Between the Saturday before Thanksgiving and the weekend after Christmas, nearly every holiday event on Stock Island is on one of two roads. College Road has the Key West Tropical Forest & Botanical Garden and the Tennessee Williams Theatre. Shrimp Road ends at The Perry Hotel & Marina, where the island's lighted boat parade, a Thanksgiving table and the Christmas menus at Matt's are scheduled. The calendar below follows those two roads in date order. On Sunday, Dec. 13, both have something going on.
College Road: the garden and the theater
The Key West Tropical Forest & Botanical Garden at 5210 College Road starts the season early. Its Pirates & Mermaids Rum Chase is set for Saturday, Nov. 21, 2026, from 5 to 9 p.m. The garden promises drinks, hidden clues, costumes and "plenty of pirate mischief" along its paths. The listing asks guests to reserve ahead and links to booking from the garden's homepage. It's an evening event for grown-ups, timed for after sunset.
Two weeks later, the activity moves up the road to the Tennessee Williams Theatre at 5901 College Road. Nutcracker Key West runs Dec. 3 to 7, 2026. The production calls itself a tropical Nutcracker, and its own description says "Sugarplum fairies trade tutus for sea fans." It is also the theater's only show in December. The next one on its schedule is in January 2027, so for this month the Nutcracker has the stage to itself.
There are six performances, and each one has its own ticket link on the official site:
- Thursday, Dec. 3, at 7 p.m.
- Friday, Dec. 4, at 7 p.m.
- Saturday, Dec. 5, at 1 p.m.
- Sunday, Dec. 6, at 1 p.m.
- Sunday, Dec. 6, at 7 p.m.
- Monday, Dec. 7, at 7 p.m.
Two of the six are 1 p.m. matinees, which helps families with young children who can't stay up for a 7 p.m. curtain. The theater has a separate ticketing policy for small children, and the Nutcracker site points families to it before they buy.
Shrimp Road: The Perry's waterfront
At the end of Shrimp Road, The Perry Hotel & Marina runs a holiday calendar that starts with Thanksgiving. Matt's Stock Island Kitchen & Bar lists Thanksgiving lunch and dinner on Thursday, Nov. 26, from 12:30 to 8 p.m. That's a long window, so an early plate and a sunset seating both fit.
The Sunday after Thanksgiving, Nov. 29, The Perry hosts the ZEN Jewelry Pop-Up by Karen Moore from 10 a.m. to 4 p.m. It's one daytime stop for the start of holiday shopping, and it's on the same island.
The biggest date on Shrimp Road is the Stock Island Holiday Lighted Boat Parade on Sunday, Dec. 13, 2026. The event is free and open to the public. Festivities start at 3 p.m. with carnival treats, games, prizes, holiday photo spots and what the listing calls "snow fun in the Florida Keys." The decorated boats parade along the waterfront at 6 p.m. The address is 7001 Shrimp Road, and the hotel's number on the listing is 877-496-8712.
Sunday, Dec. 13: both roads in one afternoon
On Dec. 13, the College Road and Shrimp Road calendars line up. The garden holds its Snowy Day Children's Winter Concert in its courtyard from noon to 2 p.m., an hour before the boat parade festivities open. The concert costs $10 per family, and Botanical Garden Society members get in free.
A family could plan the whole Sunday on Stock Island:
- Noon to 2 p.m. Snowy Day Children's Winter Concert in the garden courtyard, 5210 College Road.
- 3 p.m. Boat parade festivities open at The Perry, 7001 Shrimp Road, with games, treats, prizes and photos.
- 6 p.m. The lighted boats parade along The Perry's waterfront.
- Through 8 p.m. The waterfront festivities continue after the parade.
That gives you a children's concert, a waterfront party and a boat parade in one afternoon on one island. The concert page linked advance tickets as "coming soon," so check the garden's event page closer to the date.
Christmas week at Matt's
After the parade, Shrimp Road has the last big dates on the calendar. The Perry's holiday dining page lists two Christmas offerings at Matt's Stock Island Kitchen & Bar:
What | Dates | Hours | Price |
|---|---|---|---|
Three-course Christmas dinner | Dec. 24 and 25, 2026 | 5:30 to 9 p.m. | $99 per person |
Holiday prix fixe brunch | Dec. 25 to 27, 2026 | 8 a.m. to 1 p.m. | $62 per person |
Dinner reservations go through OpenTable or by phone at 786-862-6621. The brunch has vegetarian and gluten-free options. Brunch runs three mornings and starts on Christmas Day, so it also works for out-of-town guests who are still around the weekend after.
Weeknights between the big dates
The weeks between the dates above have their own standing schedule at The Perry. Salty Oyster Dockside Bar + Grill has live music every Friday and Saturday from 4 to 7 p.m. Happy hour is 4 to 6 p.m. daily at Salty Oyster and 5:30 to 7 p.m. at Matt's. On Wednesdays, trivia night in The Perry lobby starts at 6:30 p.m. and is free.
Here's how those regulars fit around the holidays. Friday, Dec. 4, has the Nutcracker at 7 p.m. on College Road, three hours after the Salty Oyster music starts on Shrimp Road. Wednesday, Dec. 2, has trivia the night before the Nutcracker opens. Neither night takes more than a short drive across the island.
A new name on Peninsular Avenue
There's also a new name on the island this year. The former Ocean's Edge Resort & Marina at 5950 Peninsular Avenue is now the Hilton Key West Resort & Marina, and stays under the Hilton brand began July 1, 2026. The property has 175 rooms, including 86 suites, plus marina access and six saltwater pools. Its restaurants are Yellowfin Bar & Kitchen and Ocean's Edge Café, according to the Key West Citizen. If friends or family come to stay for the holidays, that's one more Stock Island address near the parade and the theater.
I grew up a short drive from here, and seeing the Nutcracker, a children's concert and a lighted boat parade all on Stock Island in one December makes me happy. If you're making room on your calendar for Dec. 13 or have family coming for Christmas week, I'm glad to share which matinee works for little ones or how to fit both roads into one Sunday. Natallie M Liz is always happy to talk about the island we share. Let's Connect.
