Beyond the Table
Where unforgettable places bring people even closer.
At K&S Escapes, we believe the best travel memories aren’t just about where you go—but who you share them with. Whether you’re celebrating a milestone, reuniting with friends, or simply carving out time to reconnect, we design group escapes that are thoughtful, seamless, and deeply personal.
Our custom group trips are built around what matters most: time together. Picture a private villa in the hills of Tuscany, a guided adventure through the streets of Lisbon, or a coastal retreat designed just for your crew. From elegant accommodations and curated experiences to flexible pacing and stress-free planning, we handle every detail so you can be fully present in the moment.
Whether you’re a group of friends, family, or fellow travelers with a shared passion, we’ll turn your vision into a journey that feels effortless and unforgettable.
You bring the people. We’ll bring the experience.
Signature Experience - Tuscany
Where rolling hills, rich wines, and shared meals bring people together
Gather your people for a soul-stirring journey through the heart of Tuscany—designed for those who value great conversation, unforgettable flavors, and time well spent in beautiful places. The Tuscan Table is a private, curated group escape blending vineyard luxury, culinary immersion, and Italian elegance.
Whether it’s a milestone birthday, reunion, or just a long-overdue trip with friends, this escape celebrates connection—with generous tables, golden light, and a pace that invites you to truly savor the experience.
Private Villa Stay in Chianti or Val d’Orcia
Your home base is a luxury villa surrounded by olive groves and vineyards—complete with a private chef, daily breakfast, and space for group gatherings and solo downtime.
Exclusive Wine Experiences
Enjoy behind-the-scenes tours and tastings at premier Brunello and Super Tuscan producers, including private cellar access and guided pairings with local cuisine.
Market-to-Table Cooking Class
Visit a Tuscan market with a local chef, then return to your villa kitchen to prepare a multi-course meal together—followed by a candlelit group dinner under the stars.
Florence Day Trip with Private Guide
Explore Renaissance treasures, artisan shops, and hidden osterias with a local expert—plus free time for personal exploration or curated shopping.
Truffle Hunting & Picnic in the Countryside
Join a local tartufaio (truffle hunter) and his dog for a morning in the woods, followed by a rustic outdoor tasting featuring your freshly found treasures.
Seamless Planning & Personal Touches
From personalized welcome gifts and celebratory meals to airport transfers and activity coordination, we handle every detail so your group can simply show up and enjoy.
Sample Itinerary: 3 Days of The Tuscan Table
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Your group will enjoy a 3-day stay at a luxury Tuscan villa estate in Chianti or Val d’Orcia, surrounded by olive groves and vineyards. The property offers private en-suite bedrooms, panoramic terraces, and a private chef for daily breakfasts and select hosted meals.
Alternative upgrades available at boutique hotels such as Borgo Santo Pietro or Castiglion del Bosco upon request.
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Arrival at Florence Peretola Airport (FLR) or Rome Fiumicino (FCO).
Private luxury transfer to your villa in Chianti or Val d’Orcia.
Welcome reception and aperitivo at the villa, with local wines and seasonal antipasti.
Leisure time to unpack, explore the grounds, or relax by the pool.
Dinner Recommendation:
Osteria delle Tre Panche (Florence) – Known for its truffle-forward tasting menus and cozy elegance, this family-run favorite is a perfect introduction to Tuscan comfort with a touch of refinement.
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Morning:
Guided visit to a local food market (Greve in Chianti or Montepulciano) with your private chef. Taste and shop for ingredients for your cooking class.
Optional espresso stop in a nearby piazza for a classic Italian café experience.
Lunch:
Return to the villa for a hands-on cooking class and group-prepared lunch. Learn to make handmade pasta, seasonal contorni, and traditional desserts like cantucci e vin santo.
Afternoon:
Relax at the villa or enjoy an optional guided visit to a nearby hill town like Pienza or San Gimignano.
