Virgin Island Sailing
Virgin Island Sailing is a yacht charter broker founded in 1987 that arranges bareboat, crewed, captain-only, shared cabin, and superyacht charters across 30+ global destinations, serving affluent individual travelers via a free concierge model funded by charter provider commissions.
- Company typePrivate
- Founded1987
- HeadquartersTampa, United States
- Headcount11–50
- GTM typeB2C
- OfferingServices
What Virgin Island Sailing does
Virgin Island Sailing (legal entity: Charter Experts, LLC) is a yacht charter broker founded in 1987 and headquartered in Tampa, Florida. The company operates as a free, concierge-style brokerage connecting customers with global yacht charter providers, earning commissions embedded in negotiated charter rates. Its product portfolio spans five charter tiers — Bareboat (self-skippered), Crewed (all-inclusive with captain and chef), Captain Only, Shared By-the-Cabin, and Superyacht (100+ foot luxury vessels) — across four yacht types: sailing catamarans, sailing monohulls, power catamarans, and motor yachts.
The underlying technology is a website-based booking platform (virginislandsailing.com) with yacht search functionality, quote request forms, customer account management, and Calendly-based planning call scheduling. There is no mobile app, no public API, and no documented AI/ML capabilities. The core technical differentiator is the concierge service layer — human charter experts guide customers through yacht and destination selection — rather than proprietary technology.
The business model is a marketplace commission structure: the company negotiates charter rates in advance with 15+ partner charter companies (including The Moorings, Sunsail, Dream Yacht Charter, and Navigare Yachting) and retains a broker fee as compensation. Pricing is quote-based and varies significantly by yacht type, season, and destination, ranging from roughly $600/night for shared cabin charters to $49,560/week for premium bareboat catamarans. The customer base is composed of affluent individual travelers and small groups, with no disclosed enterprise contracts; revenue is not publicly disclosed.
Virgin Island Sailing firmographics
Firmographics- Name
- Virgin Island Sailing
- Legal name
- Charter Experts, LLC
- Website
- https://virginislandsailing.com
- Company type
- Private
- Founded year
- 1987
- Operating status
- Operating
- Headcount range
- 11–50 employees
- Short description
- Virgin Island Sailing is a yacht charter broker founded in 1987 that arranges bareboat, crewed, captain-only, shared cabin, and superyacht charters across 30+ global destinations, serving affluent individual travelers via a free concierge model funded by charter provider commissions.
- Ownership category
- akta.pro rank
Virgin Island Sailing industry classification
Industry- Product category
- Yacht Charter Brokerage
- NAICS
- Scenic and Sightseeing Transportation, Water (48721)
- SIC
- Water Transportation (4400)
- akta.pro primary industry
- Crewed Yacht Charters (Luxury Crewed) (THAEAEAA)
- akta.pro secondary industries
- Bareboat Yacht Charters (Self-Skippered) (THAEAEAB), Private Yacht & Luxury Boat Charters (With Crew) (THAJALAE), Cabin Charters on Private Yachts (By-the-Cabin) (THAEAEAD), Private Charters & Yacht Experiences (Crewed, Bareboat, Day Charters) (THAJAJAB)
Keywords
Where Virgin Island Sailing is headquartered
LocationHeadquarters
- HQ city
- Tampa
- HQ country
- United States
- HQ region
- North America
Offices1 record
Markets served
Virgin Island Sailing business model
Business model- GTM type
- B2C
- Offering type
- Services
- Cost components
- Personnel, Marketing or Sales, Operations, Technology or R&D, Others
Revenue model
- Broker Commission: The company negotiates charter rates in advance with yacht owners and charter companies to obtain cost-effective rates, facilitating reservations and availability. The company receives a commission from the charter provider (Broker Fee) which is included in the pre-negotiated charter rate. Broker retains the Broker Fee as compensation in arranging Charter Reservations.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Subscription | Multi-year contract | Crewed Yacht Charters - 2-4 Guests |
| Subscription | Multi-year contract | Crewed Yacht Charters - 6-8 Guests |
| Unit Pricing | Pay-as-you-go | Shared Cabin Charters |
| Unit Pricing | Pay-as-you-go | Bareboat Charters - Entry Level |
| Unit Pricing | Pay-as-you-go | Bareboat Charters - Premium |
Go-to-market motion2 records
Distribution channels3 records
Marketing channels5 records
Virgin Island Sailing product offering
Product offeringCore offering
Virgin Island Sailing is a yacht charter brokerage that matches individual travelers and travel agents with partner sailing and motor yacht charter operators worldwide. The company earns commission from charter providers rather than charging customers, functioning as a free concierge matching service. Its core activity is curating and booking bareboat, crewed, captain-only, shared by-the-cabin, and superyacht charters across sailing catamarans, sailing monohulls, power catamarans, and motor yachts in the Caribbean, Mediterranean, South Pacific, and Indian Ocean & Asia.
