Two Brothers Sailing Adventures
Book now
← All events

Bachelorette Boat Charter Chicago

Plan a private Chicago bachelorette boat day with Lake Michigan views, BYOB, and a social sail for your group.

Check Availability

Private charters from Montrose Harbor. BYOB-friendly. Restroom onboard.

Three women celebrating on a sailboat deck at sunset with pink balloons and calm water behind them

A Chicago Bachelorette Party on the Water

A private sailboat charter gives your group a fun, scenic alternative to the usual bachelorette party plan. Spend time on Lake Michigan with skyline views, drinks, photos, and a private setting that keeps the day focused on your group.

This is a strong fit for bachelorette groups who want a memorable Chicago summer experience without booking a crowded party boat or oversized yacht.

Why it's a fit

  • Your group, your music, your timeline—no competing with another party on board.

  • Daylight and skyline do most of the work for group shots and candids.

  • Stock the cooler with what you actually want to drink.

  • Feels intentional compared to a crowded public booze cruise.

  • Go big and social on the lake, or dial it back with a softer sunset sail.

Recommended Charter Options

What to Expect

  1. Meet at Montrose Harbor

    Arrive at the harbor and meet your captain near the boarding location.

  2. Board with your group and get settled

    Step aboard, get settled, and store your drinks, snacks, towels, and belongings.

  3. Store drinks, snacks, towels, and belongings

    Stage coolers, towels, and personal gear so the deck stays clear and comfortable.

  4. Review a short safety briefing

    Your captain will review basic safety information before leaving the dock.

  5. Sail Lake Michigan or cruise toward the Playpen depending on your charter

    Head toward the Playpen or stay flexible based on charter length, wind, and captain discretion.

  6. Return to the same dock

    Your charter ends back at the original boarding location.

Planning Tips

  • Bring towels if your charter may include swimming.

  • Keep food simple and easy to serve.

  • Bring layers even in summer.

  • Avoid loose decorations that can blow away.

  • Choose Playpen for a livelier day or sunset for a more elevated feel.

What's Included

  • Private use of the sailboat

  • Experienced captain / captain arrangement

  • Safety briefing before departure

  • Required safety gear onboard

  • Restroom onboard

  • Cooler/storage space

  • Boarding instructions before your trip

  • Weather monitoring before departure

Good to Know

This is a private sailboat charter, not a large party yacht. Playpen access, swimming, route, and timing depend on charter length, weather, lake traffic, and captain discretion.

FAQ

Is this good for a bachelorette party?
Yes. A private sailboat charter is a strong option for Chicago bachelorette groups looking for a more memorable lake day.
Can we bring drinks?
Yes. BYOB is allowed. Please drink responsibly and follow captain instructions.
Can we go to the Playpen?
Playpen access depends on charter length, weather, lake traffic, and captain discretion.
Can we bring decorations?
Simple decorations may be possible, but avoid anything loose, messy, or difficult to clean up.
Is there a bathroom onboard?
Yes. There is a restroom onboard.

Plan a Bachelorette Boat Day in Chicago

Book a private Lake Michigan charter with skyline views, BYOB, and a social summer feel.

Check Availability