Pensacola's sprawling network of protected waters and temperate fall and winter weather create ideal sailing conditions along Pensacola and Perdido bays. There’s almost always a suitable breeze here. Warm Gulf breezes ruffle sails before the cold fronts pass, then WHOOSH — stout northerly blasts follow.

Our bays are getting famous in the sailing world. We host a growing, happy sailing community — with old salts and newcomers welcome.

Whether you want to watch the experts, ride, relax, propose and selfie with the sunset — or if you want to take the helm — set sail here in Pensacola.


World-Class Racing Team Chooses Pensacola Bay to Train

Based at the Port of Pensacola

The storied New York Yacht Club’s American Magic racing team is once again calling Pensacola home during the late fall and winter to practice, facing the challenge of big bay sailing without having to scrape ice off the decks like they would up north.

The American Magic racing team is seeking to challenge the 2017 defending champions, the Emirates Team New Zealand, for the 36th America's Cup in Auckland in 2021. The America's Cup is the oldest international sporting trophy, older than the modern-day Olympics, and is held every four years. America's Cup sailing teams mount a campaign, many spending well over $100 million, to challenge the yacht club that won previous America's Cup.

Obviously, this is a pretty big deal. The New York Yacht Club has successfully defended the Cup 24 times.

The American Magic team could have chosen anywhere to train on their new concept sailboat: a high-performance, 75-foot foiling monohull boat called the AC75. They chose Pensacola Bay — for its perfect recipe of warm weather, flat water, steady breeze and welcoming community.  

So, if you’ve never seen a foiling sailboat — which has wing-like attachments mounted to the hull of the boat — quite literally flying over the top of Pensacola Bay at speeds over 50 knots… you’re missing quite the spectacle.

The team is based out of the Port of Pensacola, so the best viewing vantage point is Plaza de Luna.


Regattas by the Bay: Premiere Sailing League Racing Heats Up

Based at Pensacola Yacht Club


Our bays have spoken. Premiere Sailing League USA chose Pensacola as its southern headquarters and winter harbor at Pensacola Yacht Club. It will bring exciting spectator-friendly regatta racing from January through April 2020.

The teams race identical RS21 boats instead of “handicaps” as they do in many other regattas. The short, fast-paced races of windward and leeward legs will mean up to 20 races a day and are easily followed by spectators.


The first PSL Winter Exhibition is set for Jan. 3-5, 2020, with practice races held along the bay near Pensacola Yacht Club and Sanders Beach. Race days on Saturday and Sunday put the races nearshore with optimum viewing for spectators along Plaza de Luna in downtown Pensacola and the Vince Whibbs Community Maritime Park (locals call it Blue Wahoos Park) just down Main Street.


Teams and even collegiate sailing teams can charter their own RS21 boats to practice for their spring seasons. More PSL Winter Exhibitions are planned for Jan. 31-Feb. 2, March 6-8 and April 3-5, 2020. (Stay tuned. Dates could change).


Want to Crew? Join our Sailors! Pensacola Yacht Club

Think sailing is slow?

Try riding along in a regatta as the crew pops the spinnaker. It’s choreographed chaos. The boat carves a tight arc around the buoy as the crew scurries along the deck, unsheathing the spinnaker as others furiously crank winches. Canvas rustles, and then you feel a shuddering THUMP. Wind fills the colorful chute and the boat surges forward. It’s a rush.

Sailing competition is serious fun. The Pensacola Yacht Club, Pensacola Beach Yacht Club and Navy Yacht Club Pensacola all are members of the Gulf Yachting Association, which includes clubs from Houston and New Orleans to St. Petersburg. Regattas are held routinely throughout the year, hosted by clubs all along the Gulf Coast.

The first regatta of the year starts on New Year’s Day with the Hangover Regatta, and races continue with Valentine’s Regatta and so on and forth. The three clubs unite for the prestigious Maxine Series — a trio of races held by Navy Yacht Club Pensacola, Pensacola Yacht Club and Pensacola Beach Yacht Club.

Maxine #1 —Held in February by the Navy Yacht Club Pensacola.

Maxine #2 — Held by the Pensacola Beach Yacht Club in early March.

Maxine #3 — Held by the Pensacola Yacht Club in late March and when the Maxine Champion is crowned!


Sail the Condor: Sailing Adventures with Captain Kirk

Palafox Pier, Pensacola

Want to ride on the wings of a condor? One of only 21 in existence, the 40-foot, 28-foot wide Condor trimaran was born and bred in Annapolis, Md. — built to sail the Chesapeake Bay and traverse the wild ocean. Three hulls make it a breed apart for sailing. Built to withstand punishing seas, it is fast, stable and graceful — an exhilarating ride in Pensacola Bay.

Condor Sailing Adventures owner Michael “Captain” Kirk charters guests on “Dare II,” a Condor he has owned since 2002. He knows what these trimarans can do, making a 5,800-mile transatlantic crossing on the Condor “Thunderbird.”

For a max of six guests, Condor Sailing Adventures offers daily sunset cruises, engagement and wedding cruises and even customized cruises – all perfectly Instagrammable. Let Cap’n Kirk take the helm.


Take the Helm at Lanier Sailing Academy & Buccaneer Sailing Club

Palafox Pier

Sailing takes time, patience and skilled instruction. John and Kathy Struchen have taught sailing through Lanier Sailing Academy since 2001 and offer American Sailing Association certification classes in Basic KeelBoat (Beginner Course), Basic Coastal Cruising, Coastal Navigation and more.

With the hands-on certification class, certified instructors teach you what you need to know to guide a sailboat all by yourself. You steer the boat and trim the sails, cap’n.

Graduates of the basic certification course can join Lanier’s Buccaneer Sailing Club, which means you can reserve a 22-to-25-foot boat and whisk it away for the day.

Imagine having a boat without ever having to sand it, or spend a gorgeous fall day wandering aimlessly around an obscure marine supplies store.


Cats Cruise the Sound along Pensacola Beach

On Pensacola Beach, Santa Rosa Sound provides a large, protected waterway feeding Pensacola Bay. Featherlight Hobie cats are quick and nimble and a breeze to sail on this aquatic playground.

Key Sailing, located at 400 Quietwater Beach Blvd, offers two different catamaran sailboats available for rent on Santa Rosa Sound: a 13-foot Wave and 16-foot Getaway catamaran. Contact: 400 Quietwater Beach Blvd, Pensacola Beach, FL 32561. (850) 932-5520

Portofino Island Resort offers 14-16-foot Hobie Cat rentals for its guests.
Contact: 10 Portofino Drive • Pensacola Beach, Florida 32561 • Main Phone: 850.916.5000 • Toll-free: (877) 484-3405


Sailing, boating and more

Sailing and boating is all fun and games but sometimes you just want to sit back and relax. For a full list of sailing adventures including dolphin cruises and more, click here.