Woman holding four Guess Where Trips envelopes while on road trip

Best Day Trips in Rhode Island

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

Hit the road from Providence and uncover Rhode Island’s unique blend of coastal beauty and historic charm. Stroll through quaint New England towns where vintage vibes and scenic views create the perfect backdrop. Explore picturesque boardwalks, cozy cafes, and quirky spots that tell the stories of this small but mighty state. From coastal breezes to charming historic enclaves, these surprise road trips are your ticket to a true Rhode Island escape.

Browse all trips

  • NEW ENGLAND CHARM
    Vintage Vibes & Views

    Vintage Vibes & Views

    $65 USD
    Immerse yourself in quintessential New England charm as you wind along picturesque roads to a number of nature trails, cozy cafes, historic small towns and picturesque beaches.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Boston Area, Providence Area
  • BEST SELLER
    Funky Farms & Storybook Tales

    Funky Farms & Storybook Tales

    $65 USD
    It's no wonder authors flocked to this area of Massachusetts for inspiration! Head out on a picturesque drive and discover farms, boardwalk trails, lots of quirky history and much more.
    • Accessible
    • Kid-Friendly
    Can depart from: Boston Area, Springfield, MA Area, Providence Area, Hartford Area
  • PERFECT FOR SUMMER OR FALL
    Boardwalk leading to a beach.

    Coastal Connection

    $65 USD
    From seaside strolls and spooky ruins to cider donuts and historic mansions, this charming coastal road trip is full of surprises. Whether you’re wandering a 17th-century town green, petting goats at a giant book barn, or soaking in saltwater views, you’ll fall in love with Connecticut’s quirkier side.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
    Can depart from: New Haven Area, Hartford Area, Providence Area, Springfield, MA Area
  • EXPLORE CAPE COD
    Escape to the Cape

    Escape to the Cape

    $65 USD
    This road trip is full of Cape Cod charm. Think picturesque views, independent shops, heritage buildings, boardwalks and more. This trip focuses more on the hidden gems, quaint towns and history of the area.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Boston Area, Providence Area
  • returning this fall
    Witchy Wonders

    Witchy Wonders

    USD
    This road trip will have you exploring the Salem witch trials, haunted history and a few iconic Hocus Pocus locations. This trip can be done throughout the year. If you're travelling during the month of October some attractions need to be pre-booked as the area gets significantly busier.
    • Accessible
    • Kid-Friendly
    Sold out
    Can depart from: Boston Area, Providence Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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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!