23 days in Orlando, Kentucky & New York City Itinerary

23 days in Orlando, Kentucky & New York City Itinerary

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Route & dates

23 days in Orlando, Kentucky & New York City Itinerary

Start: Riyadh
Fly:  19​h 30​min
1
Orlando
— 2 nights
Fly + Drive:  5​h 15​min
2
Bowling Green
— 3 nights
Drive:  2​h
3
Louisville
— 3 nights
Drive:  1​h 15​min
4
Loretto
— 1 night
Drive:  1​h 30​min
5
Monticello
— 2 nights
Drive:  2​h
6
Slade
— 2 nights
Drive:  1​h 15​min
7
Lexington
— 3 nights
Fly:  4​h 15​min
8
New York City
— 4 nights
Fly:  15​h
End: Riyadh

2
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.
Explore hidden gems such as Disney's Typhoon Lagoon Water Park and Orlando International Premium Outlets. Venture out of the city with trips to Ponce de Leon Inlet Lighthouse & Museum (in Ponce Inlet) and Daytona Beach (Saint Demetrios Greek Orthodox Church & Beach at Daytona Beach). There's lots more to do: test your team's savvy at popular escape rooms, enjoy breathtaking views from ICON Orlando, and make an unforgettable trip to World of Disney.

For maps, reviews, more things to do, and other tourist information, go to the Orlando online trip maker .

Riyadh, Saudi Arabia to Orlando is an approximately 19.5-hour flight. You can also do a combination of flight and bus. Traveling from Riyadh to Orlando, you'll gain 8 hours due to the time zone difference. Plan for little chillier temperatures traveling from Riyadh in May, with highs in Orlando at 36°C and lows at 24°C. Finish up your sightseeing early on the 27th (Mon) so you can travel to Bowling Green.

Things to do in Orlando

Shopping Theme Parks Parks

Side Trips

Daytona Beach, Ponce de Leon Inlet Lighthouse & Museum
Highlights from your plan
Orlando International Premium Outlets ©
Room Escape Games
Disney's Typhoon Lagoon Water Park ©
Disney's Typhoon Lagoon Water Park

3
nights
Bowling Green

Bowling Green ©
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. Eschew the tourist crowds and head to Mammoth Cave National Park and Basil Griffin Park. Explore Bowling Green's surroundings by going to Dog Creek Recreation Area (in Cub Run) and Cave City (Onyx Cave & Kayaking & Canoeing). Next up on the itinerary: examine the collection at National Corvette Museum, Head underground at Lost River Cave, admire all the interesting features of E.A. Diddle Arena, and take in the spiritual surroundings of St. Joseph Catholic Church.

Quickly create a custom-made itinerary for Bowling Green using our trip planner.

You can do a combination of flight and car from Orlando to Bowling Green in 5.5 hours. Other options are to drive; or take a bus. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Traveling from Orlando in May, expect Bowling Green to be slightly colder, temps between 30°C and 16°C. Finish up your sightseeing early on the 30th (Thu) so you can go by car to Louisville.

Things to do in Bowling Green

Parks Nature Adventure

Side Trips

Cave City, Dog Creek Recreation Area, Mammoth Cave
Highlights from your plan
Mammoth Cave ©
Mammoth Cave
National Corvette Museum ©
National Corvette Museum
Lost River Cave ©
Lost River Cave

3
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Discover out-of-the-way places like Louisville Slugger Museum & Factory and Distillery Tours. The adventure continues: examine the collection at Kentucky Derby Museum, sample the fine beverages at Kentucky Peerless Distilling Co, explore the landscape on two wheels at The Parklands of Floyds Fork, and snap pictures at The Big Four Bridge.

For more things to do, traveler tips, other places to visit, and tourist information, read our Louisville trip planner .

Traveling by car from Bowling Green to Louisville takes 2 hours. Alternatively, you can take a bus; or take a bus. You'll lose 1 hour traveling from Bowling Green to Louisville due to the time zone difference. In May, daily temperatures in Louisville can reach 29°C, while at night they dip to 17°C. Cap off your sightseeing on the 2nd (Sun) early enough to travel to Loretto.

Things to do in Louisville

Parks Museums Nature
Highlights from your plan
Louisville Slugger Museum & Factory ©
Kentucky Derby Museum ©
Kentucky Derby Museum
Distillery Tours

1
night
Loretto

Loretto ©
Loretto is a home rule-class city in Marion County, Kentucky, United States. On the 3rd (Mon), contemplate in the serene atmosphere at The Abbey of Gethsemani, learn about winemaking at Jesters Winery & Cafe, brush up on your knowledge of spirits at Limestone Branch Distillery, then see the interesting displays at Lincoln Legacy Museum, and finally sample the fine beverages at Maker's Mark.