Dinner Recommendation:
Villa Chef Experience – Enjoy a multi-course dinner prepared by a local chef at the villa. Dine al fresco under the stars with estate wine pairings and candlelight ambiance. -
Morning:
Breakfast at the villa followed by private transfer to Montalcino or Montepulciano.
Visit two boutique wineries for vineyard walks, cellar tours, and reserve tastings.
Lunch:
Vineyard Lunch at a Brunello Estate – Enjoy a seasonal tasting menu with estate wines and stunning panoramic views of rolling Tuscan hills
Afternoon:
Return to the villa for leisure, packing, or a final swim.
Optional golden hour photography session for group memories.
Private transfer to Florence or Rome for your flight home—or extend your journey with a custom add-on to the Amalfi Coast, Venice, or Lake Como.
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We can extend your itinerary with:
Truffle Hunting in the Countryside: Join a tartufaio (truffle hunter) and his dog, then enjoy a truffle-themed picnic lunch.
Olive Oil Tasting & Estate Tour: Visit a family-run frantoio (olive mill) to learn about cold pressing, taste different varietals, and enjoy a rustic bruschetta lunch.
Pecorino Cheese Farm Visit: Head to Pienza for a guided tasting and tour of a working sheep farm specializing in this Tuscan delicacy.
Chianti Classico Wine Safari: A scenic, off-road tasting adventure through vineyards and medieval hamlets, with stops at boutique wineries and barrel cellars.
Sunset Aperitivo in the Vineyards: Enjoy cocktails and canapés set up exclusively for your group overlooking the hills—ideal for milestone celebrations or casual elegance.
Guided Walking Tour of Siena: Explore the famed Piazza del Campo, the Palio horse race traditions, and the striking Siena Cathedral with a local art historian.
Visit to San Gimignano: Stroll the medieval towers and artisan gelato shops in this UNESCO World Heritage site. Add a local lunch or wine tasting nearby.
Florence Artisan Studio Tour: Go behind the scenes with Florentine leatherworkers, jewelers, or perfumers—ideal for those interested in craftsmanship and shopping.
Private Opera or Classical Concert Evening: Attend a small-group concert at a historic villa or church, with optional pre-performance wine and hors d’oeuvres.
And more!
Why K&S Escapes?
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Custom Experiences, Not Cookie-Cutter Tours – Every trip is built from scratch to reflect your group’s unique interests, travel style, and pace. Whether it’s wine, golf, culture, or celebration—we craft it your way.
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Luxury Without the Logistics – From flights and transfers to villa rentals, curated dining, and exclusive activities, we handle every detail—so your group can focus on relaxing and reconnecting.
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Dedicated Planning & Support – You’ll have one expert point of contact from start to finish, plus access to our team for real-time support during the trip. No call centers. No confusion.
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Room to Be Together—and Space to Breathe – We balance shared moments with downtime, offering options for private rooms, flexible schedules, and experiences that cater to different personalities and energy levels.
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Perks, Access & Insider Privileges – Thanks to our trusted global partnerships, your group can enjoy upgrades, VIP experiences, private tastings, and behind-the-scenes moments not available to the public.
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Clear Communication & Easy Payments – We make planning simple with individual traveler invoices, deadline reminders, and collaborative tools that keep everyone in the loop—without putting all the pressure on the organizer.
Our Signature Travel Design Process
Embark on a bespoke travel journey where every detail is meticulously crafted to your discerning tastes. Schedule a personalized consultation with our expert travel designers and unlock an unrivaled world of luxury exploration. At K&S Escapes, we craft every journey with care, creativity, and a deep understanding of your travel style. Whether you’re dreaming of a romantic escape, a multi-generational adventure, or a food and wine immersion, our process ensures no detail is overlooked.
Book a Consultation
Start by scheduling a one-on-one consultation.
Speak With a Founder
You’ll speak directly with one of our founders who will guide you through inspiration, options, and the vision for your ideal escape.
Receive a Custom Proposal
We’ll craft a beautifully curated proposal. Every element is hand-selected to align with your interests, timeline, and budget.
