St. Petersburg Cruising Itinerary

A yacht charter vacation along the scenic shores of west Florida offers a favorably flexible itinerary that is easy to personalize based on the duration of your trip and your group’s unique travel preferences. Whether you charter for three days, a week, or more, the Intracoastal Waterway’s cruising ground is brimming with glimmering green-blue anchorages, laid-back seaside towns, and unforgettable memories best shared at 8 knots. With a plethora of world-class fishing locations, award-winning beaches, and quaint waterfront restaurants at your disposal, you’re free to explore Florida’s Gulf Coast paradise at your very own pace. Soak up endless amounts of radiant sunshine by day and feast your eyes on mesmerizing sunsets by night. 

Day 1
Longboat Key Florida

Longboat Key

The first pass south of Tampa Bay, after leaving the Vinoy Marina in St. Petersburg, Longboat Pass, is a superb anchorage nestled between two top-ranked vacation destinations—Anna Maria Island and Longboat Key. Just after cruising beneath the Cortez Bridge, enjoy a low-key lunch on the Intracoastal Waterway at Tide Tables Restaurant and Marina or Anna Maria Oyster Bar on the Pier. Or, continue further south for some authentic “old Florida” vibes and a signature cocktail at Mar Vista Dockside Restaurant. Be sure to visit Longboat Key Club Moorings, the Gulf coast’s largest deep-water marina, where you also have the option to dock overnight. Either way, you’ll have complete access to all the exclusive Marina Village facilities and amenities, including complimentary shuttle service to St. Armands Circle—Sarasota’s well-known promenade for prime shopping, fine dining, and upscale charm.

Highlight:
Beer Can Island on the northwest end of Longboat Key is popular among boaters for its low-key sand bar and soft white-sand beaches. You can really relax and get back to nature at Beer Can Island, where dolphin sightings are prevalent, and an abundance of seashells can be collected.

Day 2
Shark teeth found on Venice’s Caspersen Beach

Venice Inlet South

Along the way to Venice, spend some much-deserved leisure time soaking up the sun at Siesta Key—the #1 beach in America as named by TripAdvisor’s 2020 Traveler’s Choice Awards™. At the main boat entrance to the Inlet, animal lovers will be delighted by all the marine mammals spotted around North Jetty Beach. And if you take a dip in the water, you might be so lucky to actually swim with manatees that are known to frequent the jetty swim area. For dinner, enjoy a waterfront meal with stunning sunset views at Sharky’s on the Pier or The Crow’s Nest, where there is also a marina for those that wish to overnight here. To really experience Venice’s eclectic appeal, be sure to stroll through downtown, where there’s a variety of shops and restaurants, and you can satisfy your sweet tooth at the Venice Avenue Creamery, which many patrons believe serves up the “best ice cream ever!”

Highlight:
Those with a hankering for treasure hunting must visit south Venice’s Caspersen Beach—a hot-spot for finding genuine shark teeth thanks to the deep fossil layer hidden beneath the surface throughout this region of the Gulf.

Day 3
Boca Grande Florida

Boca Grande

For the swiftest passage to Boca Grande, cruise along the outer shoreline in the Gulf of Mexico, or opt to take the scenic route by way of the Intracoastal Waterway. A hidden gem sitting pretty on the southwest coast of Florida, Boca Grande is a best-kept secret vacation spot most easily accessed by boat. This darling slice of paradise is located on secluded Gasparilla Island in Charlotte Harbor—one of the top sailing destinations in the U.S. where clear-blue waters and easy-living reign supreme. Rightfully nicknamed the “Tarpon capital of the world”, Boca Grande is a haven for die-hard anglers, where up to 10,000 trophy fish have been counted at Boca Grande Pass at the same time. Onshore, pedal your way along the former railroad turned 7-mile bike path, visit the historic lighthouse, go downtown to browse the premium local shops, and of course, indulge in some first-class relaxation on the quiet silky-sand beaches. From the moment you arrive in Boca Grande, it’s easy to see why A-list celebs retreat to this perfect little hideaway, where cares are quickly forgotten, and golf carts are the main form of transportation. There are plenty of praiseworthy restaurants to choose from but two, in particular, are fan-favorites that are sure to win you over too—The Pink Elephant and Loose Caboose Restaurant (we highly recommend the house specialty “Boca Grande Wrap”).

Highlight:
Experience the wonder of the Gulf coast’s crystalline waters in a truly unique and memorable way—atop a see-through bottom kayak or stand-up paddle board from Glass Bottom Rentals. Explore the shallow aquamarine seas and sandbar on your own, join a guided eco-tour, or head out on a sunset tour complete with LED lights. 

