Things to Do in Tampa Bay This Weekend Nov 22–23, 2025

Discover the best events happening in Tampa Bay this weekend, Nov 22–23, 2025. From Winter Village at Curtis Hixon Park to holiday markets, comedy shows, and waterfront festivals, here’s your complete Tampa Bay weekend guide.

1. Winter Village at Curtis Hixon Park (Tampa)

A seasonal favorite, Winter Village at Curtis Hixon transforms downtown Tampa into a festive holiday playground — complete with ice skating, sparkling lights, waterfront activities, and boutique shopping.

When: Nov 21, 2025 – Jan 4, 2026
Where: Curtis Hixon Waterfront Park, 600 N Ashley Dr, Tampa
Cost: Free entry; skating and cruises ticketed

Why It’s a Must-See This Weekend

• Real outdoor ice skating rink (75-minute sessions)
  

• River of Lights holiday cruise along the Hillsborough River
  

• Holiday market with 20+ local vendors
  

• Curling lanes, themed skate nights, trivia, silent disco
  

• A perfect photo-op spot for families, couples, and holiday lovers

2. Sarah Millican: Late Bloomer Tour (St. Petersburg)

If you’re looking for fun things to do in St. Pete this weekend, catch internationally acclaimed comedian Sarah Millican at the Mahaffey Theater.

When: Saturday, Nov 22 at 8 PM
Where: Mahaffey Theater, St. Petersburg
Cost: Ticketed event

Why You’ll Love It

• Hilarious, warm, relatable storytelling
  

• Perfect for a date night or girls’ night
  

• One-night-only stop on the Late Bloomer tour

3. Tampa Bay Holiday Market & Expo (St. Petersburg)

Holiday shopping is officially underway! The Tampa Bay Holiday Market is one of the largest seasonal markets in the region and a top choice for unique, locally made gifts.

When: Nov 22–23 | 10 AM – 5 PM
Where: Coliseum, 535 4th Ave N, St. Pete
Cost: FREE admission & parking

What to Expect

• 100+ local makers & artisans
  

• Holiday décor, candles, handmade gifts, treats, and more
  

• Free holiday ornament for the first 250 guests each day
  

• Great for early Christmas shopping
  

  4. Italian Food & Wine Festival (St. Petersburg)

If you’re craving delicious eats and waterfront views, the Italian Food & Wine Festival is one of the top food events in Tampa Bay this weekend.

When: Friday, Nov 22 | 6 PM – 11 PM
Where: Albert Whitted Park, St. Petersburg
Cost: Free entry

Why Go

• 30+ food trucks serving pasta, pizza, cannoli & more
  

• Local vendors + craft makers
  

• Live music and family-friendly entertainment
  

• Incredible sunset views over the waterfront

5. Sanding Ovations Masters Cup (Treasure Island)

One of the biggest annual events in Tampa Bay, Sanding Ovations brings world-class sand sculptors to the beaches of Treasure Island.

When: Nov 20–24
Where: Treasure Island Beach
Cost: approx. $15

Why It’s Popular

• Massive, highly detailed sand sculptures
  

• Food vendors, live music, and kid-friendly activities
  

• Perfect for photos and beach lovers

Honorable Mentions- More Tampa Bay Events This Weekend

• St. Pete Saturday Morning Market — fresh produce + local artisans
  

• Tampa Riverwalk Holiday Lights Self-Guided Tour — perfect for an evening stroll
  

• Holiday Movies in the Park (St. Pete Pier) — free family event
  

• Ybor City Holiday Tree Lighting — seasonal kickoff 

Why Tampa Bay Locals Love Weekends Like This

Events like these are a huge reason why people love living in Tampa Bay. From waterfront views to walkable downtown districts, residents enjoy year-round festivals, outdoor activities, holiday celebrations, and vibrant nightlife — all part of the incredible lifestyle this region offers.

Thinking About Moving to Tampa Bay? Here’s What Life Here Really Feels Like

Weekends like this are one of the biggest reasons people choose to call Tampa Bay home. Whether it’s waterfront festivals in St. Pete, holiday celebrations along the Tampa Riverwalk, or community markets in our walkable downtowns, this region offers a vibrant lifestyle you won’t find anywhere else.

Living here means having:

• ✔️ Year-round outdoor events and festivals

• ✔️ Beautiful beaches just minutes away

• ✔️ Top-rated neighborhoods for families, retirees & young professionals

• ✔️ A thriving arts, food, and culture scene

• ✔️ Walkable communities with local shops, cafes & markets

If you’re considering relocating or just want to explore what it would be like to live closer to all these incredible weekend experiences…

Let’s talk! We'd love to help you find the perfect Tampa Bay home.

Whether you’re buying, selling, or relocating from out of state, I can guide you through neighborhoods, schools, market trends, and homes that match your lifestyle.

Contact us anytime for a custom list of homes near the events and communities you love.