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…

West Sumatra, Indonesia· Aug 2026

68 videos· 51 deeply analyzed

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

PublishedAug 15, 2026

Duration23:25

Views6K

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.Aug 8, 2026 · West Sumatra, Indonesia

PublishedAug 8, 2026

Duration25:30

Views26K

LocationWest Sumatra, Indonesia

Our OFF-GRID Life on a Sailboat in IndonesiaAug 1, 2026

PublishedAug 1, 2026

Duration25:41

Views5K

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

PublishedJul 25, 2026

Duration26:02

Views37K

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.Jul 18, 2026 · North Kuta, Indonesia

PublishedJul 18, 2026

Duration22:12

Views11K

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.Jul 11, 2026 · North Kuta, Indonesia

PublishedJul 11, 2026

Duration23:49

Views15K

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.Jul 4, 2026 · North Kuta, Indonesia

PublishedJul 4, 2026

Duration22:31

Views123K

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.Jun 27, 2026 · Kuta Selatan, Indonesia

PublishedJun 27, 2026

Duration25:18

Views15K

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.Jun 20, 2026 · North Kuta, Indonesia

PublishedJun 20, 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.Jun 13, 2026 · South Jakarta, Indonesia

PublishedJun 13, 2026

Duration22:40

Views17K

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.Jun 6, 2026 · North Kuta, Indonesia

PublishedJun 6, 2026

Duration25:00

Views111K

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.May 31, 2026 · Kuta Selatan, Indonesia

PublishedMay 31, 2026

Duration27:29

Views33K

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.May 23, 2026 · Kuta Selatan, Indonesia

PublishedMay 23, 2026

Duration20:03

Views21K

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.May 16, 2026 · Ban Nong Chaeng, Thailand

PublishedMay 16, 2026

Duration20:16

Views32K

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.May 9, 2026 · Kapuas, Indonesia

PublishedMay 9, 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.May 2, 2026 · Marga, Indonesia

PublishedMay 2, 2026

Duration15:54

Views62K

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.Apr 25, 2026 · Kapuas, Indonesia

PublishedApr 25, 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.Apr 18, 2026 · Marga, Indonesia

PublishedApr 18, 2026

Duration26:02

Views16K

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.Apr 11, 2026 · Sabang, Indonesia

PublishedApr 11, 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.Apr 4, 2026 · Sabang, Indonesia

PublishedApr 4, 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.Mar 28, 2026 · Cenang Beach, Malaysia

PublishedMar 28, 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.Mar 21, 2026 · Kedah, Malaysia

PublishedMar 21, 2026

Duration16:18

Views22K

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.Mar 14, 2026 · Cenang Beach, Malaysia

PublishedMar 14, 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.Mar 8, 2026 · Si Sunthon, Thailand

PublishedMar 8, 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.Feb 28, 2026 · Ban Ko Li Pe, Thailand

PublishedFeb 28, 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.Feb 21, 2026 · Sala Dan, Thailand

PublishedFeb 21, 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.Feb 15, 2026 · Ton Sai, Thailand

PublishedFeb 15, 2026

Duration17:35

Views19K

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.Feb 11, 2026 · Ban Nong Chaeng, Thailand

PublishedFeb 11, 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.Feb 8, 2026 · Si Sunthon, Thailand

PublishedFeb 8, 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.Feb 1, 2026 · Ban Nong Chaeng, Thailand

PublishedFeb 1, 2026

Duration16:23

Views23K

LocationBan Nong Chaeng, Thailand

We Sailed to One of Thailand’s Best Dive Spots | Off Grid LivingJan 25, 2026

PublishedJan 25, 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.Jan 18, 2026 · Ban Nong Chaeng, Thailand

PublishedJan 18, 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.Jan 11, 2026 · Kedah, Malaysia

PublishedJan 11, 2026

Duration12:32

Views141K

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.Jan 4, 2026 · Great Falls, United States

PublishedJan 4, 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.Dec 28, 2025 · Dranesville, United States

PublishedDec 28, 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.Dec 21, 2025 · Gunnison County, United States

PublishedDec 21, 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.Dec 14, 2025 · Padang Tengku, Malaysia

PublishedDec 14, 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.Dec 7, 2025 · Kedah, Malaysia

PublishedDec 7, 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.Nov 30, 2025 · Kedah, Malaysia

PublishedNov 30, 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.Nov 23, 2025 · Buckingham County, United States

