Visitors have the option of flying directly into the smaller Blue Grass Airport (LEX ^IATA) , in Lexington, or flying into larger airports further away. Louisville Muhammad Ali International Airport (SDF ^IATA) and Cincinnati/Northern Kentucky International Airport (CVG ^IATA) are both about 1.5 hours away from Lexington, but are served by more airlines than Blue Grass Airport.

Travellers can access the Bluegrass Region via one of the two major interstates that arc around the northern and eastern sides of Lexington. I-64 runs from east to west, connecting Lexington with the largest city in Kentucky, Louisville, to the west. I-75 runs north-south, connecting Lexington with Cincinnati and Knoxville respectively. The two interstates meet in Lexington, running together for several miles in the northeast quadrant of the city.

There are no passenger rail lines in the Bluegrass Region. Amtrak has routes that serve Eastern, Western, and Northern Kentucky as well as Cincinnati, and has bus service from Chicago to Loiusville.

Long-distance bus company Greyhound serves both Lexington and Frankfort.

• Greyhound stations:
  • 38.07236-84.478391 Lexington Station, 477 W New Circle Rd NW, Lexington, toll-free: +1 800 231-2222. (updated May 2022)
  • 38.15923-84.898682 Frankfort Bus Stop, 301 Leonardwood Dr, Frankfort, toll-free: +1 800 231-2222. (updated May 2022)

• 37.7992-84.64321 Dupree Nature Preserve, 2991 Polly's Bend Road, Lancaster, KY, 40444. A 300 acre nature preserve located 15 miles south of Lexington. This property features 5 miles of hiking trails located within the Kentucky River Palisades, a deep gorge cut by the river. 

The Bluegrass Region is home to many small towns, each with their own reason to visit.

• Danville, 35 miles southwest of Lexington, is the "City of Firsts", and the "Birthplace of the Bluegrass" since the first Constitutional Convention in the West was held at Constitution Square in 1792 and Kentucky's first Constitution was signed there.
• Frankfort, Kentucky's capital city, is 25 miles northwest of Lexington.
• Midway is a quaint and colorful railroad town halfway between Lexington and Frankfort; stop for a bite to eat and explore the antique and boutique shops downtown.
• Harrodsburg, 32 miles southwest of Lexington, is Kentucky's oldest city.
• Shaker Village of Pleasant Hill, 30 miles southwest of Lexington, is America's largest restored Shaker community, with 34 carefully restored buildings and 3,000 acres of preserved farmland.

Lexington is home to an astonishing number of independently owned restaurants at all price levels. The city's college town atmosphere and affluent lifestyle contribute to this relatively small metropolitan area's great culinary offerings. Chain restaurants, typical in most American cities and towns, can be found here, as well as a great number of privately owned and operated establishments. Lexington has an amazing variety of regional and ethnic foods. Almost any taste can be fulfilled, from Home Cookin' to Fine Dining and from Cajun to Vietnamese.

Frankfort has a wide variety of restaurants to choose from while visiting.

• 38.12119-84.694021 Wallace Station Deli & Bakery, 3854 Old Frankfort Pike, Versailles, ☏ +1 859 846-5161. 8AM-8PM Monday, 8AM-6PM Tuesday-Thursday and Saturday, 8AM-8PM Friday, 8AM-6PM Sunday. Wallace Station is a hidden local favorite, known for huge, delicious sandwiches and wonderful desserts. A small place with a real country feel. Around $10/person. 
• 37.91878-84.273342 Hall's on the River, 1225 Athens-Boonesboro Rd, Winchester (40 minutes from downtown), ☏ +1 859 527-6620. Although it's well outside Lexington (it's halfway to Richmond), the easy scenic drive down KY-418 and location on the Kentucky River make it worthwhile. Try their famous beer cheese for an appetizer, and enjoy their excellent seafood selection, or play it safe with the very large "Kentucke River" Hot Brown. 
• 37.81882-84.740293 The Inn at Shaker Village at Pleasant Hill, 3501 Lexington Road, Harrodsburg, toll-free: +1-800-734-5611. A mix of traditional southern and continental foods, served at breakfast, lunch, and dinner. Call ahead to ensure available seating. Around $15/person. 

