Browse all trips
-
Coastal Connection
$65 USDFeel the ocean breeze in your hair as you go from beaches and boardwalks to independent shops and eateries. There are a few unusual surprises in this trip that will keep you on your toes! This is a great trip to do from the New Haven and Hartford area.- Dog-Friendly
- Accessible
- Kid-Friendly
-
Funky Farms & Storybook Tales
$65 USDIt'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
-
Escape to the Cape
$65 USDThis 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
-
Vintage Vibes & Views
$65 USDImmerse yourself in quintessential New England charm as you wind along picturesque roads to a number of nature trails, cozy cafes, historic small towns and an incredibly funky garden.- Kid-Friendly
- Dog-Friendly
-
Witchy Wonders
$65 USDThis 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
![](http://guesswheretrips.com/cdn/shop/files/hero-funky-florals-women-walking-in-tulip-field-1440x1304.jpg?v=1669769692&width=1500)
![](http://guesswheretrips.com/cdn/shop/files/our-trips-archive-min.jpg?v=1667586827&width=1500)
CAN'T DECIDE?
Take Our Quiz to Find Out
Select your region and interests to find the best trip for you.
![](http://guesswheretrips.com/cdn/shop/files/contact-us-woman-on-roadtrip-leaning-out-window.jpg?v=1667845489&width=1500)
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!