When the Gulf Intracoastal Waterway canal from Mobile Bay opens into Wolf Bay in Orange Beach, Alabama, it begins crisscrossing a series of estuaries tucked behind the finest white-sand beaches in the world. This stretch of beach between here and Panama City, Florida, boasts sugar-soft sands that once were the tops of the Appalachian Mountains. Now they welcome the warm waters of the Gulf Coast.Start your journey in Orange Beach, where so many excellent restaurants sit on the water that you'll want to stay longer to sample them all. Pull into Orange Beach Marina, which is located on a fully protected harbor and accommodates vessels up to 130 feet. For fine dining, be sure to head upstairs at the marina to Fisher's, or opt for their dock-side dining for something a bit more casual. If you're in the need of service or maintenance during your stay, Saunders Yachtworks is located next to the marina and can help with any fixes. Over at Perdido Pass, boaters tie up at the Cobalt dock to dine on fresh seafood while watching the water traffic travel in and out of the Gulf.
For shopping, don't miss Orange Beach's eclectic collection of retailers and boutiques all along the docks. San Roc Cay and The Wharf both offer locally owned clothing, home decor, and specialty shops. Meanwhile, the Coastal Arts Center of Orange Beach sits on the shore of Wolf Bay in a 1920s-era hotel, and includes an art gallery. There's also an on-site glass-blowing studio and a pottery studio. If you prefer some outdoors activity, glide like a seagull on the Hummingbird Ziplines at Gulf Adventure Center at the Gulf State Park's Lake Shelby. Or opt for some paddle boarding on the lake. It's ideal for beginners without having to deal with surf and tides.
When you do head to the east, leave time to dock or pull up on the sand at the state line's Flora-Bama Yacht Club. With your feet in the sand, sip a legendary Bushwacker and enjoy ruby red shrimp, a sweeter deep-water shrimp harvested offshore. Afterwards, wander across the street to experience the legendary roadhouse bar The Flora-Bama, with its three stages of live music.
Distance: 24 nautical miles
Slip behind the rows of marching condos on Perdido Key to motor out into Pensacola Bay to Palafox Pier Yacht Harbor, just footsteps away from downtown Pensacola. Be sure to stroll down Palafox Street's brick sidewalks and breathe in more than 450 years of history. The street is the heartbeat of downtown. Chic shops, galleries and trendy restaurants populate the wroughtironed buildings. Crepe myrtles wave in the gentle sea breezes.
Take in a minor league baseball game at the adjacent stadium featuring the home team the Blue Wahoos, a Double A team for the Cincinnati Reds. If they are not in town you may want to see who is performing at the historic Saenger Theatre. Pensacola hosts many traveling concerts as well as its own symphony, opera, and ballet.
Hungry? Head over to the Atlas Oyster House or its sister restaurant, The Fish House; they both sit on the bay, and both serve locally caught mahi-mahi, grouper and other Gulf fish. Or maybe you'd prefer to cook your own. Stop at Joe Patti's Seafood Market to pick up the freshest fish in town. When the sun goes down, join the party over at Seville Quarter with its dueling pianos. Afterwards, stop by Old Hickory Whiskey Bar for a late-night nip. In the morning, grab your coffee at the Fosko Coffee Barre.
Distance: 47 nautical miles
Transit back out through the Bay and scoot in between Gulf Breeze and Pensacola Beach along the Gulf Islands National Seashore. The Gulf ICW will take you behind pristine Navarre Beach, Santa Rosa Island and Okaloosa Island before popping out into the wide Choctawhatchee Bay. You'll first come to Destin, settled as world's luckiest fishing village. These days it's a beach hub too. Families and fisher folk flock here for incredible beaches, boating and bountiful seafood. If you want to leave your boat docked, a water taxi can move you between destinations.
HarborWalk Village, tucked just under the bridge at East Pass and on Destin Harbor, has both a marina as well as a waterfront shopping and dining destination. It's the place to rent a paddle board, kayak or jet ski or to schedule a glass-bottom boat ride. Fireworks light up the night sky on weekends. There's a passel of Gulf-to-table restaurants with Brotula's Seafood House and Steamer especially notable. They will even cook your catch for you.A bit farther east is Baytowne Marina, located within the Sandestin Golf and Beach Resort. The marina staff provides concierge service, including arranging golf tee times, restaurant reservations, tram service and golf cart rentals. There are well over two dozen restaurants nearby, including casual dining, dinner cruises and fine dining, where you can enjoy a spectacular breakfast, lunch or dinner.
A favorite place to spend a day swimming and snorkeling is Crab Island. Depths around the island range from 2 to 10 feet depending on where you anchor. During the warmer seasons, a restaurant/snack barge sells hamburgers, steamed shrimp, boiled peanuts and ice cream.
Distance: 56 nautical miles
Move your boat to the east end of Choctawhatchee Bay to enter the narrow canal to West Bay, the Grand Lagoon and North Bay at Panama City. Those feed into St. Andrews Bay just past Panama City Beach, where you can tuck into Bay Point Marina at the Lower Grand Lagoon near the Pass. You'll find a lovely resort setting with a challenging Jack Nicklaus- designed golf course and a full spa at Bay Point.The nearby Capt. Anderson's Marina, also on the same lagoon, offers one of the most popular seafood restaurants in town, alongside a full fishing fleet, dive boats and cruises to Shell Island another fun spit of sand amid the emerald waters of the Gulf that's good for an hour or a full day's fun.Across St. Andrews Bay at the City Marina you can walk to many shops and restaurants in downtown Panama City. Don't miss Ferrucci Ristorante for Italian seafood dishes or Millie's Café for po'boys and beignets. Those with a taste for impeccably curated antiques will love Main Street. Afterwards, try your hand at Corner Pocket, a smoke-free pool hall that also has the city's largest selection of craft brews on tap.The charming small town of St. Andrews sits on the same bay with a host of eateries, watering holes and galleries all within two blocks of the docks. Chef Ernie Hall dishes up Latin Caribbean fare on his boat Just the Cook.On your final morning, head over to Andy's Flour-Power Café Bakery for the finest breakfast in town. Most tourists haven't found it yet, so you'll be able to score a table and sip your way into another beautiful day on the Gulf ICW.