42 days in United States Itinerary

42 days in United States Itinerary

Created using Inspirock United States visit planner

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Route & dates

42 days in United States Itinerary

Start: Sheboygan Falls
1
Sheboygan Falls
— 1 day
+2
Drive + Fly + Drive:  7​h 15​min
2
Williamstown
— 6 nights
+2
Drive + Fly + Drive:  10​h 30​min
3
North Fort Myers
— 8 nights
Drive:  3​h 15​min
4
Orlando
— 21 nights
Drive:  2​h 45​min
5
Jacksonville
— 1 night
Drive:  6​h
6
Pensacola
— 1 night
Fly:  3​h 30​min
7
Nashville
— 3 nights
Fly + Drive:  7​h 15​min
End: Sheboygan Falls

1
day
Sheboygan Falls

Sheboygan Falls ©
Sheboygan Falls is a city in Sheboygan County, Wisconsin, United States. Start off your visit on the 31st (Thu): stop by Evans, then play a few rounds at Whistling Straits Golf Course - Straits and Irish, and then admire the majestic nature at Kohler-Andrae State Park.

To see photos, reviews, where to stay, and tourist information, read our Sheboygan Falls route planner .

Use the Route module to see travel options from your home to Sheboygan Falls. In January, daily temperatures in Sheboygan Falls can reach 26°F, while at night they dip to 12°F. Cap off your sightseeing on the 31st (Thu) early enough to travel to Williamstown.

Things to do in Sheboygan Falls

Outdoors Golf Parks

Side Trips

Sheboygan, Whistling Straits Golf Course - Straits and Irish
Highlights from your plan
Kohler-Andrae State Park ©
Kohler-Andrae State Park
Evans ©
Evans

6
nights
Williamstown

Williamstown ©
Williamstown is a home-rule-class city in Grant and Pendleton counties in the U.S. Get in touch with nature at Tater Knob Pottery and Farm and Nada Tunnel. Discover out-of-the-way places like Miller's Bakery & Furniture and Kentucky Soaps and Such. Explore Williamstown's surroundings by going to EAT Gallery (in Maysville), Berea (Old Town Fudge Factory, Weston Glass Studio, & more) and Natural Bridge Sky Lift Gift Shop (in Slade). There's still lots to do: stop by Ruth Hunt Candies, browse for treasures at Irish Acres Gallery of Antiques, see the interesting displays at Oldham County History Center, and sample the fine beverages at Buffalo Trace Distillery.

To see more things to do, other places to visit, reviews, and other tourist information, read our Williamstown trip itinerary tool .

Explore your travel options from Sheboygan Falls to Williamstown with the Route module. Due to the time zone difference, you'll lose 1 hour traveling from Sheboygan Falls to Williamstown. In February, Williamstown is a bit warmer than Sheboygan Falls - with highs of 44°F and lows of 25°F. Finish up your sightseeing early on the 14th (Thu) so you can travel to Orlando.

Things to do in Williamstown

Shopping Museums Historic Sites

Side Trips

Berea, Madison, Natural Bridge Sky Lift Gift Shop, Nada Tunnel, Kentucky Artisan Distillery
Highlights from your plan
Miller's Bakery & Furniture ©
Miller's Bakery & Furniture
Ark Encounter ©
Ark Encounter
Milan '54 Hoosiers Basketball Museum ©

8
nights
North Fort Myers

North Fort Myers ©
North Fort Myers is a census-designated place (CDP) in Lee County, Florida, United States. Deepen your sense of the past at sights like Smallwood Store and Historic Spanish Point. Explore hidden gems such as Ten Thousand Islands National Wildlife Refuge and Siesta Beach. Explore the numerous day-trip ideas around North Fort Myers: Immokalee State Farmers' Market (in Immokalee), Kayaking & Canoeing (in Bonita Springs) and Big Cypress National Preserve (in Ochopee). And it doesn't end there: stop by Cw Fudge Factory LLC, enjoy the sand and surf at Coquina Beach, stroll through Boca Grande Beach, and savor the flavors at Cape Coral Farmers Market.

To find where to stay, maps, traveler tips, and tourist information, read North Fort Myers tour planner .

The Route module can help you plan travel from Williamstown to North Fort Myers. Traveling from Williamstown in February, expect North Fort Myers to be warmer, temps between 79°F and 58°F. Wrap up your sightseeing on the 15th (Fri) early enough to travel to Orlando.

