Key West in three days

Logistics

Three days is the most popular duration for a first visit to Key West. You should stay in Old Town near Duval Street so you can walk or bike and avoid parking issues. Renting bikes is suggested as an alternative to using a car.

Day one

Start your morning at the Southernmost Point buoy before 9 a.m. to beat the line for photos. Visit the Ernest Hemingway Home and Museum, which costs USD 20 and takes approximately 1h 15m. You can see polydactyl (six-toed) cats there during their daily hours from 9:00am to 5:00pm, though last entry is often at 4:30pm. For lunch, try Spanish tapas-style plates at Santiago's Bodega for USD 25 (approximately 1h). End the day at the free Mallory Square Sunset Celebration with street performers and vendors. In late October, sunset occurs around 6:15pm to 6:30pm. Follow this with dinner at Conch Republic Seafood Company for USD 35 (approximately 1h 15m).

Day two

Dedicate your second day to the Dry Tortugas. The Yankee Freedom ferry costs USD 190 and the total duration is 11h. The ferry usually departs at approximately 7:00am. After returning, have dinner at Louie's Backyard for USD 50 (approximately 1h 30m).

Day three

Start with breakfast at Blue Heaven, where you can eat in an outdoor courtyard while roosters wander between tables. It opens at 8 am, but lines often start by 8:30 am, and the meal costs approximately USD 20 (approximately 1h). If you prefer a quicker option, Cuban Coffee Queen offers grab-and-go breakfast and coffee for USD 8 (approximately 20m).

For your activities, you can visit Fort Zachary Taylor State Park for USD 8 (approximately 2h), which combines a Civil War-era fort with a beach and clear water. The park is open from 8:00am until sunset. Alternatively, you can take the Tiger Cat shark and wildlife boat tour, which departs by 10 am. This tour visits the Key West National Wildlife Refuge for sightings of dolphins, stingrays, sea turtles, lemon sharks, nurse sharks, and blacktip sharks.

Travel timing

If you visit in late October, sunset occurs between 6:15pm and 6:30pm. While hurricane season is a factor in travel timing, the specific metrics or risks associated with it are not established in the provided data.

Sources

[S1] https://www.keywestvacationcenter.com/2026/07/19/key-west-3-day-itinerary/, https://www.keywestvacationcenter.com/2026/07/19/key-west-3-day-itinerary/ [S2] https://ibx.key.com/ibxolb/login/client/index.html, https://ibx.key.com/ibxolb/login/client/index.html [S3] https://plantrip.io/itinerary/1038505, https://plantrip.io/itinerary/1038505 [S4] https://ibx.key.com/ibxolb/login/index.html, https://ibx.key.com/ibxolb/login/index.html [S5] https://destinationlesstravel.com/three-days-key-west-florida-itinerary/, https://destinationlesstravel.com/three-days-key-west-florida-itinerary/