Bourbon & Bluegrass · The Kentucky Trail

Louisville → Lexington → Nashville · 5 days · group of 16 · Wine Country

open & edit in the planner → add it to my workspace

Day 1 · Louisville

8:00 AM
Repeal Oak Fired Steakhouse meal
Start the day at Repeal Oak Fired Steakhouse, a 4.8 star favorite across 3,665 reviews.
★ 4.8 (3.7k) · (502) 716-7372
9:30 AM
Waterfront Park activity
Explore Waterfront Park, a 4.7 star favorite across 7,408 reviews.
★ 4.7 (7.4k) · (502) 574-3768
12:30 PM
Gralehaus meal
Midday, settle in at Gralehaus, a 4.7 star favorite across 1,227 reviews.
★ 4.7 (1.2k) · (502) 857-7457
2:30 PM
First Friday Hop activity
Discover First Friday Hop, rated 5 stars.
★ 5 (2)
5:45 PM
Louisville Zoo activity
Spend time at Louisville Zoo, a 4.5 star favorite across 13,120 reviews.
★ 4.5 (13.1k) · (502) 459-2181
7:00 PM
Epiphany meal
Come together for dinner at Epiphany, a 4.9 star favorite across 148 reviews.
1525 Highland Ave, Louisville, KY 40204, USA · ★ 4.9 (148) · {'endPrice': {'units': '30', 'currencyCode': 'USD'}, 'startPrice': {'units': '20', 'currencyCode': 'USD'}} · (502) 384-5758
Check-in
Drury Inn & Suites Louisville North lodging
Check in at Drury Inn & Suites Louisville North, your base for the wine country, a 4.7 star favorite across 1,204 reviews.
★ 4.7 (1.2k) · (502) 425-5500

Day 2 · Louisville

8:00 AM
In Season Harvest Kitchen meal
Start the day at In Season Harvest Kitchen, a 4.8 star favorite across 607 reviews.
★ 4.8 (607) · (502) 323-3200
9:30 AM
Louisville Mega Cavern activity
Explore Louisville Mega Cavern, a 4.5 star favorite across 8,951 reviews.
★ 4.5 (9.0k) · (502) 855-6342
12:30 PM
North of Bourbon meal
Midday, settle in at North of Bourbon, a 4.7 star favorite across 798 reviews.
★ 4.7 (798) · (502) 749-3305
7:00 PM
Mayan Cafe meal
End the evening at Mayan Cafe, a 4.7 star favorite across 1,244 reviews.
★ 4.7 (1.2k) · (502) 566-0651
Check-in
Drury Inn & Suites Louisville North lodging
Check in at Drury Inn & Suites Louisville North, your base for the wine country, a 4.7 star favorite across 1,204 reviews.
★ 4.7 (1.2k) · (502) 425-5500

Day 3 · Lexington

10:00 AM
Tabla Indian Restaurant Lexington meal
Start the day at Tabla Indian Restaurant Lexington, a 4.9 star favorite across 121 reviews.
2270 Nicholasville Rd 120 Lease, Lexington, KY 40503, USA · ★ 4.9 (121) · {'endPrice': {'units': '30', 'currencyCode': 'USD'}, 'startPrice': {'units': '20', 'currencyCode': 'USD'}} · (859) 618-3427
12:30 PM
Agave & Rye Lexington Square meal
Regroup over lunch at Agave & Rye Lexington Square, a 4.7 star favorite across 1,764 reviews.
123 N Broadway, Lexington, KY 40507, USA · ★ 4.7 (1.8k) · {'endPrice': {'units': '20', 'currencyCode': 'USD'}, 'startPrice': {'units': '10', 'currencyCode': 'USD'}} · (859) 523-1170
7:00 PM
Lost Palm meal
Sit down to dinner at Lost Palm, a 4.7 star favorite across 358 reviews.
941 Manchester St, Lexington, KY 40508, USA · ★ 4.7 (358) · {'endPrice': {'units': '50', 'currencyCode': 'USD'}, 'startPrice': {'units': '20', 'currencyCode': 'USD'}} · (859) 785-3906

Day 4 · Lexington

8:00 AM
Granddam meal
Start the day at Granddam, a 4.6 star favorite across 275 reviews.
941 Manchester St, Lexington, KY 40508, USA · ★ 4.6 (275) · {'endPrice': {'units': '90', 'currencyCode': 'USD'}, 'startPrice': {'units': '30', 'currencyCode': 'USD'}} · (859) 785-3905
12:30 PM
Naz's Halal Food - Lexington meal
Regroup over lunch at Naz's Halal Food - Lexington, a 4.8 star favorite across 412 reviews.
685 S Limestone Ste 150, Lexington, KY 40508, USA · ★ 4.8 (412) · {'endPrice': {'units': '20', 'currencyCode': 'USD'}, 'startPrice': {'units': '10', 'currencyCode': 'USD'}} · (859) 880-7553
7:00 PM
Charlie Brown's Restaurant meal
Sit down to dinner at Charlie Brown's Restaurant, a 4.5 star favorite across 961 reviews.
816 Euclid Ave, Lexington, KY 40502, USA · ★ 4.5 (961) · {'endPrice': {'units': '20', 'currencyCode': 'USD'}, 'startPrice': {'units': '10', 'currencyCode': 'USD'}} · (859) 269-5701

Day 5 · Nashville

9:30 AM
Photowalk Nashville activity
Explore Photowalk Nashville, a 5 star favorite across 748 reviews.
226 11th Ave S, Nashville, TN 37203, USA · ★ 5 (748) · (615) 924-8997
10:00 AM
The Hampton Social - Nashville meal
Start the day at The Hampton Social - Nashville, a 4.9 star favorite across 19,741 reviews.
★ 4.9 (19.7k) · (615) 622-7772
12:30 PM
The Finch meal
Midday, settle in at The Finch, a 4.8 star favorite across 5,322 reviews.
★ 4.8 (5.3k) · (615) 208-2762
3:00 PM
The Rabbit Hole VR activity
Discover The Rabbit Hole VR, a 4.9 star favorite across 396 reviews.
633 7th Ave S, Nashville, TN 37203, USA · ★ 4.9 (396) · (615) 499-6219
7:00 PM
Aba Nashville meal
Come together for dinner at Aba Nashville, a 4.9 star favorite across 3,229 reviews.
★ 4.9 (3.2k) · (629) 270-9501
9:00 PM
Bad Axe Throwing Nashville activity
Spend time at Bad Axe Throwing Nashville, a 4.8 star favorite across 1,831 reviews.
652 Fogg St, Nashville, TN 37203, USA · ★ 4.8 (1.8k) · {'endPrice': {'units': '40', 'currencyCode': 'USD'}, 'startPrice': {'units': '30', 'currencyCode': 'USD'}} · (629) 203-6158
Check-in
Holiday Inn & Suites Nashville Downtown - Broadway by IHG lodging
Check in at Holiday Inn & Suites Nashville Downtown - Broadway by IHG, your base for the wine country, a 4.7 star favorite across 3,628 reviews.
★ 4.7 (3.6k) · (615) 265-0355

This is a worked example built from real, rated vendors — open it in the planner to make it your own, or browse more example tours. Built for the people who organize group travel · turtlely.