Luxury Water Activities Near Highwood, Illinois — Private Charters & Cruises

Bella is presented as a sought-after Italian yacht available for private charters of three to six hours. The operator highlights a roomy sundeck and a swim platform that ease access to the water, plus two refrigerators and an ice chest to keep food and drinks cold. A state-of-the-art Sonos sound system provides Bluetooth audio, and the vessel’s layout accommodates social groups—bachelorette and bachelor parties, birthdays, corporate outings, and intimate celebrations were cited as typical uses.

The listing is explicit about inclusions and exclusions: a full kitchen and two bathrooms are aboard, but the captain’s fee is paid separately and gratuity is not included (the operator notes 20% as standard). The operator states the yacht meets U.S. Coast Guard safety requirements and carries required permits and insurance. Guests are advised to bring towels, sunscreen, and provisions; alcohol is permitted, and the host will provide a vetted list of captains should you need one.

The 62’ Azimut dubbed “Checkmate” is marketed as one of the more glamorous Italian yachts available for private charter. Its 4–6 hour windows make it well suited to longer daytime or early-evening cruises along the shoreline. The operator emphasizes social comfort: a generous sundeck, swim platform, two refrigerators, and a Sonos Bluetooth system keep guests at ease and entertained while cruising.

Like other motor yachts in this collection, Checkmate includes a full kitchen and two bathrooms, but the captain’s fee and gratuity are not part of the listed price. The vessel is described as compliant with USCG safety requirements and carries required permits and insurance. Guests are encouraged to bring towels, sunscreen, food, and drink; the operator allows alcohol and will provide a list of pre-approved captains for hire in accordance with USCG regulations.

This four‑hour Sail & Swim Playpen Charter departs from Navy Pier Marina and operates aboard a meticulously maintained 37' sailing yacht. The experience is structured for intimate groups—options accommodate groups up to seven or up to twelve— and is positioned as an all‑inclusive outing with complimentary snacks and beverages, a fridge with ice, and a USCG‑certified captain trained in First Aid and CPR. On route, the charter anchors at the Playpen or another suitable anchorage to allow guests to swim, float, and use provided pool floaties, noodles, and towels.

Operator notes emphasize safety and flexibility: the captain is certified, weather cancellations due to lightning or high wind are eligible for full refund, and all guests must sign a participant waiver. The listing also mentions available add-ons—alcohol for purchase, drink packages, and catering—for those who want a more curated onboard menu. The combination of sailing, a swim stop, and downtown skyline views makes this a distinct, activity-focused option for groups from Highwood seeking Lake Michigan adventure.

Rose Marie is a 47' Carver described as a modern, sporty hardtop that blends fast cruising with comfortable accommodation. The operator notes its capability to cruise efficiently at 24 knots with higher top-end performance when desired, making it a good fit for guests who want to cover more water during a limited charter window. Typical durations span three to six hours on weekdays and slightly longer on weekends.

Included amenities mirror the operator’s fleet standard: full kitchen, two bathrooms, a powerful Sonos sound system, and refrigeration. As with the other motor yachts, the captain’s fee must be paid separately and gratuity is not included. The operator confirms compliance with USCG safety requirements and outlines basic guest preparations—towels, sunscreen, and food and drinks are recommended—to maximize comfort and enjoyment during the cruise.

Pier Pressure is presented as another 47' Carver in the operator’s roster, described as modern and sporty with an emphasis on comfort and social onboard spaces. The vessel is offered for three to six hour weekday charters and four to six hour weekend charters, making it versatile for either daytime cruises or evening plans. The operator highlights the same suite of features as their other vessels: full kitchen, two bathrooms, refrigeration, and a Sonos audio system.

Operational notes reiterate that the captain’s fee is separate, gratuity is not included, and the boat meets all USCG safety and permit requirements. Guests are advised to bring essentials—towels, sunscreen, and personal food or beverages—and are permitted to bring alcohol. The operator will supply a vetted list of captains if the charterer does not provide one, consistent with USCG regulations.

The Navy Pier Fireworks Cruise is an all‑inclusive three‑hour private sailing charter aboard S/V Dragonfly, a luxury 37' sailing yacht. The operator frames it as a sunset outing that proceeds to a favorable position on the lake for an unobstructed viewing of the Navy Pier fireworks display. The charter includes complimentary ice, snacks, and drinks, with alcohol available for purchase or BYO options and a USCG-certified captain provided for the voyage.

Practical notes emphasize safety and flexibility: weather cancellations for lightning or high wind are enacted one hour prior to departure with a full refund, and the boat’s capacity is listed for small groups—up to seven or ten depending on configuration. The listing also notes that on warm nights the crew may anchor to allow guests to swim. Meeting point details are provided as Navy Pier Marina, and specific check‑in instructions follow booking confirmation.