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Waterway Wonders: 49 Must-Visit Places on America’s Great Loop

Embarking on America’s Great Loop is a journey of a lifetime, offering an unparalleled opportunity to explore the diverse landscapes, rich history, and vibrant cultures of the United States and parts of Canada.

This continuous waterway adventure encompasses the Atlantic and Gulf Intracoastal Waterways, the Great Lakes, Canadian Heritage Canals, and the inland rivers of America’s heartland.

Whether you want to spend time soaking up the sun, sightseeing, admiring historical architecture, or visiting different states, these 49 places along America’s Great Loop are worth a visit. 

Wilmington  North Carolina
Wilmington North Carolina I photo credit: Paul Brady Photography / Shutterstock

Eastern Seaboard & Atlantic Intracoastal Waterway Cities

Annapolis | Maryland

Known as America’s Sailing Capital, Annapolis is a picturesque waterfront city steeped in maritime history. Home to the United States Naval Academy, the city boasts a rich nautical tradition and a dynamic sailing community. The Chesapeake Bay provides the perfect backdrop for sailing enthusiasts, with numerous marinas and sailing events throughout the year.

Norfolk | Virginia

Norfolk stands as a naval powerhouse, serving as the home of the largest naval base in the world — Naval Station Norfolk. The city’s deep-rooted connection to the sea is evident in its impressive fleet of warships and pivotal role in supporting the U.S. Navy’s operations.

Beaufort | North Carolina

Beaufort is a riveting coastal town steeped in pirate lore and maritime charm. Renowned for its rich pirate history, the town’s waterfront is adorned with historic homes and centuries-old oak trees, evoking a sense of timeless beauty. Beaufort’s connection to infamous pirates like Blackbeard adds an air of mystery and adventure to its picturesque surroundings.

Wilmington | North Carolina

Wilmington is a captivating coastal city renowned for its scenic riverfront and historic downtown. The Cape Fear River — lined with quaint cafes and vibrant shops — serves as a focal point of the city’s allure, offering breathtaking views and a bustling waterfront atmosphere. The historic downtown area, exudes a timeless elegance, inviting exploration and discovery.

RELATED: Top 10 Cities in North Carolina To Visit

Myrtle Beach | South Carolina

Myrtle Beach is a premier coastal destination known for its pristine shoreline and world-class golf courses. The expansive stretch of golden sands and azure waters offers a perfect haven for beach enthusiasts, with endless opportunities for relaxation and recreation. The city’s golf courses, featuring lush fairways and challenging layouts, beckon golfers of all skill levels to enjoy a memorable round.

Charleston | South Carolina

Charleston exudes an irresistible blend of Southern charm and historic architecture, drawing visitors with its timeless elegance. Cobblestone streets and pastel antebellum houses reflect its rich heritage and a well-preserved historic district showcases a stunning array of architectural styles. From the iconic Rainbow Row to stately plantations, Charleston’s buildings stand as a testament to its storied past.

RELATED: Best Beaches Near Charleston South Carolina

Savannah | Georgia

Savannah is a city of enchanting beauty, distinguished by its moss-draped oaks and picturesque squares. The iconic image of Spanish moss hanging from ancient trees encapsulates the city’s timeless allure, creating a sense of romantic tranquility. Savannah’s historic squares, adorned with lush greenery and elegant fountains, offer a serene escape into the past, inviting leisurely strolls and contemplation.

St. Simons Island | Georgia

St. Simons Island is an enchanting blend of rich history and natural beauty. The island’s storied past is evident in its well-preserved landmarks, including a historic lighthouse and ruins of a 19th-century plantation. Along its pristine coastline, St. Simons Island boasts picturesque beaches, where visitors can bask in the sun, stroll along sandy shores, and enjoy a variety of activities.

Clearwater Florida
Clearwater Florida I photo credit: David Y Hyun / Shutterstock

Stops Along the Florida & Gulf Coasts

Fernandina Beach | Florida

Nestled on Amelia Island, Fernandina Beach exudes historic charm that beckons visitors to step back in time. The island’s rich history is showcased through its well-preserved Victorian architecture, quaint streets, and enchanting downtown area. The city’s maritime heritage is celebrated through its thriving waterfront and the presence of historic landmarks, inviting exploration and discovery.

