After living for several years in a compact, shoebox apartment in Midtown Manhattan, the urge for a fundamental break from high-density city life and steep rental prices became impossible to ignore. In September 2024, my partner and I made the decision to take a wild leap of faith, pack up our lives, and hit the open road. Our ambitious blueprint for the subsequent 365 days was simple yet daunting: we would live entirely out of short-term rentals, specifically utilizing Airbnb to traverse the United States, exploring cities, towns, and rural landscapes we had never previously had the opportunity to experience.
With barely a second thought, I liquidated the majority of my furniture, compressed my wardrobe and essentials into a single Samsonite suitcase, and opened the Airbnb app to begin curating a digital wishlist titled “The Next Adventure.” Among the various rental platforms available, Airbnb offered the highest degree of freedom, flexibility, and creative control, encouraging an innovative approach to mapping out our itinerary. Over the course of that transformative year, we drove more than 16,000 miles, traversing 30 states and embedding ourselves in dozens of communities. Our temporary backyards ranged from the mountainous terrain of Gatlinburg, Tennessee, and the coastal shores of Destin, Florida, to the cultural depths of New Orleans, Louisiana; Lexington, Kentucky; Austin, Texas; Santa Fe, New Mexico; and Los Angeles, California.
As a poet and writer, embarking on a Kerouac-inspired, modern-day On the Road experience felt entirely fitting. Yet, what I did not anticipate was how profoundly my perspective would shift regarding the vast natural American landscape, the practical realities of domestic long-term travel, and the intricate curation process required to select the ideal Airbnb. More unexpectedly, this intensive road trip evolved into a lifestyle that continues to fuel my creative output, inspiring me to pack my bags and hit the highway once again. Next time, I intend to lean even further into creative and unconventional lodging choices, perhaps securing a glass dome nestled high in the mountains.
Our cross-country journey challenged, excited, amazed, and continuously inspired us. One of my fondest memories unfolded during a visit to Flagstaff, Arizona, timed to coincide with International Dark Sky Week. It was there that I learned Flagstaff holds the distinction of being the world’s first designated dark sky city. As someone accustomed to the light-polluted haze of New York City, I had never before witnessed the constellations rendered with such crystalline clarity. We had intentionally chosen our Flagstaff Airbnb based on local events researched months in advance, a strategy that underscored how critical regional knowledge is before locking in a reservation. Armed with a year’s worth of hard-earned experience and intimate knowledge of how to navigate properties across the country, I began documenting the essential lessons I learned along the way.
What to look for when booking
After spending countless hours scrolling through digital listings, my primary recommendation for prospective travelers is to maximize the utility of the platform’s search filters. For our specific needs, a dishwasher was an absolute non-negotiable amenity designed to preemptively eliminate any chore-based domestic disputes, while access to a washer and dryer was an invaluable perk that spared us both time and money during month-long stays. Once our baseline requirements were filtered out, we could turn our attention to the delightful cherry-on-top amenities that elevated a good stay into a transcendent one, whether that meant a deep soaking tub, a private pool, or an expansive waterfront view.
Toggling on the "Guest Favorite" feature proved exceptionally reliable for identifying distinctive, highly rated properties that consistently delivered on their digital promises. Similarly, paying close attention to accessibility filters is vital, particularly for travelers with mobility concerns or those traveling with older family members. Features like step-free entrances and shower grab bars can be filtered with a single click. Furthermore, possessing even a rudimentary understanding of your destination city allows you to target specific neighborhoods—such as River North or Wrigleyville in Chicago—directly aligning your accommodations with your intended itinerary.
Developing a meticulous routine of reading user reviews before hitting the "reserve" button quickly became second nature. These candid assessments from past guests often reveal crucial logistical details, such as whether a coveted hot tub is secretly out of commission or if a first-floor bedroom advertised as peaceful is actually subjected to heavy overnight street noise. Additionally, utilizing the "flexible dates" function whenever possible opens up a wealth of alternative options within a given city, frequently revealing neighborhoods previously unconsidered or unlocking price points that better align with long-term budgeting goals.
How to pay less by staying for longer
We gravitated toward Airbnb primarily due to the sheer variety of its inventory and the relative ease of comparing diverse properties side by side. For a natural planner, the search phase was as thrilling as the stays themselves, offering everything from rustic farmhouses and structural A-frames to riverfront condominiums and whimsical treehouses. While the initial research phase felt overwhelming, we quickly realized that structuring our itinerary around weekly or monthly blocks rather than shorter bursts was essential for preserving both our financial budget and our sanity.
