January to March is Key West’s high season: dry, mild and booked. It opens with writers on Duval Street, fills up in the last week of January with a music festival and a food festival at once, and ends with three weeks of spring breaks. Here are the 2027 dates the organizers and the city have posted, the Dry Tortugas ferry’s days off, the ships in port, and what the weather and the water do.
The three months at a glance
| Date | What | Where |
|---|---|---|
| Thu 7 – Sun 10 Jan | Key West Literary Seminar, “Poetry” | San Carlos Institute, 516 Duval |
| Thu 7 – Sun 10 Jan | Pole Vault in Paradise | Higgs Beach |
| Sun 10 Jan | Wienerpalooza and Chihuahua Flash Mob parade | Front Street, Duval, Caroline |
| Sat 16 – Sun 17 Jan | Key West Half Marathon weekend; the half on Sunday at 7 a.m. | Higgs Beach, then Caroline Street |
| Mon 18 Jan | Martin Luther King Jr. Day | |
| Tue 19 Jan | No Dry Tortugas ferry, a maintenance day | |
| Fri 22 – Sat 23 Jan | Key West Home Tours | Old Town, from the Oldest House |
| Tue 26 – Sat 30 Jan | Mile 0 Fest, Red Dirt and Americana music | Truman Waterfront Amphitheater and around the island |
| Wed 27 – Sun 31 Jan | Key West Food & Wine Festival | Venues across the island |
| Fri 12 – Sat 13 Feb | Key West Home Tours | Old Town |
| Sat 13 – Sun 14 Feb | Florida Keys Seafood Festival | Truman Waterfront Park |
| Mon 15 Feb | Presidents’ Day | |
| Tue 16 Feb | No Dry Tortugas ferry | |
| Sat 20 – Sun 21 Feb | Key West Art & Craft Festival | The Quay, Truman Waterfront Park |
| 1 – 26 Mar | Spring breaks | The table below |
| Fri 12 – Sat 13 Mar | Key West Home Tours, and the Key West Jeep Invasion | Old Town; Truman Waterfront Park |
| Sat 13 Mar | Plein Air Key West, an outdoor painting competition | |
| Sun 14 Mar | Clocks go forward: sunset moves from 6:35 to 7:36 p.m. | |
| Wed 17 Mar | No Dry Tortugas ferry | |
| Sun 28 Mar | Easter | |
| Wed 31 Mar | Lobster season closes |
Event dates are the organizers’ own or the City of Key West’s event notices, and where both have posted one, they agree. The spring breaks are each school’s published calendar.
January: writers, runners and the fullest week of the year
The Literary Seminar, 7 to 10 January
The 44th Key West Literary Seminar takes poetry as its theme, from Thursday 7 to Sunday 10 January, every session in the 365-seat theater of the San Carlos Institute, 516 Duval Street. About twenty writers take the stage, among them Billy Collins, Kevin Young, Marie Howe, Natalie Diaz and Paul Muldoon. It opens with the keynote at 7 p.m. on the Thursday, runs all day Friday and Saturday, and closes on Sunday afternoon.
Registration is $825 for the four days, with the opening reception and a farewell lunch. After 1 December there are no refunds except for a medical emergency or bereavement, though a registration can be passed to someone else until 1 January. Some of it is free: the closing session on Sunday 10 January, 2 to 5 p.m., is open to the public, and so is “Writers on Writing” on Monday 4 January, 4:30 to 6:30 p.m., at the Helmerich Theater in The Studios of Key West, 533 Eaton Street. That is the first day of the writers’ workshops, which meet each morning from 4 to 7 January.
The half marathon, 17 January
The 29th Key West Half Marathon starts at 7 a.m. on Sunday 17 January from Caroline Street at Trumbo Road, less than two blocks from the race expo outside the Half Shell Raw Bar on Margaret Street, and finishes behind the Waterfront Brewery. That is 13 minutes before sunrise. The 8K starts at 7:30. On Saturday 16 January the 5K (7 a.m.) and the 10K (8 a.m.) start and finish at Higgs Beach, 1000 Atlantic Boulevard. Sunday afternoon is the rum stroll and a beer mile outside the Southernmost Beach Cafe.
Monday 18 January is Martin Luther King Jr. Day, so this is a three-day weekend, and the city’s Southernmost Youth Regatta has the Truman Waterfront quay wall, the playground side of the boat ramp and the gravel lot from 15 to 17 January. The city has not yet posted a street-closure notice for the half marathon, as it has for the Wienerpalooza parade.