St. Augustine | Florida

America’s oldest city, St. Augustine stands as a living testament to its rich Spanish colonial heritage, with captivating architecture serving as a window into the past. The city’s cobblestone streets, historic fortresses, and ornate buildings reflect the enduring influence of its Spanish founders, evoking a sense of Old World charm and romance.

Palm Beach | Florida

Palm Beach epitomizes luxury and sophistication, offering an opulent escape amidst pristine beaches and exclusive amenities. The island’s lavish estates, upscale boutiques, and renowned resorts exemplify its status as a premier destination for discerning travelers. Its immaculate beaches with sugary sands and turquoise waters provide a picturesque backdrop for relaxation and indulgence.

Key West | Florida

Key West exudes a laid-back atmosphere and tropical allure, owing to its idyllic location at the southernmost point of the continental US. The island’s lively energy and easygoing spirit are palpable as visitors wander through its charming streets, which are lined with pastel-hued conch houses and swaying palm trees.

Fort Myers | Florida

Fort Myers serves as a gateway to the fascinating wonders of Southwest Florida, offering a perfect launchpad for exploration and adventure. From the shell-strewn beaches of nearby Sanibel and Captiva Islands to the enchanting beauty of the Everglades, Fort Myers opens the door to a world of outdoor pursuits and ecological marvels.

Clearwater | Florida

Clearwater’s sugar-white sands and clear waters create an idyllic backdrop for sun-soaked relaxation and water activities, drawing beach enthusiasts from near and far. Clearwater’s iconic Marine Aquarium — home to rescued marine life, including dolphins and sea turtles — offers an immersive and educational experience for visitors of all ages.

Tarpon Springs | Florida

Tarpon Springs is a charming seaside city known for its rich Greek heritage and vibrant sponge docks. The sponge docks are a focal point, offering a glimpse into the city’s history as a major sponge diving hub. Visitors can explore the waterfront and witness the traditional art of sponge diving, as well as enjoy delicious Greek cuisine and lively cultural events.

Carrabelle | Florida

Carrabelle exudes the timeless charm of a quintessential fishing village, nestled along the picturesque Gulf Coast. The town’s rich maritime heritage is palpable as visitors stroll along its working waterfront where fishing boats bob in the harbor and seafood shacks offer the day’s fresh catch. Carrabelle’s unassuming beauty and relaxed pace capture the essence of a bygone era.

Apalachicola | Florida

This city’s historic downtown with well-preserved buildings and quaint streets exudes a nostalgic ambiance that harkens to a bygone era.

Apalachicola’s oyster industry — fueled by the nutrient-rich waters of Apalachicola Bay — has earned it a reputation as a seafood lover’s paradise where visitors can savor fresh oysters at local eateries and explore the town’s maritime heritage at the Apalachicola Maritime Museum.

Pensacola | Florida

Pensacola’s deep ties to the U.S. Navy are evident in the presence of Naval Air Station Pensacola — the cradle of naval aviation — and the National Naval Aviation Museum — showcasing a remarkable collection of aircraft and maritime artifacts. Pensacola’s pristine white sand beaches and emerald waters offer a picturesque backdrop for relaxation and water activities.

RELATED: 9 Family-Friendly Florida Cities to Visit

Mobile | Alabama

Mobile stands as a cultural and historic gem, captivating visitors with its rich heritage and vibrant arts scene. The city’s storied past is reflected in its well-preserved antebellum architecture, cobblestone streets, and historic districts, inviting exploration of its fascinating history.

Mobile’s thriving arts community, diverse museums, and annual cultural festivals celebrate its deep-rooted traditions and artistic vitality.

Galveston | Texas

Galveston is renowned for its stunning historic architecture, which reflects a rich tapestry of influences from Victorian to Greek Revival styles. From the elegant mansions of the East End Historic District to the iconic Bishop’s Palace, Galveston’s architectural treasures offer a captivating journey through time and stand as a testament to its storied past and resilience.

