Sunset Sail Key West
Sunset Sail Key West is a privately held sailing charter operator in Key West, Florida, running a three-vessel fleet of historic yachts. It offers shared and private sunset sails, day sails, and special-occasion cruises to tourists and visitors booking directly via its website.
- Company typePrivate
- Founded2012
- HeadquartersKey West, United States
- Headcount1–10
- GTM typeB2C
- OfferingServices
What Sunset Sail Key West does
Sunset Sail Key West is a privately held sailing charter company founded in 2010 by Captain Seth Salzmann and based in Key West and Stock Island, Florida. The company operates a fleet of three classic sailing vessels — the 80-foot historic schooner When and If (built 1939 for General George S. Patton), the 1930 schooner Malabar X (winner of the Newport to Bermuda race), and the 1980 Glander sloop High Tide — offering shared and private sailing experiences including sunset cruises, day sails, snorkeling and lilypad trips, and special-occasion charters such as proposals, weddings, and corporate events. Captain Seth's personal history (becoming the youngest schooner captain in North America at 19, transatlantic crossings, Panama Canal transit) and the documented provenance of the vessels form the core of the brand narrative.
The underlying technology stack is intentionally minimal and aligned with a service business: bookings are processed via the embedded FareHarbor reservation platform on the company website, with supplementary phone-based reservations and walk-in inquiries; marketing relies on organic social media (Facebook, Instagram, YouTube, Twitter), the company website, and earned media on TripAdvisor, where the business holds a 4.89/5 average across 1,146+ reviews. There is no proprietary software, app, or AI/ML capability disclosed; the company's primary 'technology' is the restored, USCG-certified sailing fleet itself and the operational expertise of its captain and crew.
Revenue is generated entirely on a transactional, per-trip basis: shared sunset and day sails on the schooners are sold at $109 per person with a 28-guest cap, while private charters range from $395 (90-minute harbor day sail) to $645 (private sunset sail) with capacity for up to 32 guests across the fleet. Ancillary revenue comes from add-ons such as catering, photography, BYOB options, and a small online Ship's Store offering branded merchandise. Distribution is direct-to-consumer, with no enterprise or recurring institutional customers; schooner operations are seasonal (Thanksgiving through Memorial Day), creating a concentrated revenue window that the year-round sloop and special-occasion packages partially offset.
Sunset Sail Key West firmographics
Firmographics- Name
- Sunset Sail Key West
- Legal name
- Sunset Sail Key West
- Website
- https://sunsetsailkeywest.com
- Company type
- Private
- Founded year
- 2012
- Operating status
- Operating
- Headcount range
- 1–10 employees
- Short description
- Sunset Sail Key West is a privately held sailing charter operator in Key West, Florida, running a three-vessel fleet of historic yachts. It offers shared and private sunset sails, day sails, and special-occasion cruises to tourists and visitors booking directly via its website.
