39 days in Westchester County Itinerary

39 days in Westchester County Itinerary

Created using Inspirock Westchester County trip itinerary maker

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Route & dates

39 days in Westchester County Itinerary

Start: Tampa, Florida
Fly + Drive:  8 h
— 36 nights
Drive:  30 min
— 2 nights
Drive + Fly:  8 h 15 min
End: Tampa, Florida


Yonkers ©
Yonkers is the fourth most populous city in the U.S. Your cultural itinerary includes sights like Hartsdale Pet Cemetery and John Jay Homestead. Take a break from the city and head to Hudson Hills Golf Course and Anthony's Nose. Venture out of the city with trips to Yorktown Heights (Jefferson Valley Mall, Wilkens Farm, & more), Outhouse Orchards (in Croton Falls) and North Salem (Harvest Moon Farm & Orchard & Hammond Museum and Japanese Stroll Garden). The adventure continues: play a few rounds at Doral Golf Club, contemplate the long history of Greenburgh Nature Center & Manor House, look for all kinds of wild species at Rye Nature Center, and explore the striking landscape of Croton Gorge Park.

For reviews, traveler tips, where to stay, and other tourist information, read Yonkers trip itinerary builder site .

Tampa to Yonkers is an approximately 8-hour flight. You can also drive. Traveling from Tampa in April, expect Yonkers to be cooler, temps between 62°F and 43°F. You'll set off for home on the 19th (Sun).

Things to do in Yonkers

Parks Historic Sites Wildlife

Side Trips

Tarrytown, Rye, Yorktown Heights, Peekskill, Sleepy Hollow
Find places to stay Apr 13 — May 19:
Highlights from your plan
Teatown Lake Reservation ©
Teatown Lake Reservation
Sleepy Hollow Cemetery ©
Sleepy Hollow Cemetery
Kykuit ©


Mamaroneck ©
On the 19th (Sun), don't miss a visit to Greenwich Avenue.

For photos, maps, reviews, and other tourist information, read our Mamaroneck day trip planning app .

Mamaroneck is very close to Yonkers. Traveling from Yonkers in May, expect nights in Mamaroneck to be about the same, around 51°F, while days are a bit cooler, around 69°F. You'll set off for home on the 21st (Tue).

Things to do in Mamaroneck

Beaches Parks Nature

Side Trips

Greenwich Avenue, Cradle of Aviation Museum, Freeport's Nautical Mile, Jones Beach State Park
Find places to stay May 19 — 21:
Highlights from your plan
Jones Beach State Park ©
Jones Beach State Park
Cradle of Aviation Museum ©
Cradle of Aviation Museum