Fall Boat Trips Built Around What’s in Season
Arriving anywhere by boat is a memorable experience. But arriving to a bustling waterfront festival filled with color and celebration elevates the journey. I remember anchoring our boat during one of our fall boat trips after a long sail inside the barrier islands of the Florida Keys. We took the dinghy to shore with our children and were met with an extravaganza of food, art, and culture. The streets came to life with color and music. Our kids ran from one tent to another, eyes wide from visions of cotton candy and locally prepared seafood.
Nothing could have landed better than an accidental waterfront seafood festival after a long day on the water. Why leave such moments to chance, though, when you can chart a course around them? From oyster harvests to coastal wineries, your boating itinerary can immerse you in the traditional season. What better way to get a real taste of the local flavor?
Rhode Island Is for Cider Lovers
I can’t think of anything that speaks of fall more than cider. Apple trees. Gallon jugs filled with sweet, spiced liquid. And of course, pumpkins. Rhode Island has become the place to visit for its cider options.
The Hard-Pressed Cider Co.
These cider makers specialize in non-alcoholic craft cider. You can choose a cider slushie, hot mulled cider, or a classic sweet apple cider. By the time you stop for a visit, they may have started to churn out their plan for some fermented varieties.
Where: Jamestown (pictured at top)
Docking Options: Anchor in Potter’s Cove or tie up to Conanicut Marina.
Ragged Island Brewing Co.
Ragged Island is a delightful farm brewery located in Portsmouth. After you dock your boat, make your way to the farm, which sits on 37 acres of property overlooking Narragansett Bay. Sip a craft beer or a featured hard cider as the sunset paints the sky.
Where: 54 Bristol Ferry Road, Portsmouth
Docking Options: Stone Bridge Marina, Portsmouth
Sowams Cider Works
Sowams features slow-pressed juice and small-batch fermentation craft cider, and all of the apples are grown on site. Swing by the tasting room for a flight or a glass of cider.
Where: 98 Child Street, Warren
Docking Options: Warren Town Dock
Would you rather eat your cider than drink it? Huh? Yep. Have you heard of apple cider donuts? They are a thing in Rhode Island. So don’t hesitate to take a culinary tour of this specialty treat.
Knead Doughnuts in Providence has made a name for itself as a top gourmet donut shop in Rhode Island. Hard-Pressed Cider Co. in Jamestown makes donuts directly from their cidery’s house-made apple cider. Rocky Brook Orchard in Middletown is the perfect stop for families traveling with children. This pick-your-own apple orchard has wagons for your kiddos and picker tools for apples and pears. Their apple cider donuts are highly recommended.
A Seafood Thanksgiving Before Turkey Dinner
This November, treat your palate to a medley of traditional seafood before the turkey hits the table. Florida is home to so many food-based festivals that you can pick your flavor just about any week of the year. Let’s curate a slate of local seafood tastings before the familiar Thanksgiving classics.
Tarpon Springs Seafood Festival
November 7-8, 2026
Learn about the history of sponge diving and the Greek sponge divers who settled the town. Local seafood takes a delightful Greek twist in this exciting culinary adventure.
Where: Sponge Docks in Tarpon Springs
Docking Options: Tarpon Springs City Marina and Captain Jack’s are good docking options near the Sponge Docks.
Homosassa Arts, Crafts, and Seafood Festival
November 14-15, 2026
This festival is centered around a working fishing community. The local waters support commercial harvests of seasonal fish and a variety of shellfish. Celebrate the region’s beautiful landscape alongside a seafood extravaganza.
Where: Civic Club Festival Grounds, 5530 South Mason Creek Road, Homosassa
The headwaters of the Homosassa Springs will take you all the way to the festival grounds, and beyond. This portion of Florida waterways offers some of the most amazing wildlife viewing in the entire state.
Docking Options: The Florida Cracker, Crumps Landing, McRae’s. Check out the menu at each of these while you’re there.
Don’t forget to explore Homosassa. Chassahowitzka Springs is a smaller and more diverse alternative to the ever-popular Crystal River. Bring your kayak and you will not be disappointed.
Ormond Beach Riverfest Seafood Festival
November 21-22, 2026
The Halifax River offers a scenic backdrop to a festival filled with food, entertainment, local vendors, and family activities.
If you’re traveling with children, check out the fishing clinic for young people. They will learn about casting, knot-tying, and ethical angling.
Where: Rockefeller Gardens and Fortunato Park
Docking Option: Ormond Beach Public Docks
The Bay Area for Art and Wine Lovers
Tiburon Wine Festival
October 3, 2026
Take a gastronomic tour of featured wines from both small and established production vineyards. Pair it with exceptional food from local restaurants and live music.
Where: Point Tiburon Plaza, Tiburon, California
Docking Options: Corinthian Yacht Club of San Francisco
San Carlos Art and Wine Faire
October 10-11, 2026
Attendees of this annual fair enjoy a colorful mix of local art and curated wines, with live music and family events.
Where: San Carlos Avenue at Laurel Street
Docking Options: Coyote Point Marina
Wine Tasting on the Bay at Pier 39
Any Time of Year
If your boat isn’t serving its purpose as a floating wine bar, this one will. Hop aboard Wine Therapy, a classic yacht, and the bay’s only floating wine bar. Partake in a Wine Country experience without going inland.
Where: Pier 39, the Embarcadero, San Francisco
Dock and Dine for Blue Crabs and Oysters
I don’t know which I like better: cruising on Chesapeake Bay or eating on Chesapeake Bay. In a perfect world, I can do both. And so can you. Here are some dock-and-dining options to get your fill of local oysters and blue crabs on the water.
The Point Crab House and Grill in Arnold, Maryland, is one of the bay’s favorite dock-and-dine stops. Pull your boat up directly to the restaurant where there are three slips for patron boaters. Feast on steamed Maryland blue crabs in the summer and oysters in the fall.
The Fisherman’s Crab Deck in Grasonville, Maryland, allows boaters to tie alongside the restaurant in one of 12 transient slips. Order steamed crabs by the dozen and dine while you overlook the Kent Narrows.
The Crab Claw is in historic St. Michaels, Maryland. Tie your boat to the restaurant’s dock and get ready for business. The menu is full of blue crabs, crab cakes, oysters, clams, and even lobster. Feast on whatever is in season.
Traveling for Food
No one travels by boat just for the water. We do it because we love where it takes us. Food is a gateway to culture. It invites us to experience a place just a little deeper. And what better way to try a new flavor than during a time and in a place where it is being celebrated.
Olivia de Soria
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