Strategic partnerships Partner with Island Windjammers to extend travel insurance offerings through TripMate, leveraging their existing integration and recent partnership to cross-sell protections to a niche sailing and island-hopping audience.

Cross-sell opportunities Leverage the Windjammer sailing holiday model to propose ancillary services such as on-board upgrades, premium excursion bundles, and targeted travel add-ons to a customer base interested in unique island experiences.

Tech-enabled sales Utilize their WordPress Multisite, Gravity Forms, and FareHarbor integration to streamline lead captures, bookings, and partner marketing campaigns, offering complementary tools or plugins to enhance conversion for travel partners.

Financial potential With annual revenue in the multi-million range and a voyage-focused itinerary, position premium B2B services (corporate booking portals, group travel incentives, and insured itineraries) to capture larger, recurring sales from a growing travel arrangements provider.

Market positioning Target similar cruise and sailing operators with a portfolio of 11-50 employees and mid-market revenue, highlighting scalable partnership models, co-branded promotions, and shared sustainability storytelling to differentiate from larger cruise lines.