Top 10 Winter Boating Destinations

In the winter months, when the northern boating meccas are quiet due to gray skies, freezing temperatures, ice and snow, many boaters head south for a relaxing vacation exploring warmer waters. Whether you take your own boat, charter a bareboat, or sit back and let a professional captain do the driving, there are plenty of hotspots to choose from across the U.S. and in the Caribbean. Before you go, however, be sure to familiarize yourself with the local boating (and fishing) regulations.

Here are 10 popular winter boating destinations to consider.

Trailer your boat:

  • St. John’s River. This 310-mile river, which flows north through Central Florida to Jacksonville and the Atlantic Ocean, is highly popular both for fishing and immersing yourself in nature. Birdwatching is excellent along its banks, and you undoubtedly also will see a large number of alligators. During the winter, manatees are a common sight, especially in areas with warmer waters like Silver Glen Springs in Ocala National Forest, on an offshoot of the river you can reach by boat. There are many boat ramps along St. John’s, along with marinas where you can rent a houseboat to use on the river if you don’t trailer your own boat.

  • Clearwater, Florida. The Gulf Coast of Florida is blessed with calm waters that typically stay in the mid-to upper-60-degree range in the winter months. You can stay and play on Clearwater Beach, enjoying nightly sunsets over the Gulf of Mexico from the beachfront bars, but be sure to take a day to explore the wild barrier islands to the north. Caladesi Island State Park, which has its own marina, is a can’t-miss stop featuring one of the prettiest beaches in the nation. The little, Scots-influenced town of Dunedin, just opposite, offers many shopping and dining options just a short stroll from the docks.

  • Key West, Florida. While it’s a long way to trailer a boat to the Southernmost Point in the U.S., Key West is well worth the trip. The Conch Republic has it all, from paddleboarding and snorkeling coral reefs by day to fine dining and nightclubbing at night. Sunsets are a specialty here, especially in Mallory Square where you can also enjoy the nightly street performers. There are many other famous Key West attractions to check out – all within walking distance of the marinas – including Jimmy Buffet’s Margaritaville, Sloppy Joe’s Bar, the Mel Fisher Maritime Museum, the Hemingway Home and Museum, and of course, the Southernmost Point itself.

  • Lake Austin, Texas. A 1,600-acre manmade lake on the Colorado River, Lake Austin is only a half-hour drive from Austin, Texas. Here, boaters can explore miles of scenic shoreline and also find several popular hiking trails that offer scenic views of the lake. A couple of the trails also take you to small waterfalls. Later, enjoy a meal at one of the lakeside eateries specializing in baked goods or barbecue or oysters and other seafood. Anglers love fishing for the big largemouth bass that inhabit these waters. Lake Austin is easily accessed by two concrete boat ramps.

Best by large center console, cruiser, or sailboat:

  • Georgia’s Golden Isles. Coastal Georgia is a year-round boating destination with air temperatures averaging in the mid-60-degree range. The Golden Isles region, which encompasses Brunswick on the mainland along with St. Simons, Sea and Jekyll islands, offers serene marsh scenery, broad beaches, and quaint downtown areas lined with boutiques and restaurants featuring lowcountry cuisine. Even if it’s too cold for sunbathing, you will find plenty to do in the area, including kayaking and bicycling. Be sure to visit the Jekyll Island Club and learn about its history during the Gilded Age.

  • St. Augustine, Florida. America’s Oldest City, founded in 1565, offers a wealth of attractions within walking distance of the city’s municipal marina. History buffs can tour Castillo de San Marcos National Monument, a fort built of local coquina shell in 1695, or watch a demonstration of old-time blacksmithing in the Colonial Quarter. St. George Street, open only to pedestrians, is lined with shops, restaurants, and live music venues. Anastasia State Park with its beautiful beach is just a short taxi ride away. After dark, if you are brave enough, several companies offer spooky ghost tours of this ancient city.

  • Biloxi, Mississippi. While there are many great ports to visit by boat along the coast of the Gulf of Mexico, Biloxi has a cluster of attractions right along its beachfront. A mini-Vegas, it is home to a strip of casinos that offer not only gambling but also a wide variety of dining options and live entertainment. You can take a walk along the boardwalk, tour a historic house, or visit the Hurricane Katrina Memorial, commemorating the city’s devastation by the 2005 hurricane and the resilience of its people after the storm. Biloxi also is a world-class sportfishing mecca.

  • South Padre Island, Texas. If you are heading south for a back-to-nature boating vacation, you will enjoy the miles-long barrier island, which is protected by Padre Island National Seashore. In addition to sunbathing, this is a great place for birdwatching, hiking, biking and even riding horses along the beach. Surfing and windsurfing are also popular pastimes here. While this is an ideal spot to reconnect with sand and sea, it also offers full-service marinas located inside the bay.

Charter a bareboat or a skippered yacht:

  • The Abacos, Bahamas. While the southern U.S. offers a break from the ice and snow, if you want to experience true summer temperatures during the winter months, head to The Bahamas. The Abacos chain of cays is highly popular with Florida boaters who own a boat capable of crossing the Gulf Stream, but you also can find bareboat and skippered boats – both power and sail – available to charter here. Largely recovered from the impacts of Hurricane Dorian, which hit the islands in 2019, the Abacos offer a laid-black seven-day itinerary, hopping from cay to cay along the calm, turquoise Sea of Abaco.

  • The British Virgin Islands. The BVI are considered by many to be the pinnacle of winter cruising destinations. This island chain, strung like jewels along Sir Frances Drake Channel, is so popular you probably won’t be able to find a deserted anchorage – but that’s for good reason. Island-hopping, beach bars, Caribbean cuisine, world-class snorkeling and diving – You can find it all in the BVI. Don’t miss the Soggy Dollar on Jost Van Dyke – so named by sailors who anchored in the bay and swam into this iconic beach bar with their wallets in their pockets. The Baths, a jumble of giant boulders that you can wade through on the tip of Virgin Gorda, is another must-see site. The BVI is beloved by sailors for its steady breezes, but you also can charter power catamarans there. 

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