With travel slowly resuming, it seemed only fitting to embark on a slow travel adventure now that I’m vaccinated and ready to explore again. I wanted a relaxed trip rather than a booked-solid itinerary, so to dip my toes back into travel, I chose a close-to-home destination—Florida’s Gulf Coast.
Living in Central Florida, I typically head to the St. Pete/Clearwater area, which I absolutely adore. But this time, I headed a bit further north to the under-the-radar town of Dunedin. The draw? The incredible “twin sister” islands across St. Joseph Sound.
Twin Sister Islands
When a 1921 hurricane barreled through the Gulf Coast area, it separated a strip of land into two distinct barrier islands now called Honeymoon Island and her sister, Caladesi Island. The waterway that now separates the two—fittingly named Hurricane Pass—serves as a prime spot for fishing.
According to the Florida State Parks website, more than a million people visit Honeymoon Island each year, making it the most visited state park in Florida. In comparison, roughly 200,000 people a year visit Caladesi Island. It seems like the added cost and effort it takes to get to Caladesi Island keeps throngs of visitors away, which works in your favor when you’re looking to unwind on an isolated slice of Gulf Coast paradise.
Honeymoon Island State Park
A picturesque drive over the Dunedin Causeway gives you access to Honeymoon Island State Park—four miles of undeveloped beaches that provide a tranquil respite from the bustling crowds of nearby Clearwater Beach. With no towering hotels or noisy beachfront bars competing for your attention, you can soak in the natural beauty of this 2810-acre state park that stretches along the Gulf of Mexico. Although undeveloped, Honeymoon Island brims with amenities, including a picnic pavilion, playground, concession stand, nature center, and even a pet beach at the park’s southern portion. The $8 per carload entry fee is a bargain!
Two nature trails wind through pine flatwoods and mangrove forests, inviting you to slow down for a mindful hike. Journey along the Osprey Trail, spotting ospreys (of course!), eagles, great horned owls, gopher tortoises, armadillos, and (be careful!) eastern diamondback rattlesnakes. You can take a leisurely 1.5-mile bike ride around the island’s perimeter on the paved bike trail, with rentals available for single and tandem bikes as well as covered surreys.
In case you’re wondering, Honeymoon Island got its name back in 1939, when a New York real estate developer purchased the land and partnered with LIFE magazine to hold a contest for newlyweds. The prize? Contest winners received a two-week stay in thatched bungalows for their Sunshine State honeymoon, earning the island its name.
Caladesi Island State Park
For an even more remote island experience, visit the 600-acre Caladesi Island State Park— accessible only by boat. Fortunately, you can catch a ferry at the docks situated at the southwest end of Honeymoon Island. Open daily beginning at 10 a.m., the ferry departs every 30 minutes (mid-February through mid-September) and then hourly the rest of the year. The captain will even amuse you with a bit of island history on your 15-minute voyage. A round-trip ticket costs $16 per adult, $8 for kids 6-12, and free for the under-six crowd. It’s well worth it because you’ll feel like you’ve got your own private island. Why? Ferry tickets limit guests to a four-hour stay to help control island capacity.
Once you dock, grab what you need at the concession stand before heading to the beach so you can spend an interrupted stretch of time just chillin’ on the shoreline or exploring the island. Stroll over the boardwalk, which transports you over sand dunes lined with sea oats and saw palmetto, to discover three miles of pristine beach on this stunning secluded island. Stake your claim in the sugar-white sand by renting beach chairs and an umbrella, then enjoy the incredible view as the warm gulf breezes wash over you and the turquoise waters beckon you to jump in. At low tide, you can see the reefs formed by oysters. And if you love hunting for seashells, Caladesi beach won’t disappoint—hundreds of them gently wash up with each wave.
Like its sister island, Caladesi teems with abundant wildlife. Birdwatchers can look for blue herons, great egrets, bald eagles, and bright pink roseate spoonbills on the bayside of the island. The beach itself claims a spot on the Great Florida Birding Trail, with shorebirds such as American oystercatchers, black skimmers, royal terns, and piping plovers. If you’re lucky, you might event spot dolphins, manatees, or loggerhead sea turtles. With three-mile nature trails carving through land and water, you can explore the island on foot or by boat. If you kayak through the winding trail channels, you might spot baby fish and crustaceans hiding in the tangle of red mangrove roots that poke out above the water. If you’re taking the interior island trail, you’ll be hiking through 100-year-old slash pine forest and live oak hammocks.
