Surprise New York Day Trips

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

Set out from the hustle and bustle of NYC for a road trip full of surprises. Explore charming small towns and lush landscapes just beyond the city, where historic ruins, whimsical gardens, and storybook-like streets are waiting. With scenic trails, vibrant views, and markets that offer a bit of everything, these day trips are the perfect way to uncover a different side of New York.

Browse all trips

  • Gift Card [Digital $USD]

    Gift Card [Digital $USD]

    $65.00 USD
    Instantly send the gift of a one-day surprise road trip! Digital gift cards can be sent immediately or scheduled to be sent on a specific day.
  • BEST SELLING GIFT
    Hudson River Hideaways

    Hudson River Hideaways

    $65 USD
    An iconic road trip route with a twist! We've found countless hidden hideaways along the Hudson including; crumbling ruins, quaint towns, spooky cemeteries and more.
    • Dog-Friendly
    Can depart from: New York City Area, Newark Area, Hartford Area, New Haven Area
  • Can be done in winter
    Vibrant Vistas & Picturesque Towns

    Vibrant Vistas & Picturesque Towns

    $5,565 USD
    Hit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls.
    • Dog-Friendly
    Sale
    Can depart from: Hartford Area, New Haven Area, Springfield, MA Area
  • Perfect for Families
    Enchanted Adventures

    Enchanted Adventures

    $65 USD
    Around every winding road is a world of whimsical and enchanted adventures. This family-friendly trip is perfect for those who love easy trails, farm market stops, colourful photo ops and tasty treats.
    • Kid-Friendly
    Can depart from: New York City Area, Philadelphia Area, Trenton Area

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

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Gift-a-Trip

The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!