Corpus Christi | Texas

Corpus Christi is a sun-kissed gem with excellent beaches. The city’s pristine shoreline offers a perfect playground for beach lovers and water enthusiasts, with opportunities for swimming, fishing, and water sports. Additionally, visitors can tour the USS Lexington, a historic aircraft carrier turned museum that stands as a proud symbol of the city’s naval heritage.

Chattanooga Tennessee
Chattanooga Tennessee I photo credit: Kevin Ruck / Shutterstock

Cities Along Inland Rivers & Waterways

Houma | Louisiana

The city’s proximity to the sprawling wetlands of the Mississippi River Delta offers a unique opportunity for visitors to explore the rich ecosystem and diverse wildlife of the region. Houma’s Cajun heritage is celebrated through its lively music, distinctive cuisine, and colorful festivals, providing a fascinating immersion into the area’s cultural tapestry.

New Orleans | Louisiana

The Big Easy is a bustling cultural hub renowned for its rich Creole cuisine and soulful jazz. The city’s culinary scene, influenced by Creole and Cajun traditions, offers a tantalizing array of flavors — from spicy gumbo to savory jambalaya — that creates a paradise for food enthusiasts.

The soulful sounds of jazz permeate the city, with live performances filling the air in venues across the historic French Quarter. New Orleans’ spirited festivals, such as the iconic Jazz & Heritage Festival, celebrate the city’s musical legacy.

Florence | Alabama

Florence is a musical treasure trove, deeply rooted in a rich and storied music history. The city’s legendary FAME Recording Studios and Muscle Shoals Sound Studio have welcomed iconic musicians, shaping the sounds of renowned hits.

Also, visitors can explore the Alabama Music Hall of Fame, honoring the state’s musical heritage and influential artists. The city’s vibrant music scene continues to thrive with live performances, festivals, and events.

Decatur | Alabama

Decatur is a city celebrated for its energetic festivals and rich architectural heritage. The city’s annual events, such as the Alabama Jubilee Hot Air Balloon Classic and the Riverfest, showcase its lively spirit and community camaraderie. Decatur’s historic district, with its charming antebellum homes and well-preserved landmarks, offers a captivating glimpse into the city’s past.

Chattanooga | Tennessee

Chattanooga entrances visitors with its beautiful riverfront where the majestic Tennessee River flows through the heart of the city, offering a stunning backdrop for outdoor recreation and scenic strolls. Also along the river, visitors can enjoy river cruises, waterfront dining, and a variety of water sports, immersing themselves in the serene beauty of the river.

Knoxville | Tennessee

Knoxville is a gateway to the breathtaking beauty of the Great Smoky Mountains, offering a perfect blend of urban vibrancy and natural splendor. The city’s proximity to the national park provides outdoor enthusiasts access to scenic hiking trails, cascading waterfalls, and diverse wildlife.

Knoxville’s historic downtown features charming market squares and cultural venues that complement the area’s natural allure.

Nashville | Tennessee

Music City is the heart of country music — a city where the soulful sounds of country melodies permeate the vibrant streets and iconic venues.

Nashville’s historic Ryman Auditorium and the Grand Ole Opry showcase the genre’s timeless allure, while the Country Music Hall of Fame honors its legendary artists and heritage. The city’s honky-tonk bars along Broadway and diverse music scene offer a captivating immersion into the spirit of country music.

Paducah | Kentucky

Paducah is a city of contrasts where the Ohio and Tennessee Rivers converge. The city’s waterfront, with its picturesque river views and bustling riverfront district, offers a serene escape into the heart of this natural beauty. Renowned as a global destination for quilting enthusiasts, Paducah is home to the National Quilt Museum, showcasing a stunning collection of textile art.