Things to do in North Fort Myers

Parks Outdoors Beaches

Side Trips

Matlacha, Boca Grande, Immokalee, North Jetty Beach, Coquina Beach
Highlights from your plan
Big Cypress National Preserve ©
Big Cypress National Preserve
Kayaking & Canoeing
Muscle Car City Museum ©
Muscle Car City Museum

21
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Eschew the tourist crowds and head to Stetson Mansion and Stand-Up Paddleboarding. Your itinerary includes some good beach time at Beach at Daytona Beach and Ormond Beach. You'll find plenty of places to visit near Orlando: Ponce Inlet (Lighthouse Point Park & Ponce de Leon Inlet Lighthouse & Museum), Grumbles House Antiques & Garden Shop (in Dunnellon) and Scuba & Snorkeling (in Crystal River). Pack the 26th (Tue) with family-friendly diversions at Walt Disney World Resort. Pack the 3rd (Sun) with family-friendly diversions at Universal Orlando Resort. And it doesn't end there: revel in the low prices at Orlando Premium Outlets - Vineland Avenue, stroll through Cocoa Beach, buy something for everyone on your list at The Florida Mall, and look for gifts at Ron Jon Surf Shop.

Plan my Orlando trip by asking Inpirock to come up with tips and suggestions.

Traveling by car from North Fort Myers to Orlando takes 3 hours. In February, plan for daily highs up to 75°F, and evening lows to 56°F. Wrap up your sightseeing on the 8th (Fri) early enough to drive to Jacksonville.

Things to do in Orlando

Shopping Theme Parks Outdoors

Side Trips

The Villages, Daytona Beach, Melbourne, Wildwood, Winter Park
Highlights from your plan
Stetson Mansion ©
Stetson Mansion
Stand-Up Paddleboarding

1
night
Jacksonville

Jacksonville ©
The sprawling city of Jacksonville is not only Florida's most populous city, but also the largest city by land area in the continental United States.
On the 8th (Fri), steep yourself in history at Kingsley Plantation, wander the streets of Jacksonville Landing, and then look for gifts at Sweet Pete's.

To see where to stay, other places to visit, ratings, and other tourist information, go to the Jacksonville driving holiday site .

Getting from Orlando to Jacksonville by car takes about 3 hours. Other options: take a train; or take a bus. Traveling from Orlando in March, expect Jacksonville to be little chillier, temps between 73°F and 49°F. Cap off your sightseeing on the 9th (Sat) early enough to go by car to Pensacola.

Things to do in Jacksonville

Shopping Neighborhoods Historic Sites
Highlights from your plan
Jacksonville Landing ©
Jacksonville Landing
Kingsley Plantation ©
Kingsley Plantation

1
night
Pensacola

Pensacola ©
Surrounded on three sides by water, Pensacola offers access to white-sand beaches and emerald-green ocean unspoiled by large resorts.
On the 9th (Sat), examine the collection at Foley Railroad Museum, then look for gifts at Billy's Seafood, and then enjoy the sand and surf at Gulf Shores Public Beach. Get ready for a full day of sightseeing on the next day: look for gifts at Joe Patti's Seafood Company and then brush up on your military savvy at National Naval Aviation Museum.

For maps, ratings, other places to visit, and other tourist information, read Pensacola day trip planning app .

Traveling by car from Jacksonville to Pensacola takes 6 hours. Alternatively, you can take a bus. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In March, daily temperatures in Pensacola can reach 71°F, while at night they dip to 53°F. Cap off your sightseeing on the 10th (Sun) early enough to travel to Nashville.

Things to do in Pensacola

Museums Parks Outdoors

Side Trips

Gulf Shores Public Beach, Foley Railroad Museum, Billy's Seafood
Highlights from your plan
National Naval Aviation Museum ©
National Naval Aviation Museum
Billy's Seafood ©
Billy's Seafood
Foley Railroad Museum ©
Foley Railroad Museum

3
nights
Nashville

Nashville ©
Known as the capital of country music, the thriving city of Nashville combines old-world southern charm with a progressive urban flair.
Kick off your visit on the 11th (Mon): see the interesting displays at Lane Motor Museum, then stop by Brentwood Jewelery & Gifts, and then identify plant and animal life at Radnor Lake State Park. Keep things going the next day: steep yourself in history at Lotz House Museum, then stop by Hatch Show Print, then take an in-depth tour of Tennessee State Museum, and finally appreciate the extensive heritage of Bicentennial Capitol Mall State Park.

Before you visit Nashville, use our trip planner to discover what you can do and see there.

Traveling by flight from Pensacola to Nashville takes 3.5 hours. Alternatively, you can do a combination of taxi and flight; or drive. Expect a bit cooler temperatures when traveling from Pensacola in March; daily highs in Nashville reach 61°F and lows reach 39°F. On the 13th (Wed), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Nashville

Parks Nature Museums

Side Trips

Brentwood Jewelry, T.B. Sutton General Store, Lotz House Museum
Highlights from your plan
Lotz House Museum ©
Lotz House Museum
Bicentennial Capitol Mall State Park ©
Radnor Lake State Park ©
Radnor Lake State Park

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