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Not sure which yacht?
Tell us the dates and the party size. A broker who charters here every week will shortlist three yachts for you.
A reply within 24 hoursMedian weekly rate $115,000. Base rate, before APA and tax.
Yacht charter Key West anchors you at the southernmost point of the continental United States, a sun-bleached, free-spirited island town where Hemingway’s polydactyl cats still roam the verandas of his Whitehead Street home, the nightly Mallory Square sunset celebration draws fire-eaters and tightrope walkers to the harbour’s edge, and the crystalline waters of the Florida Straits separate you from… Read more
Not sure which yacht?
Tell us the dates and the party size. A broker who charters here every week will shortlist three yachts for you.
A reply within 24 hours
The Monthly Price Index · October 2026, low season
Local knowledgeTwo seasons in one country: Florida and the Keys peak through winter, while Newport and New England take over for the northern summer.
Experience the season's highlights from the water
Holidays and school breaks that suit these waters
For the peak November to April dry season, six to nine months’ lead time is recommended, with Fantasy Fest (October), Christmas, New Year, and Key West Race Week among the highest-demand periods. Summer offers excellent fishing, warmer water, and broader vessel availability, and can typically be arranged four to five months ahead at softer rates.
Access to Dry Tortugas National Park requires a per-person entrance fee payable on arrival, and overnight anchoring in the harbour at Garden Key is limited to a set number of vessels on a first-come, first-served basis. Your Boatcrowd broker can advise on the best timing to secure a spot and ensure the yacht carries all required documentation for the 70-nautical-mile open-water passage from Key West.
The base fee covers the yacht, professional crew, insurance, and standard equipment including snorkelling gear and the tender. Fuel, provisions, beverages, dockage fees, national-park fees, and any fishing-guide services are funded through the APA (30 to 35% of the charter fee). Florida state sales tax at 7% applies, and any unspent APA is refunded at the end of the charter.
Yes, both extensions are popular. Heading north-east through the Keys via Marathon and Islamorada back to Miami is a classic week-long itinerary, while a westward detour to the Dry Tortugas adds a dramatic wilderness dimension. Your Boatcrowd broker designs the routing and manages all permits and customs logistics for whichever combination you choose.
Yacht charter Key West anchors you at the southernmost point of the continental United States, a sun-bleached, free-spirited island town where Hemingway’s polydactyl cats still roam the verandas of his Whitehead Street home, the nightly Mallory Square sunset celebration draws fire-eaters and tightrope walkers to the harbour’s edge, and the crystalline waters of the Florida Straits separate you from Cuba by just 90 miles of deep, Gulf Stream blue. Key West’s charter fleet draws from over 77 yachts across US waters: 68′-98′ motor yachts that berth at the Historic Seaport or Key West Bight, 100′+ superyachts that anchor in the deeper outer harbour, and 55′+ catamarans whose shallow drafts open up the mangrove creeks and backcountry flats between Boca Chica and the Marquesas.
November to April is peak season, dry, 24 to 27°C days, outstanding visibility on the reef tract, and the lively calendar of Hemingway Days, Fantasy Fest, and the Key West Race Week regatta. Summer brings warmer water, tarpon runs on the bridges, and more relaxed pricing. Daily rates start from $6,000/day, rising to $11,500+/day on superyachts above 89′, plus Florida’s 7% state sales tax and 30 to 35% APA covering fuel, provisions, and dockage. Key West’s irresistible appeal is its end-of-the-road character, a place where Caribbean colour, literary history, and bohemian spirit converge on a tiny island surrounded by some of the clearest water in the Western Hemisphere, with the Dry Tortugas’ Fort Jefferson and the pristine Marquesas atoll waiting a short day-sail away for guests seeking true remoteness.
Navigate harbour logistics, reef access, and the best anchorages from the Marquesas to the Dry Tortugas in our detailed Key West destination guide.
Plan your southernmost adventure with curated Key West charter itineraries linking Mallory Square, the Marquesas atoll, and Fort Jefferson in the Dry Tortugas.
Above you’ll find yachts available for Key West charters from the US fleet of over 77 vessels, motor yachts from 68′, superyachts over 100′, and catamarans from 55′. Weekly rates start from approximately $42,000. Filter by type, guest capacity, length, or rate to build your shortlist, then let Boatcrowd’s charter specialists handle Historic Seaport berth reservations, Dry Tortugas permits, and bespoke backcountry fishing and reef itineraries.
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