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Celebrate the season aboard the 105-foot Schooner America 2.0 for a 90-minute holiday sail in Key West Harbor. Enjoy live music, two drinks, hot cocoa and festive lights while cruising past the town’s lit waterfront.
Celebrate the season aboard the 105-foot Schooner America 2.0 for a 90-minute holiday sail in Key West Harbor. Enjoy live music, two drinks, hot cocoa and festive lights while cruising past the town’s lit waterfront.
The schooner slips out of the historic Key West Bight as dusk loosens the heat, Christmas lights wrapped around her rigging and a live band tuning on deck. Salt tang and hot cocoa mingle with the murmur of the harbor; palms lean like an audience as the 105-foot Schooner America 2.0 points toward open water for a 90-minute holiday sail.
Verified experiences and guided adventures in the surrounding area.
Operated by Classic Harbor Line · Key West, Florida
The schooner slips out of the historic Key West Bight as dusk loosens the heat, Christmas lights wrapped around her rigging and a live band tuning on deck. Salt tang and hot cocoa mingle with the murmur of the harbor; palms lean like an audience as the 105-foot Schooner America 2.0 points toward open water for a 90-minute holiday sail.
Key West’s maritime story runs deep — from 19th-century wrecking and sponging to modern sport fishing — and this cruise threads that history into a simple, celebratory passage around the harbor. The shallow coral flats and reclaimed mangroves that rim the island are limestone and coral outcrops worn by currents; on calm nights the water mirrors the town’s neon and Christmas bulbs. The cultural mix here is salty and playful: island music, Cuban influences a few blocks inland, and a bar scene that spills out onto the docks.
Practical details are straightforward. Boarding is dockside at Schooner Wharf Bar (plan to check in 20–30 minutes early); the cruise runs 90 minutes and includes two drinks for adults plus holiday treats. Expect a family-friendly atmosphere but bring layers — breezes intensify after sunset. Parking near William Street is limited; public transit or a short taxi ride from downtown Key West is often faster. If you get seasick, pick a seat near the center and look at the horizon; guests with infants can request specialized seats. The boat departs promptly, so keep your ID handy if you plan to drink. This is a low-effort, high-ambience evening that pairs Key West’s maritime character with holiday cheer — a practical, scenic way to celebrate the season on the water.
easy.
1–1.5 hours.
Suitable for all fitness levels; minimal mobility required for boarding stairs and deck movement
Arrive 20–30 minutes before the scheduled departure to pick up boarding passes at the ticket booth on William Street; boarding starts 10–15 minutes before departure.
Yes—two drinks are included for guests 21+. Beer, wine and champagne are offered; non‑alcoholic options are also available.
Yes. The cruise is suitable for all ages and offers holiday treats; infant seats are available on request.
For a full refund cancel at least 24 hours before departure. No refund within 24 hours of the scheduled time.
Key West’s harbor was a center for wrecking, sponging and shipbuilding in the 19th century; the Schooner America 2.0 echoes the island’s long sailing tradition.
Be mindful of the nearby coral reef ecosystems—avoid throwing anything overboard and follow crew guidance to minimize disturbance to wildlife and water quality.
Classic Harbor Line operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
The schooner slips out of the historic Key West Bight as dusk loosens the heat, Christmas lights wrapped around her rigging and a live band tuning on deck. Salt tang and hot cocoa mingle with the murmur of the harbor; palms lean like an audience as the 105-foot Schooner America 2.0 points toward open water for a 90-minute holiday sail.
The schooner slips out of the historic Key West Bight as dusk loosens the heat, Christmas lights wrapped around her rigging and a live band tuning on deck. Salt tang and hot cocoa mingle with the murmur of the harbor; palms lean like an audience as the 105-foot Schooner America 2.0 points toward open water for a 90-minute holiday sail.
Key West’s maritime story runs deep — from 19th-century wrecking and sponging to modern sport fishing — and this cruise threads that history into a simple, celebratory passage around the harbor. The shallow coral flats and reclaimed mangroves that rim the island are limestone and coral outcrops worn by currents; on calm nights the water mirrors the town’s neon and Christmas bulbs. The cultural mix here is salty and playful: island music, Cuban influences a few blocks inland, and a bar scene that spills out onto the docks.
Practical details are straightforward. Boarding is dockside at Schooner Wharf Bar (plan to check in 20–30 minutes early); the cruise runs 90 minutes and includes two drinks for adults plus holiday treats. Expect a family-friendly atmosphere but bring layers — breezes intensify after sunset. Parking near William Street is limited; public transit or a short taxi ride from downtown Key West is often faster. If you get seasick, pick a seat near the center and look at the horizon; guests with infants can request specialized seats. The boat departs promptly, so keep your ID handy if you plan to drink. This is a low-effort, high-ambience evening that pairs Key West’s maritime character with holiday cheer — a practical, scenic way to celebrate the season on the water.