Watch Sailing & Boating Adventures Around the World

Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.

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Sailing Across the Pacific – Day 27: Red Shirt Monologue #4 – With Cat
Cruising Lealea

Sailing Across the Pacific – Day 27: Red Shirt Monologue #4 – With Cat

The Red Shirt Monologues by Captain Chuck Rose. Day 27 Sailing across the Pacific. Chuck talks about the challenges of cruising aboard a small sailboat with Bree's help. For more sailing adventures see our other Playlists: "Honolulu: The Beginning" - "Cruising Lealea in Ala...
Sailing Across the Pacific – Day 24: The Red Shirt Monologues #3 “Whine”
Cruising Lealea

Sailing Across the Pacific – Day 24: The Red Shirt Monologues #3 “Whine”

Chuck complaining, again, still....Cold weather and seasickness continues to be the topic of the day. Journey along with the crew of S/V Lealea as we sail from Honolulu to Neah Bay, WA in an Albin Vega 27. For more sailing adventures see our other Playlists: "Honolulu: The Beginning" -...
Sailing Across the Pacific – Day 22:  The Red Shirt Monologues #2 – Jellyfish and Sunshine
Cruising Lealea

Sailing Across the Pacific – Day 22: The Red Shirt Monologues #2 – Jellyfish and Sunshine

At 39 degrees North the weather is starting to get us down. We encounter thousands of jellyfish, a shark and a ray of sunshine. Journey along with the crew of S/V Lealea as we sail from Honolulu to Neah Bay, WA in an Albin Vega 27. For more sailing adventures see our other Playlists: "Hono...
Sailing Across the Pacific – Day 21:  The Red Shirt Monologues #1
Cruising Lealea

Sailing Across the Pacific – Day 21: The Red Shirt Monologues #1

The Red Shirt Monologues #1 by Captain Chuck Rose. The constant bad weather is taking its toll on the crew and yes, Chuck is still seasick. Journey along with the crew of S/V Lealea as we sail from Honolulu to Neah Bay, WA in an Albin Vega 27. For more sailing adventures see our other Playlists...
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