Let These Companies Plan Your Next Road Trip

As many of us opt to hit the open road this year, there’s an easier way. Why not have someone else figure out where you’re going to stay and what you’re going to do along the way?

Let These Companies Plan Your Next Road Trip

Whether you want to focus on food, fun, history, or nature, these companies can customize an itinerary for you.

Photo by Shutterstock

Back in the day, before my husband and my kids, I was the most easygoing traveler (I swear). Any old accommodation would suffice, as long as it was relatively clean. When I took a road trip, I’d make a rough plan, but part of the fun was going with the flow and making unplanned stops along the way. Then, I had kids. Young kids, in particular, don’t really go with the flow so well. Or at least they don’t go with your flow. They have their own flow, involving naps and diaper changes, frequent snacks, and early bedtimes.

Given my band of not-so-easygoing travelers, when luxury vacation club Exclusive Resorts and custom road trip planner All Roads North invited me to test their new custom luxury road trip itineraries, my first instinct was to give them an out—I offered to sub in someone who doesn’t have tiny tots. But to their credit, they were up for the challenge even if I wasn’t sure I actually was. Ultimately, we decided to go. I mean, who better to gauge a tailor-made road trip experience than working parents with two kids under four (the latter being the ultimate ruthless critics)?

The first step was laying the groundwork. From its portfolio of 400 global properties, Exclusive Resorts reserved a beautiful three-bedroom villa in Santa Rosa, California, the pièce de résistance of which was the pool overlooking the vineyard. The house alone (really the pool) already put us in very good shape to win major points with the junior judges.


Exclusive Resorts members have access to private residences and villas such as this one in Sonoma County with a private pool overlooking a vineyard.

Courtesy of Exclusive Resorts

Then, a representative of All Roads North called to discuss the itinerary. After relaying what our typical daily schedule is (afternoon nap around 2 p.m., bedtime around 8 p.m.), All Roads North got to work plotting out the activities. And before I get into precisely what those activities were, I’ll just say this—they nailed it.

Our first night was unplanned, which was perfect. Our friendly masked concierge Dona (an Exclusive Resorts stay includes a concierge who helps guests settle in and takes care of any personal requests) welcomed us with a tour of the house and a fridge stocked with some grocery store items we had requested (eggs, milk, cheese, wine). We had ordered takeout dinner on the way to the house and were able to settle in and just relax and enjoy the pool. The next morning, per our custom itinerary created by All Roads North, we headed off to Toluma Farms and Tomales Farmstead Creamery, where the kids had so much fun petting the goats and chickens and jumping on the property’s trampoline, while their folks were thrilled to indulge in the exceptional cheese plate that ended the site tour (with required masks for all, except while eating the cheese).

On the second night, Exclusive Resorts arranged a private chef dinner through Vine Dining. Our personal chef (who wore a mask the entire time) was accommodating and understanding when we asked if we could squeeze the dinner in between bedtimes. A mother herself, she remained calm, cool, and collected as she prepared our over-the-top meal while we navigated the chaos of putting our little one to bed, settled our older kiddo in with a movie, and tried to prepare for what would be our first fine-dining experience since before the pandemic.

I actually had to hold back some tears as she set down the first (and my favorite) dish of tuna crudo with avocado wasabi, kumquat marmalade, and a ponzu reduction. Next came a ramen noodle carbonara, Akaushi bistro fillet, and finally, buttermilk panna cotta with minted strawberries and shortcake crumble, all paired with delicious wines. It felt as though I was in a dream.


Amid a pandemic, private dining is a safe way to experience fine dining.

Courtesy of Exclusive Resorts

The next morning we took it slow and eventually made our way to Meadowood Napa Valley, where we experienced the resort’s new wine education course, then had lunch and took a dip in the pool (always need to keep those wee tagalongs happy). Meadowood had recently been added to Exclusive Resorts’s hotel collection and the experience (and others like it) is something the company offers to clients. Sadly, one week after our visit the property was damaged in the Glass Fire and is now temporarily closed (with plans to rebuild and reopen in the future).

The experience we had was uber-luxurious (details below), far beyond what we are accustomed to. But what struck me even more than the luxury was how nice it was to truly let go of the planning and hand over the reins to someone else. When it comes to trip planning, I am admittedly often a control freak, or what I like to call a “martyr control freak” (the worst kind)—I decline help (because I can do it better of course) and then am annoyed that no one is helping. This custom road trip experience forced me to not decline for once. It felt so great to give in. The heightened stress, anxiety, and added responsibilities many of us are experiencing during the pandemic make relinquishing control all the more rewarding. This here tired working mom of two littles truly appreciated the break.

Companies that offer custom road trip experiences

As numerous travelers and families have turned to road trips to satisfy their wanderlust this year, several companies have stepped in to help them plan and execute truly incredible journeys. These are three of the options if you want someone to plan a curated road trip for you.

Exclusive Resorts + All Roads North


Exclusive Resorts and All Roads North will set up custom experiences for clients such as outdoor winetastings.