Lexington is a large college town, so there are many bars and nightclubs catering to all crowds. Frankfort and Richmond have their own smaller bar scenes.

Bourbon distilleries are plentiful in the area, due to the particular geology of the region that make this distinctively Kentuckian liquor possible. Many distilleries operate tours where you can learn about the processes of mashing, distilling, and aging, and often sample the product. Traveling between the distilleries is called "Taking the Bourbon Trail." Souvenir T-Shirts and Bourbon Trail "passports" are available. Each distillery has their own souvenirs available for purchase, ranging from shot glasses to Bourbon Balls.

Five distilleries are within 30 miles of Lexington.

• 38.0498-84.509481 Alltech's Lexington Brewery and Distilling Company, 401 Cross Street, Lexington, ☏ +1 859 255-2337. Tours every hour 10:00 to 4:00 Monday to Saturday, and Noon to 5:00 Sunday. $7/person. 
• 38.21673-84.87052 Buffalo Trace, 113 Great Buffalo Trace, Frankfort, toll-free: +1-800-654-8471. Tours Monday-Saturday year-round; call for times. Free. 
• 37.97339-84.897543 Four Roses, 1224 Bonds Mill Road, Lawrenceburg, ☏ +1 502 839-3436. 
• 38.03951-84.8524 Wild Turkey Distillery, 1417 Versailles Rd, Lawrenceburg, ☏ +1 502 839-2182. Free. 
• 38.11329-84.810845 Woodford Reserve, 7785 McCracken Pike, Versailles, ☏ +1 859 879-1812. Tours Tu-Sa year-round, Su April–December. For specific times, call or see web site. Tours $5-10/person; reservations may be required. 

A little farther afield:37.64687-85.348916 Maker's Mark, 3350 Burk Spring Rd, Loretto (1½ hours from Lexington), ☏ +1 270 865-2099. Tours Monday to Saturday 10:30AM-3:30PM every hour on the half-hour; Sunday March–December 1:30, 2:30, 3:30; closed some holidays. Aside from the usual distillery tour perks, Maker's Mark offers a unique souvenir: you can purchase a small bottle of bourbon and dip it yourself in their signature red sealing wax (must be 21 or older). The drive out to Loretto is also very scenic. Free. 

In addition to the Bourbon Trail, Lexington has two Breweries. Alltech's Lexington Brewery and Distilling Company, previously mentioned, and 38.05932-84.49217 West Sixth Brewing, 501 West 6th Street, Lexington. Monday to Thursday 3:00-10:00, Friday and Saturday Noon-Midnight, Sunday Noon-10:00. No tours are given at West Sixth, but they have a large tasting room onsite. 

Many Kentucky Wineries produce award winning wine. The winery business is growing, with several new vineyards starting up in the Bluegrass Region.

• 38.15861-84.6458 Equus Run Vineyards, 1280 Moores Mill Road, Midway, ☏ +1 859 846-9463. Open tastings 11:00 to 5:00 Monday to Saturday, and 1:00 to 5:00 Sunday, with extended summer hours. Tours on request. Equus Run wine has won many major awards. The vineyard features weekly events, with music and picnics in the summer. The drive is scenic. Wine tasting $2/person. 
• 37.90949-84.444859 Talon Winery & Vineyards, 7086 Tates Creek Road, Lexington, ☏ +1 859 971-3214. Open tastings 10:00 to 6:00 Monday to Friday, 10:00 to 7:00 Saturday, and Noon to 6:00 Sunday, with extended summer hours. Music and events weekly. The drive is scenic, through Kentucky's farmland.