Boardwalk leading to a beach.
Pebbly beach with water.
Woman walking along path in a woodsy park.
Box of six donuts on a wooden table.
Photo of an iPhone screen showing a photo of the beach.
Woman at a bookstore.

Coastal Connection

4.0 (2 reviews)

From $39

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.

When to Go Weds - Sun, Spring - Fall
ends near Mystic, CT

Choose your format:

  • $8 Flat-Rate Shipping
  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges

essentials for your trip

Road Trip Tote Bag

An essential tote bag for your road trip ahead. Carry everything from your surprise package...

$5

Trip Highlights

  • Explore spooky seaside ruins
  • Stroll sandy beaches and boardwalks
  • Wander a one-of-a-kind bookstore
  • See the oldest house in Connecticut
  • Discover a 19th Century mansion turned art gallery
  • Multiple recommendations included on every stop

How Long Is This Trip?

  • From New Haven, CT:

2 hours and 15 minutes / 117 miles

  • From Hartford, CT:

2 hours and 48 minutes / 152 miles

  • From Providence, RI:

3 hours and 15 minutes / 186 miles

  • From Springfield, MA:

3 hours and 36 minutes / 202 miles

  • From Worcester, MA:

3 hours and 52 minutes / 228 miles

  • From Boston, MA*:

4 hours and 53 minutes / 288 miles

  • From Yonkers, NY*:

4 hours and 27 minutes / 246 miles

*We recommend booking an overnight hotel if the driving distance is greater than 4 hours round-trip.

When Can I Go?

Days of the week: Wednesday through Sunday

Seasons: Spring through Fall

Not recommended: Mondays, Tuesdays, Holidays, Winter

Shipping & Returns

Shipping: $8 flat rate, free on orders over $100.

Standard shipping takes 4–10 business days. Need it faster? Choose the fastest option at checkout for 2–4 business day delivery.

Returns: Not the right fit? Reach out within 30 days of purchase to start a return. Products just need to be unopened, unused, and in their original packaging, return shipping is your responsibility. Digital trips, gift cards, and opened products can't be returned.

Exchanges: Want a different trip instead? Email us at questions@guesswheretrips.com within 30 days of your order, there's a small $8 reshipping fee to send your new pick out. Digital trips cannot be exchanged.

Read our full return policy →

Coastal Connection

4.0 Physical Package

Here's How It Works

Browse by location and find a surprise trip that fits your day. Every route is road-tested by our team.

Your surprise destinations stay sealed until you're ready for them. One envelope at a time on the road, all day long.

Hidden gems, local favorites, and stories you won't find on Google. That's what's waiting for you.

Explore All Road Trips

Frequently Asked Questions

View All FAQs

What People Love About Our Trips

Rated 4.9/5.0 stars

What an Amazing Day!

Our daughter gave us this for Christmas and we finally pulled it out this week, July now. We love a road trip and loved the mystery of each new step. Great things to see and experience. Great restaurants to enjoy. I’ve recommended it to all my friends. Amazing.

Donna S. 🇨🇦

First Time…There WILL be a second!

Knowing the area we went I was very pleasantly surprised. We saw things I did NOT know existed! One of the stops was closed however we were able to walk up to it for a photo.

Mary Y. 🇨🇦

Great day away!

Did this trip with my mom for Mother’s Day. Lots of quaint little stops and places to explore! They also gave a few options at each stop so you could choose your own adventure! Will definitely be doing this again, had a wonderful time!

Megan M. 🇨🇦

Road Tested by Our Team

Our team spends 40+ hours researching, driving, and vetting every route: talking to locals, discovering hidden gems, and making sure every stop is worth your day.

More Experiences You'll Love

2,328 verified reviews

See Where Our Road Trips Took Them

“It was such a fun experience!”

@traveling_foodqueen

"The most fun, stress-free way to explore Ontario”

@ thevacaygirl

“Trust me, you need to try this”

@the_winged_rhymester

“I still can’t get over how fun it was”

@her.travel.adventures

“Guess Where Trips thinks of everything”

@wanderfarspendless

We Remember Experiences, Not Things.

Research consistently shows that spending time together creates more lasting happiness than buying more stuff. Every Guess Where Trip is thoughtfully planned to help you reconnect, explore, and create memories that last long after the day is over.