Classic Day Sail Aboard Schooner America 2.0

$56 Adults - Kids Under 12 Sail Free!

Enjoy an afternoon on the water aboard Schooner America 2.0, namesake of the first sailboat to win the 1851 America's Cup Race. The stunning Schooner America 2.0 is a 105-foot sailboat built in Albany, NY in 2011. She is the namesake of the first schooner to win the 1851 America's Cup Race. ...

Key West
1.5 Hours
Adirondack Sailing, Boat Tour, Cruise / Large Boat, Day Sail, Dolphin, Sailing, Sunset Sail, Water Activities, Yacht Charter
Classic Harbor Line - Key West
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Christmas Brunch Sail aboard Schooner America 2.0

Enjoy your morning with us in Key West in style! • 2.5 Hours • From $169 per adult

Enjoy your holiday in Key West aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West as you sip champagne, dine on passed a delicious brunch, and glide through the crystal clear surrounding waters. This two-hour morning ...

Key West
2,5 Hours
Sailing
Classic Harbor Line - Key West
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Christmas Eve Sunset Sail Aboard Schooner America 2.0

$124 Adults • 2 hours

Enjoy your Christmas Eve sunset sail aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West's famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys. This ...

Key West
2 Hours
Boat Rental, Boat Tour, Sailing
Classic Harbor Line - Key West
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Christmas Day Sunset Sail Aboard Schooner America 2.0

$124 Adults | 2 hrs

Enjoy your Christmas Day sunset sail aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West's famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys. This ...

Key West
2 Hours
Boat Rental, Boat Tour, Sailing
Classic Harbor Line - Key West
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New Year's Eve Champagne Sunset Sail Aboard Schooner America 2.0

$124 Adults • 2 hours

Enjoy your New Year's Eve sunset sail aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West's famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys. ...

Key West
2 Hours
Boat Rental, Boat Tour, Sailing
Classic Harbor Line - Key West
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New Year's Day Champagne Sunset Sail Aboard Schooner America 2.0

From $124 Adults • 2 hrs

Enjoy your New Year's Day sunset sail aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West's famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys. ...

Key West
2 Hours
Boat Rental, Boat Tour, Sailing
Classic Harbor Line - Key West
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Wreckers Race aboard Schooner America 2.0

From $108 • 3 hrs

All hands on deck! Sail aboard the Schooner America 2.0 for the monthly Schooner Wharf Bar Wrecker's Cup Race! Back in the days of the yore, pirate ships from afar often ran aground on Sand Key Reef, nine miles off of the southern coast of Key West. When all the scallywags in Key West heard there ...

Key West
3 hours
Sailing
Classic Harbor Line - Key West
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Key West Champagne Sunset Sail on Schooner America 2.0

Voted 'Top Things to do on TripAdvisor!"

Enjoy your romantic sunset sail aboard Key West's most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West's famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys. This two-hour ...

Key West
2 Hours
Boat Tour, Sunset Sail
Classic Harbor Line - Key West
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Full Moon Sail Aboard Schooner America 2.0

From $64 • 1.5 hrs

Experience the serenity of Key West night sailing aboard the 105-foot Schooner America 2.0. Away from land, the dark Key West skies reveal a canvas of stars and celestial phenomena. Whether you're an astronomy enthusiast or seeking quiet reflection, stargazing aboard the Schooner America 2.0 promises ...

Key West
1.5
Adirondack Sailing, Boat Tour, Cruise / Large Boat, Day Sail, Party Boat, Sailing, Water Activities, Yacht Charter
Classic Harbor Line - Key West
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Key West Lighted Boat Parade aboard America 2.0

From $104 • 3 Hours

Join us for Key West's Annual Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the fastest, most elegant schooner, the brand new eco-friendly, America 2.0 as we parade through the Bight and Harbor of Key West! She'll be fully decorated in Holiday decor with up to 30 other ...

Key West
3 Hours
Adirondack Sailing, Boat Cruise, Boat Tour, Booze Cruise, Cruise / Large Boat, Day Sail, Evening Cruise, Sailing, Sunset Cruise, Sunset Sail, Water Activities, Yacht Charter
Classic Harbor Line - Key West
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Cocoa and Carols: Live Christmas Music Cruise aboard Schooner America 2.0

December 20th-24th only!

Happy Holidays from Classic Harbor Line! Please join us for this special Key West warm and cozy holiday cruise tailored for friends, family, and all your loved ones during the Christmas season. Step aboard our beautiful 105-foot Schooner America 2.0 in full holiday decor for a 1.5-hour cruise in Key ...

Key West
1.5 Hours
Boat Tour, Sailing
Classic Harbor Line - Key West
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New Year's Eve Dockside Bash on Schooner America 2.0

From $296 + tax/gratuity • 3 Hrs

Join us aboard America 2.0 for a wonderful New Year's Eve Bash! Enjoy this timeless celebration on the most exclusive boat in the Historic Bight, and experience VIP dockside access to the famous Schooner Wharf Bar "Lowering of the Pirate Wench" from the rig of Schooner America 2.0! This ...

Key West
3 Hours
Sailing
Classic Harbor Line - Key West
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Schooner America 2.0 Holiday Printed Glass Ornament

Add a touch of holiday magic to your cruise with our exclusive custom ornament! Crafted to commemorate your special voyage, it’s the perfect keepsake to remember your time on the water. Elegant, nautical, and personalized—this limited-edition ornament makes a beautiful addition to your tree or a ...

Key West
Classic Harbor Line - Key West
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Limited Edition MARC & Schooner America 2.0 Hat

🧢 100% of proceeds benefit MARC House, Key West! ⛵

🧢 Set Sail for a Good Cause At Classic Harbor Line, we believe everyone deserves a day on the water. That's why we've partnered with MARC House — Key West's beloved nonprofit supporting adults with developmental and intellectual disabilities — to make that happen twice a year, bringing ...

Key West
Classic Harbor Line - Key West
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