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Sunset Sail Key West

Real. Classic. Sailing.

Sunset and day sails on two historic schooners and Key West’s first charter sailboat. Join a shared sail, or take a boat for your group.

Book nowMeet the fleet

4.9 from 1,287 reviews on Tripadvisor4.8 from 377 reviews on Google

When and If at sunset, off Key West

Since 2010, Captain Seth has sailed Key West on boats with a past. The schooner built for General Patton in 1939, a schooner built to win the race to Bermuda, and the little green sloop that became Key West’s first charter sailboat.

Choose your sail

Pick a sail and a date and book online. Your confirmation, with the dock to come to, arrives by email right away.

When and If, with the sun in her rigging

The schooner sunset

Two hours under canvas as the sun goes down, with wine poured on deck.

Join a small crowd aboard one of our two historic schooners. The crew raise sail and cut the engine, and the only sound is the wind in the rigging. Haul a line, take a turn at the wheel, or settle in with a glass of the boat’s own wine and watch for dolphins. You’re back at the dock as the sky turns pink.

  • When and If

    Shared sail · 2 hours · Daily through November, timed to sunset · Historic Seaport

    $109

    per adult, plus tax

    Book →

  • Malabar X

    Shared sail · 2 hours · Daily at 4:30pm · The Perry Marina

    $109

    per adult, plus tax

    Book →
High Tide heading out for the sunset

A sunset of your own

The boat, the crew and the sky, for your party alone.

High Tide takes up to 12 from the Historic Seaport, past the crowds at Mallory Square and out into the Atlantic. Bring your own drinks; the cooler is stocked with ice. For a bigger party or a grander evening, charter one of the schooners, with Champagne on ice.

  • High Tide

    Private charter · 2 hours · Timed to sunset · Historic Seaport

    $645

    per boat for up to 6, plus tax

    Book →

  • Malabar X

    Private charter · 2 hours · 4:30pm · The Perry Marina

    $1,635

    per boat for up to 12 guests, plus tax

    Book →

  • When and If

    Private charter · 2 hours · Timed to sunset, through November · Historic Seaport

    $2,180

    per boat for up to 12 guests, plus tax

    Book →
Swim call off High Tide

Into the water

Sail to the backcountry, drop anchor and jump in.

High Tide is one of only two medium-sized sailboats in Key West that can reach the backcountry, with its sheltered, shallow spots. Snorkel over sponge beds and coral nurseries, lounge on a floating lilypad, and sail home in time for lunch, or for the sunset.

When and If on an afternoon sail

A day under sail

Morning or afternoon, out on the water in the sunshine.

Two hours on General Patton’s schooner from downtown, in the morning or with a glass of rosé in the afternoon. Blue-water sailing on Malabar X from Stock Island, or ninety minutes around the harbor islands on High Tide. Join a small group or have the boat to yourselves. Take the helm, help raise sail, or simply enjoy the ride.

Last light, off Key West

Under the stars

Out past the lights of town, engine off, heads back.

Ninety minutes on High Tide after dark. The crew sail you out beyond the lights and sounds of Key West, shut off the engine, and leave you to pick out the season’s stars.

  • High Tide

    Private charter · 90 minutes · 7pm · Historic Seaport

    $595

    per boat for up to 6, plus tax

    Book →
“When the war is over, and if I return, Bea and I are going to sail her around the world.”

General George S. Patton, of When and If

Three boats, each with a past

When and If

No. I · Schooner, 1939

When and If

Built for General George S. Patton, who meant to sail her around the world after the war. He never got the chance. Captain Seth oversaw her restoration, then bought her in 2015 to keep her in America.

Built
1939
Built for
Gen. George S. Patton
Length
80 feet
Guests
Up to 28
In Key West
November to May

Read her storySail aboard her (5)

Malabar X

No. II · Schooner, 1930

Malabar X

The yacht designer John G. Alden drew her for himself, to win the Newport Bermuda Race. She won her class in 1930 and took first place overall in 1932, smashing the record.

Built
1930
Designed by
John G. Alden
Length
73 feet
Below
Three cabins sleeping six
Sails from
The Perry Marina

Read her storySail aboard her (4)

High Tide

No. III · Sloop, 1980

High Tide

Key West’s first charter sailboat, built here in 1980. Small, quick and nimble enough for the backcountry, she takes up to 12 guests snorkeling, lilypad lounging, or out for the sunset.

