4 Easy Fall Getaways From Orlando

Clearwater Beach ©Visit Florida

Fall is finally on its way and it’s not too late to plan your getaway.

Check out some of these great deals and special destinations just a short drive from Orlando. Call or click and get ready for a great trip!

Clearwater Jazz Holiday

October 16 – October 19

The Clearwater Jazz Holiday is a four-day and four-night, world-class, live, music festival, enjoyed by thousands of fans taking place the third week of every October and now in its 46th year. The music festival has evolved from a series of concerts on the back of a flatbed truck and at venues around Clearwater into an annual, international, music festival that draws tens of thousands of visitors each year to beautiful Coachman Park in Clearwater, against the backdrop of the Gulf of Mexico, warm breezes, brilliant sunsets, and one of the world’s greatest beaches. The festival features a combination of legendary and relevant musical artists and a gathering of an amazingly diverse fan base.

Over its 46-year history, a long and impressive list of legendary jazz talents have made stops in Clearwater such as Woody Herman, Buddy Rich, Dizzy Gillespie, Herbie Mann, Dave Brubeck, Tito Puente, Stephan Grappelli, Stan Getz, and the Count Basie Orchestra. The Jazz Holiday’s modern-day, diverse line-up covers a wide array of musical styles: straight ahead and smooth jazz, swing, blues, jam band, rock, folk, Americana, funk, and Zydeco and showcases a new generation of artists, emerging stars, and classic legends including Tony Bennett, Earth, Wind & Fire, Chicago, Bonnie Raitt, Trombone Shorty, The Avett Brothers, Brandi Carlile, Gov’t Mule, Esperanza Spalding, Marcus Roberts, Mindi Abair, Dirty Dozen Brass Band, Medeski, Martin & Wood, Soulive, Christian McBride, Bela Fleck, Boney James, Brian Culbertson, Spirit Family Reunion, Amos Lee, Lake Street Dive, Edward Sharpe & the Magnetic Zeros, Buddy Guy, Gladys Knight, Commodores, Kool & The Gang, UB40, Grace Potter, Sheryl Crow, Michael McDonald and Kenny Loggins and the list goes on and on…. 46 years has shaped a unique magical and magnetic destination experience built on incredible community support.

The true magic stems from those who built, shaped and implemented the experience, many of which share a multi-generational bond with it. The festival is organized and supported by the Clearwater Jazz Holiday Foundation. The Foundation’s dedicated and engaged Board of Directors is composed of community leaders, who oversee production of the festival and various innovative education and outreach initiatives.

The Foundation also orchestrates the popular Jazz Force committee of lead volunteers who work tirelessly to operationally implement the four-day celebration every October and manage hundreds of services needed to accommodate thousands of visitors. The Foundation’s wonderful family of corporate and strategic partners and its popular High Note Society membership help to sustain and grow this timeless tradition. Clearwater Jazz Holiday programs are also funded in part by grants from the State of Florida, Department of State, Division of Arts and Culture and the Florida Council on Arts & Culture and the Pinellas County Commission through the Cultural Development Grants Program of the Cultural Affairs Department.

For more information about the 46th Clearwater Jazz Holiday, visit ClearwaterJazz.com

Shephard’s Beach Resort

Shephard’s Beach Resort is Florida’s Premier Entertainment Resort! Located on South Clearwater Beach, it features large balconies with spectacular views of the Gulf. The Resort’s centerpiece is the World-
Famous Tiki Beach Bar and Concert Stage, perched over their white sand beach. Enjoy local and international bands performing daily while watching the dramatic sunsets.

Explore the new restaurant “Cove Kitchen & Bar,” featuring a casual elevated dining experience. Dine outside at the Tiki Beach Grill. Dance the night away in the Wave Night Club, the area’s only beachside nightclub. Exclusively for the resort guests is the SOAK BAR featuring a wide variety of tropical drinks. Private poolside cabanas are available for your added enjoyment. So don’t just come for the SUN, TROPICAL POOL, WHITE SAND BEACH, WATERSPORTS, MUSIC, DANCING, TROPICAL DRINKS, GREAT FOOD, and AWESOME ROOMS; also come for the excellent service and loads of FUN!

