Table of Contents
- How Shoreline Sightseeing Started in Chicago
- Shoreline Sightseeing Timeline
- From One Speedboat to Larger Tour Boats
- A Family-Owned Chicago Boat Tour Company
- The Growth of Chicago Water Taxi Service
- Bringing Architecture Tours to the Chicago River
- A New Generation of Shoreline Sightseeing
- Shoreline Sightseeing Today
- Experience Shoreline’s History from the Water
- FAQs About Shoreline Sightseeing History
Shoreline Sightseeing has been part of Chicago’s waterfront since 1939, when the company began with a single speedboat and a simple idea: show visitors the city from the water.
What started as a small family-run boat business has grown into one of Chicago’s long-running sightseeing companies, with tours on Lake Michigan, cruises along the Chicago River, and water taxi service connecting some of the city’s most popular waterfront stops.
The history of Shoreline Sightseeing is also the story of a family business that kept evolving with Chicago. From early lakefront rides near the old Edgewater Beach Hotel, Shedd Aquarium, and Grant Park to today’s architecture tours, skyline lake tours, and water taxis, Shoreline has spent generations helping locals and visitors see the city from a different perspective.
How Shoreline Sightseeing Started in Chicago
Shoreline Sightseeing began in 1939, during the Great Depression. Jim Martin started the company with sightseeing service near the old Edgewater Beach Hotel, Shedd Aquarium, and Grant Park.
In the beginning, the business operated under the name Shoreline Marine Company before later becoming Shoreline Sightseeing. The early operation was simple: one speedboat, Chicago’s waterfront, and visitors who wanted to experience the city from the water.
At night, passengers could ride for 25 cents each. During the day, the speedboat docked near Grant Park and Shedd Aquarium. As the company grew, it became clear that Grant Park brought more foot traffic and more passengers, helping Shoreline focus its early sightseeing service around Chicago’s lakefront.
Those first years set the tone for everything that followed. Shoreline’s identity was built around the city’s shoreline, its skyline, and the idea that Chicago looks different when seen from the water.
Shoreline Sightseeing Timeline
| Year | What Happened |
|---|---|
| 1939 | Shoreline begins sightseeing service in Chicago with early operations near the old Edgewater Beach Hotel, Shedd Aquarium, and Grant Park |
| 1949 | Jim Martin purchases Blue Dog, Shoreline’s first large touring vessel |
| Around 1950 | George Martin joins the company and helps formalize the business |
| 1960 | Marlyn is built as a 300-passenger vessel and becomes one of the largest passenger vessels on Lake Michigan |
| 1961 | Charles “Mr. C” Collopy joins Shoreline and becomes part of the company’s next chapter |
| 1996 | Shoreline adds Chicago Water Taxi service to help guests move between major downtown and lakefront landmarks |
| 1999 | Shoreline launches its Architecture Tour from Navy Pier |
| 2002 | Chip and Matt Collopy become owners of Shoreline Sightseeing |
| 2016 | Shoreline adds the Michigan Avenue Dock to support more Architecture River Tours |
| Today | Shoreline continues operating Chicago river tours, Lake Michigan tours, and Chicago Water Taxi service |
From One Speedboat to Larger Tour Boats
As Shoreline grew, so did the need for larger vessels. In 1949, Jim Martin purchased Blue Dog, which became Shoreline’s first large touring vessel and marked an important step beyond the original speedboat operation.
Pictured: Blue Dog running as a water taxi service on Lake Michigan in June 2023.
Around 1950, George Martin joined Shoreline. A lawyer by trade, George helped manage and formalize the business, playing an important role in its development over the next 25 years.
The company’s fleet continued to expand. George later purchased the Shoreline, a cruiser that could carry up to 100 passengers. Although that vessel no longer operates, it helped Shoreline offer longer cruises from Grant Park and serve more guests on Chicago’s lakefront.
In 1960, Shoreline added the Marlyn, a 300-passenger vessel whose name came from a combination of “Martin” and “Lynch.” While many people assume the name refers to the fish, it actually comes from the family and business history behind the vessel.
For nearly 25 years, the Marlyn was one of the largest passenger vessels on Lake Michigan. It was also the first Shoreline tour boat to feature the red, white, and blue colors that would become associated with the fleet.
A Family-Owned Chicago Boat Tour Company
Family ownership has been central to Shoreline Sightseeing from the beginning. The company’s story began with the Martin family and continued through the Collopy family, helping give Shoreline a personal connection to Chicago’s waterfront across generations.
Charles Collopy, known to many as “Mr. C,” joined Shoreline in 1961. At that time, George Martin was helping lead the company, and Mr. C became increasingly involved in Shoreline’s future.
Mr. C had spent years in the corporate world before taking on a larger role with the family business. When George was ready for retirement, he and Mr. C discussed the future of Shoreline. One of the most memorable pieces of advice passed down was simple: “Don’t buy anymore boats and don’t raise the prices.”
Like many family businesses, Shoreline’s growth did not always follow that advice exactly. About five years after Mr. C took over, the need for a bigger boat became clear. Shoreline II was added to the fleet, carrying up to 350 passengers and helping the company meet growing demand.
That mix of family advice, practical decisions, and willingness to grow has helped define Shoreline’s history. The company has remained rooted in family ownership while continuing to adapt to the needs of Chicago visitors.
