Morning

Choose From a Hearty Menu. There are two locations for the Blue Dolphin Café — one in St. Armands Circle and one on Longboat Key — and with good reason. This neighborhood breakfast favorite offers something for everyone in the family, from fluffy Belgian waffles to rich eggs Benedict and everything in between.

Clown Around. At the Ringling Circus Museum, visitors can celebrate the history, ceremony and color of the Ringling Bros. and Barnum & Bailey Circus. From live performances to static exhibitions, the museum is a sensory delight. While you’re on the Ringling property, it’s also possible to explore the museum of art and Ca’D’Zan, the Ringlings’ 56-room mansion on Sarasota Bay.
 

Afternoon

Lounge Around. At The Ritz-Carlton, Sarasota, poolside cabanas mean the whole family can relax in the shade after splashing in the pool. Sea Breeze cabanas come equipped with crafted cocktails, a snack basket, luxury lounge chairs and a 32-inch flat-screen television with premium programming.
 

Evening

Hit the Local Ocean. With a big banyan tree outside and plenty of Southern hospitality inside, Owen’s Fish Camp is in Burns Court in downtown Sarasota. The menu, which changes daily based on anglers’ catches, features everything from crab cakes to fried green tomato salad to shrimp and oyster po’boys. Of course, a large selection of wine and craft beer rounds out the offerings.

Morning

Take Your Breakfast for a Walk.  At Siesta Key’s boardwalk-based Meaney’s Mini Donuts, you and the family can grab a bag of sweet mini doughnuts and a couple of coffees for a song. From there, walk Siesta Beach to look for shells, as well as dolphins, manatees and other wildlife.
 

Afternoon

Find Your Pedal Power. Beaches would be incomplete without beach cruisers, and POPcycles rents a variety of bicycles. Just five minutes from Siesta Key beach, this friendly shop offers Electra Townie bikes for just $30 a day. From the shop, ride 2 miles to the Legacy Trail, which runs from Sarasota to Venice, or hop to the beach to cruise.

Snag a Photo Opportunity. The “Unconditional Surrender” sculpture on the Sarasota Bayfront pays tribute to Alfred Eisenstaedt’s famous photograph of a serviceman dipping a nurse for a kiss on Aug. 14, 1945, the end of war with Japan. Artist Seward Johnson created the 26-foot-tall aluminum sculpture, and it’s a great place to snap a quirky photograph.
 

Evening

Get a Piece of the Pie. At Palermo Pizza, the crust is perfectly flaky, the toppings are made-to-order and the cheese is melted just right. This long-standing Sarasota pizza parlor also offers up decadent Stromboli and sandwiches. It’s a casual, inexpensive place to dine in, or get carryout and have a picnic on the beach.

Morning

Taste the Sun.  Back on Siesta Key, the Sun Garden Café offers a different take on breakfast. Think: sweet potato pancakes and waffles crafted with pecans and bacon. If you’re looking to expand the kids’ breakfast palate, this is the spot. Plus, parents will love the wide stone patio, tropical flowers and relaxing, airy feel.

Afternoon

Wander a Living Museum. The Marie Selby Botanical Gardens are an urban oasis tucked into Sarasota Bay. Fern gardens, tropical rainforests, butterfly and fragrance gardens, and a tidal lagoon span 9 acres on this property, once owned by Marie and William Selby of Texaco Oil. It’s a wonderful place to wander.

Have a Sweet Treat. Consistently rated one of Sarasota’s best places for dessert, Abel’s Ice Cream has been family-owned and operated since 2011. Your family will love sweet scoops of dreamy ice cream or frozen yogurt.

Evening

Taste Traditional Florida. No family trip is complete without some sort of silly experience, and Captain Curt’s Crab & Oyster Bar delivers. This popular, kitschy restaurant has been a Sarasota staple since 1979 and serves up all of the local seafood you can imagine. Curt’s clam chowder is a champion. It took first place in Newport, Rhode Island’s Great Chowder Cook-Off.

Morning

Sleep In.  Hit the snooze button once or twice and linger over an in-room breakfast at The Ritz-Carlton, Sarasota. Croissant French toast, fresh fruit and cage-free omelets can be delivered right to your door as you prepare for another day of adventure.

Afternoon

Take To Open Water. If you’re family has its sea legs, Sea Life Kayak Adventures offers a fleet of sea kayaks for rental. Or, if you’d prefer, their expert guides can lead you on a tour to document some of Sarasota’s native wildlife, including sea turtles, manatees and seabirds.
 

Evening

Catch a Show. Since 1973 Florida Studio Theatre has engaged patrons with brilliant productions — from musical theater to standard stage plays. The children’s theater presents several shows each year, while the main stage cycles through contemporary and traditional theater fare. Visit the box office or go online for tickets.

Morning

Line Up.  Although the lines at Toasted Mango Café can be long, the wait is worth it. This healthy café dishes up smoothies as well as traditional breakfast fare. And these three words will likely please the kiddos: cinnamon-roll pancakes.

Afternoon

Manatees and More. At the Mote Marine Laboratory and Aquarium, scientists work hard to understand the biology and ecology of the ocean and its creatures. You won’t have to work so hard to enjoy the aquarium, where hundreds of marine mammals and fish make their homes. A 135,000-gallon shark tank is the highlight of the aquarium, as are two touch tanks.

Evening

Until Next Time. Celebrate your last evening in town with a delicious dinner at Jack Dusty at The Ritz-Carlton, Sarasota. This exceptional restaurant combines seafood and steak, as well as salads and a raw bar, to create a memorable meal for you and your family.

