Sailing yacht charter
Vagabond — Beneteau Oceanis 393
Meet Vagabond, a private Beneteau sailing yacht used for Chicago skyline cruises, sunset sails, Playpen charters, and relaxed Lake Michigan experiences.
Book a Charter on VagabondPrivate sailing yacht from Montrose Harbor. Restroom onboard. Built for relaxed Lake Michigan charters.
- 39-foot sailing yacht
- Private charter boat
- Montrose Harbor departure
- Restroom onboard
- Ideal for skyline, sunset, Playpen, and lake cruising
A Private Sailing Yacht for Chicago Charters
Vagabond is a Beneteau Oceanis 393 sailing yacht used for private Chicago charters on Lake Michigan. It gives guests a comfortable place to relax outdoors, enjoy views of the Chicago skyline, and experience the lake from a real cruising sailboat.
The boat is a strong fit for private sailing charters, sunset cruises, fireworks nights, Playpen outings, and small group celebrations. It offers a more personal and authentic experience than a large party boat or crowded sightseeing cruise.
Photo gallery
Why Guests Like Vagabond
Real Sailing Experience
Vagabond is a true cruising sailboat, ideal for guests who want an authentic Lake Michigan sailing charter.
Private for Your Group
Your charter is reserved for your group, so the experience feels personal and relaxed.
Comfortable Outdoor Seating
The cockpit and deck areas give guests space to enjoy the lake, skyline views, and fresh air.
Cabin Space Below Deck
Guests can step below deck for additional space during the charter.
Restroom Onboard
A restroom is available onboard, which makes longer charters more comfortable.
Great for Chicago Views
Vagabond is well suited for skyline cruises, sunset sails, fireworks nights, and Lake Michigan photo opportunities.
Amenities
Comfort
- Outdoor seating
- Cabin space below deck
- Restroom onboard
- Space for small personal items
Convenience
- Montrose Harbor departure
- Return to the same dock
- Cooler/storage space
- Boarding instructions before your trip
Experience
- Private sailboat setting
- Chicago skyline views
- Lake Michigan cruising
- Great for photos and celebrations
Safety
- Safety briefing before departure
- Required safety gear onboard
- Weather monitoring before departure
- Experienced captain / captain arrangement
Best Charters on Vagabond
Private Chicago Sailing Charter
Best for first-time guests, skyline views, birthdays, date nights, and relaxed private groups.
View CharterChicago Sunset Sailing Charter
Best for golden-hour views, anniversaries, proposals, visiting guests, and memorable evenings on the lake.
View CharterChicago Fireworks Sailing Cruise
Best for summer nights, Navy Pier fireworks, skyline views, and special occasions after dark.
View CharterChicago Playpen Sailboat Charter
Best for birthdays, bachelorette groups, friend outings, and social summer boat days.
View Charter
Safety and Maintenance Confidence
Vagabond is operated by experienced local sailors and prepared for private Lake Michigan charters. Before each trip, the crew reviews weather, lake conditions, guest readiness, and onboard safety equipment so guests can relax and enjoy the experience.
Routes, timing, and lake activity may vary based on conditions and captain discretion. Safety always comes first.
Boat Specs
| Model | Beneteau Oceanis 393 |
|---|---|
| Boat Type | Monohull sailing yacht |
| Length | Approximately 39 feet |
| Beam | Approximately 13 feet |
| Departure Harbor | Montrose Harbor, Dock G — Chicago |
| Primary Use | Private sailing charters, sunset sails, fireworks cruises, Playpen charters, and Lake Michigan cruising |
| Restroom | Yes |
| Cabin Access | Yes |
| Guest Capacity | Up to 10 guests |
Good to Know Before Booking
Vagabond is a sailboat, not a luxury motor yacht or oversized party boat. The experience is private, scenic, and relaxed, with a focus on sailing, skyline views, and time on Lake Michigan.
Boarding requires stepping from the dock onto the boat. Guests should wear flat, comfortable shoes and bring layers, since conditions on Lake Michigan can feel cooler than on land.
Routes may vary based on weather, lake conditions, timing, and captain discretion.
Frequently Asked Questions
Is Vagabond private for our group?
Is there a bathroom onboard?
Can we go below deck?
Is this a sailboat or a motor yacht?
Where does Vagabond depart from?
What types of charters is Vagabond best for?
Can kids come onboard?
Can we bring drinks and snacks?
What should we wear?
Do we need sailing experience?
Ready to Sail Aboard Vagabond?
Choose your private Chicago sailing charter and enjoy Lake Michigan, skyline views, and a relaxed experience aboard Vagabond.
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