Running The Islands

You might recognize me as one of those crazy people running around the island “for fun.” As a former track and field hurdler, I do still enjoy a nice jog to stretch my legs, and what better place to run than beautiful Sanibel Island?


Not long after I started working at McCallion & McCallion, Jim discovered that I’m a “fellow runner” and graciously shared his wealth of knowledge about running on the island. He immediately pulled up a map of Sanibel and started pointing out the best trails and courses he has run in the past. I interrupted a few times to remind him I’m a former short-distance sprinter – not a long-winded miler like himself and Patty.


Did you know Patty Holston from our office is a marathon runner?! (Yeah, and you thought I was crazy.) I love hearing Patty’s stories about heading out for pre-dawn runs with her husband, Craig, as they trained for their Chicago marathon in 2013. They would rise and run the quiet streets of Sanibel and Captiva, enjoying the unique wildlife that are out and about before daylight.

Both Patty and Jim have seen everything from bobcats, gopher tortoise, rare birds, and yes, even gators while on their island runs. They mention that the wildlife animals “don’t bother you if you don’t bother them.” I told them not to worry, I have no interest in being chased by a bobcat or large bird!


Tips For Exercising on Sanibel

From my conversations with Jim and Patty, and my own experiences running on Sanibel, I’ve learned a few things that I thought are helpful for anyone jogging, walking or biking on island.

#1 – Be aware of your surroundings.
This is the most important tip I have. When running, biking, walking and driving on Sanibel you have to watch out for fellow runners, bikers, walkers and drivers!

I love the entertaining video the Sanibel Bike Club put together earlier this year with their own safety instructions about using Sanibel’s shared bike paths.


#2 – Watch your step.
Other pedestrians aren’t the only ones to keep an eye on… I sometimes find myself hurdling little lizards that decide to scurry across the path right as I run by! Be sure to watch for larger wildlife animals that might be lounging alongside the walking paths, or the lush Sanibel vegetation that sometimes obstruct a path.

#3 – Plan for the weather, but plan on it changing.
Especially in the Summer months, you can expect an afternoon shower around 3:00-4:00pm every day like clockwork. Running in the rain is actually refreshing, but if the skies start to get really dark, you might want to take cover somewhere just in case the rain and winds start to pick up.

#4 – Use the buddy system.
If you can, run with a family member or friend, or at least tell someone you’re going for a run before you leave. Did you know Sanibel has a runners club that meets at Matzaluna Italian Kitchen? Check with Matzaluna to see the next time the club will meet.

Trails on Sanibel Island

Here are a few trails that I enjoy running. I admit, that most of them are within 5 miles of our office at 1640 Periwinkle Way, since I usually run after work.

Trail past Bailey’s Homestead – This is actually a well-known trail used by a number of residents and visitors of the island looking to get in touch with nature and possibly see some of Sanibel’s unique wildlife. The trail runs from the Chamber of Commerce building when you first get on island, to Roadside Park near the Bailey homestead and the SCCF Native Plant Nursery at 1300 Periwinkle Way. From the Chamber, follow the Apple Pond Trail to the Starr D. Thomas Memorial Boardwalk, which connects to The Shipley Trail behind the homestead.


Image courtesy of

The Dunes to Sanibel Causeway – I sometimes start from The Dunes Golf & Tennis Club and run the backroads of Bay Drive. One of Jim’s favorite routes takes Bailey Road to the bay, then runs along the shoreline towards the Causeway and back up in front of the Chamber building.

Casa Ybel to the Sanibel Cemetery – When I’m feeling more adventurous, I take Casa Ybel Road from Periwinkle, and head down Middle Gulf Drive. There’s a bike path just off Middle Gulf that takes you back to the old Sanibel Cemetery. This is a cool place to check out if you are biking near Gulfside Beach one day. Depending on the weather, the trail can be a little muddy at times, so proceed with caution in the wet summer months.


These are a few of my “regular routes,” as you can see, I have a lot of island left to explore! I’d love to hear some of your favorite areas to walk or jog. Feel free to share photos and/or running stories with us on our McCallion & McCallion Facebook Page!

Tiffany Stokes About Tiffany Stokes

Meet the Marketing Secret Weapon at McCallion & McCallion. In 2015, Tiffany traded the beltway traffic of Washington, DC, for the sandy, two-lane streets of Sanibel and she hasn't looked back since!