Profitable Downtown Chicago Yacht Charter with Burnham Harbor Slip
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Three stacked assets sold as one transaction: a 42-foot luxury motor yacht, a downtown Chicago commercial slip with a transferable charter rental permit, and a profitable six-year operating business with established marketplace channels and a 1,000+ customer database.
THE STRATEGIC ASSET: PERMIT MOAT
The City of Chicago no longer issues new commercial charter rental permits at Burnham Harbor. The slip and permit pairing is functionally unobtainable for new entrants except by acquisition. Burnham Harbor sits at the foot of the downtown Chicago skyline, adjacent to Soldier Field, Museum Campus, and Northerly Island. It is the highest-demand charter address on the Great Lakes. A buyer absorbing this position inherits a moat that cannot be created with capital alone, only acquired.
THE VESSEL
2004 Sea Ray 420 Sedan Bridge. 42 feet length overall, 2,700 engine hours. Maintained by top-tier marine mechanical providers with no expense spared. Upholstery and woodwork recently refurbished. Independent 2024 marine survey value: $250,000. Naval architect work for USCG Certificate of Inspection is complete and the COI application is filed (1 of 3 milestones complete), opening a path to inspected-vessel operations under new ownership.
THE OPERATING BUSINESS
Structured to run with minimal direct owner involvement. A dedicated booking broker handles inquiries, scheduling, and customer coordination. A vetted pool of USCG-licensed captains rotates through charters. Mechanical service is contracted to top-tier marine providers. Bareboat documentation workflow is largely automated through the existing software stack.
MARKETING & CHANNEL ASSETS (TRANSFERABLE)
Top Performer and Top Owner status on the largest charter marketplaces in North America, including 5.0-star ratings across 500+ lifetime bookings and 8 consecutive Boat of the Year awards (2018 through 2025). Owned brand domain, website, and content library transfer with the business. The seller estimates an entrant building from scratch would need 12 to 24 months to replicate this channel mix.
FINANCIAL PROFILE
Three-year averages (2023 through 2025):
Revenue approximately $200,000
Gross margin 69%
Adjusted SDE $92,000
Five-year gross margin range: 67% to 73%. The business is post-cutover. Pre-pandemic years (2021 and 2022) ran higher at $253K to $318K revenue. Results have stabilized at a sustainable run-rate around $200K with high-60s gross margins. Operating expenses are largely fixed (slip, insurance, mechanical, storage), creating operating leverage on incremental revenue growth.
A live, transaction-level recast workbook is available for review under NDA.
GROWTH PATHWAYS
COI completion would unlock inspected-vessel operations and expand the addressable charter market. The existing permit and channel infrastructure can support a second vessel without duplicating overhead. The owned domain and SEO equity provide a path to reduce marketplace commission expense over time.
TRANSITION
Structured transition at no additional cost, including vendor introductions, marketplace profile transfers, and customer database integration.
PROCESS
Detailed financials, the 2024 marine survey, the COI documentation package, and the customer database are released upon execution of a mutually acceptable NDA. Inquiries handled directly by the seller's representative
THE STRATEGIC ASSET: PERMIT MOAT
The City of Chicago no longer issues new commercial charter rental permits at Burnham Harbor. The slip and permit pairing is functionally unobtainable for new entrants except by acquisition. Burnham Harbor sits at the foot of the downtown Chicago skyline, adjacent to Soldier Field, Museum Campus, and Northerly Island. It is the highest-demand charter address on the Great Lakes. A buyer absorbing this position inherits a moat that cannot be created with capital alone, only acquired.
THE VESSEL
2004 Sea Ray 420 Sedan Bridge. 42 feet length overall, 2,700 engine hours. Maintained by top-tier marine mechanical providers with no expense spared. Upholstery and woodwork recently refurbished. Independent 2024 marine survey value: $250,000. Naval architect work for USCG Certificate of Inspection is complete and the COI application is filed (1 of 3 milestones complete), opening a path to inspected-vessel operations under new ownership.
THE OPERATING BUSINESS
Structured to run with minimal direct owner involvement. A dedicated booking broker handles inquiries, scheduling, and customer coordination. A vetted pool of USCG-licensed captains rotates through charters. Mechanical service is contracted to top-tier marine providers. Bareboat documentation workflow is largely automated through the existing software stack.
