What The Windjammer Way does

The Windjammer Way, operated by Windjammer Sailing Inc. (Florida), is a boutique heritage sailing cruise company building a single-asset experiential tourism business around the 1923-built three-masted schooner SV Mandalay. The company's core product is multi-day, small-passenger-count sailing voyages through the Caribbean, primarily Grenada, the Grenadines, and St. Vincent, positioned as an antidote to mass-market cruise tourism. The underlying 'technology' is the physical restoration and refit of a 109-foot historic vessel: hull grit blasting and steel plate replacement, replacement of legacy concrete ballast with a state-of-the-art granular ballast system developed in partnership with a Portuguese cod-fishing company, and mast replacement—all designed to materially improve speed, maneuverability, and fuel efficiency relative to the vessel's prior 1980s configuration. The business is pre-revenue: voyages are not yet bookable, pricing is undisclosed, and the company is generating demand through community-driven marketing (an 'Old Salts' alumni storytelling platform, a 'Jammer Bingo' Facebook group, an email newsletter, and a partnership with US Sailing) while completing the refit.

The company monetizes through one-time voyage bookings to individual consumers, with the planned pricing structure expected to reflect a boutique, heritage experience. Target segments are layered: a primary base of adventure/heritage travelers and former Windjammer Barefoot Cruises passengers (a nostalgic 'Old Salts' cohort), Caribbean sailing tourists drawn to small islands inaccessible to large ships, and a secondary segment of special-occasion travelers (honeymoons, anniversaries, group charters). Distribution is direct-to-consumer through the company website and contact channels; the company does not use third-party travel agents at this stage. In parallel, the company is raising equity capital from its community through the Vicinity Capital marketplace via a 'Founding Windjammer Investment Program,' converting customers and fans into part-owners and creating a hybrid of capital formation and customer acquisition. Headcount is 1-10, the legal entity is Florida-incorporated, and the company is led by Founder/CEO Charles Kropke (also founder of eco-tour operator Dragonfly Expeditions and Tropic Moon Holdings) and President/COO Zack Luttrell, with legacy crew members (Captain Julian Peterson, Executive Chef Boston Brown, Head Bartender Mashup Thompson) carried over from the prior Mandalay operations.

Name

The Windjammer Way

Legal name

Windjammer Sailing Inc.

Website

https://thewindjammerway.com

Company type

Private

Founded year

2024

Operating status

Operating

Headcount range

1–10 employees

Short description

The Windjammer Way operates boutique Caribbean sailing voyages aboard the restored 1923 SV Mandalay schooner, serving heritage travelers, adventure tourists, and special-occasion guests with intimate Grenada-to-Grenadines itineraries as a direct-to-consumer alternative to mass-market cruises.

Ownership category

akta.pro rank

Product category

Heritage Sailing Cruises

NAICS

Scenic and Sightseeing Transportation, Water (4872), Ship and Boat Building (3366)

SIC

Water Transportation (4400), Services-Amusement & Recreation Services (7900)

akta.pro primary industry

Luxury Sailing Cruises (Windjammers & Tall Ships) (THAEADAB)

akta.pro secondary industries

Luxury Yacht & Small-Ship Expedition Cruises (THAEABAF), Cabin Charters & Shared Yacht Trips (THAEADAH)

Keywords

• Sailing cruises
• Heritage tourism
• Caribbean charters
• Schooner voyages
• Maritime experiences

Headquarters

HQ city

Miami

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Operations, Personnel, Infrastructure, Marketing or Sales, Technology or R&D

Revenue model

1. Voyage Bookings: The primary revenue stream will come from selling tickets for multi-day sailing voyages aboard the restored Mandalay. The voyages will be intimate experiences sailing the Caribbean from Grenada through the Grenadines, with pricing expected to reflect the boutique, heritage nature of the experience.

Go-to-market motion3 records

Distribution channels1 record

Marketing channels5 records

Core offering

The Windjammer Way restores and operates the historic 1923 three-masted schooner SV Mandalay to offer multi-day sailing voyages through the Caribbean. The company focuses on heritage tourism and intimate cultural sailing experiences on a vintage windjammer. It also offers a Founding Windjammer Investment Program allowing individuals to acquire equity in the company.

