Multigenerational Family Resorts in Tuscany: A Guide to Properties That Accommodate All Ages

Our users support our website. Therefore, we sometimes earn affiliate commissions when you click through the affiliate links on our website. Rest assured that all of our recommendations are made whole-heartedly with the intent of helping travelers like you discover the world authentically and responsibly.

Tuscany has long been a region where families come together across generations, not only to admire its celebrated cultural heritage but also to enjoy resort environments that support a wide range of interests, mobility levels, and daily rhythms. This is a place where art, food, and nature intersect in ways that comfortably accommodate both energetic children and adults seeking a steady, unhurried pace. UNESCO recognizes several of Tuscany’s historic centers, including the Historic Centre of Florence and Historic Centre of Siena, underscoring the region’s enduring cultural importance.

Many of Tuscany’s family-oriented resorts are situated between Florence and Siena, offering easy access to world-renowned cities while providing peaceful settings where families can reconnect. These properties typically include multiple accommodation types—from suites to multi-bedroom villas—so families can stay near one another while giving each generation space to unwind. Those planning broader family travel can explore BTA’s Family Travel Resources for additional insight.

Resorts designed for multigenerational travel often feature flexible dining, supervised children’s activities, wellness experiences for adults, and mobility-friendly transportation. This combination reduces the pressure on the trip organizer and allows each traveler to choose activities that match their energy level. For families comparing options across Europe, BTA’s Luxury Resort Collection is an excellent reference.

When to Visit Tuscany with Multiple Generations

Late spring (May–June) and early fall (September–October) offer the most balanced conditions, with temperatures averaging 64°F to 75°F (18°C–24°C) according to the Italian National Tourist Board. These months are ideal for gentle walks through small towns, family cycling routes, olive oil tastings, and afternoons by the pool.

Summer brings higher temperatures—often 86°F to 95°F (30°C–35°C), as documented by CNN—but families tied to school schedules can stay comfortable at higher-elevation properties or those offering indoor recreation. Children often enjoy extended pool time and ice-cream-centric outings in the nearby villages.

Winter (November–March), though cooler, offers an appealing alternative for families interested in museums, cooking classes, artisan workshops, and holiday markets. Many properties maintain full services during this period at more approachable price points.

Where to Stay: Family-Focused Resort Properties

Photo Courtesy of Borgo San Felice Resort

Borgo San Felice (Relais & Châteaux, Virtuoso Partner)

Borgo San Felice combines the feel of a small Tuscan village with amenities that suit families traveling together. Grandparents often appreciate the quiet rooms tucked into the original stone buildings, while parents and children enjoy easier access to the pool and gardens. Golf cart transportation simplifies movement for guests who prefer to avoid hills or long walks.

The property’s children’s program, separate family pool, and wide outdoor spaces allow younger guests to play freely while adults enjoy wine tastings, spa treatments, or leisurely strolls through the estate. Families planning similar hotel stays may appreciate BTA’s Italy Hotel Guides.

Photo Courtesy of COMO Castello Del Nero

COMO Castello Del Nero, Tuscany (Virtuoso Partner)

COMO Castello Del Nero sits quietly in the Chianti countryside, offering villas with private pools, full kitchens, and generous indoor–outdoor living spaces that work exceptionally well for families. It is the type of property where mornings often begin with a scenic walk, followed by activities that each generation can enjoy at their own pace.

Adults will find COMO Shambhala wellness offerings, refined lounges, and culinary experiences rooted in Tuscan tradition. Younger guests benefit from supervised play areas, nature-based explorations, garden visits, and approachable introductions to Italian cooking. Villa pools provide privacy and flexibility, while the main pool supports all swimming abilities. The concierge team specializes in creating itineraries that balance cultural outings with downtime, keeping the experience enjoyable for everyone.

Photo Courtesy of Castello di Casole Belmond

Castello di Casole (Auberge Resorts, Forbes Travel Guide Verified)

Castello di Casole’s restored hilltop estate offers a compelling environment for families who value both comfort and authenticity. The 39 suites feel residential, and the estate’s 4,200 acres create room for children to explore while adults enjoy spa experiences, cooking classes, or wine pairings. Forbes Travel Guide recognizes Auberge Resorts for exceptional service standards, making this property a strong match for families seeking thoughtful, attentive hospitality.