- Ownership category
- akta.pro rank
Sunset Sail Key West industry classification
Industry- Product category
- Sailing Charters and Maritime Tourism Services
- NAICS
- Scenic and Sightseeing Transportation, Water (487210)
- SIC
- Water Transportation (4400)
- akta.pro primary industry
- Private Yacht & Luxury Boat Charters (With Crew) (THAJALAE)
- akta.pro secondary industries
- Luxury Sailing Cruises (Windjammers & Tall Ships) (THAEADAB), Sailing Experiences (Lessons, Regattas, Day Sails) (THAJAJAG)
Keywords
Where Sunset Sail Key West is headquartered
LocationHeadquarters
- HQ city
- Key West
- HQ country
- United States
- HQ region
- North America
Offices2 records
Markets served
Sunset Sail Key West business model
Business model- GTM type
- B2C
- Offering type
- Services
- Cost components
- Personnel, Operations, Marketing or Sales, Technology or R&D, Others
Revenue model
- Charter Bookings: Per-trip and per-person charter fees for shared and private sailing excursions. Shared sails charged per person ($109pp for schooner sunset sails). Private charters charged per trip (from $395 to $645 per charter depending on duration and vessel). Additional revenue from custom experiences, catering add-ons, photography, and special occasion packages.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Unit Pricing | Pay-as-you-go | Schooner Sunset Sail - $109 per person, 2 hours, up to 28 guests |
| Unit Pricing | Pay-as-you-go | Private Sunset Sail - From $645, up to 12 guests |
| Unit Pricing | Pay-as-you-go | Chillout Lilypad Sail - From $595 |
| Unit Pricing | Pay-as-you-go | Key West Daysail - From $395, 90 minutes |
Go-to-market motion1 record
Distribution channels3 records
Marketing channels9 records
Sunset Sail Key West product offering
Product offeringCore offering
Sunset Sail Key West operates a fleet of three classic sailing vessels (two historic schooners — When and If and Malabar X — and the sloop High Tide) offering shared and private charter experiences in Key West, Florida. Offerings include shared sunset sails and day sails aboard the schooner When and If, as well as private charters for sunset sails, lilypad sails, harbor day sails, and special occasion events. Pricing ranges from $109 per person for shared sails to $645+ per trip for private charters.
Product overview
Sunset Sail Key West operates a fleet of three classic sailing vessels offering shared and private charter experiences. The portfolio consists of two historic schooners (When and If, a 1939 General Patton vessel, and Malabar X, a 1930 John Alden design) plus a 1980 Glander sloop (High Tide). Charter options include shared sunset sails ($109/person) and day sails on the schooners, as well as private charters on all vessels for sunset sails (from $645), lilypad sails (from $595), and day sails (from $395). Special occasion charters with customization options are also available. The company operates from two locations in Key West and Stock Island.
Differentiator
Problem solved
Functional benefit
Products and services
- Schooner Sunset Sail Two-hour shared sunset sail aboard the historic schooner When and If, limited to 28 guests, with complimentary boutique wine and select beers included. Available from Thanksgiving to Memorial Day. Priced at $109 per person.
- Private Sunset Sail Exclusive private sunset sailing experience aboard the USCG-certified Sloop High Tide, accommodating up to 12 guests, with customizable options including catering, music, and photography. Starting from $645 per charter.
- Chillout Lilypad Sail Private charter into Key West's wildlife preserve featuring a 6' x 18' floating lily pad for on-water relaxation and dolphin watching. Fully customizable experience. Starting from $595.
- Key West Daysail 90-minute harbor day sail experience in Key West Harbor, providing a sun-soaked Florida Keys sailing experience. Available as a private charter starting from $395.
- Schooner Day Sails Two-hour shared day sail aboard the historic schooner When and If, limited to 28 guests, with complimentary boutique wine and select beers included. Available from Thanksgiving to Memorial Day.
- Private Day Sails Private day sail options including harbor day sails and all-day snorkel and sail trips, with three classic boats available and parties up to 32 guests. Customizable for snorkeling, stargazing, or sunset experiences.
- Special Occasion Charters Custom sailing trips for special occasions including birthdays, engagements, proposals, weddings, bachelorette parties, family reunions, anniversaries, and corporate events, with options for photographer, music, champagne, and catering.
- Ship's Store Online merchandise store featuring branded apparel and sailing-related merchandise, operated through a Printify storefront.
Companies that use Sunset Sail Key West
Customer profileSegments3 records
Ideal customer profiles2 records
Sunset Sail Key West technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Integration2 records
Sunset Sail Key West partnerships and signals
Strategic signalScale indicators4 records
Recent moves6 records
Expansion highlights4 records
Sunset Sail Key West competitors and assessment
Company assessmentBroad incumbents
- Sebago Watersports: Established Key West water excursion operator offering snorkeling, sunset sails, and other marine activities. Comparable in serving Key West tourists with multi-vessel water experiences, though at broader portfolio scale.