Product overview
Virgin Island Sailing is a yacht charter broker offering a portfolio of charter products across multiple service tiers: Bareboat Charters (self-skippered rentals), Crewed Charters (all-inclusive with captain and chef), Captain Only Charters (captain with customer provisioning), Shared By-the-Cabin Charters (individual cabin bookings), and Superyacht Charters (100+ foot luxury vessels). These services are available across four main yacht types: Sailing Catamarans, Sailing Monohulls, Power Catamarans, and Motor Yachts. The company operates across 30+ global destinations spanning the Caribbean, Mediterranean, South Pacific, and Indian Ocean/Asia regions, and provides free concierge services to assist customers in selecting boats, planning itineraries, and booking travel. The company has been in operation since 1987.
Differentiator
Problem solved
Functional benefit
Products and services
- Bareboat Charters
Quantifiable outcome
- Customers report high satisfaction with booking experience and charter outcomes based on testimonial reviews
Companies that use Virgin Island Sailing
Customer profileNamed customers9 records
Segments6 records
Ideal customer profiles2 records
Virgin Island Sailing technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Feature1 record
Virgin Island Sailing partnerships and signals
Strategic signalPartnerships
15 partnerships are on record, tiered core and minor.
- The MooringscorePremier sailing charter company offering bareboat and crewed yachts. One of the most recognized names in the industry with worldwide operations.
- SunsailcoreGlobal sailing charter company providing bareboat and crewed charter options across multiple destinations.
- Dream Yacht ChartercoreWorldwide yacht charter company offering diverse fleet options across many destinations.
- Navigare YachtingcoreInternational yacht charter company with strong presence in Mediterranean and Caribbean.
- Virgin Charter YachtscoreVirgin Islands-based yacht charter company specializing in BVI and USVI charters.
- BVI Yacht CharterscoreBritish Virgin Islands specialist yacht charter company.
- Conch ChartersminorBVI-based yacht charter company offering bareboat and crewed options.
- Fun in the Sun Yacht ChartersminorYacht charter company operating in the Caribbean.
- Horizon Yacht ChartersminorCaribbean-based yacht charter company specializing in crewed yachts.
- Kiriacoulis MediterraneanminorMediterranean specialist yacht charter company with Greek island expertise.
- The Catamaran CompanyminorCatamaran-focused charter company with operations in Caribbean and other destinations.
- TMM Yacht ChartersminorYacht charter company operating in Caribbean and Mexico.
- Virgin Islands Yacht ChartersminorVirgin Islands specialist yacht charter company.
- Voyage ChartersminorYacht charter company offering various charter options.
- Waypoints Yacht ChartersminorYacht charter company providing bareboat and crewed options.
Scale indicators3 records
Recent moves6 records
Expansion highlights5 records
Virgin Island Sailing competitors and assessment
Company assessmentDirect peers
- GlobeSailor: Online yacht charter broker offering bareboat, crewed, and cabin charters across 50+ destinations worldwide. Directly competes with Virgin Island Sailing in the same commission-based brokerage model with similar product tiers.