Louisville | Kentucky

Louisville is renowned for its iconic contributions to American culture, including its status as the birthplace of bourbon and the home of the legendary Kentucky Derby. Historic distilleries and an urban bourbon trail offer an immersive journey into the art of bourbon-making. The Kentucky Derby, held at Churchill Downs, captivates visitors with its exhilarating horse races and festive atmosphere.

Pittsburgh | Pennsylvania

Pittsburgh is defined by the confluence of the Allegheny, Monongahela, and Ohio Rivers, creating a stunning natural backdrop and a spirited urban environment. The city’s iconic riverfront, with its picturesque bridges and waterfront parks, offers a captivating blend of natural beauty and metropolitan energy.

Charlevoix Michigan
Charlevoix Michigan I photo credit: Laurent Fady / Shutterstock

Places to Visit on the Great Lakes

Chicago | Illinois

The Windy City is well-known for its architectural wonders. The city’s skyline is adorned with towering skyscrapers, showcasing a blend of historic and modern architectural marvels, including the Willis Tower and the John Hancock Center. Navy Pier, a beloved waterfront destination, offers a myriad of attractions, from amusement park rides to cultural venues, against the stunning backdrop of Lake Michigan.

Door County | Wisconsin

Door County is a picturesque peninsula dotted with charming waterfront villages and bountiful orchards, creating a serene and idyllic escape. The region’s scenic coastline boasts a collection of quaint villages, each with its own unique character. Amidst the lush landscapes, visitors can explore the area’s thriving orchards, which are known for producing an abundance of cherries and other fruits.

Bayfield | Wisconsin

Bayfield serves as the gateway to the stunning Apostle Islands, offering unparalleled access to this breathtaking archipelago. The town’s proximity to Lake Superior and the Apostle Islands National Lakeshore provides a beautiful backdrop for outdoor enthusiasts and nature lovers.

Visitors can embark on scenic cruises, kayak through sea caves, and hike along pristine trails, immersing themselves in the natural splendor of the islands.

Sault Ste. Marie | Michigan

Michigan’s oldest city is a popular Upper Peninsula destination and home of the famous Soo Locks. These engineering marvels have transformed Great Lakes transportation, and visitors to “The Soo” can see the locks in action. Boat tours are available to see the locks up close or view them from a spacious viewing platform while learning about the maritime heritage in Sault Ste. Marie and the surrounding area.

Mackinac Island | Michigan

Time moves slower on this picturesque island in Lake Huron. Mackinac Island’s timeless charm makes it a popular summer tourist draw where visitors come to enjoy its famous fudge. In addition, the island is famous for the magnificent Grand Hotel and the historic Fort Mackinac.

Charlevoix | Michigan

This quaint Lake Michigan town, known as “Charlevoix the Beautiful,” offers the unparalleled small-town charm that Northern Michigan is famous for and feels like something out of a fairy tale. The more than two dozen mushroom houses of Charlevoix are 20th-century wonders from the mind of Earl Young and a joy for those who love unique architecture.

Traverse City | Michigan

The Cherry Capital of the World is a Northwest Michigan hotspot with incredible bay views, quaint vineyards, a National Cherry Festival, and much more. Visitors can enjoy Traverse City’s bustling downtown, explore the wonders of the Old Mission Peninsula, or spend time soaking up rays by Lake Michigan and Grand Traverse Bay.

Erie | Pennsylvania

Nestled on the Lake Erie shore, Erie is steeped in maritime history. The city’s rich nautical heritage is showcased through attractions such as the Erie Maritime Museum and the historic Bicentennial Tower, offering a glimpse into the region’s seafaring past. Visitors can explore Presque Isle State Park’s sandy beaches and lighthouses, further immersing themselves in the area’s maritime legacy.

Buffalo | New York

Buffalo serves as a dynamic gateway to the awe-inspiring wonder of Niagara Falls, one of the world’s most iconic natural attractions. Visitors to Buffalo can embark on a short and scenic journey to witness the majestic power and beauty of the falls, immersing themselves in the breathtaking vistas and thundering cascades.