Day 4
Shells on Sanibel Island

Captiva & Sanibel Island (Overnight at Boca Grande)

Just south of Boca Grande near Cape Coral lies a pair of small sister islands that are all about outdoor fun in the Florida sun. Collectively, Captiva Island and Sanibel Island are known as the “Shell Islands” for the abundance and variety of seashells found along their 15 miles of unspoiled shoreline. When you come to the “Sea Shell Capital of the World”, you get to bring a special keepsake home with you—a hand-picked, and perfectly in-tact, souvenir from the sea. For a truly one-of-a-kind Captiva Island dining experience, a visit to the world-famous Bubble Room is a must, where it’s Christmas all year long and the dessert slices are notoriously generous. Or, dock your yacht at the premier Sanibel Marina on the southeast end of the island to savor the fresh flavors and nautical atmosphere of Gramma Dot’s—Taste of the Island People’s Choice Award Winner seven years in a row. As dusk approaches, plan to head back north so you can drop anchor at Boca Grande or rent a marina slip for the night.

Highlight:
On your way back to Boca Grande from Sanibel and Captiva, stop off at Cayo Costa—a completely uninhabited barrier island and designated State Park that can only be accessed by way of boat or ferry. An absolutely prime place for camping, Cayo Costa is a nature sanctuary with pure white sand stretching across nine miles of undisturbed, untouched paradise. 

Day 5
Dolphins - Image credit: Naples, Marco Island and Everglades CVB

Venice Inlet North

Rich in Florida history, Italian-influenced architecture, and gorgeous sugar-sand beaches, Venice is easy on the eyes with plenty of opportunities for enjoyment both on shore and off. Animal lovers will find joy in spotting numerous manatees, dolphins, and other wildlife near North Jetty Beach, where it’s not uncommon to see people swimming in the same shallow waters as gentle “sea cows”. Head south for some fruitful shark tooth hunting at Venice’s Caspersen Beach—the longest beach in Sarasota County and the most famous spot for finding genuine shark teeth washed up on the shore and in the gentle ocean waves.

Photo Credit: Naples, Marco Island, and Everglades CVB
Day 6
Siesta Key Lifeguard Hut at Sunset Florida - Image credit: Visit Sarasota

Sarasota Bay

Venture into Sarasota Bay via the Intracoastal Waterway, where a fully-equipped cove makes it easy for boaters to enjoy three of Florida’s top-rated destinations all in the same day. Soak up some sun and relaxation at Siesta Key—named the #1 beach (again!) in the United States by the 2020 TripAdvisor Travelers' Choice™ awards. If you’re partial to the Longboat Key Club’s high-end yet easy-going appeal, spend your day unwinding at the pool with a frozen cocktail in-hand then take the shuttle service to St. Armands Circle for some uptown shopping. Located in the heart of downtown Sarasota, Marina Jacks is the perfect place to spend the last night of your unforgettable vacation. Grab a table at crowd-pleasing Owen’s Fish Camp to enjoy fresh seafood with a modern flair and an “ode to Florida” atmosphere that just feels like home.

Photo credit: Visit Sarasota
Day 7
Vinoy Hotel and Marina St. Petersburg Florida

St. Petersburg (via Egmont Key)

As you make your way back to the beautiful Tampa Bay Area, allow yourself some time to stop at secluded and historically-significant Egmont Key. Only accessible by boat, this preserved piece of land offers a unique glimpse into Florida’s past, dating back as far as the Civil War. Explore the ruins of formerly-thriving Fort Dade, visit the 160+ year-old lighthouse that still guides boat captains to safety, and immerse yourself in the natural beauty of this designated National Wildlife Refuge. Upon returning to the pretty-in-pink Renaissance Vinoy Resort Marina, not only are you free to wander the sidewalks of historic downtown St. Petersburg, but you’re also invited to indulge in the resort’s amenities. Depending on your travel dates, it’s worth spending a day or two exploring the “Sunshine City”—home of the new and improved iconic St. Pete Pier, exquisite art museums, more than a dozen local breweries, two rooftop bars with stunning panoramic views, and so much more.

Photo credit: The Vinoy Renaissance St. Petersburg Resort & Golf Club
Day 1
Aerial view of Fort de Soto in Florida

De Soto Point

A perfectly remote and relaxing anchorage spot, De Soto Point is centrally located within Fort De Soto Park’s peaceful nature haven. On your journey there, be ready to snap some photos while cruising under the Sunshine Skyway Bridge—rated #3 of the "Top 10 Bridges" in the world by The Travel Channel. Fort De Soto is highly-praised for its natural beauty, offering superb beaches, a seven-mile multi-purpose trail, and top-rated campgrounds. Visit the historic landmarks of Battery Bigelow and Battery Laidley, splash around in the wide tidal pool at North Beach, hike the scenic trails, fish from the pier, and collect sand dollars along the sea shore. Rent kayaks or a covered surrey bike (can accommodate up to 8 people) to explore the many wonders of this outdoor paradise at your own pace.