Two pools—one adults-only and one family-focused—allow everyone to enjoy the water comfortably. The kids’ club, offered year-round, provides creative programming, while shuttle services and walking paths accommodate guests with different mobility needs.

Cultural Activities for Mixed-Age Groups

Tuscany offers memorable experiences for families of all ages. Museums such as the Uffizi Gallery and Accademia Gallery are best approached with short, focused private tours that highlight a few essential works, keeping the pace comfortable for grandparents and children.

Siena’s Piazza del Campo is an excellent open space where children can move freely while adults enjoy the surrounding architecture.
The Siena Cathedral is well suited for shorter cultural stops and offers accessible routes for guests who prefer limited walking.

Families often enjoy half-day visits to San Gimignano or Volterra, where gelato shops, artisan stores, and medieval towers offer something for each generation. BTA’s Cultural Immersion Experiences showcase additional options.

Wine estates such as Antinori nel Chianti Classico now offer family-adapted visits, featuring shorter walking paths, engaging storytelling, and non-alcoholic tastings for younger participants.

Inspiring Activities for Families

Here are activities that consistently resonate with multigenerational travelers:

Hands-On Culinary Experiences

Pasta-making workshops, pizza classes, olive oil tastings, and gelato-making sessions engage all ages. Children enjoy the creativity; adults appreciate the cultural depth.

Farm and Garden Experiences

Many estates maintain working vineyards, olive groves, or vegetable gardens. Families enjoy guided garden walks, wildlife spotting for younger guests, and seasonal harvest activities that connect everyone to Tuscany’s agricultural traditions.

Scenic Outdoor Options

Flat, well-maintained walking paths, family-friendly cycling routes, and gentle hillside trails allow grandparents and children to explore at the same pace. Many resorts offer e-bikes for guests seeking additional support.

Artisan Workshops

Ceramics painting, leather crafting, and simple watercolor workshops introduce younger travelers to Tuscany’s artistic heritage while giving adults the chance to observe or participate at their own rhythm.

Village Exploration

Short excursions to nearby towns offer gelato stops, local markets, panoramic viewpoints, and relaxed wandering—activities that appeal across generations.

Dining Considerations for Family Groups

Resort dining tends to be flexible and welcoming for family schedules, with earlier seating times and menus suitable for children and adults alike. Breakfast buffets help accommodate different morning routines, and many properties offer family cooking classes designed to be interactive, educational, and accessible.

Off-property dining requires advance reservations for larger parties, especially for outdoor seating. Restaurants with simple menus—grilled meats, fresh pasta, pizza—tend to be the best fit for mixed-age groups.

Transportation and Accessibility

Family-oriented Tuscan resorts frequently offer shuttle services to nearby towns, reducing the need for multiple vehicles. Private transportation is often the simplest option for groups of six to eight, especially when accommodating grandparents’ comfort and children’s schedules.

Travelers with accessibility considerations will find broad guidance within the European Union Disability Strategy, while museums and cultural sites list detailed accessibility information on their official websites.

Terrain varies across the region. Resorts provide helpful guidance about slopes, steps, and distances so families can plan accordingly.

Practical Notes for Planning

Multigenerational trips often require booking 6–9 months in advance, especially during June–September when connecting accommodations and larger suites are in high demand. BTA’s Italy Travel Planning Resources can help families begin early and plan thoughtfully.

Travel insurance is essential for multigenerational groups, as recommended by the U.S. Department of State. Coverage should include medical evacuation, pre-existing condition protection, and trip interruption.

Clear communication about mobility needs, dietary considerations, and personal preferences enables resorts to prepare effectively. Properties that participate in Virtuoso or Forbes Travel Guide programs maintain detailed guest profiles, supporting smoother return visits.

Budget planning should include transportation, private tours, hands-on activities, and varied dining preferences. Many resorts offer structured family packages with transparent pricing.

Plan Your Multigenerational Tuscany Journey with BTA

Tuscany offers experiences that feel effortless, enriching, and memorable for every generation. BTA’s luxury travel advisors create custom itineraries that blend cultural depth, family-friendly activities, and seamless logistics—allowing families to enjoy meaningful time together without the stress of planning.

👉 Begin planning your custom Tuscany family journey by contacting your BTA Advisor.

—