The Best of the Berkshires
Sample Itineraries
Every Berkshires experience is personal — shaped by who you are, how you like to travel, and what you need most right now. The itineraries below are examples of what’s possible: thoughtfully curated, locally inspired, and designed to help you arrive, unwind, and feel connected.
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From farm-to-table dining to private chefs and boutique wineries, these culinary partners capture the flavor of the Berkshires — local, seasonal, and full of heart.
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Cozy inns, modern retreats, and storied estates — each space offers something distinct, from quiet intimacy to inspired architecture.
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Healing, movement, and mindful restoration. These partners help guests slow down, reconnect, and exhale.
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Galleries, theaters, and makers that showcase the creative soul of the Berkshires — authentic, expressive, and unforgettable
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For the ones who crave fresh air and open skies — guides, outfitters, and places that bring you closer to nature
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Trusted professionals who help second-home owners and long-term guests feel settled, supported, and inspired
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Visionary planners, musicians, photographers, and venues who turn milestones into meaningful moments
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Local storytellers, photographers, and entrepreneurs who help share the spirit of the Berkshires with the world
The Cultural Explorer
For the curious traveler who loves art, architecture, and the stories hidden between the hills.
Friday
3:00 PM — Step off the local train and into a waiting black car — your private driver takes you through winding backroads to a historic inn full of 19th-century charm.
6:00 PM — Dinner at a refined bistro where everything feels handcrafted, from the linen napkins to the local wine list.
8:00 PM — Stroll through a lively downtown with twinkle lights and jazz floating out of old brick buildings.
Saturday
8:30 AM — Breakfast featuring locally baked croissants and wildflower honey.
10:00 AM — Private gallery tour or artist studio visit — you’ll meet the maker, not the crowd.
1:00 PM — Picnic lunch beside a quiet pond surrounded by maples.
3:00 PM — Optional private photography session at a hidden sculpture park or gardens.
6:30 PM — Dinner with live music — candlelight, conversation, and something decadent for dessert.
Sunday
9:00 AM — Coffee and reading by the fire, followed by a late brunch at a sun-drenched café.
11:30 AM — Visit a century-old bookstore before catching your afternoon train home.
The Modern Minimalist
For the couple that craves quiet, simplicity, and spaces that breathe.
Friday
4:00 PM — Check into a Scandinavian-inspired hideaway surrounded by pines and stillness.
6:00 PM — Private chef-prepared dinner — three elegant courses served by candlelight.
8:30 PM — Evening sauna under the stars, followed by a cold plunge and cozy robes.
Saturday
8:00 AM — Slow coffee and local pastries on the porch.
10:00 AM — Private yoga or meditation session — movement guided by the rhythm of nature.
12:00 PM — Drive to a hidden waterfall hike — bring a thermos of tea for the summit view.
2:00 PM — Optional in-home massage or facial using locally made oils.
6:30 PM — Dinner at a modern farmhouse restaurant followed by stargazing in total quiet.
Sunday
9:00 AM — Breakfast and a late checkout — unhurried, restorative, intentional.
The Family Gatherer
For families who want connection, laughter, and little moments that matter.
Friday
4:00 PM — Arrive at a charming home with wide porches, big tables, and plenty of space to play.
6:00 PM — Family-style pizza dinner from a local wood-fired favorite.
8:00 PM — Board games and s’mores by the fire before bedtime.
Saturday
8:00 AM — Pancake breakfast made with local maple syrup.
10:00 AM — Visit a working farm to meet the animals and pick your own snacks.
12:30 PM — Picnic in a hidden field with sweeping mountain views.
3:00 PM — Optional private family photography session to capture the weekend.
6:00 PM — Private chef dinner with candlelit dessert and hot cocoa for the kids.
Sunday
9:00 AM — Late breakfast and slow packing.
10:30 AM — One last stop at a local market for baked goods and souvenirs.
The Romantic Revival
For two people who just need to disappear for a while — no schedules, no stress, just the sound of the woods and the crackle of firelight.
Friday
3:00 PM — Arrive to a tucked-away cottage with old beams, candlelight, and music playing softly.
6:00 PM — Dinner prepared on-site by a private chef — local ingredients, thoughtful pairings.
8:00 PM — Wood-fired sauna and cold rinse under the stars.
Saturday
9:00 AM — Breakfast delivered — fresh bread, local jam, and coffee roasted nearby.
10:00 AM — Scenic drive through winding country roads that end at a hidden waterfall.
1:00 PM — Lunch at a quiet café known only to locals.
3:00 PM — Couples massage followed by an afternoon nap or a soak in a clawfoot tub.
6:30 PM — Sunset wine tasting at a countryside vineyard, then dinner by candlelight.
9:00 PM — Stargazing with a blanket and a bottle of red.
Sunday
10:00 AM — Late breakfast and checkout, leaving time for a detour to an antique barn on the way home.
The Wellness Wanderer
For those seeking peace, clarity, and the simple beauty of slowing down.
Friday
4:00 PM — Step off the train and into a waiting car service — your chauffeur drives through winding backroads to your serene retreat.
5:30 PM — Herbal tea and guided meditation to arrive fully.
7:00 PM — Nourishing dinner of roasted vegetables and seasonal greens.
8:30 PM — Evening sauna, cold plunge, and candlelit rest.
Saturday
7:30 AM — Sunrise yoga and breathwork overlooking mist-covered hills.
9:00 AM — Breakfast featuring local honey, granola, and fruit.
10:30 AM — Guided forest walk to a quiet overlook — journaling or sketching time included.
1:00 PM — Lunch at a rustic farm café with garden views.
3:00 PM — Optional energy session or sound bath with a local healer.
6:30 PM — Dinner al fresco beside a small fire — music, stars, stillness.
Sunday
8:00 AM — Gentle morning stretch and breakfast.
10:00 AM — Visit to a hidden ceramics studio to pick out a keepsake mug before departure.
12:00 PM — Depart lighter, calmer, restored.
Start Planning Your Weekend
These are simply starting points — every detail can be personalized, from chauffeured pickups to private photography sessions, sunset picnics, or guided waterfall hikes known only to locals.
Whatever your pace, purpose, or people — I’ll design a Berkshires experience that feels like it was made just for you.