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Finding The Best Winter Vacation Activities Near Clearwater, Florida

Clearwater, Florida, is a vibrant destination known for its stunning white sand beaches, year-round sunshine, and crystal-clear waters. While many flock to the area during the summer months, Clearwater’s charm doesn’t fade when the temperatures drop. In fact, the winter months offer a unique opportunity to explore the city at a more relaxed pace, without the typical crowds.

Clearwater FL winter temperatures are mild, with daytime temperatures in the 60s and 70s Fahrenheit (18-24°C), making it a welcoming escape for visitors seeking warmth without the extreme heat of summer. Nights cool off to the low 50s and low 60s (10-16°C), providing a comfortable climate for outdoor exploration. Also, rain is minimal in the winter, so you’ll find clear, sunny days dominating the forecast.

Winter Vacation Florida Clearwater
A Boat Tour for you winter vacation in Clearwater, FL

Here’s a guide to some of the best wintertime sightseeing and activities you can enjoy in Clearwater, Florida.

1. Take a Winter Boat Tour with Flying Pelican Tours

Clearwater’s waterways are at their best in the winter. There are fewer visitors to the region and the waterways are open and beautiful. The comfortable temperatures make for a perfect boat tour experience while still allowing you to enjoy the warmth of the sun. Flying Pelican Tours offers a variety of options for getting out on the water, including our 3 hour or 4 hour Caladesi Island beach excursion or sunset tour. Regardless of which tour your select, you’re sure to see dolphins frolicking in the waves and a plethora of wildlife soaking up the sun rays.

2. Explore Clearwater Beach

Clearwater Beach is a must-see destination year-round, but in winter, it becomes a quieter, more serene spot to unwind. The beach, known for its soft, powdery white sand and clear turquoise waters, is often less crowded in the winter months, giving you more space to relax and enjoy the views.

With temperatures in the 60s and 70s, winter is perfect for leisurely strolls along the shore or taking a dip in the Gulf. You can also rent golf carts or ebikes and cruise around the area. Moreover, there are plenty of rental options for kayaking and paddle boarding only a short distance away in Dunedin, FL. Many beachfront restaurants and cafes have outdoor seating where you can enjoy a meal or drink while soaking in the coastal vibes. Winter sunsets are still breath-taking & a must-see item on your vacation to-do list.

3. Clearwater Marine Aquarium

The Clearwater Marine Aquarium is a family-friendly attraction that offers visitors the chance to learn about local marine life and the ongoing efforts to rescue and rehabilitate animals. During the winter, the aquarium is less crowded than in peak tourist season, making it the perfect time to take your time and explore the exhibits. You can also see other rescued animals like sea turtles, otters, and stingrays. The outdoor exhibits are especially pleasant in the cooler winter weather, and the chance to interact with the animals is a memorable experience for visitors of all ages.

4. Take a Nature Walk at Caladesi Island State Park

For nature lovers, Caladesi Island State Park is a must-visit. This pristine island, accessible only by boat, offers quiet beaches, scenic trails, and abundant wildlife. In winter, the island’s natural beauty shines even more, as cooler temperatures create a perfect environment for outdoor exploration.

You can hike the park’s nature trails through mangroves, salt marshes, and along the beach, keeping an eye out for wintering birds and other wildlife. Kayaking and canoeing are also popular activities there, and the calm waters are perfect for exploring the island’s coastline. Whether you’re walking trails, birdwatching, or simply relaxing on the beach, Caladesi Island provides an amazing winter beach escape.

5. Largo Central Park Holiday Lights

If you’re visiting during the holiday season, don’t miss the Largo Central Park Holiday Lights display. This beautiful FREE annual light display is a festive must-see for locals and visitors alike. The park transforms into a winter wonderland with over 2 million twinkling lights adorning trees, sculptures, and displays. The light show runs from late November through early January. During the day hours, Largo Central Park offers a peaceful environment for strolling, and the nearby playground and picnic areas are perfect for enjoying a relaxed afternoon with the kids.

6. Tampa Ice Skating at Winter Village

For those looking for a touch of winter magic, head to Winter Village in downtown Tampa (just a short drive from Clearwater). The seasonal ice rink at Winter Village is a fun and unexpected experience in Florida. Open from November through January, the rink is nestled among local shops, restaurants, and seasonal vendors, creating a festive atmosphere perfect for a winter evening out. Along the same downtown walking area, you’ll find Armature works, a waterfront, historic mixed-use building that breathes new life into the Heights District. Grab yourself an adult beverage or a cup of cocoa from one of the nearby vendors to create an unforgettably “warm winter experience” in the Sunshine State.

7. St. Petersburg and Tampa Day Trips

Clearwater is conveniently located close to two other exciting Florida cities: St. Petersburg and Tampa. Both are easy day trips from Clearwater and offer plenty of winter activities.

  • In St. Petersburg, you can visit the Salvador Dalí Museum with an unparalleled collection of works by renowned artist Salvador Dalí. The St. Pete Pier offers a great place to walk, shop, and dine by the water.
  • Tampa has a variety of indoor and outdoor attractions that are ideal for winter visits, including the Glazer Children’s Museum, The Florida Aquarium, and Busch Gardens. Many of the museums and attractions are less crowded during the winter, allowing you to enjoy them without the long lines.

8. Brunch in Ybor City: A Historical and Culinary Delight

A short drive from Clearwater, the historic district of Ybor City in Tampa offers a unique blend of history, culture, and culinary delights, especially when it comes to brunch. Ybor City holds a special place in Florida’s history. Originally founded by Cuban, Spanish, and Italian immigrants in the late 19th century, it became known as the “Cigar Capital of the World.” At its peak, Ybor City was home to more than 150 cigar factories, where workers rolled hand-constructed cigars in a thriving industry. Today, remnants of this vibrant past can still be seen in the historic architecture and the many buildings that date back to the early 1900s.

One of the most famous landmarks is the Ybor City Cigar Factory, where you can learn about the legacy of cigar-making and its influence on the culture and economy of the region. Ybor’s Latino roots are still visible today, particularly in the Cuban influences seen in the food & music.

Enjoy a leisurely brunch in one of Ybor City’s famous restaurants, many of which offer outdoor seating to enjoy the cooler temperatures while soaking in the area’s vibrant atmosphere. We highly recommend THE ATTIC in Ybor City for vegan pancakes and artsy brunch vibes.