Depending on the length of your sail, the greater Tampa Bay area offers a number of exciting destinations, from the pristine natural beauty of Egmont Key up to the exciting nightlife of the Keys. Whether you want to watch manatees or dolphins, shop at Gulfport, or simply sail the Bay, Simply Sailing Charters will help you pick the perfect itinerary.

Tampa Bay

Sailing around Tampa Bay is a relaxing way to get in touch with nature. At high tide, Florida’s largest open-water estuary stretches 398 square miles. As many as 40,000 pairs of birds nest in Tampa Bay every year.

Fort De Soto, a Florida State Park, has something for everyone - nationally recognized beaches, historic landmarks, nature trails, and more. Bring your family and spend the day exploring!

Little Harbor
A 350 acre Caribbean-style island resort on Tampa Bay. Secluded between Tampa and Sarasota, a resort, secluded beach, two restaurants, lounge, tiki bar, nearby golf, shopping, and attractions makes Little Harbor an ideal getaway!

Egmont Key
Egmont Key is a secluded state park reachable only by boat or ferry. Historic attractions include the Egmont Key Lighthouse and the ruins of Fort Dade. Egmont Key is a lovely place to experience untouched nature.

Longboat Key Marina
Dock in a full-service deep-water marina and spend a while relaxing on the white-sand beach. Six restaurants, 9,000 sq. ft. spa, golf, tennis and more!

Moore's Stone Crab
For a different dining experience, sail to Moore's Stone Crab Restaurant, the oldest seafood restaurant under the same ownership in Manatee County.

Siesta Key
Siesta Key is an eight-mile barrier island along Florida's Intracoastal Waterway. Visit it, and you'll find beaches which were recently named the most beautiful in the United States for their white "sugar sand" and teal-blue waters.

Boca Grande
Boca Grande, a historic town on Gasparilla Island, boasts some of Florida's best fishing and seashell hunting. Thousands of Tarpon are caught here, and beachcombers are likely to find Sharks Eye Snails, Lightning Whelks, and more.

Sanibel Island
More than half of Sanibel Island consists of wildlife refuges, the largest of which is the J. N. "Ding" Darling National Wildlife Refuge, one of the country's largest natural mangrove ecosystems. Tour these reservesor relax on the beaches.[/one_half][one_half last]

Sarasota is a lovely getaway from the everyday, with beaches, restaurants, shopping and more. Visitors can enjoy the Ringling museums - art, circus history, and the last of the Gilded Age mansions to be built.


Explore Bradenton’s Old Florida history and visit its museums, parks and preserves. Don’t miss vibrant downtown Bradenton, the RiverWalk and the Village of the Arts – a working artists community. So take a break and visit Robinson Preserve, DeSoto National Memorial Park, the Cortez fishing village and the Manatee Village Historical Park. A collection of restored, historic buildings from Manatee County's pioneer past, the historical park includes a courthouse, one-room schoolhouse, farmhouse, general store, boat shop, steam engine and a Florida cowboy bunkhouse. It’s culture and it’s fun and it’s all in Bradenton.

Anna Maria Island

Anna Maria Island is an ideal place to relax and getaway from it all. This stretch of land, 7 miles long is home to the island's three cities – City of Bradenton Beach, City of Holms Beach and City of Anna Maria. All three cities provide access to spectacular beaches, accommodations and outdoor activities -- while at the same time offering an enjoyable selection of shops, restaurants, performing arts, wildlife, history and other attractions.

Hyatt Regency Sarasota Marina
Hyatt Regency Sarasota offers a private 32-slip marina with floating docks, a dock master, power, water, laundry facilities and pump-out station.  Savor American cuisine and seafood specialties in their Currents Restaurant, or relax with beverages and cocktails

Twin Dolphins Marina

Nestled safely along the beautiful Manatee River in Bradenton, Florida. Twin Dolphin Marina is within walking distance of the historic downtown and it's quaint Old Main Street. The historic Bradenton Pier, centrally located within the marina is host to the famed Pier 22 Restaurant, Patio, and Ballroom where you can enjoy fine dining in a relaxed atmosphere. Come and enjoy the best of what the Gulf Coast has to offer. Enjoy a scenic and tranquil getaway in the heart of Bradenton, Florida. Great dining and shopping abound in the warm and inviting atmosphere of the historical downtown area. Visit Pier 22 for casual or fine dining in a relaxed setting.


Just south of Sarasota along Florida’s white-sanded Gulf Coast, Venice offers 14 miles of beaches from Casey Key to Manasota Key and plenty of recreational opportunities, including swimming, sunbathing, fishing and boating. Shelling is also a favorite pastime in Venice, and fossilized shark's teeth can be found in abundance by sifting through the sand. Golfers enjoy excellent courses in the greater Venice area. Venice also is a Florida Main Street City – its downtown graced by Northern Italian architecture and beautifully landscaped boulevards that date to the original city plans of 1925 and reminiscent of the Italian city of Venice whose name it borrowed.

Marina Jack

Marina Jack specializes in transient dockage and cruise club accommodations for visitors who want to explore nearby Downtown and events near famous Sarasota Bayfront. Take in some of the many attractions in a few nights or secure one of our 316 slips on an annual basis. The Marina includes full amenities including bathrooms, launderette, concierge shuttle, and ship’s store.