Itineraries

Over the years, we’ve learned a thing or two about crafting memorable trips, balancing exploration with relaxation, and making the most of our time on the road (and beyond).

Here, we’ll be sharing some of our favorite tried-and-tested itineraries, ranging from quick weekend getaways to more extended adventures. Whether you’re dreaming of a scenic road trip along a breathtaking coastline, a historical deep-dive into a fascinating city, or a relaxed exploration of a charming region, you’ll find a variety of suggestions to spark your wanderlust.

Consider these itineraries as starting points – feel free to adapt them to your own interests, time constraints, and travel style. We’ll try to include key highlights, potential routes, activity suggestions, and even some of our personal tips and lessons learned along the way. Let us help you turn your travel dreams into a well-planned reality!

Key West Southernmost Bouy

3 Full Days in Key West

Key West is more than just the end of U.S. 1—it’s a pocket-sized island crammed with more history, literary legends, and iconic bars than almost anywhere else in the country. Planning a full three-day escape (plus 2 travel days) here requires a good strategy, balancing the must-see historical tours with the necessary Key West traditions,

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2 Days in Myrtle Beach, SC

Our a trip to Myrtle Beach, SC, about this time last year, was a chance to visit some younger friends and check out a town my sister enjoyed. Upon arrival, I was surprised with the cold weather! Despite the palm trees and sunshine, it was far colder than we expected, even in November, necessitating an

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A Long Weekend in Ouray, CO

The idea for my most recent long weekend in Ouray was born over a casual breakfast with two girlfriends. When asked where in Colorado I’d love to go, my answer was immediate and heartfelt: Ouray. It’s a town I’ve long admired from afar, but its distance from home has always made it feel just out

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14 Day Alaska Itinerary

Memorable 14 Day Alaska Itinerary (Anchorage, Seward, & Fairbanks)

Justin’s 50th State! Woo-hoo. This trip, which doubled as our 33rd state explored together, was a two-week adventure designed to hit the highlights of the Railbelt region while balancing his initial work commitments with our favorite travel formula: a few essential pre-booked tours, plenty of flexible exploration, and necessary rest days. If you’re planning a

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Kanab UT KHill Hiking Trail Justin on ledge

8 Awesome Things to Do in Kanab, Utah

When we were planning this leg of our southwest road trip, one specific landscape kept calling our names: slot canyons. We wanted that classic Utah experience of wandering through deep, twisting, ribbon-like sandstone walls. As it turns out, Kanab is the ultimate basecamp for slot canyons. Positioned perfectly in southern Utah, it sits within striking

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Flagstaff & Surrounding Area Road Trip

Flagstaff & Beyond: Ancient Ruins, Route 66, and Desert Wonders

A short but packed stop in Northern Arizona and Southern Utah—where 900-year-old cliff dwellings, a legendary Route 66 town, one unforgettable song, and some of the Southwest’s most surreal geology made our road trip come alive. Flagstaff was a fantastic home base for us—really just two full days of exploring, sandwiched by two travel days

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Long Weekend in New Orleans Skyline

An Unforgettable Long Weekend in New Orleans: Bikes, Voodoo, Bourbon Street, and a Record-Breaking Night at the Superdome

From the moment you arrive, New Orleans wraps itself around you — the smell of something frying nearby, the faint sound of a trumpet from a few blocks away, the iron-lace balconies casting shadows on streets that feel like they belong to another century. We spent a long weekend in New Orleans in December 2019,

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