VentureSail Holidays

What VentureSail Holidays does

VentureSail Holidays is a privately-held, UK-based sailing holiday marketplace founded in 2017 and headquartered in Falmouth, Cornwall. The company curates and resells skippered sailing holidays and private boat charters on a fleet of independent vessels operated by third-party boat owners, offering customers access to 400+ voyages spanning more than 30 countries across the UK, Europe, Scandinavia, the Polar Regions, the Americas and Caribbean, and the Indo-Pacific. Its core product surface is organised around three fleet tiers (Luxury Yachts, Yachts and Catamarans, and Traditional Vessels including tall ships such as Bessie Ellen, Eye of the Wind, and Oosterschelde) and 14 experience categories ranging from expedition and wildlife voyages to family, solo-traveller, hands-on sailing, Atlantic crossings, and ski-and-sail trips.

The business operates without a proprietary technology platform, running instead on a WordPress-based website with a search-enabled voyage finder, supplemented by phone, email, and WhatsApp advisory sales, and using Mailchimp for marketing automation and Feefo for verified customer reviews. Booking protection is offered through Package Travel Regulations where applicable. Revenue is generated on a transaction-fee basis, with VentureSail earning commission on completed bookings while the underlying vessels remain owned and operated by independent partners; pricing spans from approximately £375 for short taster voyages to over £17,000 for full private catamaran charters, with quoted prices in GBP and EUR.

Customer acquisition is direct-to-consumer via SEO-optimised destination pages, blog content, social media (Facebook, Instagram, YouTube, X, LinkedIn), newsletter email campaigns, and earned media coverage from publications including The Guardian, The Sunday Times, Financial Times, and National Geographic. The company positions itself around sustainable, low-impact wind-powered travel and reinforces this through partnerships with Tree Nation (one tree planted per booking) and the Cornwall Wildlife Trust. Primary customer segments are individual travellers, couples, families, and private charter groups, with the market currently spanning consumer and small-mid private charter buyers rather than enterprise accounts.

Name

VentureSail Holidays

Legal name

VentureSail Holidays

Website

https://venturesailholidays.com

Company type

Private

Founded year

2017

Operating status

Operating

Headcount range

1–10 employees

Short description

VentureSail Holidays is a UK-based online marketplace that curates and resells skippered sailing holidays and private yacht charters on a fleet of 400+ independent vessels across more than 30 countries, serving individual travellers, couples, families, and private charter groups on a commission basis.

Ownership category

akta.pro rank

Product category

Sailing Holiday Travel Services

NAICS

Scenic and Sightseeing Transportation, Water (48721), Tour Operators (561520), Scenic and Sightseeing Transportation, Water (487210)

SIC

Services-Amusement & Recreation Services (7900), Services-Miscellaneous Amusement & Recreation (7990)

akta.pro primary industry

Sailing Experiences (Lessons, Regattas, Day Sails) (THAJAJAG)

akta.pro secondary industries

Small-Ship Expedition Cruises (Under ~500 Guests) (THAEADAC), Luxury Sailing Cruises (Windjammers & Tall Ships) (THAEADAB), Day & Short-Horizon Private Cruises (Half-Day/Day/Overnight) (THAEAEAF), Luxury Yacht & Small-Ship Expedition Cruises (THAEABAF)

Keywords

• Sailing holidays
• Crew boat charters
• Yacht charter bookings
• Expedition cruises
• Maritime travel agency

Headquarters

HQ city

Redruth

HQ country

United Kingdom

HQ region

Europe

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

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

Revenue model

1. Sailing Holiday Package Bookings: VentureSail acts as an agency/marketplace connecting customers with independent boat owners and operators. The company facilitates booking of sailing holidays across 400+ voyages worldwide, earning commission on completed bookings. Customers pay for sailing holidays that include accommodation aboard various vessel types, board (full board or half board), and crew services.

Pricing tiers

Go-to-market motion1 record

Distribution channels3 records

Marketing channels5 records

Core offering

VentureSail Holidays is an online marketplace that curates and sells crewed sailing holidays and private boat charters worldwide, offering 400+ voyages across destinations such as the Mediterranean, Caribbean, Arctic, South Pacific and the Indian Ocean. The company connects individual travellers with independent boat owners and operators, providing taster trips, festival events, family holidays, solo-traveller departures, expedition adventures, exotic wildlife voyages, Atlantic crossings, and premium private charter holidays.

Product overview

VentureSail Holidays operates as a sailing holiday marketplace and booking platform offering 400+ skippered sailing adventures across diverse global destinations. The core offering consists of three vessel fleet categories: Luxury Yachts (Chronos, Kairós, Rhea, Ombak Putih, Katharina, Skyelark), Yachts & Catamarans (Agave, Acacia, Cherokee, Emma Claire, Humla, Noonmark VI, Sea Dragon, Stravaigin, Steady, Valiente, Zorba, Zorba Cat, Zuza), and Traditional Vessels (including tall ships and classic boats like Bessie Ellen, Blue Clipper, Eye of the Wind, Noorderlicht, Oosterschelde). The company curates 14 distinct experience types spanning expedition adventures, wildlife holidays, guided activities, hands-on sailing, Atlantic crossings, relaxed sunshine voyages, ski-and-sail expeditions, taster sails, private charters, and maritime festivals. Bookings are available in pounds or euros with Package Travel Regulations protection.

