Best of Sand Key: Redington Shores, Madeira Beach & Indian Rocks Beach

By Lynn Waddell

Cast away to Redington Shores on Sand Key, the well-charted Gulf Island of Mary Ann's choosing. It's family-friendly, intimately connected to fishing and steeped in vintage charm.
 

Sit right back and you’ll hear a tale… What kid who watched Gilligan’s Island didn’t want to go there, especially if he could hang out with the cute, pigtailed farm girl who baked an incredible coconut cream pie?

Fans will be happy to know that there is a new Gilligan tale, set on a real-live island in the Gulf of Mexico. Since being rescued from Gilligan’s Island, actress Dawn Wells (a.k.a. Mary Ann) has been a part-time castaway in Redington Shores on Sand Key, Florida, an island off the coast of St. Petersburg.

The 14-mile-long barrier island stretches from Sand Key Park in the north (just across a bridge from Clearwater Beach) to the weathered shops of John’s Pass at the southern end. Along the way, it passes through well-heeled Belleair Shores, low-key Indian Rocks Beach and Indian Shores and the three retro Redingtons to fishing-focused Madeira Beach.

Like so many others who arrive in this quiet Florida beach area year after year, Wells comes to the island to slow down. Her modest 1950s beach cottage in Redington Shores, FL is her hideaway: a place to fish in the surf, enjoy sunsets and relax from her demanding theater schedule. “I love the beach and the water, the casualness of the area,” Wells said. “And when I look out over that ocean, it reminds me of how small we are in the scheme of things.”

Outside of Madeira Beach, Sand Key, Florida is generally quieter and less commercial than some other islands in the area. This has helped the island hang onto its slow pace, which makes it attractive to families and others who would rather gaze at the stars than party the night away.

But this “quiet” is not inaccessible. Five short bridges connect Sand Key to St. Petersburg and Clearwater.

Skipper’s Paradise: Madeira Beach

If you’d rather let someone else do the catching, enjoy the fruits of fishermen’s labors at local restaurants, which serve fish fresh from the docks. Dockside Dave’s on Gulf Boulevard is renowned for its fresh grouper sandwiches, and the Friendly Fisherman Seafood Restaurant dishes up fish from the boats docked right outside its dining room window. If you visit the area in October, be sure to check out the annual John’s Pass Seafood Festival, now in its 26th year.

Madeira Beach’s gritty maritime culture has receded a bit with the rise of condos and the growth of the beach’s largest tourist attraction, John’s Pass Village and Boardwalk. There you can buy everything from string bikinis to a painting of Emmett Kelly, the famous Ringling clown of the 1950s. The shops are a great place to wile away a hot, sunny afternoon; each member of the family is sure to find something he or she just can’t go home without.

The new, nonprofit National Comedy Hall of Fame in John’s Pass Village displays a wickedly elaborate dress of comedian Phyllis Diller along with the original Howdy Doody. Its gift shop, complete with Three Stooges, Gomer Pyle and Marx Brothers merchandise, has all manner of kid-friendly road-trip gags that parents appreciate.

Although party boats still run daily fishing excursions, there are plenty of other opportunities for families that want to get out on the water.

Dolphin-watching and shell-hunting excursions are popular, as are pirate cruises and a nighttime haunted cruise. Casino cruises cater to visitors who are feeling lucky.

When it comes to accommodations, you can still find retro beach lodging like the Schooner Motel and the Beach Flower, which take you back to the days when Mary Ann wore midriffs and pigtails.

Redington Beach, North Redington Beach & Redington Shores, FL

Wells wasn’t the first celebrity to set foot on Sand Key, Florida. In the 1950s, newlyweds Marilyn Monroe and Joe DiMaggio vacationed at the former Tides Hotel and Bath Club on North Redington Beach. That resort, developed by Charles Redington, put the Redingtons on the map, drawing the likes of Alfred Hitchcock and Ronald Reagan, as well as baseball legend Babe Ruth, who had spring training in St. Petersburg.

