Sailing School T-Shirts

Description: "Isn't this a breakthrough, that I'm a sailor? I sail? I sail now?" - Bob Wiley

Description: A circular emblem with horizontal stripes of yellow, orange, and red, depicting a sunset. Inside, a white sailboat is on water, with a dark tree line behind it. Above the emblem, text reads "BOB WILEY'S", and below, "SAILING SCHOOL EST. 1991". A white fish is at the top.

Description: Ahoy, I'm a sailor.

Description: We might not be the best school, but we ARE the other best school. Also, we're very close to the Giant Mistake, and that counts for something, doesn't it?

Description: Traditional Tattoo Ship and sunset Homeward Bound

Description: When you learn to sail, you have to learn the names of everything on the boat. And there are a lot of them. This design is a very silly take on sailboat terminology with funny descriptions for various boat parts. Disclaimer: All of these terms are wrong. Don't use this design as a cheat sheet for the test, you will flunk.

Description: Lake Winnipesaukee, NH Ahoy, I'm a sailor.

Description: Bob Wiley's Sailing School, Lake Winnipesaukee, since 1991. Ahoy, I'm a sailor!

Description: Ahoy, I'm a sailor.

Description: Bob Wiley's Sailing School - Lake Winnipesaukee, NH

Description: Sea Captain Gift Sail Boat Heartbeat Boat Sailing T-Shirt

Description: Funny Sailing Nautical Boating Sailboat Lover Gift Men Women T-Shirt

Description: Bold nautical graphic tee featuring a classic tall ship illustration paired with the motivational quote "Rough Waves Make A Skilled Sailor." Rendered in a striking red and navy two-tone style — perfect for sailors, sea lovers, and those who embrace life's challenges head-on. Vintage Americana meets old-school maritime grit.

Description: Christopher Cross - Retro Fan Design

Description: A bold vintage-style tee featuring a classic tall ship illustration with the powerful quote "Rough Waves Make A Skilled Sailor." Perfect for sailors, ocean lovers, and anyone who finds strength in life's challenges. Old-school tattoo aesthetic meets timeless motivation.

Description: Christopher Cross - Sailing - Original Retro Design

Description: Christopher Cross - Original Retro Fan Design

Description: Christopher Cross / Retro Aesthetic Fan Design

Description: Distressed / vintage worn effect, old school / traditional style design with sailing ship. Text reads "Captain of My Fate, Master of My Destiny".

Description: Christopher Cross - Sailing - Original Retro Fan Design

Description: Take a vacation from your problems

Description: Retro craft beer label featuring a vintage sailing ship and crew.

Description: Cool, Unique, Classic

Description: COMMANDERS OF THE POINTY END! FOREDECK UNION NON-OFFICIAL UNION WEAR. Credit to Jennifer Fortuna Design for her graphics help!

Description: Mongibello, Italy

Description: Some dreams are meant to travel, while others remain trapped in memory. The Ship Inside the Bottle is a dramatic vintage tattoo design featuring a magnificent three-masted sailing ship sealed inside a glass bottle. A mysterious skeleton sailor's hand rises from the ocean to hold it, surrounded by roses, rope, stars, a compass, and crashing waves. The banner “SOME DREAMS NEVER SAIL” adds a melancholy layer to this adventurous maritime scene. The combination of nautical romance and subtle macabre imagery makes the design feel like a forgotten piece of classic sailor flash discovered in an old tattoo shop. Bold black outlines, traditional colors, distressed texture, and strong graphic shapes make this ideal for vintage tattoo and maritime

Description: Mongibello, Italy

Description: Retro nautical brewery label featuring a sailing ship and crew on deck.

Description: Some dreams are meant to travel, while others remain trapped in memory. The Ship Inside the Bottle is a dramatic vintage tattoo design featuring a magnificent three-masted sailing ship sealed inside a glass bottle. A mysterious skeleton sailor's hand rises from the ocean to hold it, surrounded by roses, rope, stars, a compass, and crashing waves. The banner “SOME DREAMS NEVER SAIL” adds a melancholy layer to this adventurous maritime scene. The combination of nautical romance and subtle macabre imagery makes the design feel like a forgotten piece of classic sailor flash discovered in an old tattoo shop

Description: Illustration depicting a clipper ship sailing in rough water, with traditional flowers, framed in a rope.

Description: Christopher Cross - Sailing - Original Retro Fan Design

Description: A hauntingly beautiful tribute to sailors, lost love, and the call of the sea. This vintage American traditional tattoo design features a lonely sailor standing beside a storm-battered lighthouse, holding a treasured letter while a tall sailing ship disappears into the distant horizon. Dramatic ocean waves, red roses, nautical rope, an anchor, and a weathered banner complete the composition. The artwork captures the emotional side of classic sailor tattoo culture: love, separation, loyalty, adventure, and the hope of returning home. Its bold black outlines, traditional red, mustard, green, cream, and muted blue palette give it the authentic character of old tattoo flash while the storytelling adds a deeper emotional connection.

Description: Romance meets adventure in this richly detailed nautical tattoo design. At its center, a giant red rose grows from an antique compass while seven tiny sailing ships circle the flower like planets. Ocean waves, rope, stars, clouds, and a graceful swallow complete the composition. The banner “LOVE HAS NO HARBOR” gives the artwork a poetic emotional message about love that travels beyond distance, borders, and time. The combination of roses and nautical imagery creates a classic sailor tattoo aesthetic while the unusual composition gives the design its own identity. Perfect for sailors, romantics, ocean lovers, travelers, tattoo enthusiasts, and anyone who believes love is an adventure.

Description: Romance meets adventure in this richly detailed nautical tattoo design. At its center, a giant red rose grows from an antique compass while seven tiny sailing ships circle the flower like planets. Ocean waves, rope, stars, clouds, and a graceful swallow complete the composition. The banner “LOVE HAS NO HARBOR” gives the artwork a poetic emotional message about love that travels beyond distance, borders, and time. The combination of roses and nautical imagery creates a classic sailor tattoo aesthetic while the unusual composition gives the design its own identity. Perfect for sailors, romantics, ocean lovers, travelers, tattoo enthusiasts, and anyone who believes love is an adventure

Description: Retro nautical brewery aesthetic featuring sailing ships and barrels.

Description: Classic nautical themed brewery graphic featuring a tall ship, sailor, and wooden barrels.