RELATED: 4 Great Lakes Ranked in Top 10 Most Picturesque Landscapes in America

Kingston Ontario
Kingston Ontario I photo credit: SF photo / Shutterstock

Canadian Heritage Canal & Waterway Cities

Georgian Bay | Ontario

Georgian Bay is a thrilling expanse of natural beauty, offering a stunning tapestry of landscapes within the Great Lakes region. The bay’s rugged shoreline, adorned with windswept pines and granite outcrops, creates a picturesque backdrop for outdoor adventures and scenic exploration.

Visitors can discover its countless islands, pristine beaches, and clear waters, immersing themselves in the serenity of this unspoiled wilderness.

Stratford | Ontario

Stratford is a charming city renowned for its world-class Shakespearean festival, a celebration of the timeless works of The Bard. The city’s quaint streets — adorned with historic architecture and lush gardens — provide a picturesque backdrop for this extravaganza.

Stratford’s seamless blend of theatrical excellence and small-town allure creates an exciting experience that celebrates its legacy as a premier destination for Shakespearean theater.

Orillia | Ontario

Orillia is a vibrant cultural hub celebrated for its rich artistic heritage and dynamic community spirit. The city’s picturesque waterfront, nestled along the shores of Lake Couchiching and Lake Simcoe, provides a scenic backdrop for cultural events and festivals.

Orillia’s thriving arts scene — with its galleries, theaters, and live music venues — offers a diverse array of creative expression, captivating residents and visitors alike.

Peterborough | Ontario

Peterborough is celebrated for its engineering marvel — the world’s highest hydraulic lift lock, a testament to human ingenuity and industrial heritage. The Peterborough Lift Lock, a National Historic Site, showcases the city’s innovative spirit and technological prowess.

Beyond this impressive feat of engineering, Peterborough offers a picturesque blend of natural beauty, with its tranquil waterways, lush parks, and active arts scene.

Kingston | Ontario

Kingston boasts a remarkable array of well-preserved architecture that reflects its rich heritage. The city’s limestone buildings, elegant cathedrals, and stately homes stand as a testament to its colonial past and regal influence, earning it the moniker Limestone City. The city’s waterfront, lined with historic fortifications and scenic parks, further enhances its timeless allure.

Gananoque | Ontario

Gananoque is a picturesque gateway to the breathtaking Thousand Islands, a region renowned for its enchanting archipelago of emerald isles and tranquil waterways. The town’s waterfront, nestled along the St. Lawrence River, offers a serene escape into the heart of this natural paradise. Visitors can embark on scenic cruises, kayak through scenic channels, and explore the region’s rich biodiversity.

Ottawa | Ontario

Canada’s capital is a city of historic significance and natural beauty with a rich tapestry of cultural and political heritage. The city’s iconic Parliament Hill, home to the country’s legislative institutions, stands as a symbol of Canadian democracy and governance. The picturesque Rideau Canal winds through the heart of the city, offering scenic views and recreational opportunities.

Montreal | Quebec

Montreal’s rich heritage, influenced by French and North American traditions, is showcased through its historic architecture, world-class museums, and eclectic neighborhoods. The dynamic arts scene — from street art to renowned festivals like the Montreal International Jazz Festival — infuses the city with creativity and energy. Its diverse culinary landscape adds to the city’s allure as well.

Quebec City | Quebec

Quebec City gives off a captivating European feel, transporting visitors to a bygone era with its cobblestone streets, historic architecture, and fortified city walls.

The city’s Old Town features charming squares, elegant bistros, and 17th-century buildings, evoking a sense of Old World charm and romance. The iconic Château Frontenac, a grand hotel with fairytale-like turrets, adds to the city’s enchanting ambiance.

Explore Wonderful Places Along America’s Great Loop

From historic towns rich in American heritage to bustling cities and quaint villages, each stop on America’s Great Loop offers a unique glimpse into the heart and soul of the regions it represents.

Whether you’re drawn to the allure of coastal beaches, the tranquility of the Great Lakes, the charm of Canadian canals, or the majestic flow of America’s inland rivers, the Great Loop promises an unforgettable journey through some of the most picturesque and welcoming towns and cities in North America.