Differentiator

Problem solved

Functional benefit

Products and services

• Expedition Adventure Holidays Crewed sailing expedition itineraries for adventure travellers seeking remote and challenging voyages across global waters.
• Exotic Wildlife Sailing Holidays Crewed sailing voyages focused on wildlife viewing experiences in destinations such as the Galapagos and Indian Ocean.
• Guided Activity & Sailing Holidays Sailing holidays combined with guided activities and excursions at destination ports.
• Hands-on Sailing Experiences Crewed voyages that allow guests to take an active role in crewing and sailing the vessel, aimed at skill development.
• Atlantic Crossings Multi-week transatlantic sailing voyages offered as part of the catalogue's flagship expedition products.
• Relaxed Sunshine Sailing Holidays Leisure-focused crewed sailing holidays in warm-weather destinations such as the Mediterranean and Caribbean.
• Ski and Sail Expeditions Combined skiing and sailing itineraries in regions such as Norway, blending winter sports with coastal voyages.
• Taster Sailing Experiences Short introductory crewed sailing trips aimed at first-time customers and those considering longer voyages.
• Maritime Festival Events Sailing-based event trips timed around maritime festivals and cultural sailing gatherings.
• Family Sailing Holidays Crewed sailing holidays specifically tailored for families and multi-generational groups.
• Solo Traveller Sailing Holidays Crewed sailing holidays with single-cabin availability designed for solo travellers.
• Private Charter Holidays Premium bespoke charters of an entire yacht or catamaran for clients seeking private, custom itineraries.

Quantifiable outcome

• 4.9/5 Google rating based on 163 reviews
• +1 more outcomes

Segments4 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration1 record

Partnerships

Three partnerships are on record, tiered core and minor.

• Independent Boat Owners and OperatorscoreChannel Partner/ Reseller/ DistributorVentureSail partners with independent boat owners and passionate operators to build long-standing relationships. Each boat is carefully selected for sailing quality, comfort, and crew quality to deliver memorable holidays. This fleet partnership model enables access to diverse vessel types from luxury yachts to traditional tall ships.
• Tree Nation (Reforestation Partner)minorStrategic or Co-development PartnerVentureSail supports reforestation efforts worldwide by planting a tree for every booking made through Tree Nation partnership, supporting environmental sustainability commitments.
• Cornwall Wildlife TrustminorStrategic or Co-development PartnerVentureSail is proud to support Cornwall Wildlife Trust as part of their commitment to marine conservation and environmental responsibility.

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Sailing Holidays: Sailing Holidays is a UK operator of skippered sailing holidays offering similar worldwide destinations and comparable vessel types, positioning it as a head-to-head competitor in the UK sailing holiday marketplace.
• Sunsail: Sunsail is a long-established sailing holiday operator offering skippered charters and flotilla sailing worldwide, competing directly with VentureSail for the same consumer base of skippered sailing holiday seekers.
• Dream Yacht Charter: Dream Yacht Charter operates one of the world's largest sailing holiday and bareboat charter fleets, competing with VentureSail in skippered and crewed yacht holidays across similar global destinations.
• Classic Sailing: Classic Sailing curates holidays on tall ships and traditional vessels in the UK and globally, directly comparable to VentureSail's Traditional Vessels fleet which includes ships like Bessie Ellen and Eye of the Wind.
• MedSailors: MedSailors is a UK-based sailing holiday operator focused on Mediterranean flotilla and skippered week-long experiences for solo travellers, groups, and young professionals, overlapping directly with VentureSail's week-long Greece/Croatia offering.
• The Moorings: The Moorings is a major global yacht charter company with skippered and bareboat options across the Mediterranean, Caribbean, and Pacific, directly comparable to VentureSail's marketplace of skippered holidays.
• TopSail Sailing Holidays: TopSail Sailing Holidays is a UK-based traditional vessel and tall ship holiday operator with overlapping destination coverage (Mediterranean, Scandinavia, Caribbean) comparable to VentureSail's experience portfolio.

Broad incumbents

• Intrepid Travel: Intrepid Travel is a large, publicly-listed adventure tour operator with a small but growing sailing and small-ship cruise line, representing a broader incumbent that competes for the same experience-seeking traveller cohort.

Emerging players

• Seafarer Cruises: Seafarer Cruises operates small-ship and sailing cruises globally including Croatia and the Caribbean, offering skippered experiences comparable to VentureSail's yacht and traditional vessel fleet.
• Aldamar Cruises: Aldamar organizes small-ship cruises and sailing adventures in Indonesia and other off-the-beaten-path regions, overlapping with VentureSail's Indonesia spice trade route and Pacific Islands offerings.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks5 records

Key highlights7 records

Customer concentration

• Xx.com/venturesail
• YouTubeyoutube.com/@venturesailholidays/videos
• Facebookfacebook.com/VentureSail
• LinkedInlinkedin.com/company/venturesail-holidays
• Instagraminstagram.com/venturesailholidays

Revenue estimate

Valuation estimate

Number of profiles

Funding overview

Funding rounds

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 VentureSail Holidays