Airbnb automatically applies a significant discount for stays lasting 28 consecutive nights or longer, an incentive established by the platform to encourage extended travel that served as a financial lifeline for our journey. Across all cities visited, these monthly-stay savings averaged a minimum of 15 percent, with properties in New Orleans and Austin scaling closer to 25 percent. To evaluate the true bottom line—including all accumulated taxes and cleaning fees—upfront, selecting the "Reserve Now" prompt provides a comprehensive financial overview before final commitment. Many hosts also extend scaled discounts for weekly bookings.
Another practical strategy involves reaching out directly to hosts prior to booking to inquire about potential pricing flexibility. Direct communication ensures that travelers secure the most competitive rate possible, regardless of the precise duration of their stay.
Get to know the city and your host
Long before our wheels hit the pavement, my partner and I focused on cultivating intentional connections with our hosts, going well beyond standard transactional messaging. We drafted personalized introductory templates designed to break the ice, discuss pricing flexibility, and tap into local expertise regarding neighborhood bars, hidden-gem restaurants, and off-the-beaten-path activities. These early interactions invariably set the welcoming tone for each destination. We maintained this outreach strategy even with properties we ultimately chose not to book, ensuring mutual compatibility before finalizing any contracts.
Even when we opted against a specific rental, our detailed introductions frequently yielded warm hospitality, valuable travel tips, and genuine conversations with residents across the country whom we otherwise never would have met. This proactive communication served as an effective bridge, easing the transition into unfamiliar cities and enabling us to experience each location from a local perspective. Furthermore, when committing to multi-week or monthly residencies, establishing a rapport with your host beforehand ensures you are fully briefed on any quirky property nuances or unique operational details that might not be explicitly detailed in the listing description, preventing any unwanted surprises upon arrival.
Do your research
Prior to selecting our destinations or locking in specific rentals, we dedicated hours to researching regional micro-climates, seasonal offerings, and community events. One of our most memorable residencies took place in New Orleans throughout the entire month of January. We drove into the city on New Year’s Eve, celebrated at R Bar, and rang in 2025 within the historic confines of a classic shotgun-style home located in the Irish Channel—a property where our host and their family had lived for decades. Our goal was to immerse ourselves in the authentic run-up to Mardi Gras, an ambition realized when we secured tickets with the Space Vikings, marched alongside the Intergalactic Krewe of Chewbacchus, and gained access to neighborhood gatherings throughout the month.
Beyond tracking cultural events, prospective travelers should monitor seasonal weather shifts to ensure adequate preparation for regional environmental quirks, such as challenging street parking conditions or adult-only property policies. Maintaining vigilance through user reviews remains paramount. Sorting reviews from lowest to highest star rating is an efficient method for cutting through the noise of dozens of listings, allowing travelers to quickly identify recurrent complaints or praised attributes that might impact their daily living experience.
How to pack
Sustaining a nomadic lifestyle for an entire year required a masterclass in packing discipline and spatial efficiency. Essential gear included a personalized toiletries kit dedicated to skincare and cosmetics, though my daily routine leaned refreshingly makeup-free during long driving shifts. My most indispensable travel companion was a structured Dagne Dover tote bag, designed with dedicated internal compartments that kept my mobile workspace organized. As a remote worker, this tote was crucial for transporting my laptop setup to local cafes and indie shops whenever a change of scenery was required. Nestled within it was my trusty travel mug, an essential accessory for pre-dawn highway departures.
Transforming transient rentals into temporary homes also called for minor creature comforts. A pair of cozy slippers provided an immediate sense of domestic grounding upon stepping across a new threshold. Upon departure, I made it a ritual to leave a handwritten thank-you note on high-end stationery to express gratitude to our hosts. Finally, as a writer, carrying a pocket-sized travel journal was non-negotiable for chronicling the day-to-day contours of our nationwide expedition.
Reflecting on the properties that defined our route, several stand out as quintessential examples of our year on earth. In Marfa, Texas, stepping into a desert oasis felt akin to stepping back into the American West of the 1950s, complete with vintage low-rise furniture, a curated minibar of craft cocktails, and cool stone floors, all positioned a short drive from Marfa’s avant-garde art installations. In Flagstaff, Arizona, a stylish one-bedroom apartment served as an ideal basecamp for exploring Route 66 trail networks, framing dramatic snowstorms that made the interior feel like a living snow globe.
In Taos, New Mexico, a certified Earthship dwelling recognized globally as a sustainable eco-stay provided a distinct desert architecture experience centered around nightly stargazing under vast skies. Meanwhile, in Gatlinburg, Tennessee, a romantic A-frame cabin complete with a hot tub and mountain views offered the perfect backdrop for celebrating our one-year anniversary, complemented by a nearby excursion to Dollywood. Finally, our six-week residency in East Nashville placed us within walking distance of local coffee roasters and vibrant neighborhood dining spots like Noko, Bad Idea, and Xiao Bao, rounding out an unforgettable chapter of American exploration.
