Best Architecture Sailing Trips: Our Top 2

1.Manhattan Architecture Yacht Cruise

★★★★★★★★★★5.0 · 1,395 reviews · 2 hours 45 minutes (approx.) · from $113Our pick

Spend about 2 hours 45 minutes circling Manhattan aboard a 1920s-style yacht. An American Institute of Architects guide, including hosts such as John, Jenny, Ginny, or Doug on various departures, explains the city’s buildings, bridges, neighborhoods, and waterfront. Choose indoor or open-air views, with one drink included.

“We learned so much about history and architecture of NYC! Very enjoyable. We were comfortable inside boat even though wind chill was 10 degrees! Let them know when you check in if someone in your party needs extra help boarding. They were wonderful with my MIL who was in a wheelchair. She is able to walk up/down stairs with assistance so we had no problems.”

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2.Chicago River Architecture Tour Aboard a Historic Yacht

★★★★★★★★★★5.0 · 45 reviews · from $49Best value

Spend about 90 minutes on a historic wooden yacht with a captain, crew, and architecture guide. You’ll pass the Wrigley Building, Riverwalk, Michigan Avenue Bridge, and nearly 50 skyscrapers. Soda, coffee, and snacks are included, with alcoholic drinks available to buy.

“Excellent tour / trip our docent was incredibly articulate and informative - NEVER skipped a beat on the tour. Would highly recommend!”

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