Escape to the Cape
Escape to the Cape
Escape to the Cape
Escape to the Cape
Escape to the Cape
Escape to the Cape

Escape to the Cape

5.0 (4 reviews)

From $39

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.
When to Go Weds - Sun, Spring - Fall
ends near Dennis, MA

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  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges
  • No Booking Required

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

  • Beaches galore
  • Picturesque trails and boardwalks
  • Quintessential small town charm
  • Plenty of photo opportunites
  • Lots of history fun facts
  • Multiple recommendations included on every stop

How Long Is This Trip?

  • From Boston, MA:

3 hours and 20 minutes / 169 miles

  • From Providence, RI:

3 hours and 20 minutes / 177 miles

  • From Worcester, MA*:

4 hours and 15 minutes / 238 miles

  • From Hartford, CT*:

5 hours and 45 minutes / 346 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: Free shipping 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 →

Escape to the Cape

5.0 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.

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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.

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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.