Smaller dates in the first half of the month
- Pole Vault in Paradise, 7 to 10 January, on the beach between the White Street Pier and West Martello. Higgs Beach stays open.
- Wienerpalooza and its Chihuahua Flash Mob, a parade at noon on Sunday 10 January: a rolling closure from the Custom House on Front Street, along Duval to Caroline, ending at Hank’s Hair of the Dog Saloon.
The last week of January
Two festivals overlap. Mile 0 Fest, ten years old in 2027, runs from Tuesday 26 to Saturday 30 January: more than 50 Red Dirt and Americana acts, headed by Cross Canadian Ragweed, Old Crow Medicine Show, Ryan Bingham, Wyatt Flores and Kaitlin Butts, at more than ten venues. The big shows are each evening at the Truman Waterfront Amphitheater, which has almost no parking; walk, ride a bike or take a taxi.
The 18th Key West Food & Wine Festival runs from Wednesday 27 to Sunday 31 January, on the theme “Connected by the Oceans”. It is a week of separately ticketed events around the island rather than one tent: the Grand Tasting on Friday evening at the Key West Aquarium, a Friday-afternoon tasting stroll by trolley capped at 40 people, a Saturday lunch, a Sunday brunch on Duval. Every event is 21 and over, and all sales are final, with ticket insurance at checkout. Tickets have been on sale since 30 September 2026.
The Key West Home Tours open private Old Town houses on 22 and 23 January, then on 12 and 13 February and 12 and 13 March, all Fridays and Saturdays. A ticket is $55, or $45 for members of the Old Island Restoration Foundation, which runs them. It covers that month’s four homes and the Oldest House, 322 Duval Street, any time from 1 to 4 p.m. on either day, at your own pace.
February: seafood, a holiday weekend and the art show
Presidents’ Day weekend is where February’s events stack up. On Saturday 13 and Sunday 14 February the 21st Florida Keys Seafood Festival takes the Major Field at Truman Waterfront Park, 11 a.m. to 8 p.m. on Saturday and 11 to 5 on Sunday, on the city’s notice; the festival’s own site has not posted its 2027 details yet. The same Saturday a second-line parade starts at the Hog’s Breath, comes down Duval, turns onto Southard past the Green Parrot, then Whitehead and Petronia to the American Legion on Emma Street. Valentine’s Day is the Sunday, and Monday 15 February is the holiday.
The Key West Art & Craft Festival is on Saturday 20 and Sunday 21 February, 10 a.m. to 5 p.m., on the Quay at Truman Waterfront Park. It is the Key West Art Center’s 62nd annual show, juried fine art and fine craft made by the artists showing it, and since 2024 it has been the Old Island Days Art Festival and the Key West Craft Show combined.
Bush Key closes for the nesting season. Sooty terns nest on its beaches from late January to early July, the Park Service says, and the ferry operator puts the closure at February to mid-September. From the fort on Garden Key you can still watch the colony with binoculars.
March and spring break
Spring break 2027
There is no one spring break. Here are the weeks from each school’s own published calendar:
| School | Spring break 2027 |
|---|---|
| Florida International University | Mon 1 – Sun 7 March |
| University of Miami | Sat 6 – Sun 14 March |
| University of Michigan | Sat 6 – Sun 14 March (classes resume on the 15th) |
| Penn State | Sun 7 – Sat 13 March |
| University of Georgia | Mon 8 – Fri 12 March |
| University of Florida | Sat 13 – Sat 20 March |
| Florida State University | Mon 15 – Fri 19 March |
| University of Central Florida | Mon 15 – Sun 21 March |
| University of South Florida | Mon 15 – Sun 21 March |
| Monroe County schools (the Keys) | Mon 22 – Fri 26 March |
Eight of the ten fall between 6 and 21 March, and four of the six Florida universities are off in the same stretch, 13 to 21 March. The Keys’ own children are off from 22 to 26 March, the week before Easter on 28 March.
The rest of March
- 12 and 13 March: the month’s Home Tours, and the Key West Jeep Invasion at Truman Waterfront Park, 10 a.m. to 4 p.m.
- Saturday 13 March: Plein Air Key West, the Art Center’s one-day outdoor painting competition.
- Sunday 14 March: the clocks go forward. Sunset on the 13th is at 6:35 p.m.; on the 14th it is 7:36.
- Wednesday 17 March: St. Patrick’s Day, and no Dry Tortugas ferry.