Further along the trail, you can even see a bit of history, as the ruins of the Scharrer Homestead mark the spot where Swiss immigrant Henry Scharrer and his daughter Myrtle lived in the 1880s. For a deep dive into the joys and challenges of pioneer life on a remote tropical island, read Myrtle (Scharrer) Betz memoir titled Yesteryear I Lived in Paradise: The Story of Caladesi Island.
Where to Eat on the Islands
Hungry? Both islands offer casual beach fare, with two cafés on Honeymoon Island and one on Caladesi Island—perfect if you don’t want to drag along a cooler. Expect typical concession stand options like chicken tenders, fish and chips, burgers, and fried shrimp baskets, plus ice cream, soda, juice, smoothies, and even a limited selection of bottled beer and hard seltzer.
Note: the cafés also include a small store if you need beach sundries or souvenirs or if you want to rent beach umbrellas, chairs, kayaks, or bikes. You might even be able to find a copy of Myrtle’s book!
However, if you decide to pack your own lunch (think wraps, salads, fresh fruit, and subs), hit the Publix grocery store in the plaza right before you get on the Causeway.
Where to Stay
While those thatched bungalows for honeymooners no longer exist, neither do any other island accommodations. Well, technically Caladesi Island offers a 108-slip marina equipped with water and electric for overnight boat stays. But if you’re not into boat camping, you can anchor your stay at the historic Fenway Hotel in Dunedin.
Originally opened in 1927, Fenway Hotel is now part of Marriott’s Autograph Collection, a global collection of distinctive independent hotels. Back in the day, this iconic property played host to notable artists, explorers, musicians, and politicians. The Fenway also provided a home base for the first radio station in Pinellas County, which began broadcasting from the hotel’s roof in 1925. Guests can read all about the Fenway’s musical heritage, as framed newspaper clips adorn the first-floor hallway and a “hidden stairway” reveals the password-required speakeasy once housed in the basement.
This boutique property completely embraces its musical background, immersing guests in themed décor, live music, and aptly named Hi-Fi Rooftop Bar. The timeless rhythm begins in the lobby, showcasing live music most nights. You can even reserve a table near the stage and enjoy a glass of wine and a meal with a front-row seat to the artist du jour. In the guest rooms, you might find a cymbal on the wall or a funky nightstand inspired by travelling musicians’ trunks. Cap off the night with jazzy drinks at Hi-Fi. Try the Jam Session—a thirst-quenching blend of Jamming with Redemption Bourbon, house berry jam, and lemon. Sit back, sip, and soak in the breathtaking views of the twin sister islands across St. Joseph Sound.
What to Do
While the twin sister beaches could consume the bulk of your trip (as they should!), carve out time to explore Dunedin’s historic downtown just a few blocks from Fenway Hotel. It boasts a quaint history center, an independent bookstore, charming boutiques, specialty stores, and gift shops, and some amazing restaurants.
I loved people watching during lunch on the patio of Café Alfresco, which abuts the Pinellas Trail. For dinner, head to the colorful Casa Tina for a killer mojito, authentic Mexican fare, and a lively atmosphere. If you’re a fan of craft breweries, you’ll find eight within a few miles of Fenway Hotel, including Dunedin Brewery—Florida’s oldest microbrewery.
Within roughly a 30-minute drive, you’ll also find plenty to do in nearby towns. Carve out time to tour two hidden gems in Largo—both free! Stroll through the 150-acre Florida Botanical Gardens dotted with specialty gardens, native landscapes, boardwalks, and ponds. Then travel back in time at the adjacent Heritage Village, a living museum dotted with restored historic homes and buildings, museums, exhibits, and “demonstration sheds” like the sugar cane mill and blacksmith and woodworking areas.
Get your Greek on in Tarpon Springs, where you can stroll down the blue-and-white themed Dodecanese Boulevard lined with Greek restaurants and gift shops across from the world-famous sponge docks. Then head to Safety Harbor to check out the volunteer-driven Safety Harbor Art and Music Center, which hosts community art and music events throughout the year, from concerts and art workshops to open mic nights and literary events.
While you’re in town, take a tour of the unique Whimzeyland property, the incredibly colorful home of the founding artists behind the art and music center.
Lisa Beach is a seasoned freelance writer. Her work has been published in The New York Times, USA Today Go Escape, Good Housekeeping, Eating Well, and dozens more. Check out her writer’s website at www.LisaBeachWrites.com.