Stella Overboard

48 located videos · tap a dot to watch · Basemap © Wikimedia Commons · CC BY-SA 4.0

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…

Canggu· Jul 2026

64 videos· 48 analysed

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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 · Canggu

Published18 Jul 2026

Duration22:12

Views5K

LocationCanggu

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 · Canggu

Published11 Jul 2026

Duration23:49

Views13K

LocationCanggu

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 · Canggu

Published4 Jul 2026

Duration22:31

Views100K

LocationCanggu

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 · Uluwatu

Published27 Jun 2026

Duration25:18

Views13K

LocationUluwatu

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 · Canggu

Published20 Jun 2026

Duration20:01

Views9K

LocationCanggu

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 · CANGGU STREET PIZZA BLOK M SQUARE

Published13 Jun 2026

Duration22:40

Views17K

LocationCANGGU STREET PIZZA BLOK M SQUARE

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 · Canggu

Published6 Jun 2026

Duration25:00

Views91K

LocationCanggu

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 · Bingin Beach

Published31 May 2026

Duration27:29

Views30K

LocationBingin Beach

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 · Uluwatu

Published23 May 2026

Duration20:03

Views20K

LocationUluwatu

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 · Thailand

Published16 May 2026

Duration20:16

Views32K

LocationThailand

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 · Indonesia

Published9 May 2026

Duration21:15

Views24K

LocationIndonesia

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 · Bali

Published2 May 2026

Duration15:54

Views61K

LocationBali

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 · Indonesia

Published25 Apr 2026

Duration14:43

Views7K

LocationIndonesia

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 · Bali

Published18 Apr 2026

Duration26:02

Views14K

LocationBali

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

Published11 Apr 2026

Duration20:22

Views17K

LocationSabang

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

Published4 Apr 2026

Duration24:57

Views18K

LocationSabang

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 · Rebak Island Resort & Marina, Langkawi

Published28 Mar 2026

Duration13:30

Views11K

LocationRebak Island Resort & Marina, Langkawi

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 · Langkawi Island

Published21 Mar 2026

Duration16:18

Views22K

LocationLangkawi Island

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 · Rebak Island Resort & Marina, Langkawi