- Fury Key West: Largest water sports and excursion operator in Key West, offering a wide portfolio including sunset cruises, snorkeling, parasailing, and party boats. Comparable as a Key West water-based experience competitor though it operates at much larger scale and broader portfolio.
Direct peers
- Classic Harbor Line: Operator of classic and historic vessels offering sailing and harbor cruises in multiple U.S. cities. Comparable heritage-vessel charter model focused on scenic and sunset sailing experiences.
- Sunset Sail Salem: Sister company in the Friends of SSKW network offering comparable historic sailing experiences in Salem, Massachusetts. Operates on the same brand playbook (heritage vessels, shared/private charters) in a different geographic market.
- Schonerer When and If: Direct affiliate vessel operating under the Friends of SSKW network, sailing the same flagship schooner that Sunset Sail Key West operates. Closely comparable in offering sunset and day sails aboard a historic schooner in a heritage sailing market.
- Key West Sailing Adventures: Local Key West sailing charter offering sunset sails, day sails, and private charters. Direct comparable in the small-operator Key West sailing charter category.
- Danger Charters: Key West sailing charter operator offering half-day and full-day sailing, snorkeling, and sunset trips aboard traditional sailing vessels. Direct competitor in the Key West authentic sailing charter segment.
Emerging players
- Barefoot Sailing Adventures: Smaller Key West sailing charter offering private and small-group sailing experiences. Comparable niche operator competing in the authentic Key West sailing charter segment.
Regional players
- Schooner Appledore: Operator of traditional tall ships offering sailing excursions in Key West and elsewhere. Comparable in classic sailing vessel experiences but primarily serves other markets.
- Maine Windjammer Association: Association of traditional schooner and tall ship operators offering multi-day windjammer cruises in Maine. Comparable in the historic tall ship sailing experience category but operates in a different geographic market (New England).
Market position
Strengths4 records
Weaknesses4 records
Competitive moat3 records
Key risks6 records
Key highlights6 records
Customer concentration
Sunset Sail Key West social profiles
Digital presenceSunset Sail Key West financial estimates
Financial estimateRevenue estimate
Valuation estimate
Sunset Sail Key West leadership team
Management profileNumber of profiles
Profiles1 record
Sunset Sail Key West funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Sunset Sail Key West M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Sunset Sail Key West
What does Sunset Sail Key West do?
Sunset Sail Key West operates a fleet of three classic sailing vessels (two historic schooners — When and If and Malabar X — and the sloop High Tide) offering shared and private charter experiences in Key West, Florida. Offerings include shared sunset sails and day sails aboard the schooner When and If, as well as private charters for sunset sails, lilypad sails, harbor day sails, and special occasion events. Pricing ranges from $109 per person for shared sails to $645+ per trip for private charters.
Is Sunset Sail Key West a public or private company?
Sunset Sail Key West is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was Sunset Sail Key West founded?
Sunset Sail Key West was founded in 2012. It employs 1 to 10 people.
Where is Sunset Sail Key West based?
Sunset Sail Key West is headquartered in Key West, United States, in the North America region.
How does Sunset Sail Key West make money?
One revenue line is on record: charter Bookings.
Who are Sunset Sail Key West's main competitors?
Broad incumbents on record are Sebago Watersports and Fury Key West. Direct peers are Classic Harbor Line, Sunset Sail Salem, Schonerer When and If, Key West Sailing Adventures and Danger Charters. Barefoot Sailing Adventures is listed as an emerging player. Regional players are Schooner Appledore and Maine Windjammer Association.
Does Sunset Sail Key West have an API?
No public API is recorded for Sunset Sail Key West.
What industry is Sunset Sail Key West in?
Sunset Sail Key West's product category is Sailing Charters and Maritime Tourism Services. Its primary akta.pro industry code is THAJALAE, Private Yacht & Luxury Boat Charters (With Crew), with a secondary code of THAEADAB, Luxury Sailing Cruises (Windjammers & Tall Ships). Its NAICS code is 487210 and its SIC code is 4400.