16 days in Wisconsin & Chincoteague Island Itinerary

Created using Inspirock United States vacation planner
Make it your trip
— 4 nights
Fly to Baltimore, Bus to Salisbury, MD, Taxi to Chincoteague Island
Chincoteague Island
— 3 nights
Taxi to Salisbury, Fly to Spring Green
Spring Green
— 2 nights
— 1 night
Baileys Harbor
— 2 nights
Chippewa Falls
— 2 nights
Drive to Minneapolis–Saint Paul International Airport / Wold–Chamberlain Field, Fly to Bengaluru


Milwaukee — 4 nights

Brew City

Pabst Mansion and Riverwalk will appeal to history buffs. Do your shopping at Historic Third Ward and Milwaukee Public Market. Change things up with these side-trips from Milwaukee: Two Brothers Wines (in Pewaukee), Wind Point Lighthouse (in Racine) and Holy Hill (in Hubertus). There's lots more to do: indulge your thirst for a good beer at Lakefront Brewery, see the interesting displays at Harley-Davidson Museum, admire the striking features of Kneeland-Walker House, and take in the spiritual surroundings of Basilica of St. Josaphat.

To see reviews, other places to visit, where to stay, and more tourist information, use the Milwaukee trip itinerary maker.

Bengaluru, India to Milwaukee is an approximately 23-hour flight. You'll gain 11.5 hours traveling from Bengaluru to Milwaukee due to the time zone difference. Expect little chillier temperatures when traveling from Bengaluru in September; daily highs in Milwaukee reach 27°C and lows reach 17°C. Finish your sightseeing early on the 27th (Wed) so you can travel to Chincoteague Island.
Historic Sites · Shopping · Neighborhoods · Wineries
Side Trips

Chincoteague Island — 3 nights

Get some cultural insight at The Ugly Oyster Tour Co. and Sturgis One Room School Museum. Shop till you drop at Tryfan Gallery and Wine Cheese & More. Explore the numerous day-trip ideas around Chincoteague Island: Furnace Town Living Heritage Village (in Snow Hill) and Boxwood Gardens (in Princess Anne). Spend the 28th (Thu) exploring nature at Chincoteague National Wildlife Refuge. Next up on the itinerary: see majestic marine mammals with a dolphin and whale watching tour and don't miss a visit to Chincoteague Cultural Alliance.

For where to stay, more things to do, other places to visit, and other tourist information, read Chincoteague Island driving holiday planning tool.

Getting from Milwaukee to Chincoteague Island by combination of flight, bus, and taxi takes about 7.5 hours. Other options: drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Milwaukee to Chincoteague Island. Plan for a bit warmer temperatures traveling from Milwaukee in September, with highs in Chincoteague Island at 31°C and lows at 20°C. Cap off your sightseeing on the 30th (Sat) early enough to travel to Spring Green.
Wildlife · Parks · Nature · Tours
Side Trips

Spring Green — 2 nights

Start off your visit on the 1st (Sun): contemplate the long history of Folklore Village, learn about winemaking at Wollersheim Winery & Distillery, and then stop by Carr Valley Cheese. Get ready for a full day of sightseeing on the 2nd (Mon): admire the landmark architecture of Taliesin Preservation: Frank Lloyd Wright Visitor Center , browse the exhibits of The House on the Rock, and then sample the tasty concoctions at New Glarus Brewing Company.

To see ratings, where to stay, more things to do, and more tourist information, read our Spring Green trip maker tool.

You can do a combination of taxi and flight from Chincoteague Island to Spring Green in 7.5 hours. Other options are to drive; or do a combination of taxi, bus, train, and car. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. Traveling from Chincoteague Island in September, Spring Green is slightly colder at night with lows of 14°C. Finish your sightseeing early on the 2nd (Mon) so you can drive to Sheboygan.
Breweries & Distilleries · Wineries · Shopping · Historic Sites
Side Trips

Sheboygan — 1 night

On the 3rd (Tue), admire the masterpieces at John Michael Kohler Arts Center, then tee off at Whistling Straits Golf Course - Straits and Irish, then tee off at Blackwolf Run, and finally look for gifts at Cedar Valley Cheese.

For more things to do, ratings, where to stay, and tourist information, use the Sheboygan online day trip planner.

Drive from Spring Green to Sheboygan in 3 hours. In October, plan for daily highs up to 18°C, and evening lows to 6°C. Wrap up your sightseeing on the 3rd (Tue) to allow time to drive to Baileys Harbor.
Golf · Outdoors · Nightlife · Museums
Side Trips

Baileys Harbor — 2 nights

Start off your visit on the 4th (Wed): enjoy the sea views from Cana Island Lighthouse, then hunt for treasures at Schartner's Farm Market, then view the masterpieces at Plum Bottom Gallery, and finally learn about winemaking at Harbor Ridge Winery. Get ready for a full day of sightseeing on the 5th (Thu): learn about winemaking at Stone's Throw Winery, view the masterpieces at Edgewood Orchard Galleries, then look for gifts at Wood Orchard, and finally view the masterpieces at Off The Wheel Pottery.

For ratings, other places to visit, where to stay, and tourist information, refer to the Baileys Harbor road trip planner.

Drive from Sheboygan to Baileys Harbor in 2.5 hours. In October, daytime highs in Baileys Harbor are 16°C, while nighttime lows are 8°C. Cap off your sightseeing on the 5th (Thu) early enough to go by car to Chippewa Falls.
Shopping · Wineries · Museums · Historic Sites
Side Trips

Chippewa Falls — 2 nights

On the 6th (Fri), do a tasting at Autumn Harvest Winery and Orchard, then indulge your thirst for a good beer at Jacob Leinenkugel Brewing Company, and then indulge your thirst for a good beer at Leinie Lodge.

To find where to stay, more things to do, photos, and other tourist information, go to the Chippewa Falls travel route tool.

You can drive from Baileys Harbor to Chippewa Falls in 4 hours. Traveling from Baileys Harbor in October, plan for little chillier nights in Chippewa Falls, with lows around 4°C. You will have some time to spend on the 7th (Sat) before leaving for home.
Breweries & Distilleries · Wineries · Museums

Wisconsin travel guide

Specialty Museums · Water Parks · Zoos
The Badger State
Wisconsin is known as "America's Dairyland" because of its status as the nation's most famous producer of milk and cheese. A growing favorite with foreign tourists, the state is a perfect holiday destination for nature lovers, offering year-round outdoor activities like fishing, boating, kayaking, and hiking. Dotted with thousands of inland lakes and waterways alongside apple and cherry orchards, Wisconsin also offers numerous urban tourist attractions, its cities hosting renowned beer and art festivals each year.