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Captain

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Browse Michigan Boat Rentals

4.9

(4,612 Reviews)

Page 3 of 15 • 343 listings

Sailing in Chicago · 10 guests

37' Luxury Sailboat with Captain in Chicago, Illinois

5.0

Superowner

$400hour

Events in Chicago · 13 guests

Maxum Yacht 44' in Chicago

5.0

Superowner

Best of 2023

$268-$300hour

Powerboats in Chicago · 12 guests

40ft Yacht w/ Huge open seating area!

5.0

Superowner

Best of 2023

$210-$240hour

Events in Chicago · 13 guests

Book now Searay Sundancer Cruiser 36' LOA with Fuel

5.0

$250hour

Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0

$150hour

Events in Chicago · 12 guests

Multi Level LUXURY Yacht Rental in Chicago - Water toys are included! (M)

4.9

Superowner

Best of 2023

$250hour

Powerboats in Pewaukee · 8 guests

21ft SeaRay SunDeck for Pewaukee Lake. Other lakes by request.

5.0

Snoozed - Active 01 Jun 2024

Events in Chicago · 12 guests

52’ Beautiful Sunseeker Portofino Pristine Condition Weekday Special Rates!!

5.0

$250hour

Events in Chicago · 12 guests

Sea Ray 38 Sundancer - Motor Yacht for Charter in Chicago, Illinois

5.0

Superowner

Best of 2023

$400hour

Events in Chicago · 13 guests

Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois

5.0

Best of 2023

$400hour

Events in Chicago · 12 guests

Enjoy Chicago! 46' Beautiful Sea Ray Yacht - Perfect for Parties

5.0

Best of 2023

$400hour

Instant Book

Events in Chicago · 12 guests

42FT Regal Commodore Express Cruiser

5.0

Superowner

Best of 2023

$245-$275hour

Events in Chicago · 12 guests

Gorgeous Sea Ray Sundancer 40 in Chicago with Stunning Interior

5.0

Superowner

Best of 2023

$245-$275hour

Events in Chicago · 11 guests

42' Luxury Mediterranean Yacht Charter w/ Captain in Chicago

5.0

Superowner

$400hour

Events in Chicago · 12 guests

44' Luxury Sundancer Yacht Rental! Includes Floating Island!

4.8

Superowner

$399hour

Powerboats in Chicago · 10 guests

Downtown Chicago, Party on the Lake!

4.9

$270hour

Events in Chicago · 12 guests

46' Spacious Portofino Party Yacht in Chicago For Every Occasion

5.0

$250hour

Events in Chicago · 13 guests

44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois

4.9

Superowner

$399hour

Events in Chicago · 12 guests

50 ft Double Decker Yacht | Sea Ray Bridge Express

5.0

$100person

Events in Chicago · 12 guests

62' $2M Italian Luxury Yacht with Party up to 12

5.0

Superowner

Best of 2023

$800hour

Instant Book

Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

4.8

$115-$120hour

Events in Chicago · 12 guests

55' Sea Ray Luxury Yacht in Chicago

5.0

$325hour

Events in Chicago · 12 guests

Sea Ray 45' Chicago Playpen, River, Winery, Lilly Pad

5.0

Superowner

Best of 2023

$375-$450hour

Events in Chicago · 12 guests

Sea Ray Express 390 Luxury Charter in Chicago, Illinois

5.0

$300hour

Top Destinations Nearby

Michigan Reviews

Anthony
May, 2024
Maxum Yacht 44' in Chicago
Chris and Captain Kelly were great all around from initial booking, communication leading up to the trip, and of course the trip itself. Highly recommended for any trips in the Chicago area!
Jenna
May, 2024
50 ft Double Decker Yacht | Sea Ray Bridge Express
Great boat with good communication. Didn't love the captain but that was separate.
Kaitlin
March, 2024
44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois
Highly recommend! Jimmy was very nice and he even rescheduled us to the following day due to bad weather. He made my birthday very special and I would definitely book with him again in the future!
MC
Megan
June, 2023
37' Luxury Sailboat with Captain in Chicago, Illinois
Greg was an amazing captain - he sent a very helpful document that outlined all the details about the boat ahead of time, he was on time and willing to be flexible in wherever we wanted to go. We had an amazing time and I would definitely hire him again!
Sara
July, 2022
37' Luxury Sailboat with Captain in Chicago, Illinois
My fiancé and I planned a engagement photoshoot, however, due to weather conditions not cooperating, Greg was so flexible at rescheduling with us. He made us feel very comfortable and gave tips on how to take the most beautiful photoshoot out of the beautiful scenery of the city. Would totally recommend him! By the way, the boat was spotless, so clean and so so beautiful😍
GM
Gerald
September, 2021
37' Luxury Sailboat with Captain in Chicago, Illinois
We had an awesome experience on Dragonfly. Greg arrived on time to pick us up and we immediately headed out onto the lake. Greg listened to what we needed as a new sailing couple and really delivered. Greg is extremely knowledgeable and a good teacher. We had a lot of fun, highly recommend Greg and Cait. We will be back aboard the next time we're in Chicago.