Morning

Get An Early Start.Travel to Fort Myers Beach to catch the Key West Express, a high-speed ferry to the southernmost city in the continental United States. The ferry departs at 8:30 a.m., so give yourself ample time to travel to Fort Myers by car or coach.  
 

Midday

Be Late (or Early). Enjoy a late breakfast or early lunch at Azur, a Mediterranean-inspired restaurant in Old Town Key West. Here, crab cake Benedict and Key lime French toast are the stars of breakfast, while handmade gnocchi and innovative sandwiches steal the lunchtime show.  

Find Your Way to Hemingway. 907 Whitehead St. was the home of Key West’s most famous resident, author Ernest Hemingway. Now a museum, the house is a haven for more than 40 six-toed cats, a favorite of Hem’s. It’s also a stunningly preserved tribute to the writer, his work and his love of architecture, nature and Florida.

Afternoon

Shop the Seaport. Key West’s historic Seaport District includes more than 50 shops, galleries, restaurants and bars. It’s a great place to pick up a souvenir, sample some local rum or pick up a piece of world-famous Key lime pie. What’s more, should you want to head back out on the water, there are plenty of watersport rental shops and boat charters to choose from.  

Pick Yourself Up. You were up early, which means you might need an afternoon coffee jolt. Before you head back to the ferry, visit Cuban Coffee Queen for a café con leche or Cuban frappe. You can also pick up a few savory Cuban sandwiches to eat during the ride back to Fort Myers. The Key West Express departs at 6 p.m.

Evening

Settle In. Once you return to The Ritz-Carlton, Sarasota, settle in for a drink or two at the Lido Key Tiki Bar. Situated on the beach, just behind The Ritz-Carlton Beach Club, this charming bar features wine, beer and cocktails right on the Gulf of Mexico. Sit back and enjoy the sounds of the sea before turning in and gearing up for tomorrow’s travels.  

Morning

Freshen Up. Visit either of Crop Juice’s two Sarasota locations for fresh, cold-pressed, ultra-healthy juices. For a hearty dose of kale, spinach, romaine, cucumber, celery, green apple and lemon, try the Green with Envy. It contains six cups of leafy greens — just what the doctor ordered before a day of wine tasting.

Hit the Road. The roughly 40-mile drive from Sarasota to St. Petersburg takes less than an hour and runs along the coast. Should you choose to make a quick stop in Ellenton, visit Gamble Plantation Historic State Park, once an antebellum home and sugar plantation.  
 

Midday

Take Your First Sip. It’s not often that you hear of wine being made along the beach, but that’s exactly the case at St. Petersburg’s Florida Winery. Even better? The winery’s tasting room is open all day and offers free samples of the vintner’s award-winning blends. In addition to cabs and pinots, Florida Winery has a selection of sangria, mead and more.

Lunch at the Mill. Voted St. Petersburg’s best new restaurant in 2017, the Mill has a lunch menu that will complement the remainder of your wine-tasting excursion. Light bites include cider-braised mussels and sweet pea hummus, while sandwiches like La Cosa Nostra will fill you up. It’s loaded with chicken, Sicilian giardiniera, goat cheese croquettes, arugula, tomato aioli and fig jam.
 

Afternoon

Find Clearwater. Head up the road to Clearwater and Murielle Winery. This family-owned, boutique endeavor specializes in blends that include fruit such as apricot, peach, dragonfruit and boysenberry.

Go North. From Murielle, travel north to Aspirations Winery, where the motto is “headaches not included.” That’s because this family-owned micro-winery specializes in low-sulfite creations.
 

Evening

On the Waterfront. Before heading back to The Ritz-Carlton, Sarasota, stop for dinner at Clearwater’s Island Way Grill. With harbor views and island-inspired cuisine with an emphasis on fresh seafood, it’s a great way to end your day trip to St. Petersburg and Clearwater.

Morning

Cruise the Causeway.  Just two hours south of Sarasota, Sanibel Island is a mecca of relaxation, water sports and beautiful beaches. After an in-room breakfast at The Ritz-Carlton, Sarasota, take Interstate 75 south for 104 miles to unlock a day of exploration.

Midday

Take Refuge. The 6,354-acre J.N. “Ding” Darling National Wildlife Refuge is home to 220 bird species, 50 types of reptiles and more than 32 mammal species. Walk its winding paths, take a 4-mile scenic drive or canoe the perimeter to explore this lovely refuge.

Have a Cow. One of the most popular restaurants in Sanibel Island, the Island Cow is a must-stop for outdoor games, live entertainment and, of course, “udderly great” food. The menu is massive, so prepare to spend more than a minute selecting your meal.

Afternoon

Stand Up. Work off those lunch calories by renting a stand-up paddle board and hitting the beach. Paddle Board Sanibel offers one- to three-hour rentals and will even deliver to your location. If paddle boarding isn’t your speed, kayaks are also available.

Pick Up a Souvenir. Periwinkle Place features unique gift shops and galleries. Pick up a T-shirt from Tiki Jim’s or select a few bottles of Sanibel olive oil for loved ones back home.

Evening

Dine Before You Dash. Make a stop on your way back to The Ritz-Carlton, Sarasota for rum and dinner at Doc Ford’s Rum Bar & Grille. This airy, beautiful restaurant makes a mean mojito, as well as delicious seafood paella and island-style shrimp and grits.