Tampa Bay has some of the most beautiful barrier islands and sandbars in Florida — and most of them are only accessible by boat. From pristine wildlife preserves to historic island forts, the waters around St. Petersburg, Clearwater, and Sarasota are packed with destinations that feel a world away from the mainland. As a captain who has been running charters through these waters for years, here are the ten best islands to visit by boat in the Tampa Bay area.
1. Shell Key — Why Is Shell Key the Best Island Near St. Pete?
If you only visit one island by boat in Tampa Bay, make it Shell Key. This pristine barrier island preserve sits just south of Pass-a-Grille at the southern tip of St. Pete Beach, and it is everything that Florida used to be before the condos went up. No development, no buildings, no roads — just white sand, shallow turquoise water, and more shells than you can carry home.
Shell Key is part of the Shell Key Preserve, a protected habitat managed by Pinellas County. The shallow sandbars surrounding the island are perfect for anchoring, and on a calm day the water is crystal clear and barely waist-deep for hundreds of yards. Dolphins are regulars here — they cruise through the channels between the sandbars, and it is not uncommon to see them feeding within 30 feet of the boat.
The shelling is excellent, especially on the Gulf-facing side of the island. Look for lightning whelks, fighting conchs, sand dollars, and an endless variety of smaller shells. The birding is equally impressive — Shell Key is a nesting ground for least terns, black skimmers, and American oystercatchers, so parts of the island are seasonally restricted to protect nesting sites. Respect the posted boundaries and you will have plenty of beach to explore.
From our marina in St. Petersburg, Shell Key is about a 30-minute cruise, making it an easy addition to any half-day or full-day charter.
2. Egmont Key — What Makes Egmont Key Worth the Trip?
Egmont Key is one of those rare places that delivers on every front: history, nature, snorkeling, and pure untouched beauty. This 440-acre island sits at the mouth of Tampa Bay, about 30 minutes by yacht from St. Petersburg, and it is only accessible by boat — there is no ferry service and no bridge.
The island is home to the ruins of Fort Dade, a Spanish-American War era military installation that was active from 1898 through World War II. The crumbling brick structures, overgrown gun emplacements, and abandoned roads give the island an atmospheric, almost eerie quality that is fascinating to explore. A brick road still runs the length of the island, disappearing into the tropical vegetation.
The snorkeling around Egmont Key is some of the best in the Tampa Bay area. The old seawall and pier pilings on the bay side of the island create artificial reef habitat that attracts a surprising diversity of fish, including sheepshead, snapper, grouper, and the occasional sea turtle. The water clarity on calm days is exceptional for this part of the Gulf Coast.
Speaking of sea turtles — Egmont Key is a major nesting site for loggerhead sea turtles. During nesting season (May through October), you may see nesting crawls on the beach. The island is also home to a still-operational lighthouse, first lit in 1858, and a large population of gopher tortoises that roam the interior trails unbothered by the handful of daily visitors.
Our Egmont Key charters are among our most popular trips. We typically anchor on the bay side for snorkeling and swimming, then cruise around the island for views of the lighthouse and Gulf-side beaches before heading back through the bay for sunset.
3. Caladesi Island — Is Caladesi Island the Best Beach in Florida?
According to Dr. Beach's annual rankings, yes — Caladesi Island has been named the number one beach in the United States multiple times, and it consistently lands in the top ten. Located just north of Clearwater Beach, Caladesi Island State Park is a pristine barrier island with powdery white sand, calm Gulf waters, and a three-mile mangrove kayak trail that winds through the interior of the island.
While there is a ferry from Honeymoon Island that brings day-trippers, arriving by private yacht is an entirely different experience. You can anchor off the Gulf side and take the tender to shore, or dock at the marina on the bay side (slip availability varies — arrive early on weekends). The beach stretches for nearly three miles, and the further north you walk from the main area, the more secluded it becomes.
The mangrove kayak trail is worth the effort. It is a flat, easy paddle through tunnels of mangrove canopy with excellent bird watching — herons, egrets, ospreys, and roseate spoonbills are common. Kayak rentals are available at the marina. For Clearwater-area charters, Caladesi makes an excellent stop on a full-day itinerary.
4. Beer Can Island (Longboat Key) — What Is Beer Can Island?
Beer Can Island is not really an island — it is a shallow sandbar at the north end of Longboat Key, near the entrance to Longboat Pass between Anna Maria Island and Longboat Key. But it has become one of the most famous boating destinations on Florida's Gulf Coast, and for good reason.
On any given weekend, dozens (sometimes hundreds) of boats anchor in the shallow water around Beer Can Island, creating a floating social scene that is part beach party, part boat show. The water is shin-deep in places, so people wade between boats, set up chairs in the sand, and socialize in a way that feels uniquely Floridian. The vibe is relaxed, fun, and very social.
Beer Can Island is located near Sarasota, making it a great stop on a Sarasota-area charter. It is best visited on weekends when the sandbar is buzzing with energy, or on weekdays if you prefer a quieter experience with more space to spread out. The water is warm, shallow, and perfect for swimming.
5. Passage Key — Why Is Passage Key a Hidden Gem?
Passage Key is a tiny, crescent-shaped island sitting right at the mouth of Tampa Bay, between Egmont Key and Anna Maria Island. It is a National Wildlife Refuge and a designated bird sanctuary, which means landing on the island is not permitted. But that does not mean you cannot enjoy it.