“Come Chill With Us!”

Use the code “CHILL” when you book 2+ nights, and you will receive $75.00 in Food & Beverage credit. Promo ends Dec. 20, 2025.

Call 800.237.8477 or visit Shephards.com – Use Promo Code: CHILL

Martin County

In a world overrun by chatbots and algorithms, Martin County invites you to unplug from the noise and reconnect with what’s real. Here, A.I. doesn’t mean Artificial Intelligence. It stands for Appetizing Indulgences, Amazing Islands, Adventurous Itineraries, Artistic Inspiration, Alluring Invitations, and so much more.

Tucked along South Florida’s Atlantic Coast, Martin County offers the kind of human-powered paradise that no machine could replicate. With more than 22 miles of uncrowded beaches and over 115,000 acres of parks and conservation lands, it’s a destination defined by nature…not code. Here, you won’t find any high-rises, just scenic shorelines, charming seaside towns, and plenty of room to roam.

Fall is the perfect time to discover our warm coastal waters, locally owned restaurants, colorful boutiques, and family-friendly attractions. Or embark on a free, guided eco-tour with our award-winning ecotourism program, Explore Natural Martin (developed in partnership with Leave No Trace). With oceanfront resorts, quaint inns, and trusted national brands, there are lodging options to suit every style and price point.

In Martin County, you’ll uncover a true getaway where real people create unforgettable memories, where nature’s beauty remains untouched by algorithms, and where genuine connections always outshine digital interactions.

What does A.I. mean to you? Find out at noaineeded.com

Let’ Shine Photoshoot

Escape to Florida’s Gulf Coast and Discover St. Pete-Clearwater

This year, escape to Florida’s Gulf Coast and discover St. Pete-Clearwater, home to 35 miles of America’s Favorite Beaches. From lively, family friendly Clearwater Beach to the peaceful shores of Fort De Soto Park, every stretch of sugar-white sand offers its own unique charm. Whether you’re seeking energetic beach vibes or quiet seclusion, the perfect spot is waiting for you.

Photos from Let’s Shine Photoshoot.

But St. Pete-Clearwater offers so much more than beautiful beaches. With year-round sunshine, there are endless opportunities for outdoor adventure. You can paddle through lush mangrove tunnels at the Weedon Island Preserve, bike along scenic coastal trails on Honeymoon Island or venture out on an offshore fishing excursion from John’s Pass in Madeira Beach, the “Grouper Capital of the World.” To make a deeper connection with Florida wildlife, plan a visit to Clearwater Marine Aquarium, a working research facility and rehabilitation center that cares for injured dolphins, sea turtles and more.

When it’s time to fuel up, you can indulge in fresh, Gulf-to-grill seafood at a waterfront eatery and then raise a glass to breathtaking views from a rooftop bar. Thirsty for more local flavor? Follow the Craft Beer Trail to discover innovative new breweries and longstanding favorites like Dunedin Brewery—Florida’s oldest microbrewery.

Photos from Let’s Shine Photoshoot.

Craving culture? Marvel at surreal masterpieces at the world-renowned Salvador Dalí Museum, explore the stories of the American West at The James Museum of Western & Wildlife Art and take in a live performance at Ruth Eckerd Hall, an iconic venue famous for its near-perfect acoustics.

Of course, no trip to St. Pete-Clearwater would be complete without a visit to St. Pete Pier, where live music, bustling open-air markets and crimson sunsets set the stage for the perfect evening. From thrilling outdoor escapades to inspiring art, serene relaxation to exceptional cuisine, St. Pete-Clearwater has it all.

Start planning your sunny escape today at VisitSPC.com.