Built
1980, Key West
Built by
Admiral Finbar
Length
33 feet
Guests
Up to 12
Sails from
Historic Seaport

Read her storySail aboard her (6)

What our guests say

4.9 from 1,287 reviews on Tripadvisor4.8 from 377 reviews on Google

“Compared to the other boats we saw leaving the harbor for sunset sail, this one felt the most relaxed and uncrowded, which was exactly what we were looking for.”
travelleromaha, on Tripadvisor
  • “I had no idea that I would be sailing on a historically significant schooner, manned by a three person crew who actually live aboard. You can go below and see the crew quarters, galley, the inner workings, help hoist the sail (I wanted to but my elbows are shot) or even steer the vessel.”
    Michael M., on Google
  • “Family and I celebrated my 80th aboard the When & If—wonderful birthday present! The schooner is gorgeous and historic.”
    Nancy P, on Tripadvisor
  • “We had an amazing experience with Captain Chase and First Mate Jamie. They were very informative as to the area, local wildlife and, since it was our first sailing adventure, the boat and how it all works.”
    timsonefelt, on Tripadvisor

A proposal to remember

Champagne on ice, the sun on the horizon, and a crew who’ve done this before and will catch it all on your camera. Every package can be changed to suit you.

  1. Coral

    on High Tide

    $825

    • Your own boat with a captain and crew
    • Korbel sparkling wine
    • A single red rose
    • Eight pieces of cupcake sushi
    • Crew ready to photograph or film the moment

  2. Pearl

    on Malabar X

    $2,200

    • Your own schooner with a captain and crew
    • A bottle of Dom Pérignon
    • A dozen red roses
    • A gourmet cheese platter
    • Cupcake sushi for two

  3. Diamond

    on Malabar X

    $7,450

    • A professional photographer
    • Discreet live background music
    • Dom Pérignon and commemorative flutes
    • A luxury red rose bouquet
    • A gourmet cheese and iced seafood platter
    • Cupcake sushi for two

    Two weeks’ notice

Book the proposal sunset sail

Or plan it with us: (305) 587-4488

For the love of sailing

Captain Seth found his way to the Key West docks as a boy, cleaning boats before school. At 14 he was crewing on High Tide with Captain Pam. At 17 he made his first transatlantic crossing, and at 19 he became the youngest schooner captain in North America.

He sailed professionally along the Eastern Seaboard and in the Caribbean, across the Atlantic to Italy and through the Panama Canal, and started Sunset Sail Key West in 2010.

The idea hasn’t changed since: real sailing around Key West, on classic boats, away from the crowds and noise of party boats and booze cruises. We love making new friends, and hopefully inspiring a few new sailors along the way.

  1. 1930Malabar X is built for the yacht designer John G. Alden.
  2. 1939When and If is built for General George S. Patton.
  3. 1980High Tide becomes Key West’s first charter sailboat.
  4. 2010Captain Seth starts Sunset Sail Key West.
  5. 2013He takes the helm of When and If and oversees her 18-month restoration.
  6. 2015He buys When and If and keeps her in America.

Two docks. Check yours.

Every sail on this site says which dock it leaves from, and so does your confirmation.

  • Historic Seaport

    High Tide, and When and If’s downtown sails

    202 William St, Key West, FL 33040

    High Tide is in front of Schooner Wharf Bar. When and If leaves from the end of E Dock.

    Pay-to-park lot a minute away at 800 Caroline St, or the garage a block away at 300 Grinnell St. Be on the dock 15 minutes before you sail.

    Directions

  • The Perry Marina

    Malabar X

    7011 Shrimp Rd, Stock Island, FL 33040

    Malabar X is on H dock, in front of the pool by Bad Boy Taqueria.

    Park in the marina lot and allow five to seven minutes to walk through the marina. Be on the dock 15 minutes before you sail.

    Directions

Not sure? Call (305) 587-4488.

Before you go

Anything else? Call us at (305) 587-4488.

Where do we board?

It depends on the boat. High Tide and When and If’s downtown sails leave from the Historic Seaport, 202 William St. Malabar X sails from the Perry Marina on Stock Island, 7011 Shrimp Rd. Every sail on this site says which dock, and so does your confirmation.

Please be on the dock 15 minutes before you sail.

How do we book?

Pick a sail and a date and book online; your confirmation comes by email right away. You can always call us at (305) 587-4488 instead.

Can we bring drinks?

On High Tide, yes. Bring any drinks and snacks you like, and the coolers are stocked with ice. The schooners serve their own wine and beer (included on shared sails), so please don’t bring your own aboard When and If or Malabar X.

Can I sail the boat?

Weather and traffic permitting, everyone who wants to gets a turn at the helm and a chance to help raise sail.

Are children welcome?

Yes. Children must be supervised by an adult for the whole trip, and children 6 and under wear a life jacket on board, which we provide. On shared sails, ages 3 to 12 pay a child’s fare and under 3s sail free.

All 10 questions
Plan a custom charterWeddings, birthdays, anniversaries and company outings, for up to 32 guests across three classic boats. Add a photographer, music, catering or your favorite Champagne. Tell us what you have in mind.Tell us your plansGive a sailA gift certificate for any sail, from a schooner sunset to a private charter. It supports a small family company keeping a fleet of classic boats on the water.Buy a gift card
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