The Florida Gulf Coast stretches 550 nautical miles from Cape Sable, at the southern tip of the Everglades, to Perdido Key, which is the western border of the state’s panhandle. The Gulf of Mexico offers both enjoyable and challenging cruising. In the winter, on days when the winds are light, power boats rule. However, when a cold front passes through, the blustery northwest winds leave the waters free for experienced sailors with a reef in both their mainsail and genoa. During the summer, thermal heating onshore creates towering thunderheads and spectacular lightning displays in the early evening. That is the perfect time to be safely tucked in at the dock sipping a favorite cocktail. Fortunately for boaters, the Gulf Intracoastal Waterway allows for safe cruising on back bays behind the barrier islands when the weather turns foul. Except for the open water passage across the Big Bend, the Gulf Intracoastal Waterway provides a protected route from Sanibel Island to Perdido Key. The estimated mileages between destinations for this itinerary are calculated running coastwise on the Gulf.

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  1. - Estimated Mileage: 0

    Everglades Isle Marina

    Everglades Isle Marina in Everglades City Florida on Marinalife

    Everglades City, FL



    Everglades City, as the name suggests is surrounded by Everglades National Park, the second largest national park in the country. Navigating through Indian Key Pass surrounded by innumerable mangrove islands has a wilderness feel about it. Airboats are plentiful, and strapping in for an airboat tour complete with alligator sightings and high-speed drift turns are worth the price of admission.

  2. - Estimated Mileage: 30

    Marina at Factory Bay

    Marco Island, FL



    Marco Island began as many coastal Florida communities did, a developer’s dream in the 1960’s. In the 1940’s, Goodland, the small fishing camp at the eastern tip of Marco was a vacation getaway for Miami residents. At sunset the mosquitos were so thick on the cottage screens that they blotted out the setting sun. Today, modern mosquito control has made Marco Island not only habitable, but a premier vacation paradise with a two mile Gulf beach fronted with high rise condominiums and high end resorts. Marco’s numerous marinas are best accessed through Capri Pass. Pay close attention to the channel marks, as the sandy shoals are constantly changing in size. Dinghy over to Snook Inn for a fun Old Florida lunch or dinner.

  3. - Estimated Mileage: 15

    Naples Bay Resort & Marina

    Naples, FL



    Nestled up the Gordon River, four miles from the Gulf of Mexico, Naples is known as the “Palm Beach of the Gulf Coast”. A wide array of luxury boutiques, art galleries and couture await the shopping aficionado on both Fifth Avenue South and Third Street South. Many of the best restaurants in southwest Florida are located in both these shopping districts. Meander through Tin City and have lunch there, and try Sea Salt for dinner.

  4. - Estimated Mileage: 30

    Pink Shell Beach Resort & Marina

    Pink Shell Beach Resort Marina | Marinalife

    Fort Myers Beach, FL



    Estero Island, also known as Fort Myers Beach, is a barrier island on the Gulf of Mexico that lies just south of the junction that marks the western end of the Okeechobee Waterway and the beginning of the Gulf Intracoastal Waterway. Fort Myers Beach has a rich history dating back 2,000 years to the Calusa Indians. Begin your tour of the island with a bit of time travel at the Mound House. Walk inside a Calusa Indian shell mound and discover the indigenous culture that Ponce de Leon met as he searched for the Fountain of Youth. Since the 1950's, Fort Myers Beach has been home to a large fleet of shrimp trawlers that harvest “pink gold” from the Gulf of Mexico. Dinghy over to San Carlos Island to visit the shrimp boats. Take a self-guided walking tour of working shrimp fleet and don't forget to buy some fresh pink shrimp right at the shrimp docks.

  5. - Estimated Mileage: 25

    Tween Waters Island Resort & Spa

    Tween Waters Island Resort & Spa - Captiva Island, Florida - Florida Marinas - Marinalife

    Captiva Island, FL

    239-472-5161 ext 3


    Folklore has it that Captiva Island, just north of Sanibel Island, was named because the pirate Jose Gaspar kept his female captives there for ransom. Watching a fabulous sunset from its beaches is what captivates vacationers these days. Take a day trip to Sanibel for shelling. If you are new to shelling, you will soon learn the “Sanibel stoop” as you walk along the beach bending down in hope of finding that rare junonia shell. A visit to Captiva is not complete without dinner at The Bubble Room. Words cannot describe the eclectic nature of this restaurant, seeing is truly believing. And do save room for dessert!

  6. - Estimated Mileage: 18

    Boca Grande Marina

    Boca Grande, FL



    Boca Grande, on Gasparilla Island, looks like a quaint Midwestern town dropped down onto a sandy island. Katherine Hepburn made Boca Grande her winter home and for the former Presidents Bush and their families it is a favorite Christmas holiday destination. Boca Grande Pass, at the south end of the island, is the nexus of professional tarpon fishing tournaments, and you may want to try your hand at catch and release with one of the many local fishing charter captains. While dinner at the Main Dining Room of the Gasparilla Inn is a must, you can also enjoy lunch at Inn's Pink Elephant Restaurant.

  7. Venice, FL

    941-484-7661 ext 2


    Long white sugar sand beaches are the principal attraction in Venice. At the end of the day, take a stroll along the beach to search for a fossil shark's tooth, which is a common find for beachcombers. There have been so many of these fossils found, that Venice has earned the title of “Shark’s Tooth Capital of the World”.