- Burgess Yachts: Luxury superyacht charter broker and management company. Directly comparable for the superyacht tier, and increasingly competing for high-end crewed charter customers that Virgin Island Sailing serves.
- Camper & Nicholsons: Historic yacht charter broker and management firm specializing in luxury and superyacht charters. Competes for the same UHNW crewed and superyacht customers with comparable concierge positioning.
- Boatbookings: Yacht charter broker specializing in luxury crewed and bareboat charters in the Mediterranean and Caribbean. Operates a similar concierge brokerage model serving affluent travelers.
- CharterWorld: Yacht charter broker for crewed, bareboat, and superyacht charters globally. Direct competitor in the same niche brokerage space, with similar destination coverage and supplier network.
Others
- Dream Yacht Charter: Worldwide yacht charter company offering bareboat, crewed, and by-the-cabin charters. Both a core distribution partner and a direct competitor via its own consumer marketing.
- The Moorings: One of Virgin Island Sailing's largest charter partners, but also a direct competitor via its own consumer-direct booking channel for bareboat and crewed yachts worldwide. Represents the structural partner-versus-competitor dynamic.
- Navigare Yachting: International yacht charter operator with strong Mediterranean and Caribbean presence. Listed as a partner of Virgin Island Sailing and simultaneously a direct booking alternative for the same end customers.
- Sunsail: Global sailing charter operator and key Virgin Island Sailing partner, but operates its own direct-to-consumer booking platform. Demonstrates the supplier-disintermediation dynamic the broker must navigate.
Emerging players
- YACHTICO: Online yacht charter marketplace with global inventory of bareboat and crewed yachts. Competes on digital booking UX rather than phone-based concierge, representing the more tech-enabled version of the brokerage category.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat3 records
Key risks6 records
Key highlights7 records
Customer concentration
Virgin Island Sailing social profiles
Digital presenceVirgin Island Sailing financial estimates
Financial estimateRevenue estimate
Valuation estimate
Virgin Island Sailing leadership team
Management profileNumber of profiles
Virgin Island Sailing funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Virgin Island Sailing 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 Virgin Island Sailing
What does Virgin Island Sailing do?
Virgin Island Sailing is a yacht charter brokerage that matches individual travelers and travel agents with partner sailing and motor yacht charter operators worldwide. The company earns commission from charter providers rather than charging customers, functioning as a free concierge matching service. Its core activity is curating and booking bareboat, crewed, captain-only, shared by-the-cabin, and superyacht charters across sailing catamarans, sailing monohulls, power catamarans, and motor yachts in the Caribbean, Mediterranean, South Pacific, and Indian Ocean & Asia.
Is Virgin Island Sailing a public or private company?
Virgin Island Sailing is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was Virgin Island Sailing founded?
Virgin Island Sailing was founded in 1987. It employs 11 to 50 people.
Where is Virgin Island Sailing based?
Virgin Island Sailing is headquartered in Tampa, United States, in the North America region.
How does Virgin Island Sailing make money?
One revenue line is on record: broker Commission.
Who are Virgin Island Sailing's main competitors?
Direct peers on record are GlobeSailor, Burgess Yachts, Camper & Nicholsons, Boatbookings and CharterWorld. Others are Dream Yacht Charter, The Moorings, Navigare Yachting and Sunsail. YACHTICO is listed as an emerging player.
Does Virgin Island Sailing have an API?
No public API is recorded for Virgin Island Sailing.
What industry is Virgin Island Sailing in?
Virgin Island Sailing's product category is Yacht Charter Brokerage. Its primary akta.pro industry code is THAEAEAA, Crewed Yacht Charters (Luxury Crewed), with a secondary code of THAEAEAB, Bareboat Yacht Charters (Self-Skippered). Its NAICS code is 48721 and its SIC code is 4400.