Glide beneath a full moon aboard Schooner America 2.0 and watch Key West’s harbor turn silver. This 1.5-hour nighttime sail blends easygoing maritime history with starry views and two included drinks for 21+ guests.
Glide beneath a full moon aboard Schooner America 2.0 and watch Key West’s harbor turn silver. This 1.5-hour nighttime sail blends easygoing maritime history with starry views and two included drinks for 21+ guests.
The schooner slips away from the dock as the moon lifts over Key West, painting the water silver and pushing a cool night breeze across the deck. On a 1.5-hour full-moon sail aboard Schooner America 2.0, passengers trade street lights for constellations, while the boat cuts a steady wake that hushes the harbor and draws your focus to the horizon.
Verified experiences and guided adventures in the surrounding area.
Operated by Classic Harbor Line · Key West, Florida
The schooner slips away from the dock as the moon lifts over Key West, painting the water silver and pushing a cool night breeze across the deck. On a 1.5-hour full-moon sail aboard Schooner America 2.0, passengers trade street lights for constellations, while the boat cuts a steady wake that hushes the harbor and draws your focus to the horizon.
Key West’s maritime past — from sponge and wrecking fleets to rum-running schooners — hangs in the air; the island’s low coral substrate and reef-lined coastline mean the sea is shallow and luminous, and the shoreline lights of Fort Zachary Taylor and Old Town give the night depth. Locals still celebrate evenings on the water, and a moonlit sail feels like a continuation of that waterfront culture: unhurried, social, and tuned to tides.
Expect calm, coastal conditions suitable for all experience levels: gentle rolling swells rather than open-ocean chop. Dress in layers for the breeze, bring motion-sickness prevention if you’re sensitive, and keep cameras ready for reflections and silhouetted palm lines. The cruise includes soda, water, and two alcoholic drinks for guests 21+, with additional purchases available.
Practical notes: arrive early for boarding and brief safety orientation; stanchions and railings offer solid handholds, and the crew manages lines and navigation. The trip is short and accessible — a reliable option for date nights, families, or anyone wanting a low-effort way to experience Key West after dark.
Most nighttime sails board from Key West harbor near the historic downtown docks; check your booking confirmation for the exact pier and arrive early.
Soda and water are included; the cruise includes two alcoholic beverages for guests 21 and older, with additional drinks available for purchase by card.
The trip is rated easy and suitable for most ages; there is a short gangway to board and some standing on deck—contact the operator about specific mobility needs.
For a full refund cancel at least 24 hours before departure; bookings canceled within 24 hours are typically non-refundable.
Classic Harbor Line operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.




The schooner slips away from the dock as the moon lifts over Key West, painting the water silver and pushing a cool night breeze across the deck. On a 1.5-hour full-moon sail aboard Schooner America 2.0, passengers trade street lights for constellations, while the boat cuts a steady wake that hushes the harbor and draws your focus to the horizon.
The schooner slips away from the dock as the moon lifts over Key West, painting the water silver and pushing a cool night breeze across the deck. On a 1.5-hour full-moon sail aboard Schooner America 2.0, passengers trade street lights for constellations, while the boat cuts a steady wake that hushes the harbor and draws your focus to the horizon.
Key West’s maritime past — from sponge and wrecking fleets to rum-running schooners — hangs in the air; the island’s low coral substrate and reef-lined coastline mean the sea is shallow and luminous, and the shoreline lights of Fort Zachary Taylor and Old Town give the night depth. Locals still celebrate evenings on the water, and a moonlit sail feels like a continuation of that waterfront culture: unhurried, social, and tuned to tides.
Expect calm, coastal conditions suitable for all experience levels: gentle rolling swells rather than open-ocean chop. Dress in layers for the breeze, bring motion-sickness prevention if you’re sensitive, and keep cameras ready for reflections and silhouetted palm lines. The cruise includes soda, water, and two alcoholic drinks for guests 21+, with additional purchases available.
Practical notes: arrive early for boarding and brief safety orientation; stanchions and railings offer solid handholds, and the crew manages lines and navigation. The trip is short and accessible — a reliable option for date nights, families, or anyone wanting a low-effort way to experience Key West after dark.