The triplet towns, Redington Beach, North Redington Beach and Redington Shores, FL, make up a four-mile stretch along Gulf Boulevard and are small enough that you might miss one. The sleepiest sibling, Redington Beach (the original Redington), remains primarily residential. Restaurants, motels and the Doubletree Beach Resort are just steps north in the busier North Redington Beach.

For those who prefer an Old Florida lodging experience, there are two options: the Malibu Resort Motel, which allows pets, and the 1940s-style cottages of Park Circle Bed & Breakfast, both across the street from the Gulf on North Redington Beach.

They may not serve their drinks in coconuts at the Key West-style Conch Republic Grill & Raw Bar, but the libations flow and the crew is entertaining. If upscale dining is your priority, try the Wine Cellar, a traditional restaurant known for its gourmet menu.

Wells loves to cook (and often catches her dinner) but when she does eat out, one of her favorite restaurants, the Lobster Pot, is just down the road from her teal beach cottage in Redington Shores, FL. Her home is within walking distance of the locals’ fishing spot, the Redington Long Pier.

Nachman’s Native Seafood & Marina, a family-owned restaurant on the docks, serves up fresh fish at its own restaurant and provides fresh-caught fish to many other restaurants in the area. Visitors who have kitchenettes and want to cook local fish can check out the offerings at the family’s fish house.

Flashback: Indian Rocks Beach

Winding north through Indian Shores and Indian Rocks Beach, the island narrows to a spit of land, with the Intracoastal Waterway hugging one side of the road and the Gulf visible on the other. Life is slower here, and the weathered bungalows and small motels that have been mainstays here illustrate what most of these beaches were like when Wells moved here in the early 1970s.

No high-rises are allowed on Indian Rocks Beach, making it possible for smaller hotels to survive. The Great Heron Inn and Sun Burst Inn are the kind of (good) kitschy mom-and-pop places that harken back to the days when Gilligan’s Island was filmed. With fewer than 20 rooms each, they are mid-century gems with efficiencies opening up to a central courtyard and pool. If you’re looking for something modern with that same open, Old-Florida style, check out the Colonial Court Inn.

Perhaps no place on the beach embodies the live-and-let-live spirit of the place more than Mahuffer’s, an eclectic bar on Indian Shores, where resident cats sleep in overhead fish nets and a table top rests on a snowmobile. You may find scruffy, grey-haired Sloppy John, as John Susor likes to call himself, inside at the bar, where you are required to tip the bartender every time you swear.

Susor, a fixture on Indian Shores for decades, sells videos of himself and his eclectic home decorated with recycled mementos (he lives on the property). Since losing a race for mayor by a few votes in 1998, Susor has been battling with the man who won. You can read about them in the newspaper articles plastered on the bar’s walls. Look for the colorful old car with a makeshift canopy parked out front.

At the other end of the spectrum, the fire-grilled seafood at the Salt Rock Grill on Indian Shores qualifies it as one of the best high-end dinner spots in the Tampa Bay area.

North of Indian Rocks Beach, the area turns upscale. Three-story mansions line the shore, and about the only similarity between the beaches of Belleair Shores and the southern portion of Sand Key island is the beach itself, with its white sands and shimmering blue surf. The beach is private, but the sightseeing drive is free and worth it for what lies at the island’s north end.

Aside from the retro Belleair Beach Resort Motel, lodging in Belleair Shores includes the upscale resorts of the Clearwater Beach Marriott Suites on Sand Key and Sheraton Sand Key Resort. It’s not until you have nearly left the island that the quintessential castaway beach comes into view (and our tour ends) at Sand Key Park.

While it’s not truly deserted since there are bathrooms and showers and beach cabana rentals, Sand Key gives visitors a sense of seclusion. Nine boardwalks lead to the wide, white-sand beach, and beyond the sea oats-dappled dunes are palms and salt marshes. Grills and picnic tables accommodate your crew for dinner. A dog park, added in 2003, welcomes the canine members of your family.

With 95 acres of undeveloped coastline to explore, this is as close as you can get to being a true castaway and as close as most want to be.