Vintage Vibes & Views
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Vintage Vibes & Views

Vintage Vibes & Views

$65.00 CAD
Sale Sold out

One trip is required per group.

* "PDF Instant Download" means the trip will be sent by email as a PDF document, and not by mail (the email is sent immediately after completing your purchase)

WHAT TO EXPECT

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 an incredibly funky garden.

Trip Highlights

  • A cozy cafe in an old mill
  • Boardwalks, beaches, and botanical gardens
  • An idyllic European-style winery
  • Scenic winding roads
  • Timeless small towns

AVAILABLE TO DEPART

Days of the week: Tuesday through Sunday

Seasons: Year-round

Not recommended: Monday and Holidays

SUGGESTED FOR

  • Families
  • Photographers
  • Seniors
  • Outdoor Adventurers
  • Foodies
Vintage Vibes & Views
Vintage Vibes & Views
Vintage Vibes & Views
Vintage Vibes & Views
Vintage Vibes & Views

Itinerary

STOP 1

Before getting your steps in to start the day, check out a quaint and historic hamlet. Drive time to the second stop is 15 minutes.

STOP 2

Pick your preferred trail, grab a sweet treat, or head to a local winery and enjoy all that this region has to offer. Drive time to the third stop is 20 minutes.

STOP 3

Lunch in a unique destination, a beach or boardwalk trail, or a cute small town? The choice is yours! Drive time to the fourth stop is 25 minutes.

STOP 4

We have picked the most amazing destination to finish your surprise road trip! Think tons of epic eateries, a quirky museum, a colorful stroll and more.

Region

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Can depart from

Boston Area, Providence Area

Before you go

What You'll Need to Bring

  • Bug Spray
  • Camera
  • Cash
  • Walking Shoes
  • Water
  • Reusable Shopping Bags
  • Road Trip Snacks
  • Sunscreen (lots of easy outdoor activities)

Additional Details

  • Kid-Friendly
  • Dog-Friendly

FREQUENTLY ASKED QUESTIONS

We're here to help!

Please see the approximate driving distances below. Please note this just includes round-trip driving distances and not time spent at stops.

  • From Boston, MA:

3 hours and 10 minutes / 146 miles

  • From Providence, RI:

2 hours and 10 minutes / 85 miles

  • From Worcester, MA:

3 hours and 25 minutes / 161 miles

  • From Springfield, MA:

4 hours and 50 minutes / 253 miles

  • From Hartford, CT*:

4 hours and 55 minutes / 242 miles

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

This trip is best done Tuesday - Sunday, and can be done year-round.

We recommend leaving anytime between 8:30 am and 9:00 am from the Boston area.If you are leaving from Providence you can leave between 9:00 am and 9:30 am!

This trip is somewhat pet-friendly! At every stop there will be at least one option for you to explore with your furry friend, but it will limit you from going into a handful of shop and restaurant suggestions.

We recommended bringing up to 5 people on your surprise road trip.

If you're bringing a larger group, we highly recommend having one person in charge of booking reservations at restaurants and attractions in advance. Please see the previous page for a copy of the digital itinerary.

First Stop: No fee

Second Stop: No fee

Third Stop: No fee

Fourth Stop: One of our featured suggestions requires a significant entrance fee per person ($), but it is so worth it! We’ve provided many free alternatives as well.

*Please note: gas, tolls, and food may be additional costs.

After booking your trip, we'll send you a confirmation email with a few recommended accommodation options.

Customer Reviews

Based on 3 reviews
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K
Katie Johnson
Overall, how would you rate this trip?:
I would not recommend this trip
Excellent! I would definitely recommend this trip
Rate how active the trip was:
Not very active
Very active
Rate how accessible the trip was:
Not very accessible
Very accessible
Rate how 'unique' the stops were:
Not really
Yes, very unique!

We had so much fun with this trip!

E
Emily
Overall, how would you rate this trip?:
I would not recommend this trip
Excellent! I would definitely recommend this trip
Rate how active the trip was:
Not very active
Very active
Rate how accessible the trip was:
Not very accessible
Very accessible
Rate how 'unique' the stops were:
Not really
Yes, very unique!
The best day - and we didn’t get to half the stops!

My sister got this for my birthday, and we went with my 5yo son for Mother’s Day. We had such a great time. We didn’t make it to all the stops because we got a late start and the little one ran out of steam, but even so it was so well thought out and full of special spots we had such a great time and made so many memories. I can’t wait to go back and do the second half! And because there are options, you could do several different versions too. Lots of options for different ages/abilities. I would definitely do in the fall or spring because summer traffic might make this less pleasant. Please make more trips in New England! I can’t wait to do another one

N
Nutan Mathew
Overall, how would you rate this trip?:
I would not recommend this trip
Excellent! I would definitely recommend this trip
Rate how active the trip was:
Not very active
Very active
Rate how accessible the trip was:
Not very accessible
Very accessible
Rate how 'unique' the stops were:
Not really
Yes, very unique!
The most fun Father's Day!

We loved our experience with Guess Where Trips. Each stop was new to us, and we have lived in Massachusetts for 20 years. That was probably the coolest part. We had two kids with us, ages 10 and 12. Everyone enjoyed it. We had plenty of outdoor time, and had choices on how active we wanted to be. We had delicious eats and treats and fell in love with new parts of our beautiful state. The language in the packet was so thoughtful- especially considering our nation's history and the land where we live. I was so touched and impressed by the thoughtful approach by the creators. It's the little things that make the biggest impact. We loved the QR codes and we learned that the times are definitely right on point. We ran out of time- but that means we just have to go back! Happily!! :)