Purpose

This is the playbook we use at Borgo Santolina to design, coordinate, and deliver activities and experiences. The objective is not to fill the calendar. It is to understand what the group wants from the trip, create a thoughtful starting plan, and then keep adapting as the week unfolds. Guests should feel that we know them, that the experiences were chosen for a reason, and that they can change their minds without feeling they have disrupted the operation.

Principles

• Guests should feel seen. An activity is successful when it’s truly enjoyed by the group, not simply well executed.
• Do not over-program. We prefer a slower or balanced pace and leave meaningful unscheduled time. We explain our slow travel philosophy to guests during our pre-arrival planning calls.
• Choose local over generic. We look first for experiences that connect guests to the Val de Merse countryside, its people, food, history, craft, and rhythms.
• Every activity is a hospitality moment. A drink at the bocce court, a picnic for a hike, or a well-timed story can matter as much as the activity itself.
• Make logistics and cost obvious. Guests should understand timing, meeting place, travel, dress, cancellation terms, extra costs, and gratuity expectations before they need to ask.
• Host the experience, even when someone else delivers it. We remain responsible for how the experience feels, make the handoff warm, and solve problems without asking the guest to negotiate with a vendor.
• Safety and fit come before novelty. We do not offer or improvise an experience if we cannot deliver it safely, professionally, and without weakening the rest of the stay.

Roles & Ownership

One person may hold several of these roles, but each responsibility needs a clear owner.

Activities / Experience Owner

• Own the activity catalog, vendor relationships, guest-facing activity information, scheduling standards, pricing and cancellation information, and the quality of the overall experience.
• Maintain the operational notes behind each activity, including why it is appropriate for a guest, execution details, backup plans, and opportunities for personalization.

Guest Journey / Pre-Arrival Host

• Use the pre-arrival planning process to learn the group’s goals, pace, interests, constraints, and must-dos. Activities should not require a second long preference process.
• Carry useful information from the guest record into the activity plan so the guest does not have to repeat it.

Hosts & Activity Leaders

• Deliver staff-led experiences, help guests start self-service activities, make warm partner handoffs, notice opportunities to improve the moment, and record useful feedback afterward.

Manager on Duty

• Own real-time schedule changes, cross-team coordination, vendor failures, service recovery, and exceptions that require judgment or spending authority.

Supporting Teams

Food and beverage, transportation, housekeeping, property operations, and other teams own the parts of the experience they deliver. Activities owns the coordination so the guest experiences one seamless event rather than a set of departments.

Guest & Group Discovery

We use the Guest Pre-Arrival Planning Call in the Guest Journey, Sales & Marketing Playbook as the primary discovery conversation. The activities portion should gather enough information to curate well without turning the vacation into homework.

We usually establish:

• What the group wants from the trip overall and from its time at the property.
• Any ideas, reservations, or experiences they already have booked or want us to book.
• Preferred pace: slow, balanced, or full. We generally discourage a full schedule unless the group clearly wants it.
• Ranked interests such as food and wine, nature, wellness, culture, adventure, craft, history, or sport.
• Whether the group expects to move together or has different interests that may call for parallel plans.
• Children and family dynamics that affect timing, transportation, attention span, or activity choice.
• Special occasions.
• Openness to spontaneous experiences.
• Mobility, stamina, allergies, accessibility needs, or other physical considerations.
• Comfort with drives from the property.
• Must-dos versus nice-to-haves.

Presentation & Refinement

After the planning call, we prepare the proposed itinerary and send it to the primary guest as a live digital link along with a PDF or printable version. We offer a call to walk through it if that is easier for the guest.

The presentation should:

• Explain the reasoning behind the schedule rather than simply listing activities.
• Make clear how the plan reflects what we learned about the group.
• Identify assumptions that still need confirmation.
• Ask a small number of focused questions that will materially improve the plan.
• Make the next step clear.

One round of refinement is ideal. If we need more than two substantial iterations, we review whether our discovery process missed something or whether we are failing to understand the guest’s underlying priorities.

