Sailing Florida

Updated: Oct 20

Sailboat in the waters of Southwest Florida

Who doesn’t love Florida’s award-winning beaches and world-renowned attractions?

For residents, many staycations are often centered around them. But there’s another way to experience the Sunshine State: from the outside in. A sailing excursion, whether it’s for a few hours or a few days, provides a splashy perspective and unique memories to last a lifetime.

Wake up to the aroma of freshly brewed coffee and step on deck to greet the day. Plunge into Florida’s sparkling waters before breakfast and get face-to-face with a colorful fish or two. While under sail, catch some rays with a pina colada in hand. Most charter companies encourage you to bring along your jam; my genre of choice is Jimmy Buffett or Bob Marley. When cruising — especially with captain and crew —“don’t worry ’bout a ting”becomes my mantra.

Barbecue grill on the back of a sailboat

Have you ever barbecued on the back of a boat? A succulent steak tastes even better when prepared with a backdrop of a setting sun as red as the flames of the grill. At night, fall asleep to the sound of gentle waves rhythmically caressing the hull.

If time allows for an overnight trip or longer, plan to bring enough food and beverages for the duration of your trip. You will most likely receive a grocery list beforehand, so you can select what you want to be stocked on board and waiting for you. It is customary to provide the same for your captain and/or crew if you won’t be sailing the boat yourself. Note: It’s also

customary to tip your captain and take him or her out to dinner the last night of your trip.

Packing couldn’t be easier. Toss some casual clothes, bathing suits, hats and light-soled shoes into a duffel bag or soft-sided luggage. Don’t forget insect repellant and sunscreen, as you will be living outdoors most of each day.

If you can’t commit to more than a day’s sail, consider a half-day or evening sail as an add-on to a land-based vacation. You will be astounded at the sight of a sunset from the beautiful bay, gulf or ocean.

You don’t have to travel far to experience our paradise from the water. Dolphin Landings Charter Boat Center, tucked behind a jumble of condos and shopping centers along Gulf Boulevard in St. Pete Beach, offers access to more than 40 boats throughout Tampa Bay. Dolphins is a hub for a variety of charter experiences, from sunset sails, fishing and party boats to weeklong private charters. They also offer complimentary sailing trips the first Sunday of each month for people with health challenges and their caregivers, as part of the Soothe Our Souls (SOS) program.

Three dolphins leaping out of the water together

Escape for a short dolphin sighting sail aboard the Fantasea, a 46-foot Morgan with a ketch rig (i.e., two masts). The Captain and his first mate deftly maneuvered the boat through the waters of Boca Ciega Bay. Only minutes after leaving the dock, they raised the sails and cut the motor. Silence, gentle breezes and … dolphins! They rode along- side us for most of the two-hour sail, leaping and rolling.

Farther south, Key Sailing is rated as Sarasota‘s No. 1 sailing charter. Capt. Tim and his wife, Jan, offer two- to four-hour cruises along the gulf coastline aboard Key Breeze, their 41-foot Morgan. A favorite is the sunset sail, accompanied by Jan’s descriptions of the waterfront homes of famous area residents, Brian Johnson and others.

The tiny barrier islands of Lee County are strung together like pearls, with a com- mon thread of reverence for nature. One of the most desirable sailing destinations in the country, here we experienced everything from jungle-like wilderness to refined elegance. We met up once again with our finned friends, as the waters of Pine Island Sound boast the largest population of Atlantic bottlenose dolphins in the world. Other companions you’ll enjoy throughout your sail are brown pelicans, cormorants, terns and osprey.

Sanibel Island is home to J.N. Ding Darling National Wildlife Refuge, teeming with birds, bobcats, otters and more. Cayo Costa State Park is one of the largest unin- habited barrier islands in Florida, where you can wander through the mangroves into a picture-perfect postcard of sea oats, sand dunes, clear gulf waters, miles of white-sand beach and a kaleidoscope of seashells glistening along the shore.

Inside the restaurant at Cabbage Key - walls and ceiling covered in dollar bills

Nearby Cabbage Key is the place to stop for a meal. Rustic and welcoming, the Cabbage Key Inn and Restaurant looks much as it did when it was built in 1938 by playwright Mary Roberts Rinehart, with one exception: The walls of the restaurant and bar are covered with thousands of signed dollar bills, all left by visitors over the last 65 years. Money that falls off the wall is donated to local children’s charities and marine research. Jimmy Buffett and Julia Roberts are among the signatures you’ll see. In contrast, the private island of Useppa presents fine dining in a gentrified ambiance. Guests of Southwest Florida Yacht Charters are privy to this exclusive experience.

Sailing with Florida Yacht Charters out of Key West should be on your list of must- dos. The bedroom alone of the 45-foot Hunter was more spacious and well-appointed than in some luxury hotels. This aft cabin featured a queen-size bed, cushioned sitting area, desk and mirrored vanity, shower with built-in seat and all bath amenities.

The first stop after an easy two-hour sail was Sands Key, about 8 miles southwest of Key West. Part of the only living coral reef in the country, stretching from Miami to the Keys, Sands Key is home to an old lighthouse and some of the best snorkeling in the world. And since the Keys are warmed by the Gulf Stream, the water is temperate year-round. Continue south to the little-known islands of Woman Key and Man Key before heading back to Key West for Mallory Square’s famous sunset celebration.

If you love being out in the fresh air, swimming in turquoise waters and living the life of a castaway with amenities, nothing can compare.

IF YOU GO