Highlight:
Allow yourself some time to stop off at nearby Egmont Key. Only accessible by boat, this preserved piece of land offers a unique glimpse into Florida’s past, dating back as far as the Civil War. Explore the ruins of formerly-thriving Fort Dade, visit the 160+ year-old lighthouse that still guides boat captains to safety, and immerse yourself in the natural beauty of this designated National Wildlife Refuge.

Day 2
Fire pit at Little Harbor Florida - Credit Harborside Suites Ruskin

Little Harbor

Enjoy a relaxing sail across the bay to Ruskin’s Resort & Club at Little Harbor—a Caribbean-style island resort featuring its own private beach, a full-service marina, and an array of recreational activities. Go swimming in one of the three heated pools, cast your line off the 250-foot fishing pier, and come sunset, chill out Adirondack-style around a private fire pit. With several waterfront restaurants located on site, you can choose the menu that appeals to you most while taking in breathtaking views of Tampa Bay. You can even rent wave runners to satisfy your adrenaline-rush craving or go on a guided jet ski tour.

Highlight:
If you head a bit northwest of Little Harbor Marina, you can visit Tampa Electric’s Manatee Viewing Center at Apollo Beach during the winter months—a protected marine reserve with a boardwalk, 50-foot observation tower, trails, and a butterfly garden. You can also enjoy a superior lunch or dinner dining experience at Circles—Tampa’s most storied, iconic, and award-winning waterfront restaurant with reserved slips for patrons.

Day 3
Dolphins playing at Tierra Verde Florida

Tierra Verde

Make your way back west to the exclusive island of Tierra Verde, a celebrated boating community where you can enjoy the new 10-acre PORT 32—a premier resort-style marina with exceptional service and facilities. For some much-deserved but undisturbed rest and relaxation, head to Tierra Verde’s Shell Key Preserve—a truly secluded getaway spot only accessible by boat. Dine at a local hot-spot and top-rated seafood restaurant located on site—The Island Grille & Raw Bar, and for dessert, stop by Andy’s Ice Cream Shop for a double-dipped sweet treat in your favorite flavor.

Day 4
Top rated Clearwater Beach in Florida

Clearwater Beach

Journey up the coast to beautiful Clearwater, enjoying incredible coastal scenery along the way. Soak up the Florida sunshine on world-renowned Clearwater Beach, which boasts the distinct Blue Wave Beach classification, a fantastic assortment of shops, and plenty of island-inspired restaurants, including a dockside fish shack called the Bait House and the always-popular Frenchy’s, where they serve up their famous fresh-caught grouper sandwich six different ways. Set sail on a treasure-hunting pirate cruise, explore the bustling streets of Clearwater by bicycle, or go on a wake-making jet ski adventure. You can also visit Winter the dolphin in her new and improved home at the Clearwater Marine Aquarium, where you can meet rescued animals, feed stingrays, and more.

Day 5
Sponges for sale at a shop in Tarpon Springs Florida

Tarpon Springs (Overnight in Clearwater)

From Clearwater venture up to Tarpon Springs for the day to visit the “Sponge Capital of the World”, which is also known as “Greektown” for its authentic Greek culture and restaurants. Along the way, stop off at Dunedin’s Honeymoon Island Beach and marvel in four miles of unspoiled white sand paradise. Pull up to Rusty Bellies Waterfront Grill for some delicious eats, fun tiki drinks, and a delightful atmosphere from a place with an average Google rating of 4.6 out of over 5,300 reviews. Visit the historic district of Tarpon Springs to stroll the brick-paved streets lined with antique stores, art galleries, and specialty shops.

Day 6
Kayaking in the mangroves around Gulfport Florida

Gulfport

Anchor in the “old Florida” town of Gulfport, St. Petersburg’s hidden gem, where the vibe is always laid-back, and the local community is delightfully funky. On your way there, just south of the Treasure Island Causeway and Paradise Island, you can pick up some fun souvenirs from the popular tourist attraction, The Florida Shell Shop, and craft beer enthusiasts can enjoy some locally-brewed IPA’s at Sea Dog Brewing Co., which features a bayside patio, boat dock, billiard tables, and merchandise store. Dock your boat at the Gulfport Municipal Marina then head to Beach Boulevard to explore the row of eclectic shops, art merchants, and restaurants. 

Highlight:
Plan to spend some time at Pass-A-Grille, a quaint little beach town and historic district with watersports rentals, darling shops, laid-back restaurants, and plenty of pristine white-sand for superb relaxation under the Florida sun.

Day 7
Paddleboarding at night in St. Petersburg Florida

St. Petersburg

Upon returning to the pretty-in-pink Renaissance Vinoy Resort Marina, not only are you free to wander the sidewalks of historic downtown St. Petersburg, but you’re also invited to indulge in the resort’s amenities. Depending on your travel dates, it’s worth spending a day or two exploring the “Sunshine City”—home of the new and improved iconic St. Pete Pier, exquisite art museums, more than a dozen local breweries, two rooftop bars with stunning panoramic views, and so much more.