Boston Day Trip Box
Regular price $89
What's Inside
20 sealed surprise day trips
Adventure Length
Approx. 4-6 hours each
Twenty surprise day trips, all within reach of Boston. One day you're browsing a seaside fishing village, the next you're walking Revolutionary-era history or winding through New England farm country and covered bridges. Pick an envelope by mood, season or direction, reveal your 3-stop route and go.
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- Free Shipping on Orders $100+
- 30-Day Returns & Exchanges
What's Inside
• 20 sealed adventures to hidden gems, small towns, scenic spots and local favourites
• A pre-planned itinerary in every envelope
• A QR code for an interactive map, full trip details and our latest recommendations
• Dimensions: 8.5 x 5.5 x 1.5"
How Much Is a Surprise?
What you’ll know: Each envelope shares an overview of the adventure, so you can choose based on your mood, the season, or the direction you feel like heading.
What’s a surprise: The full itinerary, including your stops, stays sealed until you open the envelope.
Day Trip or Getaway Box?
• Day Trip Boxes: Each adventure takes 4-6 hours, with 3 curated stops and short drive times from the city on the box.
• Getaway Boxes: Each adventure takes you to an iconic destination worth making a weekend of, with suggestions for what to do, eat, see and where to stay. Available for Ontario and New York State.
Shipping & Returns
Buy with confidence! Return your product within 30 days.
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.
Exchanges: Want a different item instead? Email us at questions@guesswheretrips.com within 30 days of your order.
Boston Day Trip Box
Here's How It Works
Each one shows the duration, best season to go, and a hint at the theme.
Reveal your day at a glance and scan the QR code for the full digital itinerary.
Follow your itinerary stop to stop, with maps and directions built right in.
Frequently Asked Questions
What’s the difference between the Road Trip Boxes and your Classic Surprise Road Trips?
Our Classic Day Trips are a full day with 4 stops, and they keep the mystery going all day long. You'll open a new envelope at each stop, so every reveal is a surprise.
Our new Day Trip & Getaway Boxes flip that: open one of the 20 sealed cards and your whole itinerary is revealed at once. You get a little mystery up front, then a fully mapped-out itinerary, which is great if you'd rather plan ahead than wing it stop by stop.
Is there any overlap with your Classic Road Trips?
There is some overlap between our Day Trip Collection Boxes and our Classic Road Trips, as they explore similar regions. The amount of overlap will vary depending on which box you’re looking at and how many classic trips you’ve already completed in that area.
That said, each box contains 20 cards with a variety of stops to explore, so even if you’ve done a number of our classic trips, there will still be new destinations, travel tips, and more to discover; it’s a whole new experience!
If you’ve already completed several of our Classic Road Trips and aren’t sure which box is the best fit for you, feel free to reach out to us directly, we’re happy to help point you in the right direction!
How much of the trip is a surprise?
As much as you want it to be! Before opening an adventure, we'll give you just enough information to help you choose — including the general direction, best season and a few other helpful details. Once you've chosen, unseal the envelope to reveal where you're going and what you'll be doing along the way. You can look at this in advance or open it the morning of.
Where do I start and how do I find driving directions?
Each adventure will tell you where to begin and guide you from there. You'll also find a QR code inside your envelope that takes you to your digital itinerary and interactive map, making it easy to navigate between stops throughout the day.
Are there additional costs during the trip?
Yes. The cost of food, gas, accommodations, admission fees and any optional activities along the way are not included with your Road Trip Box. We try to provide as many options at each stop with a mix of free and paid recommendations so it can fit any budget!
How long does each road trip take?
Our Day Trip Collection adventures are approximately 4–6 hours, although you're always welcome to slow things down, add extra stops and make a full day of it.
Our Getaway Collection adventures are designed as overnight escapes and can be customized depending on how long you'd like to stay and explore.
Can I bring my kids or dog? Are the trips accessible?
Absolutely! Just keep in mind that depending on who you’re travelling with, you may not be able to experience 100% of every trip. We include a variety of options at each stop, so there should still be plenty to choose from. We recommend using the clues on the front of each envelope to help choose an adventure that’s the best fit for your group.
Another tip? Have the driver take a quick peek at the itinerary before you head out. They can help choose the activities and stops that work best for your family without spoiling the surprise for everyone else! And remember, there’s no pressure to do everything. You can always skip a stop, choose an alternative, or save something for another adventure.
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.
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.
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!
More Experiences You'll Love
2,328 verified reviews
See Where Our Road Trips Took Them
"Would you try a surprise day trip?”
“Each box is curated and packed with local intel.”
"I love that I can just grab and envelope and we have the entire day planned.”
“None of them tell you where you're going, just when to open it!”
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.
