About this tour
When Lily from our team booked a private sailing charter on Lake Michigan, we found ourselves on a sleek sailboat with just our group and a US Coast Guard licensed captain steering from Navy Pier. Two hours gliding past Chicago's skyline—skyscrapers rising from the water, the city sprawling behind us—felt less like a sightseeing tour and more like having a mate's boat for the afternoon. Up to six people, three daily departures, and the freedom to pick your own music and route. The captain's happy to chat about what you're seeing, but the vibe is relaxation rather than rapid-fire facts.
Highlights
- Private boat means no tourist crowds or scheduled commentary
- Chicago's downtown skyline reflected across the water, genuinely striking
- Bluetooth speakers let you set the soundtrack for your sail
- Captain knowledgeable but low-key—talks only if you ask
- Flexible routing; you're not locked into a fixed path
- Suits all fitness levels; mostly sitting and soaking it in
- Three departure slots daily means easier scheduling
- US Coast Guard licensed captain steers a tight ship
What to expect
You'll arrive at Navy Pier and meet your captain before boarding. The first chunk is getting comfortable on deck, finding your spot, and letting the boat slip into the rhythm of the lake. The skyline hits differently from the water—closer, taller, more human somehow. Your captain will handle the actual sailing while you relax; if you want to know about a building or the history of the area, ask. The wind and waves do their thing, so expect some gentle rocking, but nothing dramatic on a Lake Michigan day sail. Two hours moves quickly—feels like you've barely settled in before it's time to head back. The whole experience is low-key; there's no schedule of activities, no forced group moments, just your crew and the water.
Good to know
Dead straightforward if you want breathing room from crowds or guided tours. Brilliant for couples, small groups, or anyone who likes to sit quietly with good views. The captain's a pro and knows the lake well. Customisation is the real win—your playlist, your route, your pace.
It's pricey for what is essentially a two-hour sit-down. Seasickness can hit on the water; stay topside if it does (below deck is off-limits for this reason, and there's a cleaning fee if you're sick down there). No swimming on a two-hour charter. No glass bottles, no smoking, no pets. Food and drinks aren't included, so bring your own (non-glass containers, plastic cups). Parking isn't included; public transit nearby is your best bet. Late arrivals will shorten your sail with no refund. The captain can cancel if weather turns or the boat has issues. Gratuities aren't included in the price, so factor that in.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BugBitten summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.