PublishedNov 23, 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.Nov 16, 2025 · Hawaiʻi County, United States

PublishedNov 16, 2025

Duration5:20

Views4K

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.Nov 9, 2025 · Gunnison County, United States

PublishedNov 9, 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.Nov 4, 2025 · Glen Burnie, United States

PublishedNov 4, 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.Oct 30, 2025 · Ban Nong Chaeng, Thailand

PublishedOct 30, 2025

Duration16:55

Views24K

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.Oct 22, 2025 · Ban Nong Chaeng, Thailand

PublishedOct 22, 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.Oct 15, 2025 · Gunnison County, United States

PublishedOct 15, 2025

Duration34:21

Views77K

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.Oct 3, 2025 · Buckingham County, United States

PublishedOct 3, 2025

Duration8:08

Views17K

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.Sep 25, 2025 · Fresno County, United States

PublishedSep 25, 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.Sep 17, 2025 · Australia

PublishedSep 17, 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.Sep 10, 2025 · Padang Tengku, Malaysia

PublishedSep 10, 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.Sep 3, 2025 · Padang Tengku, Malaysia

PublishedSep 3, 2025

Duration5:26

Views4K

LocationPadang Tengku, Malaysia

We Finally Got a New Dinghy! Unboxing & Testing the True Kit DiscoveryCamille and Jesse unbox and water-test the True Kit Discovery dinghy delivered to their island in Malaysia.Aug 26, 2025 · Kedah, Malaysia

PublishedAug 26, 2025

Duration4:40

Views14K

LocationKedah, Malaysia

Learning to Sail Our Boat in Malaysia’s Wild Islands | Fjords, Secret Beaches & Hidden AnchoragesCamille Milligan and Jesse navigate the Langkawi fjords and manage a 30-knot squall while anchored on Stella.Aug 18, 2025 · Kedah, Malaysia

PublishedAug 18, 2025

Duration12:05

Views11K

LocationKedah, Malaysia

Meet the Couple in Their 20s Who Bought a 39’ Foot Sailing Yacht | With No ExperienceCamille Milligan and Jesse are refitting their 39-foot Genosun Odyssey for a voyage to Indonesia.Aug 10, 2025 · Byron Bay, Australia

PublishedAug 10, 2025

Duration2:53

Views192K

LocationByron Bay, Australia

Boat Project: Sirocco Fan + a Furry AssistantCamille Milligan and Jesse install a Sirocco fan by routing marine-grade wire through the boat's electrical board.Aug 4, 2025 · Kedah, Malaysia

PublishedAug 4, 2025

Duration4:09

Views9K

LocationKedah, Malaysia

A Day in the Life Living on a Sailboat | Hospital, Fixing & AloneCamille Milligan performs daily boat maintenance and manages a leg infection while living aboard her sailboat.Jul 27, 2025

PublishedJul 27, 2025

Duration9:32

Views12K

How We Installed Our Bilge Pump | Johnson Pump Wiking Power 16 – Boat Life DIY!A Johnson Pump Wiking Power 16 bilge pump replaces an undersized unit in a tight hull compartment.Jul 20, 2025

PublishedJul 20, 2025

Duration3:57

Views2K

INSANE Sailing Adventure – Jellyfish Sting, Popped Tender, Overboard Phone & 7 Knot Mayhem!The crew repairs a deflated tender and seeks medical treatment for a jellyfish sting near Singa Basar.Jul 13, 2025

PublishedJul 13, 2025

Duration13:19

Views13K

Off-Grid Sailboat Tour | Jeanneau Sun Odyssey (39i)Camille Milligan tours the interior and storage layout of the 2007 Jeanneau Sun Odyssey 39i named Stella.Jul 6, 2025 · Kedah, Malaysia

PublishedJul 6, 2025

Duration5:24

Views7K

LocationKedah, Malaysia

Alone on My Sailboat in Malaysia | While Jesse Works in the MinesJun 29, 2025

PublishedJun 29, 2025

Duration5:16

Views11K

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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 States1Gunnison County, United States3Hawaiʻi County, United States1Kapuas, Indonesia2Kedah, Malaysia8Kuta Selatan, Indonesia3Marga, Indonesia2North Kuta, Indonesia6Padang Tengku, Malaysia5Sabang, Indonesia2Sala Dan, Thailand1Si Sunthon, Thailand2South Jakarta, Indonesia1Ton Sai, Thailand1West Sumatra, Indonesia2