To Tuscany

What To Tuscany does

To Tuscany is a UK-based, founder-owned villa rental agency that curates and intermediates private holiday villa bookings across Tuscany and Umbria, Italy. Founded in 1998 by Sean and Sabina Caulfield, who relocated from the UK to Tuscany and converted a restored Chianti winery into their first rental property, the company has built a portfolio of 266+ private pool villas spanning more than 10 regions (Arezzo and Cortona, Florence and Chianti, Grosseto and Maremma, Lucca and Viareggio, Pisa and Valdera, Siena and Chianti, Pistoia and Montecatini Terme, Livorno and Coast, plus Orvieto, Perugia, and Viterbo in Umbria/Lazio). The business serves leisure travellers — primarily families, couples, luxury travellers, and small groups — through a direct-to-consumer model with no OTA resellers in the distribution chain.

The core product is a multilingual villa search and booking platform (to-tuscany.com, plus dedicated German, Polish, Dutch, and French country domains) that allows guests to filter by date, party size, region, and amenities, view villa floor plans and photo galleries, and submit enquiries to a team of villa specialists available seven days a week in UK and US hours. Trust signals are institutionalised through a Feefo Platinum Trusted Service integration (4.6/5 across 18,948 guest reviews, with 10 consecutive years of Feefo Trusted status), ABTOI membership, and a 2026 Condé Nast Traveller Readers' Choice Awards nomination. The company supplements its core booking revenue with concierge/experiences services (private chefs, wine tastings, cooking classes, wellness), a curated travel journal of 100+ editorial articles, and a weekly email newsletter.

Revenue is generated through commissions on completed villa bookings, with pricing set per villa per week on a seasonal basis (sample villas range from ~$3,105/week off-peak to $21,465+/week in peak season, plus a tourist tax of approximately €2 per person per night). The company maintains an 11–50 headcount and is headquartered in Whitstable, UK, with on-the-ground operations in Tuscany where the team conducts twice-yearly property visits. To Tuscany carries no external institutional investors or parent company and operates as an independent, profitable lifestyle business.

Name

To Tuscany

Legal name

To Tuscany Ltd.

Website

https://to-tuscany.com

Company type

Private

Founded year

1998

Operating status

Operating

Headcount range

11–50 employees

Short description

To Tuscany is a UK-based, founder-owned direct-to-consumer villa rental agency curating 266+ private villas across Tuscany and Umbria, Italy. Founded in 1998, it serves families, couples, and luxury travellers across European and US markets via a five-language website, personalised villa specialist support, and concierge experiences.

Ownership category

akta.pro rank

Product category

Villa Rental Services / Leisure Accommodation

NAICS

Travel Agencies (561510), Other Traveler Accommodation (72119)

SIC

Real Estate Agents & Managers (For Others) (6531)

akta.pro primary industry

Luxury Villa Resorts & Branded Villa Communities (THAMAEAI)

akta.pro secondary industry

Resort & Branded Residence Vacation Rental Management (BPAJAIAE)

Keywords

• Villa rentals Tuscany
• Private pool villas
• Tuscany holiday accommodation
• Umbria villa bookings
• Curated villa specialist

Headquarters

HQ city

Whitstable

HQ country

United Kingdom

HQ region

Europe

Offices2 records

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure

Revenue model

1. Villa Rental Booking Commissions: To Tuscany earns revenue by facilitating villa rentals between property owners and travellers. The company represents a curated collection of villas across Tuscany and Umbria, earning commissions on completed bookings. Pricing is per-villa, per-week, with rates varying by season, villa size, and features. The company takes a service fee and acts as an intermediary, providing guest support, villa matching, and on-ground coordination.

Pricing tiers

Go-to-market motion1 record

Distribution channels3 records

Marketing channels7 records

Core offering

To Tuscany is a villa rental travel agency that curates and facilitates bookings for 266+ private villas across Tuscany and Umbria, Italy. The company connects property owners with leisure travellers through a multilingual website and personalised villa specialist support, offering weekly villa rentals with seasonal pricing, an Feefo-integrated review platform, and supplementary concierge services (private chefs, wine tastings, cookery classes, car hire, travel insurance).

Product overview

To Tuscany operates as a villa rental marketplace and travel services company offering over 266 private villa properties across Tuscany and Umbria, Italy. The core product is the villa rental platform where guests can search and book accommodations ranging from apartments to luxury villas. The portfolio includes specialized villa types (family villas, luxury villas, romantic retreats, Chianti villas, coastal villas, dog-friendly villas, agriturismo) and properties with specific amenities (private pools, heatable pools, heating included). Supporting services include a Villa Finder enquiry form with personalized Villa Specialist recommendations, To Tuscany Experiences/concierge services featuring wine tastings, cooking classes, and private chefs, a Travel Agency service for car hire and insurance, and an editorial Travel Guide/Journal with local content. The company also offers an email newsletter for ongoing customer engagement.

