North America
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Select Itineraries are available for single purchase, others are only available to All Access Members. You’ll notice we have quite a few itineraries ‘in the works’. There’s even more coming! Sign up for an All Access Membership to be notified of, and have access to, all new itineraries.
Unless otherwise specified, Estimated Trip Cost is for two people’s flights, lodging, transportation, activities, and food.
The Trip Length simply refers to the number of fully ‘built out’ days included in the itinerary. Actual length is up to you.
Breckenridge, CO (Winter)
There’s a lot to know when you’re planning a ski trip to Breckenridge, including details about lift tickets, ski rentals, and available overnight parking.
Use this itinerary as your guide and easily adjust to accommodate a shorter weekend trip or amount of skiing days. Don’t want to hit the slope? There’s also ideas for other winter activities.
Alternative Ideas + Trip Template included.
Duration: 6 days
Est. Trip Cost: $1,500 per person
Recommended Months: November - March (Ski Season)
Denver, CO & Aspen, CO
It’s hard to beat summer in Colorado. This long weekend itinerary includes the best of Denver and Aspen, with a short stop along the way.
Maroon Bells (beautiful scenic area in the Elk Mountains), Independence Pass (another scenic area with an overlook), and other attractions await!
Alternative Ideas + Trip Template included.
Duration: 5 days
Est. Trip Cost: $1,500 - $3,000
Recommended Months: May - October
Savannah, GA
From fishing, live music (including karaoke, dueling pianos, and jazz), countless parks (okay, 22), historical museums, art galleries, shops, and even ghost tours. Pick your poison and unwind in the charming “Hostess City of the South”. The restaurants won’t disappoint!
Alternative Ideas + Trip Templates included.
Duration: 4 days
Est. Trip Cost: $1,000 - $2,000
Recommended Months: Anytime
The Carolinas
Greenville, Asheville, & Charleston.
This trip involves cycling, hiking, a beautiful boutique hotel, and complimentary luxury vehicles (really!).
See the Great Smoky Mountains, enjoy the great outdoors, visit the coast, and indulge in nationally acclaimed Charleston restaurants.
Alternative Ideas + Trip Template included.
Duration: 7 days
Est. Trip Cost: $2,000 - $4,000
Recommended Months: March - October
Watercolor, FL
Originally planned as a Bachelorette trip, this is fun for a girls trip, or even a trip with a large family.
Stay at a picturesque Watercolor home, enjoy a fireside meal on the beach and experience the best this area has to offer. This trip is priced for a large group (such as a bachelorette).
Alternative Ideas + Trip Template included.
Duration: 4 days
Est. Trip Cost: $750 - $1,000 per person (assuming group of 10 people)
Recommended Months: Anytime
Coming Soon:
Big Sky, MT
There’s a reason a show was based on this area - it’s beautiful.
With input from locals, use this itinerary to get the best out of winter in Montana. Includes a visit to Yellowstone National Park and fly-fishing on a river near Big Sky.
Cannot guarantee a Justin Timberlake siting, but we can still hope for it.
Duration: 5 days
Est. Trip Cost: $2,000 - $2,500
Recommended Months: June - October
Boston, MA
Do you like spending time in museums, or do you avoid them at all costs? Don’t worry, This isn’t your typical history class.
Tour America’s oldest city where you’ll learn a lot, but have a great time while doing it. You might even get the chance to enjoy America’s favorite past-time, baseball.
As always, the food recommendations are amazing!
Duration: 4 days
Est. Trip Cost: $1,000 - $1,500
Recommended Months: Anytime
Charleston, SC
We highlight Charleston in our The Carolinas Itinerary, but Charleston, SC deserves an Itinerary of its own.
Perfect for a weekend romantic getaway, girls trip, or Bachelorette weekend - this Itinerary gives the absolute best recommendations for food and drinks in this charming corner of the world.
Duration: 4 days
Est. Trip Cost: $750 - $1,500
Recommended Months: Anytime
San Diego, CA
California is a good idea any time of year. With this insider’s look, you can stay away from the crowded tourist traps and instead see San Diego the best way - like a local.
Duration: 4 days
Est. Trip Cost: $1,500 - $3,000
Recommended Months: Anytime
Scottsdale, AZ
This itinerary is a melting pot of bachelorette flair, romantic getaway, and family retreat. No matter which route you choose, you can’t go wrong with a long weekend in Scottsdale.
Duration: 4 days
Est. Trip Cost: $1,500 - $3,000
Recommended Months: Anytime
Can’t choose just one? Choose them all.
All Access Membership: $29.99 per year
Note: Joining as an All Access Member grants you access to ALL Itineraries, even as we continue to add new ones. Seriously.