To see where to stay, other places to visit, reviews, and other tourist information, you can read our Loretto trip maker tool .

Drive from Louisville to Loretto in 1.5 hours. Traveling from Louisville in June, Loretto is little chillier at night with lows of 19°C. Wrap up your sightseeing on the 3rd (Mon) early enough to travel to Monticello.

Things to do in Loretto

Breweries & Distilleries Museums Wineries

Side Trips

Lebanon, Lincoln Legacy Museum, The Abbey of Gethsemani
Highlights from your plan
Maker's Mark ©
Maker's Mark
Limestone Branch Distillery ©
Limestone Branch Distillery
The Abbey of Gethsemani ©
The Abbey of Gethsemani

2
nights
Monticello

Monticello ©
Monticello is a home rule-class city in Wayne County, Kentucky, in the United States. Start off your visit on the 4th (Tue): identify plant and animal life at Wolf Creek National Fish Hatchery and then head outdoors with Lake Cumberland. Get ready for a full day of sightseeing on the next day: get outside with Mill Springs Mill, identify plant and animal life at Cumberland Point Recreational Area, and then take an in-depth tour of Wayne County Historical Museum.

To find reviews, other places to visit, photos, and more tourist information, refer to the Monticello road trip planning site .

Getting from Loretto to Monticello by car takes about 2.5 hours. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. In June in Monticello, expect temperatures between 34°C during the day and 19°C at night. Finish your sightseeing early on the 5th (Wed) to allow enough time to travel to Slade.

Things to do in Monticello

Outdoors Parks Wildlife

Side Trips

Lake Cumberland, Cumberland Point Recreational Area, Wolf Creek National Fish Hatchery
Highlights from your plan
Mill Springs Mill ©
Mill Springs Mill
Wayne County Historical Museum ©
Wayne County Historical Museum

2
nights
Slade

Slade ©
Start off your visit on the 6th (Thu): hike along Auxier Ridge Trail #204, then hike along Rock Bridge Trail #207, and then get outside with Kentucky Rock & Adventure Guides. On the 7th (Fri), you'll have a packed day of sightseeing: contemplate the waterfront views at Buckhorn Lake, then admire the majestic nature at Natural Bridge State Resort Park, and then make a trip to Nada Tunnel.

To find out how to plan a trip to Slade, use our trip itinerary maker.

Drive from Monticello to Slade in 2.5 hours. Due to the time zone difference, you'll lose 1 hour traveling from Monticello to Slade. In June in Slade, expect temperatures between 32°C during the day and 19°C at night. Finish your sightseeing early on the 7th (Fri) to allow enough time to travel to Lexington.

Things to do in Slade

Parks Outdoors Nature

Side Trips

Kentucky Rock & Adventure Guides, Buckhorn Lake, Nada Tunnel
Highlights from your plan
Natural Bridge State Resort Park ©
Kentucky Rock & Adventure Guides ©
Nada Tunnel ©
Nada Tunnel

3
nights
Lexington

Lexington ©
Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Explore hidden gems such as Aviation Museum of Kentucky and Keeneland. Explore the numerous day-trip ideas around Lexington: EarthJOY Tree Adventures (in Germantown), Ark Encounter (in Williamstown) and Woodford Reserve Distillery (in Versailles). The adventure continues: admire the majestic nature at Kentucky Horse Park, make a trip to Daniel Boone's Grave, and brush up on your knowledge of spirits at Buffalo Trace Distillery.

To see traveler tips, reviews, maps, and tourist information, read Lexington day trip website .

Traveling by car from Slade to Lexington takes an hour. In June, daytime highs in Lexington are 34°C, while nighttime lows are 20°C. Cap off your sightseeing on the 10th (Mon) early enough to travel to New York City.

Things to do in Lexington

Museums Parks Fun & Games

Side Trips

Frankfort, Ark Encounter, Woodford Reserve Distillery, EarthJOY Tree Adventures
Highlights from your plan
Aviation Museum of Kentucky ©
Aviation Museum of Kentucky
Keeneland ©
Keeneland
Kentucky Horse Park ©
Kentucky Horse Park

4
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: take in the pleasant sights at Central Park, admire the striking features of Grand Central Terminal, wander the streets of Times Square, and explore the world behind art at The Metropolitan Museum of Art.

To see traveler tips and more tourist information, use the New York City attractions planning website .

You can fly from Lexington to New York City in 4.5 hours. Alternatively, you can do a combination of flight and bus; or drive. Expect a daytime high around 31°C in June, and nighttime lows around 21°C. Finish your sightseeing early on the 14th (Fri) so you can travel back home.

Things to do in New York City

Parks Museums Historic Sites
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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