The Best Fall Destinations to Explore by Boat

Last Updated on October 16, 2024 by Boatsetter Team

Leaf peepers travel near and far to witness one of the world’s most unique natural phenomena, its the most affordable time to travel in the US, and cooler water temperatures increase water temperatures unlocking a behemoth of fishing opportunities just to name a few things that make fall so special. From one the most haunted lighthouse in the US to cozy country escapes, and urban getaways, wander through the best fall destinations by boat for a unique perspective to one of the most magical times of the year.

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San Diego, California

By fall San Diego becomes a pleasantly warm destination perfect for outdoor activities like sailing, especially on a 1972 classic sailboat. Sail around Point Loma, cruise around the San Diego Bay for breathtaking views of the San Diego skyline, or bring your surf board aboard and anchor down at Cabrillo Point to practice your pop-up technique. 

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Boston, Massachusetts

Explore the Freedom Trail, attend fall festivals, and savor a cup of clam chowder while taking in the city’s picturesque fall foliage. Boston’s picturesque harbor is best enjoyed from the deck of a rented boat. Sail past the historic Boston Tea Party ships, the USS Constitution, and the vibrant Seaport District. For a unique experience, explore the Boston Harbor Islands, where you can anchor and swim, hike, or enjoy a picnic with breathtaking views of the city.

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St. Augustine Lighthouse

Many of the most haunted places just happen to be lighthouses and people love to visit them. The St Augustine Lighthouse is known as one of the oldest and most haunted structure in the US. 225,000 mortals come here annually to climb up its spiral staircase and communicate with the ghosts of these hollow grounds. If you’re looking for uniquely experience haunting experience, why not use the public boat ramp on property arrive to this lighthouse by boat?

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Chicago, Illinois

Take advantage of the last good months of boating before the waters here begin to freeze in November. Capture stunning photography of the most iconic buildings of the birthplace of modern architecture— from TheMart, formerly the largest building in the world, to The St. Regis Chicago, the tallest building in the world designed by a woman. Dock for hand-stretched pizza at Pizza Portofino, go to RPM Seafood for caviar, or book a captained cruise and bring the charcuterie and champagne aboard.

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New York City, New York

Grab your pumpkin spice latte to go, meet your captain at the dock and take views of the Statue of Liberty and the fall foliage against the city. If you’re for a nature escape nearby the city, cruise over to Jamaica Bay Refuge, a breathtaking 9155-acre natural preserve known as the home of more than 330 bird species. Expect views of dunlin, cerulean warblers, short-eared owl and several other wildlife

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San Francisco, California

Put on your favorite sweater and cruise the Bay Area to enjoying several views of landmarks like the Golden Gate Bridge, or head over to Natural Bridges State Park for views of the last remaining natural arch of this area. From late October to November, thousands of monarch butterflies migrate west making their homecoming here. 

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Whidbey Island

As you reach the Whidbey Scenic Isle Way part of the Cascade Loop, consider stretching your legs out on a boat and get a unique vantage point to Whidbey Island. Dock at Possession Beach Park, a great fall beach with brilliant yellow, orange, and red foliage and sightings of orcas.

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Providence, Rhode Island

Whether you’re taking advantage of oneof the most affordable times to travel in the US or you’re a local looking for something new to do in your area, hop on the Providence River for a unique vantage point of the colonial-style architecture. Enjoy IG-worthy shots of the WaterFire, a unique art installation that lights up the river with bonfires during autumn evenings.

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Pictured Rocks National Lakeshore 

It should come as no surprise Michigan’s rural Upper Peninsula is one of the best places to see fall foliage. A popular summer destination for its resembling Caribbean turquoise waters, come fall, red, yellow, and orange blanket the treetops of Pictured Rocks Lakeshore turning it into one of the most breathtaking fall destinations.  Go for a scenic cruise with views of picturesque sandstone cliffs with fall color trees atop.

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Sleepy Hollow, New York

Sleepy Hollow’s reputation for being a haunted and mysterious place goes as far back as to the Dutch Settlers of the 1600s. Known as the birthplace of “The Legends of Sleepy Hollow” tales and the final resting place of William Irving, Sleepy Hollow is one of the most popular haunted destinations accessible by boat. Take in the views of fall foliage along the Hudson Valley along the way, pass by William Irvings waterfront estate and Lyndhurst Mansion, a 19th-century gothic castle.

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Jamestowne

Get on the James River to get picturesque views of fall foliage and several views of rural and early colonial America sites such as the Historic Jamestown, which features the Jamestown Settlement. Go to Archer’s Hope Historical Plaque to scavenger for gold, or anchor by a nearby secluded cove to take in the natural beauty.

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Salt Lake City, Utah

Nestled against the stunning backdrop of the Wasatch Mountains, Salt Lake City offers a mix of outdoor adventures and urban exploration. Hike in the nearby canyons, sip apple cider in cozy cafes, and admire the mountain’s changing colors. While not known for its coastal waters, Salt Lake City offers a unique boating experience on Great Salt Lake. Rent a kayak or paddleboard and float on the lake’s briny waters, enjoying the unique experience of buoyancy and the surrounding salt flats and distant mountains.

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New Orleans, Louisiana

Enjoy gumbo, jazz performances, and the lively ambiance of the French Quarter, all while experiencing a different side of the city during the fall season. Rent a boat in New Orleans to explore Mississippi River or venture into the nearby swamps and bayous. Take a swamp tour to witness the fascinating wildlife, including alligators and exotic birds, or enjoy a leisurely cruise on the mighty Mississippi, where you can soak up the city’s rich history.

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Nashville, Tennessee

Fall on the water is harmonious in The Music City. Renting. Cruise along the Cumberland River, taking in the iconic Nashville skyline, including views of the famous Batman building.  Head northeast to Old Hickory Lake and anchor at one of the secluded coves to reflect among the fall foliage or visit the Historic Rock Castle, the oldest castle in Tennessee. 

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Savannah, Georgia

Renting a boat in Savannah offers a delightful escape into the heart of this coastal gem. The Savannah River, which gracefully flows along the city’s edge, provides a serene setting for exploration. Cruise along the river and fall in love with its historic riverfront, where old cotton warehouses have been transformed into shops and restaurants. Don’t forget to take pictures of the Talmadge Memorial Bridge, an iconic gateway to the city. 

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