Trip to Anywhere

Olsen-O'Leary X Luxury Road Trips

From Rancho Mirage to the Sonoran Desert

Explore the Sonoran Desert in the picturesque American southwest during this six-day trip.

Begin in Palm Springs, discovering the unique landscape during a horseback ride and then on a mountain bike trip through the desert. From there, travel to Scottsdale to explore the dynamic culinary and art scene before experiencing the other side of Arizonan culture by partaking in a classic cattle drive. Leave the city environs to descend more than six stories into the earth, accompanied by a geologist, to eyewitness some fantastic cave formations such as stalactites and stalagmites. End your journey in Tucson. The burgeoning street art scene will be detailed by an artist, uncovering the history of the city through its myriad murals. Finally, you’ll have a hand at creating one yourself before traveling home.

The Classic


California is oft associated with the open road, and for a good reason—discover why along this six-night, action-filled scenic journey.

Discover San Francisco’s Northern Californian treasures, from Haight Ashbury to the Golden Gate Bridge to Alcatraz, viewing the famous sunsets from a sailboat and seaplane atop the Bay Area. From there, travel south to picturesque Santa Barbara. Explore the myriad experiences the area has to offer, maximizing the abundance of natural beauty; from relaxing on the beach to kayaking through sea caves to mountain biking. Finally, journey to Laguna Miguel to master the classic California sport: surfing.

An immersive experience in a local artist colony will end your travels with creative inspiration, sure to accompany you long past your travels home.

From Country to Coastal California


The perfect country to coastal road trip, this six-night trip starts against the backdrop of Lake Tahoe, an adventuresome year-round destination immersed in natural beauty. Water-based fun, with kayaking and a boat trip, allow for some rest and relaxation before a city break in San Francisco. There, a private cable car ride will visit significant sites of interest, while seeing the city at sunset from a seaplane will ensure an unforgettable evening. A change of pace ensues just under an hour away in Half Moon Bay. The area boasts five distinct regions, including a host of wineries to explore. You will take advantage of the natural glory on your doorstep with surfing lessons and a horseback riding session on the beach, complete with a photoshoot, to round out this action-packed vacation.

From Deep South to Music City


Travel within America’s culturally-rich south before ending up in Music City USA—Nashville, Tennessee—during this six-night excursion.

Explore some of the natural highlights of Georgia’s beautiful Savannah, via kayak down Ebenezer Creek just outside of the city. Then, visit one of Charleston’s many plantations with a tea taster, refining your own tea preferences, before visiting Charlotte and The Duke’s Mansion. After enjoying a picnic in their extensive gardens, master a skill you can take home: that of barbecue. A classic element of American cuisine, you’ll learn from an experienced pit master the elaborate processes of smoking meat. In Nashville, capitalize on the city’s musical prowess by custom-building a guitar to your preferences. Lastly, taste some fine whiskeys at the Jack Daniels estate in Lynchburg.

Best of the Sunshine State


This six-night trip down the coast of the Sunshine State offers the perfect balance of languid days, adrenaline-filled adventure and cultural discovery. Begin in Miami’s South Beach, soaking up the sun whilst admiring the area’s art deco architecture and vibrant culinary scene. Next, venture deep into the Floridian Everglades, the tropical wetland region that is home to many endangered species. Then, a seaplane will then take you to Key West, the southernmost point of the US, famous for its candy-colored cottages, eclectic Duvall Street and the former home of author Ernest Hemingway. Move on to Naples, where you will spend time on the water and discover the local art scene on chic Third Street South. Finally, complete your journey in Sarasota, exploring the tropical paradise and turquoise gulf from a private yacht charter.

From the Dolomites to Lake Geneva