Courtesy of Exclusive Resorts

The high-touch, uber-exclusive, and totally catered to your needs experience that Exclusive Resorts offers in partnership with custom road trip provider All Roads North is no small investment. Exclusive Resorts is a membership-based vacation club. There’s a one-time initiation fee of $150,000 for a 10-year membership, or $250,000 for a 30-year membership, as well as annual dues of around $20,000 to $40,000 to have access to between 15 and 30 days of lodging (which comes out to about $1,395 per day). All Roads North typically charges a $500 planning fee, which has been waived for Exclusive Resorts members. The planning services include an introductory call to figure out what the members are interested in doing and seeing, and an initial sketch of the trip, followed by a detailed proposal (that covers how much all the activities and inclusions will cost) accompanied by a finalized custom itinerary guide outlining the entire road trip.

While All Roads North tackles all the excursions, outings, tastings, and fine-dining experiences, Exclusive Resorts offers the accommodations and a concierge (who welcomes you and who you have access to via their personal cell phone) to make sure that your stay at your luxe residence is complete—the concierge can order groceries ahead, book private chef experiences, and also help with local reservations for parks and attractions. There are many additional perks and inclusions (for example, members have access to preferred pricing from companies like private car service provider Savoya, yachting club Barton & Gray, and private jet provider Sentient Jet). Members are invited to exclusive events where they can meet other members and exchange travel tips and experiences.



CrushGlobal partners with unique properties such as Tourists in Massachusetts to host its road trippers.

Courtesy of Tourists

CrushGlobal is a travel company founded by travel journalist Kristin Braswell. The company recently launched eight road trip guides across the United States with routes that stretch from Northern to Southern California, from the Northeast to the South. Examples include the Southern Food and History Guide (which includes a guided tour of the birthplace of Dr. Martin Luther King Jr.), the national park–centric Northern California Outdoor Escape, and the Southern California Coastal Wine Lover’s Road Trip for the oenophiles out there. These are pre-set travel guides that you can purchase online starting at $30 each.

CrushGlobal can also create fully customized road trip itineraries that cater to travelers’ specific interests and budgets. The company sends a questionnaire to travelers to get a sense of what they want to see, eat, drink, and experience on their trip and, based on the responses, will set out to create a personalized road trip agenda. For this service, the fee begins at $299.

To build these curated trips, the CrushGlobal team has partnered with unique accommodations such as a stand-alone tree house in a California forest, or a bed-and-breakfast in the heart of Atlanta. They also work with well-known chefs, restaurateurs, sommeliers, and vineyards to offer unique and private dining experiences to guests. Examples include a wine and food pairing in a Sonoma Valley vineyard and a private cocktail flight prepared by two mixology experts in Charleston.

The focus for both the guides and the custom itineraries is on following COVID-19 safety protocols while also supporting minority-owned businesses in each destination. Braswell said that she created these inclusive road trips to provide her audience with an alternative way to travel, support local travel and tourism partners, and highlight Black- and POC-owned businesses along the routes during the pandemic.

Marriott International and Quintessentially


This partnership combines road tripping adventures with luxury stays.

Courtesy of the Ritz-Carlton Bacara, Santa Barbara

Imagine a road trip where you only stay at luxury hotels and resorts. That’s the concept behind Marriott International’s new partnership with the luxury concierge company Quintessentially. The companies have handcrafted several itineraries throughout the United States and Europe where clients stay at properties in Marriott’s luxury portfolio, which includes the Ritz-Carlton, St. Regis Hotels & Resorts, the Luxury Collection, Edition, and W Hotels.

Here are a few examples:

  • “Country to Coastal California,” which includes stays at the Ritz-Carlton, Lake Tahoe; the Ritz-Carlton, San Francisco; and the Ritz-Carlton, Half Moon Bay. The itinerary features kayaking and a private boat trip on Lake Tahoe, a private seaplane ride over San Francisco, and surfing and horseback riding in Half Moon Bay.
  • “Best of the Sunshine State,” with stays at the Miami Beach Edition; the Ritz-Carlton, Naples; and the Ritz-Carlton, Sarasota. Experiences include an Everglades airboat excursion, a private seaplane flight from Miami to Key West, a sunset sail around Naples, and an electric bike tour of downtown Sarasota.
  • “The Rockies,” featuring accommodations at the Ritz-Carlton, Denver; the Ritz-Carlton, Bachelor Gulch; and W Aspen. This itinerary includes hiking the Boulder Flatirons and the Vail backcountry (with a llama), fly fishing in Vail Valley’s Eagle River, and a starlight dinner on Snowmass Mountain.
  • “Rancho Mirage to the Sonoran Desert,” with stays at the Ritz-Carlton, Rancho Mirage; the Phoenician, a Luxury Collection Resort, Scottsdale; and the Ritz-Carlton, Dove Mountain. Horseback riding along the Agua Caliente Indian Reservation, mountain biking in Palm Springs, and experiencing a classic cattle drive in Scottsdale, are all on the agenda.

The road trips start at $15,000 for two guests and include all experiences.
>> Next: The 14 Best Road Trips in the U.S. to Take in 2020

Michelle Baran is the senior travel news editor at AFAR where she oversees breaking news, travel intel, pandemic coverage, airline, cruise, and consumer travel news. Baran joined AFAR in August 2018 after an 11-year run as a senior editor and reporter at leading travel industry newspaper Travel Weekly.
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