MARKETING & CHANNEL ASSETS (TRANSFERABLE)
Top Performer and Top Owner status on the largest charter marketplaces in North America, including 5.0-star ratings across 500+ lifetime bookings and 8 consecutive Boat of the Year awards (2018 through 2025). Owned brand domain, website, and content library transfer with the business. The seller estimates an entrant building from scratch would need 12 to 24 months to replicate this channel mix.
FINANCIAL PROFILE
Three-year averages (2023 through 2025):
Revenue approximately $200,000
Gross margin 69%
Adjusted SDE $92,000
Five-year gross margin range: 67% to 73%. The business is post-cutover. Pre-pandemic years (2021 and 2022) ran higher at $253K to $318K revenue. Results have stabilized at a sustainable run-rate around $200K with high-60s gross margins. Operating expenses are largely fixed (slip, insurance, mechanical, storage), creating operating leverage on incremental revenue growth.
A live, transaction-level recast workbook is available for review under NDA.
GROWTH PATHWAYS
COI completion would unlock inspected-vessel operations and expand the addressable charter market. The existing permit and channel infrastructure can support a second vessel without duplicating overhead. The owned domain and SEO equity provide a path to reduce marketplace commission expense over time.
TRANSITION
Structured transition at no additional cost, including vendor introductions, marketplace profile transfers, and customer database integration.
PROCESS
Detailed financials, the 2024 marine survey, the COI documentation package, and the customer database are released upon execution of a mutually acceptable NDA. Inquiries handled directly by the seller's representative
About the Business
- Years in Operation
- 6
- Employees
- Operated through independent contractors: dedicated booking broker / manager, ve
- Facilities & Assets
- A 2004 Sea Ray 420 Sedan Bridge (42 ft LOA, 2,700 engine hours), independently surveyed at $250,000 in 2024. Maintained by top-tier mechanical providers with no expense spared. Upholstery and woodwork recently refurbished.
Burnham Harbor commercial slip in downtown Chicago, with a transferable commercial charter rental permit. The City of Chicago no longer issues this permit class. The slip and permit pairing is functionally unobtainable for new entrants except by acquisition.
Naval architect work for USCG Certificate of Inspection is complete, and the COI application is filed with the USCG (1 of 3 milestones complete), providing a clear path to inspected-vessel operations.
1,000+ customer database. Established marketplace profiles on the three largest charter platforms transfer with the business, along with an owned brand domain and content library. - Market Outlook / Competition
- Burnham Harbor sits at the foot of the downtown Chicago skyline, adjacent to Soldier Field, Museum Campus, and Northerly Island. It is the highest-demand charter address on the Great Lakes.
The City of Chicago no longer issues new commercial charter rental permits at Burnham Harbor, freezing the supply of available operators. A buyer absorbing this business inherits a market position that cannot be replicated by greenfield investment regardless of capital.
The seller estimates an entrant building from scratch would need 12 to 24 months to replicate the marketplace presence and channel mix transferring with the business. - Opportunities for Growth
- 1. COI completion. Naval architect work is done and the USCG application is filed (1 of 3 milestones complete). Completing COI unlocks inspected-vessel operations and expands the addressable charter market.
2. Operating leverage. Operating expenses are largely fixed (slip, insurance, mechanical, storage). Incremental bookings flow through at near-gross-margin contribution.
3. Second vessel. The existing permit and channel infrastructure can support an additional vessel without duplicating overhead.
4. Direct booking channel. The owned domain and SEO equity provide a path to reduce marketplace commission expense over time.
About the Sale
- Seller Motivation
- Owner moving out of state
- Transition Support
- Structured transition at no additional cost. Includes vendor introductions for mechanical, storage, and broker relationships; transfers of all marketplace profiles; customer database integration; and walkthrough of the booking and bareboat documentation workflow. Seller available for ongoing support during a defined transition period.
Listing Info
- ID
- 2508397
- Listing Views
Business Location
Listing ID: 2508397 The information on this listing has been provided by either the seller or a business broker representing the seller. BizQuest has no interest or stake in the sale of this business and has not verified any of the information and assumes no responsibility for its accuracy, veracity, or completeness. See our full Terms of Use. Learn how to avoid scams.
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