The Growth of Chicago Water Taxi Service
In 1996, Shoreline added Chicago Water Taxi service to help guests travel between some of the city’s most visited landmarks. The water taxis gave visitors and locals another way to experience Chicago from the water while moving between downtown and lakefront destinations.
The water taxi fleet also brought some personality to the river and lakefront. Shoreline named several vessels with playful, fast-moving names, including Shake A Leg, Gotta Go Now, ASAP, and Lickety Split.
Those names reflect the practical purpose of the service: helping people get where they are going while enjoying the views along the way.
Today, the Chicago Water Taxi continues to connect major downtown and lakefront stops, including areas near Michigan Avenue, Navy Pier, Willis Tower, Museum Campus, Buckingham Fountain, and Union Station.
Bringing Architecture Tours to the Chicago River
In 1999, Shoreline launched its Architecture Tour from Navy Pier, adding a new chapter to the company’s sightseeing history. Chicago’s architecture is one of the city’s defining features, and the river offers one of the best ways to see how that architecture fits together.
The Architecture Tour helped Shoreline expand from lakefront sightseeing into a deeper storytelling experience along the Chicago River. Guests could see the city’s buildings up close, learn about the people and ideas behind them, and experience downtown from below the bridges.
In 2016, Shoreline added the Michigan Avenue Dock to support more Architecture River Tours. That dock put the company in the heart of downtown, making it easier for guests to board near the Magnificent Mile, the Chicago Riverwalk, and some of the city’s most recognizable riverfront views.
Today, Shoreline’s Architecture River Tour remains one of the clearest connections between the company’s history and its present-day tour experience.
A New Generation of Shoreline Sightseeing
In 2002, a new generation took over when Mr. C’s sons, Chip and Matt Collopy, became owners of Shoreline Sightseeing. Both had started with the company as deckhands in 1979, giving them hands-on experience with the boats, the crews, and the rhythm of Chicago’s sightseeing season.
Under the next generation, Shoreline continued to grow its fleet, docks, tours, and water taxi service. The company expanded its presence along the Chicago River and Lake Michigan while staying connected to its family-owned roots.
In 2019, Matt Collopy retired, and Chip Collopy became the sole owner of Shoreline Sightseeing.
Shoreline Sightseeing Today
Today, Shoreline Sightseeing continues to show Chicago from the water through river tours, lake tours, history-focused cruises, and water taxi service. The company now operates multiple docks, with some serving both tour departures and water taxi routes.
Guests can experience Chicago through several different Shoreline options:
- The Architecture River Tour for guided views of downtown buildings, bridges, and Chicago River landmarks
- The Skyline Lake Tour for Lake Michigan views and wide skyline perspectives
- The Chicago History Tour for a route that connects the Chicago River, the Chicago Harbor Lock, Lake Michigan, and the city’s history from the water
- The Chicago Water Taxi for convenient transportation between major downtown and lakefront stops
What has changed is the size of the fleet, the number of docks, and the range of experiences. What has stayed the same is the original idea: Chicago is best understood when you see it from the water.
Experience Shoreline’s History from the Water
Shoreline’s history is not just something to read about. It is something guests can experience from the water today.
Every tour connects back to the company’s roots on Chicago’s shoreline, whether you are cruising along Lake Michigan, learning about architecture on the Chicago River, passing through the Chicago Harbor Lock on the Chicago History Tour, or using the water taxi to move between waterfront landmarks.
For generations, Shoreline has helped visitors and locals see Chicago’s skyline, architecture, lakefront, and river from a different point of view. That same perspective is still at the center of the experience today.
Ready to see Chicago from the water? Compare Shoreline Sightseeing tours and choose the river, lake, or history-focused experience that fits your visit.
FAQs About Shoreline Sightseeing History
Shoreline Sightseeing was founded in 1939. The company began as a small Chicago sightseeing boat operation with early service near the old Edgewater Beach Hotel, Shedd Aquarium, and Grant Park.
Shoreline Sightseeing has been in business since 1939, making it one of Chicago’s long-running boat tour companies.
Yes. Shoreline Sightseeing has family-owned roots dating back to its early history with the Martin family and later generations of the Collopy family.
Shoreline Sightseeing was started by Jim Martin in 1939. The company later grew with help from George Martin, Charles “Mr. C” Collopy, and later generations of the Collopy family.
Shoreline Sightseeing began along Chicago’s lakefront, with early operations near the old Edgewater Beach Hotel, Shedd Aquarium, and Grant Park.
Blue Dog became Shoreline’s first large touring vessel when Jim Martin purchased it in 1949.
Shoreline added Chicago Water Taxi service in 1996 to help guests travel between major downtown and lakefront destinations.
Shoreline launched its Architecture Tour in 1999, originally departing from Navy Pier. The Michigan Avenue Dock was later added in 2016 to support more Architecture River Tours.
Today, Shoreline Sightseeing offers Chicago architecture river tours, Lake Michigan skyline tours, Chicago history tours, and Chicago Water Taxi service.
Shoreline Sightseeing tours depart from multiple Chicago waterfront docks, including locations near Michigan Avenue and Navy Pier. Some docks also serve Chicago Water Taxi routes.