Product overview

The Windjammer Way operates as a boutique sailing cruise company offering intimate Caribbean voyages aboard the historic SV Mandalay, a 102-year-old three-masted schooner. The company provides a single core product: small-group sailing experiences focused on cultural immersion and maritime heritage. The SV Mandalay serves as both the vessel and the centerpiece of the offering, with voyages departing from Grenada and sailing through the Grenadines. Additionally, the company offers an investment program allowing individuals to become founding owners while supporting the vessel's restoration.

Differentiator

Problem solved

Functional benefit

Products and services

• Multi-Day Sailing Voyages aboard the SV Mandalay Multi-day small-ship sailing voyages through the Caribbean aboard the restored 1923 three-masted schooner SV Mandalay, sold directly to individual travelers seeking an intimate, heritage-style tall-ship sailing experience tied to the Windjammer Barefoot Cruises legacy.
• Founding Windjammer Investment Program Equity investment opportunity offered through the Vicinity Capital marketplace that allows individuals to become part-owners of The Windjammer Way while supporting the restoration of the SV Mandalay.

Segments3 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

One partnership is on record.

• US SailingcoreStrategic or Co-development PartnerThe Windjammer Way is the Official Travel Sailing Partner of US Sailing, the national governing body for sailing in the United States. The partnership aims to create programs, events, and stories that keep maritime heritage at the helm, combining the company's historic sailing experience with US Sailing's reach into the American sailing community.

Scale indicators3 records

Recent moves6 records

Expansion highlights6 records

Direct peers

• Star Clippers: Star Clippers operates tall-ship sailing cruises globally, including the Royal Clipper (5-masted barque) — directly comparable to the Mandalay concept of multi-masted sailing cruise vessels with small passenger capacity. Most direct tall-ship sailing competitor.
• Sea Cloud Cruises: Sea Cloud operates authentic tall-ship luxury sailing cruises (Sea Cloud and Sea Cloud II), emphasizing heritage vessels, small guest counts, and windjammer-style itineraries including Caribbean routes — directly analogous to The Windjammer Way's offering.
• Windstar Cruises: Windstar Cruises runs a small fleet of motorized sailing yachts (Wind Star, Wind Surf, Star Breeze) carrying 150-310 guests on intimate, sail-assisted itineraries — closely overlapping the boutique sailing cruise niche in the Caribbean.
• Club Med 2: Club Med 2 is a five-masted sailing cruise ship offering all-inclusive small-ship cruises with sail-and-motor capability — directly comparable as a boutique, heritage-feeling Caribbean sailing cruise.
• Variety Cruises: Variety Cruises operates small-capacity (under 150 guests) yachts and motor-sailers on Caribbean and worldwide itineraries, competing for the same boutique, less-crowded, alternative-to-mega-cruise travelers.

Broad incumbents

• Ponant: Ponant is a larger luxury small-ship expedition cruise line with Caribbean sailings, offering an overlapping customer base (affluent experiential travelers) but on motor vessels rather than sailing yachts.
• Lindblad Expeditions: Lindblad operates small-ship expedition cruises in partnership with National Geographic, attracting affluent experiential travelers seeking heritage/educational sailing experiences — overlapping customer profile though typically motorized.

Emerging players

• Dream Yacht Charter: Dream Yacht Charter is a global yacht charter operator offering bareboat and crewed charter sailing holidays in the Caribbean — partially overlapping customer base but a different distribution model (charter vs scheduled sailing).
• The Moorings: The Moorings is a major Caribbean yacht charter operator with crewed and bareboat sailing vacations — adjacent peer serving the same experiential Caribbean sailing traveler, mainly via self-charter versus scheduled voyage.

Regional players

• Sailrock Resort: Sailrock is a boutique luxury resort on Anegada in the BVI offering sailing-inclusive upscale Caribbean experiences — a comparable heritage-feel, low-density, nature-anchored Caribbean competitor for the same affluent experiential traveler.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks5 records

Key highlights7 records

Customer concentration

• Facebookfacebook.com/TheWindjammerWay
• LinkedInlinkedin.com/company/thewindjammerway

Revenue estimate

Valuation estimate

Number of profiles

Profiles6 records

Funding overview

Funding rounds1 record

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about The Windjammer Way