2 hours · Private · Up to 6
Private Harbor Sunset Sail
High Tide out of Schooner Wharf at sunset, your group only. Bring your own drinks; cooler, ice, water and soda aboard.
| Whole boat | $693 |
|---|
Editorial spotlight · Perry Marina, Stock Island and Schooner Wharf, Key West
2026 Conch Shell Awards nomineeBest Sailing Experience
Sunset Sail Key West
An 80-foot schooner built for General Patton in 1939, sailed by the man who restored her. Winter sunset sails from Stock Island, and a 33-foot sloop for private harbor sails downtown all year.
- Private sails from
- $693
- Schooner sail
- $117
- Tripadvisor
- 4.9
- Flagship built
- 1939
Editorial spotlight. Sunset Sail 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 captain
Youngest schooner captain in North America at 19
Seth Salzmann started crewing on High Tide at 14, crossed the Atlantic at 17 and had his schooner license at 19. He bought and restored Conch West in 2010 to start the company, restored When and If in 2013 and bought her in 2015.
The business splits the year: When and If sails Salem, Massachusetts in summer and Key West from November to May. High Tide, the first charter sailboat in Key West, stays at Schooner Wharf year-round for private sails.
“When the war is over, and if I live through it, Bea and I are going to sail her around the world.”
Owner and captain
Capt. Seth Salzmann
- K
Captain
Capt. Kelsey
- D
Captain
Capt. Dan
Captains Kelsey and Dan are named by guests in reviews; Sunset Sail Key West confirms the current roster. Owner bio on the About page.
The flagship
When and If
John Alden designed her and F.F. Pendleton built her in 1939 for George Patton, who planned to sail her around the world after the war. She is 80 feet, wooden, and carries up to 28 guests on the sunset sail with boutique wine, beer, seltzer and a champagne toast included.
Guests can take the wheel and help raise sail. She sails Key West from November through May from the Perry Marina on Stock Island, where parking is free.
| Shared sunset sail, 2 hours | $117 adult, $48 child |
|---|---|
| Shared day sail, 2 hours | $81 adult, $42 child |
Prices include tax as shown by FareHarbor on September 30, 2026. Winter calendar opens by month; December dates were the first listed at this check.
Check AvailabilityThe boats
Two Alden schooners and the sloop
The schooners are the winter fleet on Stock Island. High Tide is the year-round downtown boat and the one to book for a private sail for up to six.
When and If
- Type
- 80 ft Alden schooner
- Built
- 1939, F.F. Pendleton, for Gen. Patton
- Guests
- Up to 28
- Berth
- Perry Marina, 7009 Shrimp Rd, Stock Island
Malabar X
- Type
- Alden wooden schooner
- Built
- 1930
- Guests
- 6 overnight, 3 cabins
- Note
- Won the Newport–Bermuda race in 1930 and 1932
High Tide
- Type
- 33 ft sloop
- Built
- 1980, Key West
- Guests
- Up to 6 private, 12 certified
- Berth
- Schooner Wharf, 202 William St
Book it
Sails
Shared sails are per person on the schooner in season. Private sails are for the whole boat. Prices as FareHarbor shows them on September 30, 2026, tax included.
3 hours · Private · Up to 6
Private Chillout Lilypad Sail
Sail out, anchor, float on the lily pad, sail back. Mornings and afternoons.
| Whole boat | $747 |
|---|
2 hours · Shared · Nov–May
Schooner Sunset Sail
When and If at sunset with wine, beer and a champagne toast. Seats open by the month through winter.
| Adult | $117 |
|---|---|
| Child 3–12 | $48 |
2 hours · Shared · Nov–May
Schooner Day Sail
An afternoon on the schooner without the sunset premium. No dates listed yet at this check.
| Adult | $81 |
|---|---|
| Child 3–12 | $42 |
2 hours · Private
Proposal Sunset Sail
A private sunset sail built around the question, in three packages.
| Coral | $887 |
|---|---|
| Pearl | $2,365 |
| Diamond | $8,009 |
Private charters of When and If for groups larger than six are booked by phone: (305) 587-4488.
Before you go
Know before you go
Where to board
Schooner sails: Perry Marina, 7009 Shrimp Road, Stock Island, with free parking. High Tide private sails: Schooner Wharf Bar, 202 William Street in the Historic Seaport. Check in at the boat 15 to 30 minutes before departure; your confirmation names the dock.
Season
When and If is in Key West from November to May and sails Salem, Massachusetts the rest of the year. High Tide sails Key West all year.
Included
Schooner sails: boutique wine, select beers, water, seltzer and a champagne toast. High Tide: BYOB with a cooler, ice, water and soda aboard.
Kids
Welcome and supervised by you. Children six and under wear a life jacket.
Reviews
What guests say
- 4.9TripadvisorRating as of September 30, 2026
- #31of 397Boat tours and water sports in Key West, Tripadvisor
- 2010FoundedOwner-operated since
Reviewers write about the crew telling the boat's history, getting to steer and raise sail on a real 1939 yacht, and the wine being generous. The recurring comparison is that it feels smaller and quieter than the big catamaran sunset cruises.
Questions
Good to know
Is When and If really Patton's boat?
Yes. He commissioned her in 1939 from John Alden and named her for the plan to sail her around the world when the war was over and if he survived it. Sunset Sail Key West restored her in 2013 and bought her in 2015.
When can I sail on the schooner?
November through May. She spends the summer in Salem, Massachusetts. The Key West calendar opens month by month.
What sails all year?
High Tide, the 33-foot sloop at Schooner Wharf. Private sunset and lily-pad sails for up to six.
What does it cost?
Schooner sunset sail $117 per adult; private sails on High Tide from $693 for the boat; proposal packages from $887. Tax included as FareHarbor shows it on September 30, 2026.
Can we bring drinks?
On High Tide, yes, it is BYOB. Schooner sails include wine, beer and a champagne toast.
Sail Patton's schooner
Winter sunsets on When and If from Stock Island, private sails on High Tide downtown all year.
Check Availability