailboat (DIY Boatyard Refit) - TRUDesignReplacing seized bronze through-hulls with TruDesign composite fittings improves safety and prevents future corrosion-related structural failure.8 Mar 2026 · Si Sunthon, Thailand

Published8 Mar 2026

Duration14:31

Views14K

LocationSi Sunthon, Thailand

Life on a Sailboat in Thailand | Family, Snorkeling & Island LivingA couple hauls out their 39-foot sailboat in Malaysia after two months cruising Thailand's islands.28 Feb 2026 · Ban Ko Li Pe, Thailand

Published28 Feb 2026

Duration18:54

Views20K

LocationBan Ko Li Pe, Thailand

Living on a Sailboat in Our 20s | A Real Day at Sea in ThailandThai officials fine boats 5,000 baht for missing check-in paperwork at a Railay anchorage.21 Feb 2026 · Sala Dan, Thailand

Published21 Feb 2026

Duration14:46

Views49K

LocationSala Dan, Thailand

Everything Broke at Sea… Engine, Toilet & Watermaker FailureEngine air lock, toilet pump failure, and watermaker fix on a 39-foot sailboat in Thailand.15 Feb 2026 · Ton Sai, Thailand

Published15 Feb 2026

Duration17:35

Views18K

LocationTon Sai, Thailand

Sailing Into a New Country 🇹🇭 | Customs, Immigration & the Reality of Boat LifeClearing into Thailand by sailboat requires three separate offices in Krabi, including a tidal river entrance.11 Feb 2026 · Ban Nong Chaeng, Thailand

Published11 Feb 2026

Duration10:09

Views5K

LocationBan Nong Chaeng, Thailand

IS THIS PLACE EVEN REAL?! Sailing Thailand’s Incredible IslandsThailand's hongs are only passable by tender at low tide, with cave ceilings inches overhead.8 Feb 2026 · Si Sunthon, Thailand

Published8 Feb 2026

Duration16:28

Views15K

LocationSi Sunthon, Thailand

Wild Voyage Through Thailand by SailboatStella sails Malaysia to Koh Lanta with six aboard, finding Koh Ha too exposed for its underwater caves.1 Feb 2026 · Ban Nong Chaeng, Thailand

Published1 Feb 2026

Duration16:23

Views23K

LocationBan Nong Chaeng, Thailand

We Sailed to One of Thailand’s Best Dive Spots | Off Grid Living25 Jan 2026

Published25 Jan 2026

Duration14:15

Views7K

Sailing From Malaysia to Thailand | Point of View Sailing — Feel Like You’re OnboardFirst reef ever attempted on a Malaysia-to-Koh-Lipe passage in 22-knot winds with swell.18 Jan 2026 · Ban Nong Chaeng, Thailand

Published18 Jan 2026

Duration34:58

Views12K

LocationBan Nong Chaeng, Thailand

Buying a Sailboat in Malaysia: Tax-Free, Cheap Repairs & Easy SailingCustom davits in Langkawi cost a quarter of equivalent Australian or U.S. prices, with no import tax on boats.11 Jan 2026 · Kedah, Malaysia

Published11 Jan 2026

Duration12:32

Views142K

LocationKedah, Malaysia

Chasing Freedom at Sea — Best, Worst & Scariest Moments of 2025 | Raw & Real40-knot winds and 3-meter swells force a monsoon-season abort back to Lanta during Thailand sailing.4 Jan 2026 · Great Falls, United States

Published4 Jan 2026

Duration52:23

Views8K

LocationGreat Falls, United States

Boat Maintenance in a Foreign Country: Diesel Engine ServiceDiesel engine service in Langkawi includes oil change, filter swap, belt replacement, and a slipping halyard clutch fix.28 Dec 2025 · Dranesville, United States

Published28 Dec 2025

Duration15:42

Views9K

LocationDranesville, United States

Sailing With Parents Was Harder Than We ExpectedA recurring jib furler jam on Stella is traced to a jib halyard slipping its clutch off Langkawi.21 Dec 2025 · Gunnison County, United States

Published21 Dec 2025

Duration23:19

Views12K

LocationGunnison County, United States

Young Couple Buys a Sailboat… 6 Months Later This Is Their LifeA rigging error jammed the headsail in 40-knot winds, forcing an underway mast climb to drop it manually.14 Dec 2025 · Padang Tengku, Malaysia

Published14 Dec 2025

Duration24:57

Views18K

LocationPadang Tengku, Malaysia

Sailors From All Over the World Come to This Deserted Island for a BBQSailors built a brick barbecue on Singapasar beach; cruisers from Langkawi gather there every other Friday.7 Dec 2025 · Kedah, Malaysia

Published7 Dec 2025

Duration21:48

Views9K

LocationKedah, Malaysia

Sailing Remote Islands: First-Time Crew, Remote Wilderness… and a Night We Won’t Forget (Aliens??)Langkawi circumnavigation includes a night anchorage at a remote beach with unexplained lights onshore.30 Nov 2025 · Kedah, Malaysia

