Winter is the season Longboat Key was made for. The weather is milder, the heated pool stays open, and the calendar fills with concerts, markets and ballgames. If you’re planning your first winter stay, or your fifteenth, this guide covers the best things to do on Longboat Key in winter, month by month.
Sand Cay has been on Longboat Key since 1974, so we’ve kept the list to places we’d send a friend. Dates change from year to year, so we’ve linked official sources and flagged anything you should double-check.
The Short Version
- December on Longboat Key is about holiday lights, tree-lighting events and the first snowbird arrivals; the 2025 Light Up Longboat kickoff was held Nov. 22 at Town Center Green.
- The Sarasota Farmers Market sets up every Saturday from 7 a.m. to 1 p.m. in downtown Sarasota, an easy weekly routine for longer winter stays.
- Sarasota Opera’s 2027 Winter Festival runs Feb. 6 to March 21 and includes four productions: La traviata, H.M.S. Pinafore, Ariadne auf Naxos and Jenufa.
- Spring training baseball returns to Ed Smith Stadium in Sarasota in February, with 15 Orioles home games on the 2027 schedule.
- Sand Cay offers nightly, weekly and monthly stays in 60 Gulf-front condos, so book early for the dates you want.
What Is Winter Really Like on Longboat Key?
Winter here means milder days and cooler evenings than the rest of the year. Sand Cay’s heated pool stays open year-round, and the beach is still a daily habit for many guests.
It’s also a busy stretch for resorts and restaurants, so book your condo and dinner reservations early.
What Can You Do on Longboat Key in December?
December is the holiday month. Longboat Key kicks off the season with Light Up Longboat, a tree-lighting evening on the Town Center Green with caroling, Santa and cookies. The 2025 edition was held on Nov. 22, so the 2026 date may land just before December.
Past years have also included Christmas in the Garden, a free evening display of lights and music at Longboat Island Chapel on Gulf of Mexico Drive, and the Night of Lights on St. Armands Circle with a 60-foot Christmas tree. Both ran in December 2024, so check the dates before you plan around them.
Outside the events, December is great for a quiet walk on the beach at sunset or a lap around the shops at St. Armands Circle. See our holiday events post for more.
What Can You Do on Longboat Key in January?
January is the month to settle in. Many monthly guests build a routine: morning walks, pickleball or tennis on the property, and a Saturday at the market.
The Sarasota Farmers Market sets up every Saturday, rain or shine, from 7 a.m. to 1 p.m. around Main Street and Lemon Avenue in downtown Sarasota. The market’s own site has the details at sarasotafarmersmarket.org.
If you’re staying longer than a week, our guide to monthly stays explains how it works.
What Can You Do on Longboat Key in February?
February is when the calendar fills up. Sarasota Opera opens its 2027 Winter Festival on Feb. 6 with a new production of La traviata, and the festival runs through March 21. The line-up also includes H.M.S. Pinafore, Ariadne auf Naxos and Jenufa, all at the Sarasota Opera House on North Pineapple Avenue.
February is also baseball season. The Baltimore Orioles play 15 home games at Ed Smith Stadium in Sarasota in 2027, and the Pittsburgh Pirates play in Bradenton. We cover game days in more detail in our spring training guide (coming in January). Check the teams’ official schedules before you buy tickets, because dates can shift.
What Can You Do on Longboat Key in March and April?
March is a busy month for the arts. The opera’s Opera Lovers Weeks run in early to mid-March, and anyone who sees all four operas in one series gets 10% off tickets, according to Sarasota Opera. Call the box office at (941) 328-1300 to book.
April brings the Sarasota Film Festival, which was held April 10 to 19 in 2026. The 2027 dates haven’t been announced yet, so watch sarasotafilmfestival.com. April is also a good month for beach days before summer heat arrives.
Month-by-Month Cheat Sheet
| Month | Highlights | Check first |
|---|---|---|
| December | Light Up Longboat, holiday lights, St. Armands Circle | 2026 event dates |
| January | Saturday farmers market, monthly guests arrive | Market hours on holiday weekends |
| February | Opera Winter Festival opens Feb. 6, spring training begins | Game and show tickets |
| March | Opera Lovers Weeks, peak crowds | Dinner reservations |
| April | Sarasota Film Festival, calmer beaches | 2027 festival dates |
Where to Stay on Longboat Key for the Winter
Sand Cay has 60 privately owned, fully furnished two-bedroom, two-bath condos directly on the Gulf. Each has a full kitchen, which matters when you’re staying for weeks. The beach is semi-private, the pool is heated all year, and there are tennis and pickleball courts on site.
Rates change by season, so check the rates page and the individual unit pages for your dates. Stays are three-night minimum, and monthly stays are available. Pets aren’t allowed anywhere on the property, including the beach.
Our concierge page lists local discounts, such as 10% off a Sarasota Alfresco beach picnic. You can also watch today’s conditions on our live beach camera before you leave home. Wondering how Longboat Key compares to its neighbor? See our Longboat Key vs. Siesta Key post.
Frequently Asked Questions
Is Longboat Key busy in winter?
Yes. Winter is a busy stretch for resorts and restaurants, so book your condo and your dinner reservations early.
Can I stay a full month at Sand Cay?
Yes. Sand Cay offers nightly, weekly and monthly stays with a three-night minimum on short stays.
Is the pool open in winter?
Yes. The pool is heated and open year-round.
Are pets allowed?
No. Pets aren’t allowed anywhere on the property, including the beach.
What’s the best month to visit?
It depends on what you want. January suits quiet routines, February and March suit events, and April suits calmer beaches before summer.
Ready to plan your winter stay? Check rates and availability or call reservations at (800) 843-4459 ext. 102.