Confirmation

• Send the final itinerary as soon as the guest approves the plan.
• Reconfirm the schedule approximately 10 to 14 days before arrival.
• Review the current schedule again on arrival and continue to update it throughout the stay.

Schedule Design

The schedule is a starting point for the week, not an attempt to maximize the number of activities. For each meaningful scheduled experience, capture internal notes in the activity in Cortile if useful:

• Why was this experience selected for this guest or group.
• What matters most to execution.
• How it connects to a known interest, person, occasion, or goal.
• Any opportunity to surprise or delight the guest without announcing it in advance.

Schedule design guidelines:

• Generally limit the group to one off-property activity per day, depending on its preferred pace.
• Plan multiple on-property days so the week does not become a series of car rides.
• Favor nearby and distinctly local experiences whenever they are as good as a more distant alternative.
• Allow the group to split when interests differ rather than forcing every guest into the same itinerary.
• Balance higher-effort or staff-intensive experiences with easy, self-directed time.
• Leave meaningful unscheduled time and make ad-hoc activities easy to add.
• Plan meal flow deliberately. Protect enough time for lunch and other meals rather than squeezing food between activities.
• Consider allergies, dietary needs, children’s food, high chairs, and other meal-related needs when the schedule affects food service.
• Respect seasonality. Avoid an experience when the season makes it meaningfully worse, or have a credible alternative.
• Check for special events during the stay, including local festivals, markets, races, celebrations, and other one-time opportunities.  Cortile does this automatically and will provide a curated list of suggestions in the guest schedule page.
• Build weather alternatives for experiences that are vulnerable to rain, heat, wind, or other conditions.  Cortile does this automatically.
• For families, consider whether the activity will be fun for the children and manageable for the parents. Avoid back-to-back demanding experiences without time to reset.
• Break up long drives when children, older guests, or the group’s energy make that useful.

Schedule Delivery & Communication

The live digital itinerary is the source of truth. Guests are encouraged to bookmark it so they can always see the current schedule.  At the same time, recognizing many of our primary guests will be older individuals not comfortable with technology, we always provide a PDF over email and a printed schedule while onsite.

Guest-facing schedule information should be available in three useful forms:

• Live digital itinerary: the current schedule, updated whenever plans change.
• In-room activity binder or guide: background on experiences, departure instructions, regional context, dress or etiquette, location, approximate duration, travel expectations, and other information that does not need to be rewritten every time a time changes.
• Daily printed schedule: a simple, current copy posted in an appropriate central location such as the café, dining area, or reception.

If a schedule change materially affects guests, update the digital itinerary, the posted daily schedule, the affected guests, and the internal team. Do not create operational work by reprinting every binder for minor timing changes when the live schedule already governs.

Changes, Cancellations & Real-Time Adjustments

We are deliberately adaptable, especially with staff-led and on-property experiences. The first question is why the guest wants to change the plan. Understanding the reason often makes the best alternative obvious.

When plans change:

• Make a genuine effort to accommodate the request, even when the answer may ultimately be no.
• If the change cannot be accommodated, explain the constraint briefly and propose the best alternatives.
• If the change can be made, identify any cascading effects on meals, transportation, staffing, other activities, or the rest of the group and communicate them clearly.
• Update the internal team immediately and trigger any required schedule, transportation, kitchen, or vendor workflows.
• Update the guest-facing itinerary and daily schedule.

For activities with cancellation or modification limits:

• Tell the guest the policy when the activity is booked.
• Show the policy in the activity brief or itinerary.
• Proactively remind the guest before the cancellation window closes when the cost is meaningful.  If a massage must be cancelled 12 hours in advance, 14 hours before the massage, find or message the guest reminding them of their upcoming massage and confirm they’d like to continue with it.
• Keep both the vendor’s formal policy and our real-world experience with that vendor in the vendor profile.

We try to predict changes before the guest has to ask. Check the weather at least daily when activities are weather-sensitive, and watch the group’s energy. If a group requested a full schedule but is clearly exhausted, propose a lighter day before the problem becomes obvious.