Published30 Nov 2025

Duration29:05

Views16K

LocationKedah, Malaysia

American Girl Living Alone on a Sailboat in Southeast Asia… With Her Cat Routine boat maintenance includes water filtration, cleaning Bimini clears, engine testing, and defrosting the freezer.23 Nov 2025 · Buckingham County, United States

Published23 Nov 2025

Duration20:12

Views7K

LocationBuckingham County, United States

A Tale of Two Young Surfers Who Bought a Sailboat to Chase Waves Around the WorldCamille Milligan and Jesse leave land with little sailing experience to chase waves and off-grid freedom.16 Nov 2025 · Hawaiʻi County, United States

Published16 Nov 2025

Duration5:20

Views5K

LocationHawaiʻi County, United States

Birthday at Sea Gone Wild: Captain’s Big Surprise in a Storm!Camille Milligan and Jesse navigate a 54-nautical-mile passage from Thailand to Langkawi while dodging fishing pots.9 Nov 2025 · Gunnison County, United States

Published9 Nov 2025

Duration13:41

Views10K

LocationGunnison County, United States

Scared for My Life | Our Worst Storm Yet in 40 Knot Winds (New Sailors)A couple aborts a passage to Koh Lanta after encountering 40-knot winds and 3-meter swells.4 Nov 2025 · Glen Burnie, United States

Published4 Nov 2025

Duration13:56

Views9K

LocationGlen Burnie, United States

We Survived Phi Phi Islands: Paradise or Total Chaos? Jellyfish, Boat Wrecks & PiratesCamille Milligan and Jesse navigate heavy boat traffic and underwater wrecks while anchoring Stella at Phi Phi Islands.30 Oct 2025 · Ban Nong Chaeng, Thailand

Published30 Oct 2025

Duration16:55

Views23K

LocationBan Nong Chaeng, Thailand

Sheltering from the Monsoon | Life at Port Takola Marina, ThailandPort Takola Marina in Krabi provides protected berthing, easy customs access, and proximity to major provisioning stores.22 Oct 2025 · Ban Nong Chaeng, Thailand

Published22 Oct 2025

Duration9:13

Views6K

LocationBan Nong Chaeng, Thailand

From Beginners to Bluewater: Sailing to Thailand and learning through experienceA fishing net wraps Stella's prop in Thai waters; Jesse dives and clears it in ten minutes.15 Oct 2025 · Gunnison County, United States

Published15 Oct 2025

Duration34:21

Views78K

LocationGunnison County, United States

Sailing Through Islands In Thailand: Diving Reefs & Catching Our Own DinnerCamille Milligan and Jesse sail from Malaysia to Thailand to snorkel and spearfish off their boat.3 Oct 2025 · Buckingham County, United States

Published3 Oct 2025

Duration8:08

Views16K

LocationBuckingham County, United States

Owning a Sailboat in Your 20s: Freedom, Chaos & Endless ProjectsCamille Milligan and Jesse repair a leaky gearbox and clogged holding tank on their new Malaysian sailboat.25 Sept 2025 · Fresno County, United States

Published25 Sept 2025

Duration3:30

Views6K

LocationFresno County, United States

Van Life to Sailboat Life | The Secret to True Freedom and a Life of AdventureCamille Milligan and Jesse moved from a van to a 39-foot sailboat to access remote island anchorages.17 Sept 2025 · Australia

Published17 Sept 2025

Duration3:31

Views5K

LocationAustralia

Living on a Sailboat in Our 20s | Off-Grid Storms, Islands & Boat ProjectsCamille Milligan and Jesse troubleshoot a jammed jib furler while circumnavigating Langkawi Island on their boat, Stella.10 Sept 2025 · Padang Tengku, Malaysia

Published10 Sept 2025

Duration12:20

Views12K

LocationPadang Tengku, Malaysia

The Sailing Kitten | We Rescued a Kitten… Now She Lives on Our Sailboat!Camille Milligan and Jesse integrate a rescued kitten named Shelly into life aboard their sailboat Stella.3 Sept 2025 · Padang Tengku, Malaysia

Published3 Sept 2025

Duration5:26

Views4K

LocationPadang Tengku, Malaysia

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Australia1Ban Ko Li Pe, Thailand1Ban Nong Chaeng, Thailand6Buckingham County, United States2Byron Bay, Australia1Cenang Beach, Malaysia2Dranesville, United States1Fresno County, United States1Glen Burnie, United States1Great Falls, United States2Gunnison County, United States5Hawaiʻi County, United States2Kapuas, Indonesia5Kedah, Malaysia9Kuta Selatan, Indonesia3Marga, Indonesia3Margaret River, Australia2North Kuta, Indonesia6Padang Tengku, Malaysia6Sabang, Indonesia2Sala Dan, Thailand1Si Sunthon, Thailand2South Jakarta, Indonesia1Ton Sai, Thailand1West Sumatra, Indonesia3Western Australia, Australia1