Buckle up — this isn't your typical road trip. Hike, shop, dine, and sail your way through New England with a custom itinerary from our partner, All Roads North. Immerse yourself in Maine's seafaring history while hauling traps on a lobster boat, drive up Mount Washington on the famed 7.6-mile Auto Road, detour in Vermont to meet and work alongside local cheese and maple syrup producers, and more. Travel south on Route 100 following the Mad River Valley through the Southern Green Mountains to the far western edge of Massachusetts. You’ll get your culture fix in the Berkshires, home to acclaimed institutions including Tanglewood, the Clark Institute and Mass MOCA. Stay in hotels and inns delivering five-star New England hospitality along the way.

Discover the heart and soul of the Kentucky Derby with an exclusive Members-only weekend. From the moment you land in Louisville, embrace the epitome of Southern hospitality with a private transfer to The Brown Hotel. Begin the adventure with an enchanting sunset farm tour, featuring a hands-on Mint Julep class and an elegant Southern dinner under the stars. Enhance your Derby wardrobe and craft your own hat masterpiece at a unique millinery session led by a renowned Derby milliner. Experience the electric atmosphere of Oaks Days from a private suite at Churchill Downs, offering gourmet dining and premium beverages, before immersing yourself in the pinnacle of the weekend — Derby Day.

Experience The Ranch’s award-winning, highly structured, and results-oriented wellness program and retreat at its first East Coast property. Spanning 200 acres of history, this private lakefront estate is less than an hour from New York City and offers an immersive experience like no other. With a focus on results and structure, the award-winning wellness program provides options for either a 3- or 4-night escape. Each day is thoughtfully curated with The Ranch's renowned activities, including mountain hikes, dynamic strength training classes, rejuvenating yoga sessions, deep tissue massages, and nourishing organic, plant-based meals. Tailored to individual abilities and needs, the program delivers noticeable improvements in both physical and mental well-being.

Cruising through New England aboard XOXO, a stunning 118-foot custom yacht, is the only way to drink in the culture of Newport, the history of Nantucket, and the relaxed local feel of Martha’s Vineyard. XOXO provides ample entertainment, including a deck jacuzzi for enjoying the scenery with your favorite drink. Your personal chef awaits, ready to treat you to succulent freshly caught lobster or a steaming bowl of aromatic clam chowder as you navigate the islands. Whether you prefer the lively energy of bustling marinas or the tranquil seclusion of hidden inlets, the choice is yours to make, creating a truly tailored experience.