Differentiator

Problem solved

Functional benefit

Products and services

• Villa Rentals in Tuscany and Umbria Holiday villa rentals across Tuscany and Umbria, Italy, offering a curated portfolio of 266+ private villas in categories such as family, luxury, romantic, Chianti, coastal, dog-friendly, agriturismo, apartments, and properties with private pools. Pricing is per villa per week with seasonal variation. Intended for leisure travellers and groups seeking self-catering villa accommodation.
• Villa Finder Enquiry Form / Villa Specialist Consultation Personalised villa recommendation service where Villa Specialists assist guests in finding suitable properties based on preferences such as group size, region, villa type, and amenities. Available 7 days a week via enquiry form and toll-free phone (1-929-445-5929). Targets travellers seeking tailored villa recommendations before booking.
• To Tuscany Experiences / Concierge Service Curated local experiences and concierge services including wine tastings, cooking classes, private chefs, and activities to enhance villa stays. Recommended add-on to villa bookings for guests seeking authentic Tuscan experiences.
• Travel Agency Services Travel planning assistance including villa selection guidance, car hire recommendations, and travel insurance for villa holiday guests. Provides one-stop travel support alongside villa booking.
• Weekly Email Newsletter Weekly newsletter delivering villa recommendations, travel tips, and Tuscan inspiration to subscribers. Subscription-based engagement channel for prospective and past guests.

Quantifiable outcome

• 4.6 out of 5 aggregate review score across 18,948 guest reviews on Feefo
• +3 more outcomes

Named customers10 records

Segments5 records

Ideal customer profiles5 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration3 records

Feature3 records

Partnerships

Five partnerships are on record, tiered core and minor.

• ABTOI (Association of British Travel Organisers to Italy)coreStrategic or Co-development PartnerABTOI membership reflects To Tuscany's commitment to professionalism, transparency, and high standards of service as an established Italy travel specialist. ABTOI works closely with Italian tourism bodies, keeping members informed about regional developments and strengthening local relationships. For To Tuscany, this membership reinforces their positioning as a trusted UK-based Italy specialist and provides networking, industry recognition, and access to Italian tourism intelligence.
• FeefocoreTechnology or IntegrationFeefo is the independent review platform used by To Tuscany to collect and display guest reviews across villa listings. To Tuscany holds Feefo Platinum Trusted Service status with 4.6/5 aggregate score from 18,948 reviews. Feefo's review widget is integrated across the website and serves as a key trust and credibility signal for prospective guests.
• Cantina FregnanminorStrategic or Co-development PartnerCantina Fregnan is a boutique winery near Bibbiena, Casentino, known for sparkling wines made using the Metodo Classico. The winery is within walking distance of Tenuta Seriole 10, and guests at To Tuscany villas are recommended to enjoy wine tastings or aperitivo at this venue. This partnership enhances the guest experience at select villas.
• Alessio Berrioni (Private Chef)minorStrategic or Co-development PartnerAlessio Berrioni is a private chef offering fine dining experiences at To Tuscany villas. He holds a hotel management diploma from Assisi, has worked in Michelin-starred restaurants under chefs including Alain Ducasse and Gordon Ramsay, and provides smoked haddock and other recipes featured on the To Tuscany journal. Chef services are recommended to villa guests seeking private dining experiences.
• Susan Gardner (Wellbeing Expert)minorStrategic or Co-development PartnerSusan Gardner is a meta-wellbeing expert who collaborated with To Tuscany to create wellbeing content for the travel journal, including the '15 Ways to Focus on Your Wellbeing This Holiday' article. This partnership positions To Tuscany as offering holistic travel experiences beyond accommodation.

Scale indicators4 records

Recent moves6 records

Expansion highlights6 records

Direct peers

• Quality Villas: Family-run villa rental agency curating luxury villas across Europe. Comparable in business model (commission-based intermediary, hand-picked inventory, family business ethos) and premium leisure customer base.
• Oliver's Travels: UK-headquartered curated luxury villa rental agency focused on Europe and the Mediterranean. Directly comparable to To Tuscany in customer base (UK/European luxury travellers), curated independent-villa model, and personal villa specialist service.
• The Thinking Traveller: Boutique UK-based specialist curating luxury villa holidays in Italy (Sicily, Puglia, Sardinia). Comparable in operating model — hand-picked villas, in-country teams, concierge-led service, and a focus on quality over volume.
• CV Villas: Long-established UK villa rental agency offering curated villas across Italy and the Mediterranean. Overlaps with To Tuscany on Italian villa rentals, customer demographic (UK/European leisure travellers), and commission-based intermediary model.
• Tuscany Now: UK-based villa rental agency specifically focused on Tuscany. Most directly comparable peer in terms of geographic specialism, portfolio size, and villa curation approach.
• BoutiqueHomes: Curated collection of boutique and luxury villas, apartments, and chalets worldwide. Comparable in curated-villa approach, focus on design and quality, and direct-to-consumer booking model.
• Italian Villas Direct: UK specialist offering privately owned villas across Italy. Overlaps with To Tuscany in Italian villa specialism, UK customer base, and curated booking service.

Broad incumbents

• Airbnb: Global vacation rental marketplace with a substantial Tuscan villa inventory. Competes for the same end customer but at much larger scale, lower curation, and a self-serve model rather than specialist villa advisory.
• Vrbo: Major vacation rental marketplace (part of Expedia Group) with significant Italy villa supply. Operates as a broad incumbent competing for villa bookings via self-serve listings rather than curated advisory.
• Booking.com: Global OTA with growing vacation rental and alternative accommodation inventory. Competes with To Tuscany for short-stay bookings in Italy, especially via its alternative accommodation verticals.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/ToTuscany
• Facebookfacebook.com/ToTuscany

Compliance1 record

Revenue estimate

Valuation estimate

Number of profiles

Profiles2 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about To Tuscany