Under our current broader guest-recovery policy, managers may approve up to €1,000 when a guest is genuinely surprised or disappointed and a thoughtful recovery is warranted. The guest should never be made to feel at fault for asking to change the week.

Pricing, Inclusions, Gratuities & Extra Costs

Self-service and staff-led activities that are part of the Borgo Santolina stay are generally included unless we have clearly said otherwise. Partner-delivered activities and off-property experiences are often additional and should be presented with complete pricing before the guest commits.

Payment & Credits

• For pre-planned tours and other discrete paid activities, collect payment before arrival when practical.  We typically create a single invoice for the entire week to reduce guest paperwork.
• Restaurants are normally paid by the guest directly unless we have a specific arrangement with the restaurant. Explain Italian tipping culture and suggestions.
• When plans change, show unused funds, credits, reallocations, and balances clearly.
• If an additional balance is due, collect it before the activity through an approved payment method. If an approved card on file is available, offer to use it rather than creating another payment step.

Current working rule for card fees on paid activities:

• If our negotiated vendor economics provide enough margin or commission, we absorb the card fee.
• If they do not, first ask the vendor whether the price can be adjusted to offset the fee.
• If the vendor will not adjust the price and the activity is more than €5,000, offer direct vendor payment or a transparent card-fee markup rather than hiding the cost.

Gratuities for 3rd Party Providers

Gratuities are a friction point because guests often do not know whether a tip has already been handled or is expected.

• Tell the guest in advance whether gratuity is included, not expected, or their responsibility.
• Repeat the expectation in the activity brief or shortly before the experience when there is any chance of ambiguity.
• When we have paid the gratuity on the guest’s behalf, confirm with the provider that it has been received so the guest is not left in an awkward tipping moment.
• Ask preferred partners to acknowledge a prepaid gratuity naturally when useful, without turning the interaction into a discussion about money.

The accounting treatment of commissions, card fees, refunds, and vendor settlement is covered in Finance & Administration.

Experience Delivery Models

The common thread across all five models is hosting. For us, a hosted experience means that we stay responsible for how it feels even when a partner delivers the activity. Hosting may include setting context, making a warm introduction, preparing the guest well, arranging transportation, anticipating a favorite drink or picnic, staying close enough to catch problems, and solving issues without asking the guest to manage the vendor.

On-Property - Self-Service

• Make the activity obvious and easy to start. Equipment should be where guests expect it whenever practical, such as bocce balls at the bocce court.
• If equipment must be requested or checked out, make the process simple and approachable.
• Give clear timing, access, return, cleaning, etiquette, or safety instructions when needed.
• Prepare selected activities so they feel inviting rather than merely available. For example, a firepit can already be lit with blankets and something appropriate to eat or drink.
• Staff should suggest self-service activities when they fit the guest’s mood and provide a quick introduction when useful.
• Look for contextual ways to improve what the guest is already doing, such as bringing wine to the bocce court or packing a picnic for a hike.

On-Property - Staff-Led

• Use clear but flexible start and end times.
• Make the meeting point and late-arrival plan obvious.
• If someone is late, message them when useful rather than leaving the group or guest uncertain.
• Use guest contact information already maintained in the approved CRM or messaging system.
• When possible, give the experience a story, point of view, or educational thread rather than simply supervising an activity.
• Schedule staff-led activities only when the team has the skill and capacity to deliver them without weakening other guest service.

On-Property - Partner-Led

• Confirm start and end times, meeting place, provider, and late-arrival plan.
• Make a warm introduction and handoff.
• A host is generally present when that improves the experience and remains accountable for quality even when not physically present throughout.
• Work with the provider in advance on opportunities to personalize or enhance the experience.
• Do not make the guest negotiate, coordinate logistics, or solve service problems directly with the provider.
• No sales pitches or opportunistic upselling to our guests.