Refine & Approve
We’ll work together to perfect the details until it feels just right.
Confirm & Book
Once your trip is approved, we handle all the bookings.
Enjoy White-Glove Support
Before, during, and after your travels, we’re here for anything you need—adjustments, recommendations, or just peace of mind. You’ll receive a digital itinerary and access to our destination guides, curated packing lists, and personalized tips.
Start Your Journey With Us
Ready to travel beautifully?
At K&S Escapes, we believe in travel that feels as effortless as it is extraordinary. When you book an appointment with us, you're not just scheduling a call—you’re beginning a collaborative process to design a journey entirely tailored to you.
What This Includes:
A one-on-one consultation with one of our founders
A full discovery of your travel preferences, goals, and priorities
Preliminary destination research and inspiration
A curated proposal that reflects your unique vision
Expert insights on timing, logistics, and luxury touches
This consultation fee secures your spot on our calendar and allows us to devote time, attention, and expertise to the initial design phase of your trip. Should you choose to book your journey with us, this fee is applied toward your total planning package.
Because luxury starts with intention.
Let’s create something unforgettable—just for you.
✺ Frequently asked questions ✺
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Every group trip we plan for you is 100% custom. Whether you're organizing a milestone birthday, a reunion, a golf or wine-focused journey, or a friends' retreat, we create an experience tailored to your group’s preferences, pace, and purpose. No templates—just thoughtful, personalized travel.
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We typically plan custom group trips for 6–30 travelers, but we’re happy to discuss smaller or larger groups depending on your goals and destination. From intimate friend getaways to larger family gatherings or corporate retreats, we’ll design something special.
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Your group trip can include luxury accommodations, all private transfers, curated dining experiences, custom excursions, wine tastings, spa days, golf outings, cultural experiences, group concierge services, and more. Flights and travel insurance can also be included. We’ll tailor everything to your group’s vibe and vision.
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Absolutely. From milestone birthdays and anniversaries to reunions or “just because” escapes, we specialize in turning group travel into a shared story. We can add thoughtful details like private dinners, live music, décor, gifts, photography, and other surprise-and-delight moments.
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Yes. We make the planning process easy by offering split payments, individual traveler invoices, and clear timelines. That way, no one person is responsible for collecting funds, and everyone can manage their own portion.
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That depends on your goals! We frequently plan group travel to destinations like Tuscany, the Amalfi Coast, Portugal, the South of France, Napa Valley, South Africa, and beyond. Whether you're looking for a villa retreat, a food and wine adventure, or an active cultural experience, we’ll recommend destinations that match your group’s style.
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For group travel, we recommend starting the planning process at least 6–9 months in advance, especially if you want to travel during peak seasons or book exclusive villas or experiences. However, we can move quickly for shorter lead times if needed.
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Yes. Every group trip includes ongoing support from our team before and during travel. We’re available to answer questions, help with last-minute needs, and adjust details in real time so your group experience runs smoothly.
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Absolutely. We’ll manage the fine details like room pairings, arrival times, dietary restrictions, and balancing different energy levels within the group. We make sure everyone feels seen, comfortable, and included.
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We offer a high-touch, design-forward approach to group trips that combines luxury, personalization, and seamless execution. You’re not getting a generic group tour—you’re getting a tailored experience with curated properties, immersive experiences, and thoughtful touches throughout. We blend expert planning with a deep understanding of how people travel together.
Make It a Group Affair
Travel together. Celebrate together. Let us handle the details.
Looking for a luxury group trip that blends connection, culture, and unforgettable experiences—without the stress of organizing it yourself? Join one of our expertly curated group escapes designed for travelers who crave meaningful moments, refined itineraries, and a sense of belonging.
Each journey includes handpicked accommodations, exceptional dining, immersive local experiences, and seamless logistics—all arranged by our expert team. Whether you're joining just as a couple, or an entire family branch, you'll be welcomed into a group of like-minded travelers who appreciate authenticity, exploration, and a touch of indulgence.
You just pack—we’ll handle the rest.