The waters around Passage Key are stunningly beautiful — shallow, clear, and teeming with marine life. You can anchor nearby and swim, snorkel, or simply float in water so clear you can see the bottom from the flybridge. The island itself is a nesting site for thousands of shorebirds, and watching the flocks from the water is a remarkable sight, especially during spring and early summer nesting season.
Passage Key is best visited as part of a longer charter that includes Egmont Key or the Anna Maria Island area. The two islands are close enough to visit on the same trip, giving you a mix of exploration (Egmont) and pure natural beauty (Passage Key).
6. Three Rooker Island — Where Can You Find a Private Island Feel?
Three Rooker Island (also called Three Rooker Bar) is a small barrier island located between Clearwater Beach and Tarpon Springs, just off the coast of Honeymoon Island. It is one of the most secluded-feeling islands in the Tampa Bay area, largely because it requires a boat to reach and there are no facilities of any kind — no restrooms, no shade structures, no nothing. Just sand, water, and sky.
The shelling on Three Rooker is excellent, rivaling Shell Key on a good day. The island shifts shape with the tides and storms, so the landscape is always slightly different from one visit to the next. On low tide, extensive sandbars emerge that are perfect for wading and shell hunting. The water on the bay side is calm and shallow, ideal for families with kids.
Three Rooker is best reached from the Clearwater area and pairs well with a stop at Caladesi Island or Anclote Key for a full day of island hopping.
7. Anclote Key — What Is Waiting at Anclote Key?
Anclote Key Preserve State Park is a four-mile-long barrier island located about three miles off the coast of Tarpon Springs. The island is completely undeveloped and only accessible by boat, which gives it a wild, frontier feeling that most Florida beaches lost decades ago.
The southern tip of Anclote Key features the Anclote Key Lighthouse, built in 1887 and no longer operational but still standing as a photogenic landmark. The beaches here are wide, the water is clear, and the island is long enough that you can walk for miles without seeing another person, even on busy weekends.
The waters around Anclote Key offer good snorkeling and fishing. The grass flats on the bay side hold spotted sea trout and redfish, while the Gulf side has better snorkeling around the rocky outcroppings near the lighthouse. If your charter departs from the north end of the Tampa Bay area, Anclote Key is a must-visit.
8. Pine Key — What Makes Pine Key Perfect for a Quick Stop?
Pine Key is a small sandbar island located near Fort De Soto Park in southern Pinellas County. It does not get the attention of Shell Key or Egmont Key, but that is part of its charm. Pine Key is a quick, easy anchorage with calm, shallow water that is perfect for swimming, floating, and simply relaxing on the sandbar.
The island is small enough that you can walk the entire perimeter in 15 minutes, but the water surrounding it is beautiful — warm, clear, and sheltered from the Gulf chop by the surrounding islands. It is an ideal lunch stop on a charter that is heading to or from Egmont Key or Shell Key, and kids love the shallow water where they can wade and play safely.
Pine Key is located within a short cruise of our St. Petersburg marina, making it easy to incorporate into virtually any charter itinerary.
9. Fort De Soto — Is Fort De Soto the Best Beach Day Destination?
Technically, Fort De Soto is not an island hop in the traditional sense — it is connected to the mainland by a bridge and you can drive there. But anchoring off the beaches of Fort De Soto by yacht is an entirely different experience than driving in with everyone else, and it earns a spot on this list for that reason alone.
Fort De Soto Park encompasses five interconnected islands (keys) at the southern tip of Pinellas County. North Beach has been ranked among the best beaches in the country, and the historic fort itself — a Spanish-American War era installation similar to Fort Dade on Egmont Key — is worth exploring. The park also has excellent kayak trails, a fishing pier, and some of the best bird watching in the Tampa Bay area.
By yacht, you can anchor off North Beach or the Gulf-side beaches and tender to shore, avoiding the parking lots and crowds entirely. On a weekday, it feels like your own private beach. Fort De Soto is also the jumping-off point for Shell Key and Egmont Key, so it works beautifully as part of a multi-island charter day.
10. The Bahamas — Can You Really Reach the Bahamas from Tampa Bay?
Yes. And it is closer than you think. Bimini, the westernmost island in the Bahamas, sits roughly 180 nautical miles from Tampa Bay. On our 52ft Marquis Flybridge with a 600-mile cruising range, Bimini is a realistic and comfortable multi-day destination.
The crossing from Tampa Bay to Bimini typically involves an overnight run across the Gulf of Mexico and the Gulf Stream, arriving in the crystal-clear turquoise waters of the Bahamas by morning. Bimini offers world-class snorkeling, diving, deep-sea fishing, and some of the most beautiful water on Earth. From Bimini, you can continue south to Nassau, the Exumas, or the Berry Islands depending on your itinerary and timeframe.
A Bahamas yacht charter from Tampa Bay is a once-in-a-lifetime experience. Most groups book three to five days for a Bimini trip, which allows time for the crossing, two to three days of island exploration, and a comfortable return. It is the ultimate extension of a Tampa Bay yacht charter — taking the same boat, the same captain, and the same luxury experience and stretching it across international waters to one of the most beautiful island chains in the world.
Ready to Start Island Hopping?
Whether you want a half-day trip to Shell Key, a full-day adventure to Egmont Key and Caladesi, or a multi-day crossing to the Bahamas, Yacht Away Now can build the perfect island-hopping itinerary for your group. Captain Josh knows every anchorage, every sandbar, and every hidden spot on this coastline — and he loves sharing them with guests.
Explore our destination-specific charter pages for St. Petersburg, Clearwater, and Sarasota, or contact us directly to tell us which islands are on your list. You can also call Josh at (727) 609-2248 to start planning your trip.