- 31 March: the last day of the regular lobster season, which reopens on 6 August.
The Conch Republic Independence Celebration comes after, from 16 to 25 April 2027.
Dates still to be posted
- Schooner Wharf’s Wreckers Cup races, a seven-mile “all-in-fun” sailing race to Sand Key. In 2026 they ran on the last Sunday of January, February and March, with a captains’ meeting at the bar the night before. The bar’s events page still shows 2026.
- The Conch Shell Blowing Contest, in the Oldest House garden on a Saturday in early March, run by the Old Island Restoration Foundation. The 2027 date is not out.
- The Literary Seminar’s full schedule, which it releases in early December, and its literary walking tours.
- The half marathon’s street closures, on the city’s special-events calendar.
The Dry Tortugas ferry in peak season
The Yankee Freedom sails every day except its maintenance days, and three fall in this season: Tuesday 19 January, Tuesday 16 February and Wednesday 17 March. The operator says plainly that the trip sells out weeks in advance. On 16 October 2026 its own calendar still had seats on every January date but 1 to 4 and 18 to 20, and on every sailing day in February and March. The Viator ticket below had none of those dates: it had no date after 31 October on sale, which is Viator’s allocation, not a full boat. Its sales are non-refundable from the start; the operator’s own are final 60 days before the trip.
If the date you want is gone, standby is a sign-up sheet at the terminal, 100 Grinnell Street, from 6:30 a.m. on the morning; no-shows are released at 7:45. In January, check-in at 7 a.m. is before sunrise, which is at about 7:10. The Dry Tortugas page has the rest, and the hotels near the ferry put you a walk from it.
Ships in port
The Pier B calendar has a ship on most days:
| Month | Pier B calls | Days with no ship |
|---|---|---|
| January | 26 | 1, 2, 14, 26, 30 |
| February | 23 | 6, 18, 20, 23, 27 |
| March | 24 | 2, 9, 11, 13, 14, 18, 22 |
Most are in from 8 a.m. to 5 p.m. A few stay until 7 p.m., past sunset: the Carnival Dream on 18 January, 1 and 15 February and 1 March; the MSC Explora 1 on 28 January and Explora 3 on 4 February; and the Margaritaville Islander on 16 and 28 February. The Celebrity Summit, listed as a charter, has a tentative stay from 7 a.m. to 11 p.m. on 10 March.
The city’s Mallory T-Pier calendar is the small ships: the American Pioneer, American Ranger and American Maverick, each in for two nights at a time. In January and February one is at the pier every evening except Sundays; in March, on 18 of the 31 evenings. The cruise-days page shows how to read both calendars.
Weather, water and sunset
| Month | High / low °F | Rain, in | Water °F | Sunset, first to last day |
|---|---|---|---|---|
| January | 76 / 66 | 1.8 | 72 | 5:50 to 6:12 p.m. |
| February | 77 / 67 | 1.5 | 75 | 6:13 to 6:29 p.m. |
| March | 80 / 69 | 1.5 | 78 | 6:29 to 7:43 p.m. |
Air and rain are the National Weather Service’s 1991–2020 normals for Key West, and these are the three driest months of the year. The water is NOAA’s Key West harbor station, averaged across 2023 to 2025. Sunset is the U.S. Naval Observatory’s.
A cold front is the thing to watch. February 2026 averaged under 70°F in the harbor, and in its first week the water stayed below 65°F for six days running. March, not January, is the windiest month of the year. Both decide whether the reef trip and the Tortugas crossing are pleasant, so put them early in the stay, with a spare day behind them.
Where to stay
For the festivals, stay in Old Town: the Literary Seminar, the Food & Wine Festival’s venues, the Home Tours and Mile 0 Fest’s amphitheater are all a walk or a short ride from Duval, and you do not need a car in Key West. Book early. The Literary Seminar holds a limited block of rooms at partner hotels for registrants, with cutoff dates. If it is a vacation rental, check the address against the city’s list of licensed properties before you pay; the where-to-stay page has the check and the other areas. The Downtown Key West list and the full Key West list are at the end of this page. Flying in, driving down or taking the ferry from Fort Myers Beach, how to get to Key West has each route.
On the water
Winter is when Honest Eco runs its dolphin search and sunset sail, mid-October to April only, and the 6 p.m. sunsets of January and February put it and any sunset sail before dinner. The sunset sail page compares them, and the dolphin page explains the season. December has its own page, and the best-time page goes month by month for the rest of the year.
.jpg){kind=link}
