Waterside Bliss
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Waterside Bliss

Waterside Bliss

Regular price $65.00 USD
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)


Boardwalks, beaches and bites make this charming itinerary the ultimate road trip!

Trip Highlights

  • Beautiful sandy beaches
  • Historic mansions to explore
  • Easy strolls
  • Charming small town vibes
  • Epic places to eat


This itinerary can be used any day from Spring - Fall.


  • Couples
  • Outdoor Enthusiasts
  • Active Families



Whether you want a marina meal, quick cafe stop, or a market visit for a beach picnic, we've rounded up some of the best waterside eats for you to start the day. Drive time to the second stop is 10 minutes.


Just a short drive away are a bunch of historic homes & hot spots for a pretty photo op. Drive time to the third stop is 25 minutes.


An easy outdoor adventure awaits with winding paths, gardens and an interesting story to tell. Drive time to the fourth stop is 20-35 minutes.


With so much to see and do, we've recommended a few of our favorite things. Think beaches, epic eateries and a weekend winery.



Can depart from

Washington DC Area, Baltimore Area

Before you go

What You'll Need to Bring

  • Bathing Suit
  • Beach Towel
  • Cash
  • Sunscreen (lots of easy outdoor activities)
  • Road Trip Snacks
  • Walking Shoes
  • Camera

Additional Details

  • Kid-Friendly
  • Dog-Friendly


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 Washington:

2 hours and 25 minutes / 85 miles

From Baltimore:

2 hours and 15 minutes / 90 miles

From Leesburg:

3 hours and 30 minutes / 172 miles

From Frederick:

3 hours and 15 minutes / 165 miles

From Cambridge:

3 hours and 15 minutes / 144 miles

From Dale City:

2 hours and 24 minutes / 130 miles

  1. This trip can be done any day from Spring - Fall.

We recommend leaving anytime between 9:30 am and 10:30. The later you leave, the less time you may have to complete all of the stops.

This trip is pet-friendly! At every stop there will be at least one option for you to explore with your furry friend.

Please note that our boardwalk suggestion on stop three does not allow dogs. There is an alternative paid recommendation.

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 the restaurants and attractions in advance. In your confirmation email, you'll receive a copy of the itinerary.

First Stop: No fee

Second Stop: No fee

Third Stop: One recommendation is $11 per adult. This is the only activity available on Sunday.

Fourth Stop: No fee

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

Customer Reviews

Based on 1 review
Stacey M.
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Great day on the water

We had a fantastic day on the Waterside Bliss trip! There were enough optional trips to go back another day. It was a really fun experience. We had been to the main town before but not the attractions suggested so it was new to us. The last stop was a blast because we met new people and enjoyed sitting outside in the beautiful weather.