Chicago Tribune - Lake Vacation

A great Lake Vacation along Michigan’s Harbor Towns

Lake Michigan Yacht Vacation

Lots of Chicagoans flock to the shores of Southwest Michigan in the summer.

Many of them skip the best part of a lake vacation: that is, getting out on the lake, in a boat.” – Capt. Rich Greenwood

Explore Michigan’s Clear Water and Quaint Harbor Towns

After retiring from his job as a Chicago-based natural resource manager with the U.S. Fish and Wildlife Service, Greenwood launched a second career as a licensed captain. He takes people to explore Michigan’s clear water, secluded beaches and quaint harbor towns aboard his sailboat, Third Coast.

“I just love introducing people to the beauty of Lake Michigan and to sailing,” Greenwood said. “So many people have said they feel like they’re in the Caribbean.”

– Capt. Rich Greenwood

From its home port in St. Joseph, a 90-minute drive from Chicago, Third Coast can take up to nine passengers on the charter sailboat that has two bedrooms and a full kitchen. Rates start at $195 for a short, introduction to sailing excursion for up to four people and climb to around $1,000 a day for overnight cruises at maximum capacity;

Licensed captains like Greenwood are waiting for passengers in many of Michigan’s harbor towns. You can also rent your own boat through local marinas. And just as Airbnb revolutionized the hotel industry, the internet’s causing a sea change in the boat rental market. Booking apps like GetMyBoat, which boasts some 58,000 vessels in 169 countries, list dozens of privately owned boats in Chicago and Southwest Michigan. Filters let you browse the inventory based on type of boat, size and price.

Most boat-booking websites rent only for the day or half-day, but Yachtico specializes in overnight charters. It has sailboats in Chicago and will set you up with a captain for an additional $200 a day; If you have several days, you can cruise over to Michigan, visit the coastal towns and skip the drive through the industrial corridor of Indiana.

Whether traveling in your own boat, renting for an afternoon or chartering overnight with a captain, here’s how to plunge into some of Michigan’s most popular ports close to Chicago.

Some of Michigan’s Most Popular Ports Close to Chicago

Northside Marina South Haven - Michigan

South Haven
This haven for boaters is a two-hour drive from Chicago’s Loop or a four-hour sail from St. Joseph with Capt. Greenwood, who’s happy to drop anchor and let passengers take a dip. Black River cuts through the town, providing plenty of waterfront dining as well as dock space.

Where to dock: South Haven has four municipal marinas. Renovated in 2013, Northside has the best amenities, including a clubhouse with computers, a large TV and comfy furnishings. Southside Marina has the most slips — 39 — for visiting boaters, and it’s just steps from both downtown and South Beach and its iconic red lighthouse. A few complimentary bicycles are available at each of the four marinas.

Getting out on the lake: Michigan is second only to Florida in fishing tourism, according to the American Sportfishing Association. Angling to try it out? Brothers Chad and Jim Bard come from three generations of fishermen and guarantee you’ll catch fish on It Il Do charters; “We’ve only had one time in the last five years where we didn’t catch anything,” Jim said. “If that happens, we’ll take you back out for free.” What’s the secret? “I’ve got 10 pieces of equipment I use, but it really comes down to knowledge and gut feeling,” he added. “If you’re serious, we leave shortly before sunrise, because fish want to eat when they wake up. Just depends on what’s more important to you … catching fish or drinking beer?” The price ranges from $450 to $550 for a five-hour excursion with four to six people.

The iconic red Lighthouse at South Haven's South Beach
The iconic red Lighthouse is a landmark at South Haven’s South Beach.  (Andrea Guthmann / Chicago Tribune)

On land: Learn about the area’s rich boating history at the Michigan Maritime Museum. South Haven also claims to be the blueberry capital of the U.S. The annual National Blueberry Festival takes place Aug. 11-14; ( Have your pick of the fruit year-round at The Blueberry Store, which sells every imaginable product tied to the fruit; (

Dining: Climb aboard the stationary Idler Riverboat for shrimp tacos and waterfront views. Clementine’s ( is a local favorite, and Captain Lou’s seafood shack serves fresh perch and live music on the weekends.

New Buffalo
In the heart of what savvy tourism strategists branded “Harbor Country,” New Buffalo lures city dwellers with its casual beach vibe and proximity. Roughly 40 nautical miles from Chicago, it’s reachable by motorboat in an hour or two.

Where to dock: New Buffalo Public Marina has 30 transient slips for visiting boaters. It costs $10 for three hours or $51 overnight for a 37-foot boat like Third Coast. It’s in a prime location at the end of the town’s main walking and shopping street, steps from the public beach .

Getting out on the lake: Anyone over 21 with a driver’s license can rent a motorboat, along with inner tubes and water skis, from Oselka Marina. Staff members help with the hard part — docking. Oselka also charters a larger power boat that comes with a captain;

On land: If surfing Lake Michigan sounds totally rad, stop by Third Coast Surf to rent a surfboard or sign up for lessons (

Dining: Families line up at The Stray Dog, but only adults can head up to the rooftop bar and patio (

Nicknamed the Art Coast of Michigan, this hip resort town is stocked with galleries, boutiques, excellent dining and lively nightlife.

Where to dock: Downtown marinas are fully booked for the season. Head a mile and a half away, across the Kalamazoo River, to the beautifully landscaped Tower Marine, with its heated pool, barbecues and playground. Saugatuck’s public transit system, the Interurban, gets you downtown for $1. There are no bus stops. Just call for your ride and the shuttle arrives within 20 minutes. Or walk 1 mile to the hand-cranked 1838 chain ferry, which also takes you across the river for $1.

Oval Beach Saugatuck close to Chicago
Oval Beach in Saugatuck, Mich. (Felicia Fairchild / Saugatuck-Douglas Visitors Bureau)

Getting out on the lake: Savor the slower pace of summer by renting a pontoon boat and gliding down the Kalamazoo River. Big Lake Outfitters ( and Makin’ Waves ( recommend a two-hour rental and cruising over to a secluded beach known as The Cove. Surrounded by dunes and blessed with warmer water, it’s the last stop before Lake Michigan.

On land: Climb the 282 steps to the top of the Mount Baldhead sand dune. The trailhead is a 10- to 15-minute walk from the chain ferry. You’ll get a bird’s eye view of the area, and the descent lands you at Oval Beach, with its powder-soft sand surrounded by dunes and forest.

Dining: Take a seat at the counter of the Saugatuck Drug Store, and you’ll get a taste of the town’s Norman Rockwell side, served up via a classic malt or ice cream soda; no website, 269-857-2300. Another sweet nostalgia trip is watching fudge being made at Kilwin’s Chocolates ( The Mermaid Bar & Grill ( offers casual waterfront fare, and Everyday People Cafe — despite its name — is the place for fine dining (

@Chicago Tribune by Andrea Guthmann

Chicago Tribune