Superior Charters, Inc.

What Superior Charters, Inc. does

Superior Charters & Yacht Sales is a family-owned sailing charter company founded in 1979 in Bayfield, Wisconsin, operating from Port Superior Marina on the Apostle Islands National Lakeshore. The company runs the largest sailboat charter fleet at a single Great Lakes harbor, with 22+ vessels ranging from 31' to 49' from manufacturers including Jeanneau, Beneteau, Lagoon, and Catalina. Its customer base spans individual sailing enthusiasts, families, group charters, sailing students, and yacht buyers/sellers across the U.S. recreational sailing market.

The business is structured around five revenue streams: (1) bareboat and captained sailing charters on Lake Superior, priced from $935 for a 2-day small-boat bareboat up to $8,866 for a week-long 40' catamaran, with seasonal pricing tiers (Early, Spring, Prime, Late); (2) NauticEd-certified sailing instruction including Bareboat Sailor, Intermediate, Advanced, and Cruising Catamaran certifications ($1,195–$1,526 per course); (3) yacht sales and brokerage including new Jeanneau vessels and a charter-to-own program; (4) yacht management services for boat owners; and (5) ancillary lines including boom truck lifting services in the Chequamegon Bay region and the Superior Racing J/70/J/125 program. Distribution is direct-to-consumer via the FareHarbor online booking platform and direct office contact, with marketing through the company website, Facebook, Instagram, TripAdvisor, an email newsletter, and a blog.

The technology layer is operationally simple: third-party booking via FareHarbor, a WordPress website, and standard social media channels. No proprietary platform, mobile app, or AI/ML capabilities are evident. The company is privately held under the Kalow family (Dick and Cindy Kalow as owners, with son Alec as Fleet Manager), supported by a small team (1–10 employees) including a Director of Operations, Fleet Supervisor, Operations Coordinator, Fleet Captain, boat brokers, and 8+ USCG-licensed captains. The business operates seasonally from May through October.

Name

Superior Charters, Inc.

Legal name

Superior Charters & Yacht Sales

Website

https://superiorcharters.com

Company type

Private

Founded year

1979

Operating status

Operating

Headcount range

1–10 employees

Short description

Family-owned sailing charter and yacht sales company founded in 1979 in Bayfield, Wisconsin, operating the largest sailboat charter fleet at one Great Lakes harbor with 22+ vessels serving recreational sailors, families, and sailing students on Lake Superior's Apostle Islands.

Ownership category

akta.pro rank

Product category

Sailing Charter Services

NAICS

Deep Sea, Coastal, and Great Lakes Water Transportation (48311)

SIC

Water Transportation (4400)

akta.pro primary industry

Private Charters & Yacht Experiences (Crewed, Bareboat, Day Charters) (THAJAJAB)

akta.pro secondary industries

Bareboat Yacht Charters (Self-Skippered) (THAEAEAB), Private Yacht & Luxury Boat Charters (With Crew) (THAJALAE), Crewed Yacht Charters (Luxury Crewed) (THAEAEAA)

Keywords

• Sailing charter rentals
• Yacht brokerage services
• Sailing instruction courses
• Yacht management services
• Captained sailing vacations

Headquarters

HQ city

Bayfield

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

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

Revenue model

1. Sailing Charters: Revenue from renting sailboats to customers for bareboat and captained sailing vacations. Pricing varies by boat size, duration, and season (Early, Spring, Prime, Late). Includes packages for 4-person and 6-person groups with captain.
2. Sailing School & Certification: Revenue from teaching sailing certification courses including Bareboat Sailor Certification, Intermediate Sailor, Advanced Sailing, and Cruising Catamaran Certification. NauticEd Sailing School Partner.
3. Yacht Sales & Brokerage: Revenue from selling and brokering yachts and sailboats, including new Jeanneau sales and brokerage boat sales.
4. Yacht Management: Revenue from managing yachts for owners who want their vessels maintained and chartered when not in personal use.
5. Boom Truck Services: Revenue from boom truck lifting services for local contractors, marinas, and businesses in the Chequamegon Bay region including Bayfield, Washburn, and Ashland.

Pricing tiers

Go-to-market motion1 record

Distribution channels2 records

Marketing channels7 records

Core offering

Superior Charters rents sailboats from a 22-vessel fleet for bareboat and captained sailing vacations on Lake Superior's Apostle Islands, departing from Bayfield, Wisconsin. The company also delivers NauticEd-certified sailing instruction, sells and brokers new Jeanneau and pre-owned sailboats, manages privately owned yachts, and provides boom truck lifting services to local contractors and marinas.

