For Sale By Owner
The Boat. The Business. The Brand.
Miss Penny Sportfishing — Islamorada, Florida Keys
Owner Jack Philip is selling the complete operation: the 43′ Tiara Express Miss Penny, the charter business, and the website — including its Google Search Console, Google Analytics, and AI-citation footprint. Everything below is real operating data, published in full.
The Opportunity At A Glance
A turnkey Upper Keys charter operation with a proven online footprint. Established August 2023. Operating 7 days a week out of Robbie's of Islamorada, Mile Marker 77.5.
Estimated Fair Market Value
An honest, evidence-backed starting point — compiled Sep 2026 from live market comps and published small-business multiples. The asking price is set by the owner; qualified buyers receive full financials for their own valuation.
How the Boat Was Priced
- 2011 Tiara 4300 Open (twin 715 HP Cummins, private-owner spec, North Key Largo): $599,000 asking
- 2019 Tiara 4300 Open (QSM11s, 775 hrs): $779,000 asking
- The 4300 Open resale market is thin: five listings in three years, averaging 281 days on market with ~8% off original asking
- Adjustments down from private-owner comps: charter duty cycle, 661 HP (not 715 HP) engines, unknown engine hours pending survey; adjusted up for the $-heavy 2023/24 refit (rewire, AC, upholstery) and complete charter fit-out a buyer-broker would otherwise add $60K+ to install
How the Business Was Priced
- Charter operations trade at 2–3× seller's discretionary earnings; published marina/fishing benchmarks span 1.6–5.4× earnings (BizBuySell, 2026)
- Recent local comps: Upper Keys charter packages asking $175K–$250K including boat at ~$120K revenue — those operations run decades-old hulls and generic websites
- Miss Penny's premium over those comps is the digital moat: page-one Google rankings, cited-in-AI content, booking automation, and a documented 47% YoY organic growth curve the comps cannot match
- SDE itself is not published here — it is shared with qualified buyers under NDA via the FareHarbor dashboard and tax returns
This is an indicative estimate for orientation, not an appraisal or an offer. Final price is negotiable and contingent on marine survey, engine-hour verification, entity and slip transfer terms, and reviewed financials. A formal appraisal (marine + business) is recommended for financing and is straightforward to arrange through Jack.
The Vessel
A Tiara 4300 Express bought in August 2023 and refurbished over roughly 20 weeks: new upholstery, complete rewire, all-new air conditioning. This is a charter-ready, air-conditioned, tournament-rigged boat — not a project.
Hull & Machinery
| Make / Model | Tiara Yachts 4300 Express (Open) sportfisherman |
| Length | 43′ hull, ~45′11″ LOA with bow roller |
| Beam | 15′ 2″ |
| Engines | Twin Cummins QSM11 diesel, 661 HP each |
| Fuel / Water | ~550 gal / ~130 gal (factory spec, verify at survey) |
| Passengers | 6 anglers licensed, A/C cabin, full head |
| Condition | 20-week refit completed 2024: rewired, new AC, new upholstery |
Charter Fit-Out
- ● Custom outriggers + tuna tower
- ● Full Raymarine electronics suite with FLIR thermal night vision
- ● Hooker Electric variable-speed live-well pumps
- ● Mariteak rocket launcher on Safe-Floor decking
- ● 100% custom rods; Shimano + Avet reels; Lindgren-Pitman electric reels for swordfish deep-drop
- ● Full lure library: Joe Yee, Moyes, Koya, Marlin Magic, GZ, Luremonger
- ● JL Audio throughout
Specifications compiled from owner records and public listings. Buyers should verify documentation, engine hours, and service history with a marine survey of their choosing. Sold as-is, where-is.
The Business
Miss Penny Fishing Charters runs a diversified menu from a slip position at Robbie's of Islamorada — one of the highest-traffic visitor destinations in the Florida Keys — with three sales channels: direct online bookings, the Robbie's booth, and the DirtyBoat affiliate fleet.
Home Port
Slip 8 at Robbie's Marina, 77522 Overseas Hwy, Islamorada (MM 77.5). The marina's own booth sells split charters on the guest's behalf — walk-up demand you don't have to buy.
Brand Story
Veteran-owned, named for owner Jack Philip's mother Penny. "Built on a Mother's Legacy" is a genuine, memorable brand that drives reviews, media, and tournament goodwill.
Specialties
Daytime swordfish deep-drop to 1,400–1,800 ft, catch-and-release sailfish, and a high-margin split-charter seat program — the niche the internet (and AI engines) cite this boat for.
Current Rate Card
| Trip | Duration | Price | Target Market |
|---|---|---|---|
| Half Day Reef | 4 hours | $1,200 | Families, first-timers |
| 3/4 Day Offshore | 6 hours | $1,800 | Mixed reef + big game |
| Full Day Sportfishing | 8 hours | $2,200 | Gulf Stream: mahi, wahoo, tuna, sailfish |
| Daytime Swordfish | 10 hours | $2,700 | Serious anglers, tournament teams |
| Split Charter | Varies | $450 / seat | Solo travelers; fills otherwise-empty days |
Included in every trip: fuel, tackle, fresh bait, ice, Florida fishing licenses, bottled water, and fish cleaning at the dock. Bookings run through FareHarbor (account transfers with the sale); payment history and booking records are available in the dashboard during due diligence.
The Website & Digital Assets
misspenny.com is not a template site. It is a hand-built, security-hardened marketing asset that already outranks most of the Upper Keys fleet and is one of the few charter websites actual AI assistants cite by name.