  8. - Estimated Mileage: 18

    Marina Jack

    Sarasota, FL



    Sarasota has consistently been rated as one of the top places to retire. It has the benefits of a big city while keeping the laid back atmosphere of a small town. John Ringling, of the Ringing Bros. and Barnum & Bailey Circus, made Sarasota his winter home. Along with his wife Mable, they became the preeminent patrons of fine arts in Sarasota. Their legacy, The Ringling, includes their restored 56-room palazzo on Sarasota Bay, called Ca’ d’Zan, that was built in 1924 . Their estate also includes the State Museum of Art, the Circus Museum and Bayfront Gardens.

  9. - Estimated Mileage: 12

    Seafood Shack Marina

    Cortez, FL



    Across the sound from Anna Maria Island is Cortez, one of the last remaining commercial fishing villages in Florida. The historic working waterfront has been restored to include the Florida Maritime Museum and a nature preserve.

  10. The Vinoy Renaissance Resort & Golf Club - St Petersburg, Florida - Marinalife

    St. Petersburg, FL



    Downtown St. Petersburg, on Tampa Bay, has been a popular snowbird destination since the 1920’s. Today, it has a thriving arts, music and restaurant scene near and along the waterfront. The marina at the Vinoy is located in the Historic Old Northeast neighborhood, a beautiful residential area with colonial revival and Mediterranean style homes, as well as Craftsman style bungalows.

  11. - Estimated Mileage: 65

    Tarpon Landing Marina

    Tarpon Springs, FL



    Back in the first half of the 20th century the Gulf of Mexico was home to a thriving sponging industry, which was centered at Tarpon Springs. Sponge divers from Greece were recruited to harvest sponges wearing hardhat diving suits while walking along the seabed. Tarpon Springs, located up the Anclote River, has the highest percentage of Greek Americans of any city in the U.S. Visiting the old sponge docks complete with Greek restaurants is the perfect way to spend a day.

  12. - Estimated Mileage: 60

    Pete’s Pier Inc.

    Crystal River, FL



    Breaking up the long passage across the Big Bend of the Gulf of Mexico into shorter hops provides for peace of mind should the weather forecast call for strong winds. It also allows for exploration of Florida’s Nature Coast with a step back in time to the real Old Florida. Crystal River is a well-known manatee haven thanks to the clear warm water that flows from numerous inland springs. Kayak tours are a great way to explore the backwaters of this area.

  13. - Estimated Mileage: 80

    Sea Hag Marina

    Steinhatchee, FL



    Steinhatchee is best known as Florida’s hot spot for recreational bay scallop harvesting. The season runs from June 25th through September 24th, with a daily bag limit of 2 gallons of whole scallops in shell per person. Mullet is another Steinhatchee favorite, and there is no better place to have it prepared then at Fiddlers Restaurant. Make sure to order it fried, as it is the tastiest way to eat mullet.

  14. - Estimated Mileage: 57

    Shields Marina

    St. Marks, FL



    Originally an important shipping port for the cotton trade in the 19th century, St. Marks became popular for both commercial and recreational fishing. Surrounded by the St. Marks National Wildlife Refuge and the Apalachicola National Forest, St. Marks is at the confluence of the Wakulla and St. Marks Rivers. The town caters to the nature lover and paddling enthusiast. There is also an abandoned railroad line that serves as a popular bicycling and horseback-riding trail.

  15. - Estimated Mileage: 70

    Miller Marine

    Apalachicola, FL



    When you think of Florida oysters, you think of Apalachicola…period. It harvests almost 90 percent of the oysters eaten in Florida. “Shut up and shuck!” is the motto of Boss Oysters, located on the waterfront. Fresh oysters are gathered from the bay, chilled and brought by boat directly to the restaurant and served on the half shell. It doesn’t get any fresher than this.

  16. - Estimated Mileage: 80

    Bay Point Marina

    Bay Point Marina - Panama City Beach, FL - Marinalife

    Panama City Beach, FL



    Located on the Grand Lagoon on the bayside of Panama City Beach, Baypoint Marina is wonderfully suited to explore this popular Spring Break destination. Beach events, scheduled throughout the year, make it a fun spot to visit whether you are seven or seventy years old.

  17. - Estimated Mileage: 50

    HarborWalk Marina

    Destin, FL



    Aquamarine waters, sugary white sand, and a laid back vibe make Destin the location of choice for beachgoers in this part of Florida. Use caution when entering East Pass to proceed into Destin Harbor due to strong currents and frequent shoaling. Negotiating the tricky entrance is well worth the effort to enjoy walking along the Gulf at Henderson Beach State Park. Natural features of the park include sand pines, scrub oaks, and dune rosemary.

  18. - Estimated Mileage: 55

    Palafox Pier Yacht Harbor

    Pensacola, FL



    When entering Pensacola Bay from the Gulf of Mexico, Fort Pickens stands to starboard on the western end of Santa Rosa Island. This pentagonal fort was one of the few U.S. forts in the South to remain in Union hands throughout the War Between the States. Taking a tour through this brick fort makes Civil War history come alive. However, the must see attraction in the area is the National Naval Aviation Museum at the Naval Air Station. It easily rivals the experience found at the Smithsonian National Air and Space Museum in Washington, DC.

  19. - Estimated Mileage: 30

    Orange Beach Marina

    Orange Beach, AL



    Orange Beach is on the west side of Perdido Pass and the dunes of Perdido Key, so it is technically in Alabama. But boaters don’t quibble about that distinction. They have made Orange Beach the most popular cruising destination between Pensacola and Mobile Bay. The annual Fishing Rodeo and National Shrimp Festival are big draws for visitors. No cruise here would be complete without spending an evening at the Flora-Bama. This famous bar is built on the Florida-Alabama state line on Perdido Key. And don’t forget to stand when the house band plays Dixie!