Product overview

Superior Charters & Yacht Sales is a family-owned sailing charter company operating on Lake Superior's Apostle Islands from Bayfield, Wisconsin, since 1979. The company offers a unified service platform comprising sailing vacation charters (both bareboat and captained), sailing school courses (NauticEd-certified), yacht sales/brokerage, yacht management, boom truck services, and Superior Racing team. The core charter offering is built around a fleet of 22+ sailboats ranging from 31' to 49' in length, primarily from Jeanneau, Beneteau, and Lagoon manufacturers. Sailing vacations are available as self-skippered bareboat charters for certified sailors or captained packages for inexperienced sailors, including the Four Person Package (39' Beneteau for 4 people) and Six Person Package (38' catamaran or 43'-49' monohull for 6 people). The sailing school includes Bareboat Sailor Certification, Intermediate and Advanced Sailing Certification, Cruising Catamaran Certification, and Women's Sailing Course. The company also operates Superior Racing, a J/70 and J/125 race team representing the Wayzata Yacht Club's Apostle Islands Station.

Differentiator

Problem solved

Functional benefit

Named customers4 records

Segments5 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

Five partnerships are on record, tiered core and minor.

• NauticEdcoreStrategic or Co-development PartnerNauticEd is a sailing education platform. Superior Charters is a NauticEd Sailing School Partner, offering NauticEd certification courses including Bareboat Sailor, Intermediate, Advanced, and Cruising Catamaran certifications.
• FareHarborcoreTechnology or IntegrationFareHarbor provides the online booking platform for Superior Charters, enabling customers to book charters, gift cards, and sailing courses directly through the company's website.
• Wayzata Yacht ClubminorChannel Partner/ Reseller/ DistributorSuperior Charters sponsors the Apostle Islands Station of the Wayzata Yacht Club and sponsors two C&C30 One Design sailboats for racing events.
• Pikes Bay MarinaminorOthersLocal marina partnership providing live webcam feed for weather and conditions monitoring for Superior Charters customers.
• JeanneaucoreChannel Partner/ Reseller/ DistributorSuperior Charters sells new Jeanneau sailboats and offers charter-to-own program where charter fees can be applied toward purchase of a new Jeanneau within 6 months.

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Broad incumbents

• Sunsail: Sunsail is a long-established global sailing charter brand (owned by Travelopia) offering bareboat and skippered charters worldwide. Like Superior Charters, it combines charter, sailing school, and yacht ownership pathways, but at global scale and focused on warm-water destinations.
• Dream Yacht Charter: Dream Yacht Charter is one of the largest global yacht charter operators with bareboat, crewed, and by-the-cabin offerings plus yacht sales and management. It is closely comparable to Superior Charters across the full charter-to-own-to-manage value chain, but at international scale.
• The Moorings: The Moorings is a global yacht charter company operating crewed and bareboat sailing vacations primarily in the Caribbean and Mediterranean, with a much larger fleet and broader geographic footprint than Superior Charters. It is directly comparable as a sailing-charter business model but operates at a very different scale and geography.

Emerging players

• Boatsetter: Boatsetter is a peer-to-peer boat rental platform with both sail and power listings, including captained options. It is an indirect competitor and complementary channel to traditional charter operators like Superior Charters.
• Sailo: Sailo is a peer-to-peer boat rental marketplace that aggregates private sailboats and yachts for charter, similar in end customer to Superior Charters' bareboat bookers. Not a direct fleet operator, but increasingly competitive on discovery, pricing transparency, and last-minute booking.

Others

• NauticEd: NauticEd is a global sailing education and certification platform; Superior Charters is a NauticEd Sailing School Partner. Comparable as a sailing-school authority and curriculum provider, and a partner/ecosystem peer rather than a direct charter competitor.

Direct peers

• MedSailors: MedSailors runs cabin-charter and flotilla sailing vacations in the Mediterranean, similar to the company’s four/six person package concept of group captained sailing trips. Comparable as a packaged group sailing-vacation product, though focused on warm-water Mediterranean routes.
• Anacortes Yacht Charters: Anacortes Yacht Charters operates bareboat and skippered sailing charters out of Anacortes, WA, providing access to the San Juan Islands and Pacific Northwest cruising. Comparable in model (bareboat + captained fleet at a single harbor) and in cold-water, island-cruising experience, but on a different coast.
• Navigare Yachting: Navigare Yachting operates a yacht charter and yacht ownership / charter-to-own program focused on the Caribbean and Mediterranean. It mirrors Superior Charters' integration of charter fleet operation with boat sales and ownership programs, making it one of the closest business-model peers.
• Windworks Sailing Center: Windworks is a Pacific Northwest sailing center combining ASA-certified sailing school with charter and brokerage services. It is directly comparable as a multi-revenue sailing school + charter + brokerage operator in a cold-water, protected-water cruising environment similar to Lake Superior.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks7 records

Key highlights7 records

Customer concentration

• Facebookfacebook.com/superiorchartersinc
• Instagraminstagram.com/superiorcharters

Revenue estimate

Valuation estimate

Number of profiles

Profiles17 records

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 Superior Charters, Inc.