2 hours · Shared
Champagne Sunset Sail
Beer, wine, champagne, soft drinks, cheese, veggies and shrimp cocktail, and the sunset off Mallory Square from a real schooner.
| Adult 13+ | $112 |
|---|---|
| Child 2–12 | $68 |
Editorial spotlight · Schooner Wharf, Historic Seaport, Key West
2026 Conch Shell Awards nomineeBest Sailing Experience
Classic Harbor Line
A 105-foot schooner built as a tribute to the yacht that won the first America's Cup, with electric motors under the deck. Champagne sunset sails, day sails with kids free, and the Wreckers Race, from the Historic Seaport every winter.
- Sunset sail
- $112
- Day sail
- $58, kids free
- Tripadvisor
- 4.9
- Guests
- Up to 85
Editorial spotlight. Classic Harbor Line Key West is a nominee in the 2026 Conch Shell Awards. They did not pay for this page and had no say in it. We earn a commission when you book through the links here; your price is the same.
The company
Built by the family that sails her
Classic Harbor Line is the Scarano family of Albany, New York, who have designed, built and operated their own schooners since the 80-foot Adirondack in 1994. The fleet works New York, Boston and Newport in summer; America 2.0 comes to Key West for the winter, November through May.
The crew are 100-ton captains with sailing endorsements plus mates, and the company runs 364 days a year across its ports. Reviews name the Key West captains and mates individually.
“Voted top things to do on Tripadvisor.”
- J
Captain
Capt. Janet
- T
Captain
Capt. Tom
- R
Crew
Ray
- J
Crew
Jade
- D
Crew
Dan
- H
Crew
Heather
Crew as named by guests in Tripadvisor reviews; the current roster is Classic Harbor Line's to confirm. Company crew page: sail-keywest.com/our-crew.
The boat
America 2.0
Scarano Boat Building delivered her in 2011 as a modern take on the 1851 America: 105 feet overall, carbon masts sheathed in cedar, 3,600 square feet of sail, a winged lead keel, and two electric motors on lithium batteries with a diesel backup. She has hit 17 knots and won the Great Chesapeake Bay Schooner Race more than once.
Certified for 85 guests, which is why the sunset sail feels like a ship and not a boat. Not wheelchair accessible.
| Champagne sunset sail, 2 hours | $112 adult, $68 child |
|---|---|
| Classic day sail, 1.5 hours | $58 adult, kids 2–12 free |
| Full moon sail, 1.5 hours | $64 |
Prices checked against FareHarbor on September 30, 2026. Key West season is November to May; the calendar opens by month.
Check AvailabilityThe boat
One schooner, four ports
America 2.0 is the only Classic Harbor Line boat in Key West. The sister schooners Adirondack and the Manhattan yachts stay north.
America 2.0
- Length
- 105 ft overall, 86 ft on deck
- Built
- 2011, Scarano Boat Building, Albany NY
- Sail
- 3,600 sq ft, carbon masts
- Power
- Hybrid electric, diesel backup
- Guests
- USCG-certified for 85
- Berth
- Behind Schooner Wharf Bar, 202 William St
Book it
Sails
Public sails are per person. Season runs November to May; November and December dates are open at this check. Checked against FareHarbor on September 30, 2026.
1.5 hours · Shared · Kids free
Classic Day Sail
An afternoon sail of the harbor and the reef line. Soda and water included; children 2 to 12 sail free.
| Adult | $58 |
|---|---|
| Child 2–12 | Free |
1.5 hours · Shared · Monthly
Full Moon Sail
Out after dark on the full moon. Next dates in November.
| General admission | $64 |
|---|
3 hours · Shared · January
Wreckers Race
Sail in the Key West Wreckers Race aboard America 2.0. January 31, 2027 at this check.
| Adult | $112 |
|---|---|
| Child 2–12 | $62 |
1.75 hours · Shared
Astronomer-Guided Stargazing Cruise
A night sail with an astronomer aboard. No dates listed at this check; the season calendar opens by month.
| Per person | $82 listed |
|---|
Holiday sails (Christmas brunch and sunset sails, New Year's Eve champagne sail, Valentine's) are on the calendar in season. Private charters of America 2.0 are quoted on the booking page; up to 85 guests.
Before you go
Know before you go
Where to board
The dock behind Schooner Wharf Bar, 202 William Street, in the Historic Seaport. Check-in details come with the booking.
Parking
Municipal lots by the seaport, card only, by the hour or the day. Parking trouble is not grounds for a refund, per their FAQ, so leave time.
Included
Sunset sail: beer, wine, champagne, soft drinks and light bites. Day sail: soda and water. Cocktails for purchase. No BYOB.
Kids and access
Children 2 to 12 are child fare; under 2 free. Kids sail free on the day sail. The boat is not wheelchair accessible.
Reviews
What guests say
- 4.9TripadvisorRating as of September 30, 2026
- #6of 397Boat tours and water sports in Key West, Tripadvisor
- 1994SinceClassic Harbor Line founded
Reviewers compare it with the catamaran sunset boats and land on the same word, quieter: a real sailing ship, a smoother ride, and crew who talk to people. The drinks and snacks get called generous, and the Wreckers Race sails are the ones people come back for.
Questions
Good to know
When does America 2.0 sail Key West?
November through May. She spends the summer in New York. The Key West calendar opens month by month.
Where does it leave from?
Behind Schooner Wharf Bar at 202 William Street in the Historic Seaport.
Is it a real sailboat?
Yes. A 105-foot schooner with 3,600 square feet of sail and electric motors for the harbor. She sails when the wind allows.
What does it cost?
Champagne sunset sail $112 per adult, day sail $58 with kids 2 to 12 free, full moon sail $64. Checked September 30, 2026.
Can we bring our own drinks?
No. The sunset sail includes beer, wine and champagne; the day sail includes soda and water.
Sail America 2.0
Winter sails from the Historic Seaport, November to May.
Check Availability