Chicago Takes the Lead as Top Boating Destination in the U.S. with Stunning Lake Michigan Views and Diverse Water Activities for 2025

Published on November 24, 2025

Chicago has risen to the top of the U.S. boating destinations for 2025, taking the lead with its breathtaking views of Lake Michigan and an impressive variety of water activities. Known for its iconic skyline and vibrant waterfront, the city offers boaters an unmatched experience with everything from architectural cruises on the Chicago River to sailing at Monroe Harbor and kayaking under the historic bridges. Chicago’s diverse water experiences, paired with its stunning lakefront, make it the perfect destination for boating enthusiasts. This recognition reflects a broader trend of inland cities like Chicago emerging as key players in the U.S. boating scene, proving that top-tier boating is no longer confined to the coast.

The analysis, which used Google Maps data to assess a variety of factors like scenic beauty, water accessibility, available activities, and overall boating experience, paints a clear picture of why Chicago has risen to the top. The city’s distinctive blend of natural beauty and urban charm—highlighted by its iconic skyline, historic architecture, and thriving waterfront—provides a backdrop for a diverse range of water activities. From architectural boat tours along the Chicago River to peaceful sailing at Monroe Harbor and adventurous kayaking beneath historic bridges, Chicago offers an extensive variety of experiences for boating enthusiasts of all types.

Perhaps one of the most surprising takeaways from the study is the emergence of inland cities as major players in the boating world. Traditionally, U.S. boating culture has been concentrated in coastal areas, but the BoatBooker study underscores how inland cities are capitalizing on their lakes and rivers. For example, Jackson, Wyoming, ranks #18 thanks to its serene glacial lakes surrounded by stunning mountain vistas, offering a peaceful escape for nature lovers. Madison, Wisconsin, at #15, shines with its expansive chain of lakes, perfect for paddleboarding and leisurely pontoon rides. Even Oklahoma City (#18) is gaining traction, with its riverfront developments and growing interest in kayaking.

While these inland cities are gaining ground, Chicago’s position at the top highlights how the city has leveraged its urban landscape to offer an unrivaled boating experience. The Chicago lakefront is not only an important recreational hub but also a focal point for cultural and architectural exploration by boat. The city’s boating scene is as diverse as its neighborhoods, offering everything from casual kayaking to upscale sailing excursions, all within view of Chicago’s stunning skyline.

Following Chicago, other cities with prominent boating cultures include Honolulu, Hawaii, which takes second place, thanks to its inviting tropical waters and year-round boating opportunities. Austin, Texas, follows closely at number three, with Lady Bird Lake serving as the centerpiece for recreational boating in the city. Seattle, Washington, rounds out the top four, with its picturesque Puget Sound providing the ideal environment for both sailing and motor boating.

The Gulf Coast is also represented, with Orange Beach, Alabama (#5), and Virginia Beach, Virginia (#6), offering expansive coastal waters perfect for a laid-back boating experience. The historic city of Newport, Rhode Island, at #7, attracts boaters with its charming, colonial-era ports and beautiful coastal routes. In contrast, New York City, ranking #9, provides a more urban boating experience, with iconic trips around the Statue of Liberty and along the Hudson River offering boaters unrivaled views of the city’s skyline.

Interestingly, the rankings also show a notable shift in the popularity of inland destinations. Madison’s chain of lakes has made it a top choice for boaters seeking tranquil waters, while Oklahoma City’s revitalized riverfront has transformed the city into an up-and-coming boating hub. These inland cities, with their beautiful lakes and rivers, offer unique experiences that rival those of coastal areas. From Jackson’s stunning mountain views to the modern riverfronts in Oklahoma City, the report underscores that America’s boating culture is diversifying and reaching new areas.

Here’s a snapshot of the top 20 U.S. boating destinations according to BoatBooker’s 2025 analysis:

1. Chicago, IL
2. Honolulu, HI
3. Austin, TX
4. Seattle, WA
5. Orange Beach, AL
6. Virginia Beach, VA
7. Newport, RI
8. Slidell, LA
9. New York, NY
10. Nashville, TN
11. Kailua-Kona, HI
12. Biloxi, MS
13. Boston, MA
14. Charleston, SC
15. Madison, WI
16. Cape May, NJ
17. Oklahoma City, OK
18. Portland, ME
19. Jackson, WY

The findings reflect a broader shift in American boating culture, with new regions emerging as significant players in the boating scene. Whether it’s Chicago’s urban waterfront, Madison’s lakes, or Jackson’s mountainous waters, these destinations are setting the stage for the next wave of boating tourism in the U.S. The diversity of boating experiences, from cityscapes to serene natural escapes, showcases the expanding and evolving nature of boating across the country. With inland cities rising in prominence, the future of American boating is more diverse than ever.

Chicago has claimed the top spot as the U.S.’s leading boating destination for 2025, offering stunning views of Lake Michigan and a variety of water activities, from architectural cruises to sailing and kayaking. The city’s vibrant waterfront and diverse boating experiences make it the ultimate destination for water enthusiasts.