D. Off-Property - Partner-Led

• We manage the logistics and remain the guest’s point of contact.
• Give the guest a written brief in advance with the experience overview, meeting and departure details, dress or etiquette, approximate duration, travel time, cost, gratuity expectations, and cancellation terms.
• Buffer transportation generously enough that the guest does not arrive stressed.
• Maintain backup transportation options. Our working approach is to call alternative preferred providers first and use a dependable rental van only as a last resort when staff driving is legally, safely, and operationally appropriate.
• Enhance selected off-property experiences with a thoughtful property gesture when it fits naturally.

Off-Property - Staff-Led (Rare)

We lead an off-property activity ourselves only when all of the following are true:

• It is an unusual situation, such as a vendor failure, or a specific experience we can genuinely deliver better ourselves.
• There is no better partner alternative.
• We can deliver it without materially reducing the guest experience elsewhere.
• The burden on the team is reasonable.
• The activity and any transportation are safe, lawful, and fully covered by the required insurance.

Vendor Scheduling & Relationship Management

We treat strong local partners as an extension of the guest experience, while keeping the guest relationship with us.

Vendor records live in our CRM (Cortile), and should include:

• Preferred-partner tier and status.
• Primary and backup contacts.
• What the provider does well and for which guests it is a good fit.
• Current pricing and our negotiated economics.
• Payment terms.
• Cancellation and modification policy.
• Our real-world experience with the provider’s flexibility when it differs from the written policy.
• Gratuity expectations and whether we normally handle them.
• Specific providers or guides to request or avoid when the business has multiple people.
• Operational notes, meeting points, transportation requirements, and known failure points.

With every booking, reconfirm at minimum:

• Cost.
• Cancellation and modification policy.
• Specific provider or guide when relevant.
• Date, start time, duration, and meeting point.
• Transportation responsibility.
• Any guest-specific requirements or personalization the partner has agreed to.

We invest in preferred relationships. Our partner playbook describes partner tiers and a recognition program that can include thank-you notes, birthday cards, holiday gifts, or other thoughtful recognition. The point is not a formal loyalty scheme; it is to deepen relationships with the small number of people we trust with our guests.

Always give partners feedback. Share praise when an experience went especially well and direct, useful feedback when something could improve.

Quality Control & Training

What We Review

• Did the activity fit the guest and the reason it was selected?
• Was the schedule accurate and easy to understand?
• Were cost, cancellation, transportation, dress, and gratuity expectations clear?
• Did the guest ever have to coordinate or negotiate directly with a vendor because we failed to own the process?
• Did transportation and meal timing work without rushing the guest?
• Did the partner or staff member deliver the expected tone and quality?
• Were changes handled early and calmly?
• Was there an opportunity to personalize or enhance the experience that we missed?
• Would we confidently recommend the activity again?

Post-Activity Feedback & Continuous Improvement

• After any meaningful activity, note execution issues, guest reactions, and opportunities to improve the experience.
• Record guest-specific feedback in the CRM when it is useful for the remainder of the stay or a future visit.
• Update the activity-specific checklist, playbook, or master activity record when the lesson is operational rather than guest-specific.
• Review activity and vendor notes quarterly. Improve, redesign, replace, or stop offering under-performing experiences.
• Use repeated guest requests as signals for new experiences, but do not add an activity simply because it sounds interesting.

Training

Team members involved in activities should understand:

• Our activity philosophy and why we avoid over-programming.  They are able to explain slow travel.
• The current activity list and which experiences are included versus extra.
• How to use the guest record and live itinerary.
• How to brief guests without overwhelming them.
• How to make a partner handoff feel hosted.
• How to handle late guests, weather changes, vendor delays, cancellations, and group splits.
• When to improvise and when not to.
• Pricing, cancellation, gratuity, and service-recovery authority relevant to their role.
• When safety, insurance, transportation, or legal questions require escalation.

Scenario practice should include a vendor no-show, sudden rain or extreme heat, a guest who wants to cancel after the deadline, a child who is exhausted, a late guest, a group that wants to split, an experience that disappoints, an unclear gratuity situation, and a last-minute request that the team cannot safely deliver.