Platform & Stack
- Astro static build on Netlify (fast, cheap, near-zero maintenance)
- Self-hosted fonts, deferred third-party scripts, inline critical CSS
- Custom AI concierge chat widget with a Telegram back-office bot for booking ops
- Automated daily QA sweep (booking links, sitemap, structured data) and monthly SEO audits
- Complete source code, build scripts, and deployment pipeline transfer at closing
Technical Health (automated audit, Sep 29, 2026)
1 critical · 1 high · 31 med · 57 low
- Technical SEO: 88/100
- AI-answer readiness (GEO): 87/100
- On-page: 67/100 — the headroom is documented and fixable in a weekend
Google Search Console & Analytics
Pulled directly from the property's Search Console (domain property misspenny.com) and Google Analytics 4. 28-day window ending Sep 26, 2026. Full account access is granted during due diligence.
Top Search Queries (28 days)
| Query | Impr. | Avg Pos |
|---|---|---|
| islamorada fishing charters | 113 | 14.6 |
| islamorada fishing charter | 61 | 14.1 |
| women-only fishing tournaments marathon | 57 | 3.2 |
| florida keys deep sea fishing | 37 | 12.6 |
| split charters islamorada | 36 | 6.4 |
| fishing charter islamorada florida | 34 | 13.7 |
| deep sea fishing florida keys | 27 | 13.1 |
Top Landing Pages (28 days)
| Page | Clicks | Impr. |
|---|---|---|
| / (home) | 27 | 838 |
| /split-fishing-charters | 9 | 340 |
| /blog/deep-sea-vs-reef-fishing-florida-keys | 2 | 362 |
| /blog/womens-fishing-tournaments-florida-keys | 2 | 122 |
| /tournaments | 2 | 245 |
| /blog/what-fish-are-in-season-islamorada | 1 | 350 |
| /reviews | 1 | 28 |
Year-Over-Year Trajectory
Same 28-day window, 2025 vs 2026: clicks 30 → 44 (+46.7%), average position 48.2 → 13.0, CTR 0.99% → 1.71%. The site went from page five to page one-and-a-half for its core market in twelve months. Seasonality is real (August ran 66 clicks vs. July's 92 as summer traffic dipped); winter is this market's peak season, and the swordfish and sailfish programs are winter products.
AI Citations & Share of Voice
Tracked Sep 28, 2026 across 51 real buyer prompts asked of ChatGPT, Gemini, and Claude (17 prompts per engine), scored against the local competitive set.
Where Miss Penny Stands
- 17.6% AI share of voice among Upper Keys charter brands (mentioned in 9 of 51 prompts)
- Cited in 7 AI answers with links back to the site
- By engine: Gemini 4 mentions / 3 citations · Claude 3 / 3 · ChatGPT 2 / 1
- Competitive set: DirtyBoat 33.3%, Bud N' Mary's 21.6%, Miss Penny 17.6%, Sea Horse 13.7%, Robbie's 11.8%
Pages The AI Engines Actually Cite
/split-fishing-charters— 5 citations/split-charter-vs-private-charter— 2 citations/(home) — 1 citation/blog/womens-fishing-tournaments-florida-keys— 1 citation
When ChatGPT recommends an Islamorada split charter, this site is one of the handful it names. That position compounds with age.
Documented Headroom (the seller did the diagnosis for you)
- GA4 key events are not configured — booking clicks aren't attributed. One afternoon of setup unlocks real ROI measurement.
- 11 of 51 AI prompts never mention the brand — the audit lists exactly which pages close those gaps.
- On-page score 67/100 — meta descriptions, Twitter cards, and one legacy 404 (/contact-us) are the bulk of the fix list.
- Split-charter queries at position 6.4 with 36 monthly impressions — page-one-topping content already exists; ranking it top-three is the single highest-leverage move.
- Social channels are under-worked relative to the review quality — the content library (fishing reports, blog, video) is ready to repurpose.
What Transfers At Closing
Included
- ✓ The vessel Miss Penny (43′ Tiara 4300 Express) with all charter fit-out, tackle, and lure inventory
- ✓ The charter business entity (Miss Penny Fishing Charters LLC) or an asset sale, buyer's preference
- ✓ Slip position at Robbie's Marina, Slip 8 (subject to marina consent for lease assignment)
- ✓ misspenny.com domain, full website source code, Netlify hosting, and deployment pipeline
- ✓ Google Search Console domain property and Google Analytics 4 property with full history
- ✓ Google Business Profile, Facebook page, and Instagram presence
- ✓ FareHarbor booking account with payment and booking history
- ✓ Photo, video, and fishing-report content library; review history; future booking calendar
- ✓ The chat widget and booking-ops automation, documented and transferable
Verify In Due Diligence
- • Vessel documentation/number, engine hours, and service records — independent marine survey recommended
- • Florida charter licensing, sales-tax permit, and entity good-standing certificates
- • Operator credentials: the buyer must hold (or hire) a USCG master's license; charter insurance to be re-underwritten
- • Slip agreement terms and assignment conditions with Robbie's management
- • FareHarbor contract terms and the DirtyBoat affiliate-fleet arrangement (at the fleet's discretion)
- • Continuing crew arrangements (captain/mate services are not automatically included — discuss staffing with Jack)
Serious About Buying?
Talk directly with the owner. Jack Philip will walk you through the boat, the books, and the numbers above — and open full account access for qualified buyers.
Call Jack — 305-290-1404Boat & Business For Sale By Owner · Islamorada, Florida Keys