A sunset sailing trip along Sarasota Bay.

A sunset sailing trip along Sarasota Bay.

Sail Away

Cut the engine and hoist your sails to enjoy a tranquil trip around the Intracoastal or out into the Gulf.

Jan Hamel Solomon leads charter sailing trips with her husband, Tim Solomon, aboard a 41-foot Morgan yacht that is stored at Marina Jack. She says sailing combines both art and science. To be good at it, you have to have a command of the physics of how sails work, as well as an instinctual feel for how the wind is behaving.

Key Sailing, the company the Solomons own, can accommodate groups as large as 12 for trips that last from two to four hours. If you’re bringing the kids, go early and try to spot dolphins. If you’re hoping for some romance, book a sunset cruise and cuddle on the deck. Kathleen D Sailing Catamaran offers similar adventures aboard a catamaran cruiser. Some trips will also include lunch and the chance to kayak, too.
Trips can go either south or north from downtown, but Solomon says the destination doesn’t matter as much as the experience of quietly sailing in the bay. Whatever cares are weighing on your mind will float away. “You get on that boat, you throw that junk up in the wind and don’t let it fall back on you,” says Solomon.

Duration: 2-4 hours     

Cost: $390-$630 per trip

Tip: Want to race? The Sarasota Sailing Squadron hosts multiple regattas throughout the year.

A day spent puttering down the Intracoastal is one well-spent.

A day spent puttering down the Intracoastal is one well-spent.

Putter Down the Intracoastal

For a low-key day on the water, visit CB’s Saltwater Outfitters near the southern end of Siesta Key. People who have previously owned a boat or rented one several times can rent a deck boat or pontoon boat and take it for a spin along the Intracoastal.

The company will provide you with a detailed map that highlights some of the best spots to hit up. One of the most popular destinations, according to CB’s co-owner Aledia Tush, is the old Midnight Pass area. “You pull the boat up on the beach and walk across to the beach side,” says Tush. “A lot of people like to do that. It’s like your own little island.” You can pack a meal or keep heading south and grab a meal at Casey Key Fish House, Pop’s Sunset Grill or The Crow’s Nest. If you do continue south, make a stop at Snake Island, a sliver of beach and woods near the Venice jetties.

If you’d rather head north, putter up to Sand Dollar Island, a small outpost right in the middle of Big Pass, but be sure to check on the conditions because of the dredging underway nearby. And stay inside the channel markers, Tush warns. “There are some very shallow spots,” she says.

Duration: 4-9 hours   

Cost: $169-$449 per trip

Tip: There’s an app for that. If you want to fish the Intracoastal, download the state’s Fish | Hunt FL app, which lets you purchase a license online.

Cannons Marina organizes group trips to Useppa Island,  located near Boca Grande.

Cannons Marina organizes group trips to Useppa Island,  located near Boca Grande.

Spend the Night

Cannons Marina on Longboat Key organizes long-distance group trips for its members.

Lucile Capo Miller, the marina’s president, says her favorite destination is Useppa Island, located near Boca Grande, Cayo Costa and Pine Island. You can either travel along the Intracoastal in a boat as small as 20 feet or go out to the Gulf if you have a larger boat, around 45 feet. Cannons sells a range of Grady-White boats and also offers rentals to marina members.

Useppa is a private island, with no bridge connecting it to the mainland, which gives it a secluded, removed air. There are plenty of luxury accommodations, from suites in swanky resorts to big standalone homes and cottages.

You can go by yourself, but Miller says it’s more rewarding to travel with a group. Cannons will organize cocktail parties, but aside from that, guests are free to do what they please once they arrive on the island. “Our goal is to do a couple events a year, just to keep in touch and keep the spirit of boating alive,” says Miller.

Duration: 2-3 days   

Cost: Accommodations cost $140-$1,200 per room per night

Tip: No Time for an overnight? Cruise to nearby Cabbage Key for a famous Jimmy Buffet cheeseburger at the Cabbage Key Inn and then head home.

Family fun at Longboat Pass.

Family fun at Longboat Pass.

Party on the Sandbar

The Sarasota area is blessed with a number of stunning passes where you can drop your anchor and hop overboard to cool off. “We’re spoiled,” says Miller of Cannons Marina. If you own a boat, this trip is a cinch. Plenty of companies also offer rentals that can get you where you need to go.

The shallow sandy beach area on the north side of New Pass, between Lido Key and Longboat Key, is perhaps the area’s best known sandbar party destination. If the sun’s out and the water’s warm, you’ll find dozens of boats anchored there, plus plenty of people sipping salt-rimmed drinks while blissing out in an inner tube. The aquamarine water almost glows when conditions are right, and hanging out here with friends feels like a quick getaway to a Polynesian resort.

Farther north, Longboat Pass is where you want to go if you’re looking for a good time. The beach that curls around the northern tip of Longboat Key is always populated by boats on warm days, and parts are shallow enough that you can explore the area on foot. Be sure to pack a sixer of your favorite beer, some floating noodles and toys for the kids, and stay late to catch the sunset.

Duration: 2-10 hours     

Cost: $150-$800 to rent a boat

Tip: Takes all kinds. A fancy powerboat is great for cruising to the sandbars, but a basic deck boat or skiff will work, too.

Deep sea fishing trips can take you anywhere from 10 to 150 miles offshore.

Deep sea fishing trips can take you anywhere from 10 to 150 miles offshore.

Go Deep

Leave land behind and enjoy the majesty of the Gulf of Mexico by booking an extended offshore fishing voyage. Charter businesses can whisk you out between 10 and 20 miles so you can spend a day catching delicious grouper and hogfish, or you can strap in for a longer trip.

Sarasota Offshore Fishing Charters, for example, operates a family-friendly 40-foot sport fishing boat that departs from Marina Jack. Close to shore, you can land snapper, amberjack and tuna. Farther out, you might find wahoo or mahi-mahi or even a shark.

If you own a boat, Tommy Butler of Xtreme Fishing & Consulting can lead you on a more challenging fishing trip that goes as far out as 150 miles and focuses on catching trophy fish, like massive swordfish or other bucket list species. Deeper runs can be squeezed into one long day or can even cover two days.

Butler has spent decades accumulating precise coordinates that show where the fish bite, and he shares those locations with his clients. He also provides all the rods and tackle you need and demonstrates how to use them. “It’s years and years of knowledge that you’re passing on,” says Butler.

Duration: 4-12 hours

Cost: $700-$1,800 per trip

Tip: Get a good night’s sleep. A successful fishing trip means getting up well before sunrise. Plan on setting out by 6 a.m.

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