On Sunset Key, every holiday plan starts with the ferry. Opal Collection's published schedule has the ferry leaving the Marina at Opal Key Resort at 15 and 45 minutes past the hour, from 6:45 a.m. to 10:45 p.m. Boats leave the Sunset Key dock on the hour and the half hour, and after 11 p.m. the boat runs by request. The crossing takes about seven minutes, and the landing sits near Mallory Square in Old Town.
Between Thanksgiving and New Year's Eve, almost everything on the 2026 calendar ends before that last scheduled departure. The island's own holiday dinners come first, then a group of December evenings on the same blocks of Front Street as the dock, and finally the one night when Key West saves its main event for after the boats stop.
Three Holiday Dinners at Latitudes, No Ferry Needed
Latitudes has posted menus for Thanksgiving, Christmas Day and New Year's Eve 2026. Reservations are required for all three, by phone at 305.292.5394. Thanksgiving falls on Thursday, November 26, two weeks after this post goes up.
| Holiday | Hours | Selected dishes from the posted menu |
|---|---|---|
| Thanksgiving Day | Noon to 9 p.m. | Heritage turkey $50, 12-ounce prime rib $58, pumpkin pie $15 |
| Christmas Day | Noon to 9 p.m. | Slow-roasted prime rib $68, lobster ravioli $36 |
| New Year's Eve | 5 to 10 p.m. | Maine lobster stuffed deviled eggs $24, yuzu-glazed scallops $50, grilled bone-in K.C. strip $78 |
Prime rib is on both the Thanksgiving and Christmas menus. It's a 12-ounce cut at $58 in November and slow-roasted at $68 on December 25. The New Year's Eve menu is built differently. It runs in courses with a suggested pour beside each dish: J Vineyards Cuvée with the deviled eggs, a Caymus Cabernet Sauvignon with the K.C. strip, and Cloudy Bay Sauvignon Blanc with the scallops.
On December 31, dinner service ends at 10 p.m., 45 minutes before the last scheduled boat leaves Opal Key.
Front Street, Within a Few Doors of the Dock
The ferry lands at Opal Key Resort, 245 Front Street. Several of December's best Old Town evenings happen on that same street, or at the dock itself. In date order:
- Tuesday, December 1. The ReMARCable Decorated Table Top Tree and Wreath Auction takes place at Opal Key Resort, hosted by DJ Sanaris and presented by First Horizon Foundation. The preview opens at 5:30 p.m. and the live auction starts at 7 p.m. The ferry landing and the auction share a property, so the walk is the length of the marina.
- Monday, December 7, through Sunday, December 27. Old Town Trolley's Holiday Lights & Sights Tours leave from Mallory Square several times each night and carry caroling passengers through the decorated streets, according to the Key West Chamber of Commerce's Holiday Fest roundup.
- Friday, December 11, 5 to 8 p.m. The Holiday Concert & Bazaar at the Key West Museum of Art & History fills the Custom House at 281 Front Street with artisans, music and choirs, plus food and libations. It's free and open to the public, and a light show is projected onto the Custom House façade.
- Saturdays and Sundays, December 12–13 and 19–20, 1 to 3 p.m. The Key West Cooking Show hosts Santa at the Shops at Mallory Square, 291 Front Street. Guests are asked to bring their own cameras, and the Chamber's listing welcomes furry friends as well as children.
The Custom House bazaar wraps up at 8 p.m. A Front Street evening that starts on the 5:15 or 5:45 boat from the island and ends there still leaves several scheduled crossings home before the last 10:45 departure. Every item on this list fits easily inside the published schedule.
Farther Afield, Still Home Before the Last Boat
A few December events are a longer walk from Opal Key. Their start and end times also fit within the schedule.
The Truman Little White House
The Key West Harry S. Truman Foundation's second annual Great Gingerbread Build runs Saturday, December 19, from 11 a.m. to 2 p.m. It's free and open to the public. Guests RSVP for an arrival time, and a limited number of kits are available to buy. The Foundation also offers evening holiday décor tours with a presentation of presidential holiday cards on Tuesday, December 22 and Wednesday, December 23. Tours start at 6, 6:45 and 7:30 p.m. within a 6 to 8 p.m. window, and tickets are $20 for members and $35 for nonmembers.
The Historic Seaport and the Boat Parade
Schooner Wharf Bar, at 202 William Street, is the judges' stand for the Lighted Boat Parade on Saturday, December 12. Festivities start along the Harbor Walk at 6 p.m. with the Bahama Village Music Program's "House of Pan" steel band, and the parade begins at 8 p.m. in Key West Bight and Harbor. The Chamber suggests arriving early to walk the Key West Harbor Walk of Lights before the boats go by. The lights stay up nightly through New Year's Eve.
The same weekend has a daytime option at the Seaport. On Sunday, December 20, the Florida Keys Southernmost Car Club holds its free Holiday Classic Car Show and Toy Drive in the Conch Republic Seafood Company lot at Greene and Elizabeth Streets. Attendees are asked to bring an unwrapped toy.
The Hometown Holiday Parade
On Saturday, December 5, the Key West Hometown Holiday Parade travels along Truman Avenue and Duval Street with floats, marching groups, and what the Chamber calls "assorted hoofed and whiskered friends." It's free to watch.
Christmas Day, Two Ways
On Christmas morning, Schooner America 2.0 runs a 2.5-hour brunch sail from 10 a.m. to 12:30 p.m., serving spiral ham, smoked salmon, quiche, pastries and champagne. Latitudes begins Christmas dinner service at noon and serves until 9 p.m. With those hours, a day can include the brunch sail in the harbor and a later dinner reservation back on the island.
New Year's Eve Peaks After the Last Scheduled Boat
All month the calendar ends ahead of the ferry. On December 31 it doesn't.
Key West's best-known New Year's traditions all happen at midnight. Sloppy Joe's has confirmed its 33rd annual Conch Shell Drop for December 31, 2026, at Duval and Greene, with the shell coming down at midnight. Bourbon St. Pub, at 724 Duval Street, lists its 29th annual High Heel Shoe Drop from 8 p.m. to 1 a.m. Schooner Wharf's events calendar lists a New Year's Eve party and the Lowering of the Pirate Wench at midnight at the Historic Seaport. According to the Keys Weekly New Year's Eve guide, watching from the street is free, and VIP balcony and indoor-party options are ticketed.
Here's how the evening lines up against the ferry:
- 5 p.m. Latitudes opens for New Year's Eve dinner on the island.
- 8 p.m. The Bourbon St. Pub event opens on Duval.
- 10 p.m. Latitudes ends dinner service.
- 10:45 p.m. The last scheduled ferry leaves Opal Key for Sunset Key.
- 11 p.m. onward. The boat runs by request.
- Midnight. The conch shell, the shoe and the Pirate Wench come down.
Dinner at Latitudes ends 45 minutes before the last scheduled boat leaves Opal Key. Each of the three midnight drops comes more than an hour after that departure. On New Year's Eve, then, Sunset Key residents decide between staying on the island and staying in Old Town until midnight, and staying in Old Town means a by-request boat home after the countdown.
If you're spending the holidays on the island and wondering how your home might fit into next season's plans, the team at Ocean Sotheby's International Realty works across Sunset Key and Old Town and would be glad to help. Request a Home Valuation, and we'll prepare a confidential review of your Sunset Key property at whatever pace suits your season.
