Day 1, Sarasota to Key West
- 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.
- 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.
- 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.
- 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.
Day 2, Wine Tasting in St. Petersburg and Clearwater
- 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.
- 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.
- 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.
- 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.
Day 3, Sanibel Island
- 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.
- 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.
- 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.
- 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.