Published14 Mar 2026

Duration12:18

Views17K

LocationRebak Island Resort & Marina, Langkawi

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 · Phuket

Published8 Mar 2026

Duration14:31

Views14K

LocationPhuket

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 · Ko Lipe

Published28 Feb 2026

Duration18:54

Views20K

LocationKo Lipe

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 · Ko Lanta

Published21 Feb 2026

Duration14:46

Views48K

LocationKo Lanta

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 · Phi Phi Islands

Published15 Feb 2026

Duration17:35

Views18K

LocationPhi Phi Islands

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 · Thailand

Published11 Feb 2026

Duration10:09

Views5K

LocationThailand

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 · Phuket

Published8 Feb 2026

Duration16:28

Views15K

LocationPhuket

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 · Thailand

Published1 Feb 2026

Duration16:23

Views23K

LocationThailand

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

Published25 Jan 2026

Duration14:15

Views—

Location—

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 · Thailand

Published18 Jan 2026

Duration34:58

Views12K

LocationThailand

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 · Langkawi Island

Published11 Jan 2026

Duration12:32

Views141K

LocationLangkawi Island

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 · Reston

Published4 Jan 2026

Duration52:23

Views8K

LocationReston

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 · 11801 Leesburg Pike

Published28 Dec 2025

Duration15:42

Views9K

Location11801 Leesburg Pike

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 · United States

Published21 Dec 2025

Duration23:19

Views11K

LocationUnited 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 · Malaysia

Published14 Dec 2025

Duration24:57

Views18K

LocationMalaysia

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 · Pulau Singa Besar

Published7 Dec 2025

Duration21:48

Views9K

LocationPulau Singa Besar

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 · Langkawi Island

Published30 Nov 2025

Duration29:05

Views16K

LocationLangkawi Island

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 · Virginia

Published23 Nov 2025

Duration20:12

Views7K

LocationVirginia

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 · Hawaii

Published16 Nov 2025

Duration5:20

Views4K

LocationHawaii

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 · United States

Published9 Nov 2025

Duration13:41

Views9K

LocationUnited 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 · Maryland

Published4 Nov 2025

Duration13:56

Views9K

LocationMaryland

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 · Thailand

Published30 Oct 2025

Duration16:55

Views23K

LocationThailand

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 · Thailand

Published22 Oct 2025

Duration9:13

Views6K

LocationThailand

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 · United States

Published15 Oct 2025

Duration34:21

Views77K

LocationUnited 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 · Virginia

Published3 Oct 2025

Duration8:08

Views16K

LocationVirginia

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 · California

Published25 Sept 2025

Duration3:30

Views6K

LocationCalifornia

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 · Malaysia

Published10 Sept 2025

Duration12:20

Views12K

LocationMalaysia

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 · Malaysia

Published3 Sept 2025

Duration5:26

Views4K

LocationMalaysia

We Finally Got a New Dinghy! Unboxing & Testing the True Kit DiscoveryCamille Milligan and Jesse assemble and sea-trial a new True Kit Discovery inflatable dinghy in Malaysia.26 Aug 2025 · Langkawi Island

Published26 Aug 2025

Duration4:40

Views14K

LocationLangkawi Island

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.18 Aug 2025 · Langkawi Island

Published18 Aug 2025

Duration12:05

Views11K

LocationLangkawi Island

Meet the Couple in Their 20s Who Bought a 39’ Foot Sailing Yacht | With No Experience10 Aug 2025

Published10 Aug 2025

Duration2:53

Views—

Location—

Boat Project: Sirocco Fan + a Furry Assistant4 Aug 2025

Published4 Aug 2025

Duration4:09

Views—

Location—

A Day in the Life Living on a Sailboat | Hospital, Fixing & Alone27 Jul 2025

Published27 Jul 2025

Duration9:32

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How We Installed Our Bilge Pump | Johnson Pump Wiking Power 16 – Boat Life DIY!20 Jul 2025

Published20 Jul 2025

Duration3:57

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INSANE Sailing Adventure – Jellyfish Sting, Popped Tender, Overboard Phone & 7 Knot Mayhem!13 Jul 2025

Published13 Jul 2025

Duration13:19

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Location—

Off-Grid Sailboat Tour | Jeanneau Sun Odyssey (39i)6 Jul 2025

Published6 Jul 2025

Duration5:24

Views—

Location—

Alone on My Sailboat in Malaysia | While Jesse Works in the Mines29 Jun 2025

Published29 Jun 2025

Duration5:16

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Anchoring, Sailing and Surviving our First Night on Our Sailboat22 Jun 2025

Published22 Jun 2025

Duration7:36

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Buying, Breaking & Figuring Out Our First Sailboat (Welcome to Boat Life)15 Jun 2025

Published15 Jun 2025

Duration5:49

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We Bought Our First Sailboat in a Foreign Country (and Moved Aboard!)9 Jun 2025

Published9 Jun 2025

Duration0:56

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Selling it All for Waves: The Quest for Our Dream Sailboat Throughout Asia19 Apr 2025

Published19 Apr 2025

Duration4:57

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Van life Hawaii : The best way to travel and surf the Hawaiian islands23 Mar 2025

Published23 Mar 2025

Duration7:31

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Take a tour of our house on wheels : Toyota Troopcarrair30 Jan 2025

Published30 Jan 2025

Duration2:35

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What a week looks like living out of our car in Australia! The best way to always be adventuring!15 Jan 2025

Published15 Jan 2025

Duration10:06

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Living out of our car in Australia! Just some daily adventures and activities of life on the road26 Dec 2024

Published26 Dec 2024

Duration7:54

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Location—

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11801 Leesburg Pike1Australia1Bali2Bingin Beach1California1Canggu5CANGGU STREET PIZZA BLOK M SQUARE1Hawaii1Indonesia2Ko Lanta1Ko Lipe1Langkawi Island5Malaysia3Maryland1Phi Phi Islands1Phuket2Pulau Singa Besar1Rebak Island Resort & Marina, Langkawi2Reston1Sabang2Thailand6Uluwatu2United States3Virginia2

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