diff --git a/packages/main/src/Calendar.ts b/packages/main/src/Calendar.ts
index a362831dd106..7028f9313a37 100644
--- a/packages/main/src/Calendar.ts
+++ b/packages/main/src/Calendar.ts
@@ -78,6 +78,7 @@ type CalendarSelectionChangeEventDetail = {
 type SpecialCalendarDateT = {
 	specialDateTimestamp: number;
 	type: `${CalendarLegendItemType}`;
+	tooltip?: string;
 };
 
 /**
@@ -274,7 +275,7 @@ class Calendar extends CalendarPart {
 	 * @public
 	 * @since 1.23.0
 	 */
-	@slot({ type: HTMLElement })
+	@slot({ type: HTMLElement, invalidateOnChildChange: true })
 	calendarLegend!: Array<CalendarLegend>;
 
 	/**
@@ -409,6 +410,11 @@ class Calendar extends CalendarPart {
 			return isTypeMatch && dateValue && this._isValidCalendarDate(dateValue);
 		});
 
+		validSpecialDates.forEach(date => {
+			const refLegendItem = this.calendarLegend.length ? this.calendarLegend[0].items.find(item => item.type === date.type) : undefined;
+			date._tooltip = refLegendItem?.text || "";
+		});
+
 		const uniqueDates = new Set();
 		const uniqueSpecialDates: Array<SpecialCalendarDateT> = [];
 
@@ -420,7 +426,8 @@ class Calendar extends CalendarPart {
 				uniqueDates.add(timestamp);
 				const specialDateTimestamp = CalendarDateComponent.fromLocalJSDate(dateFromValue).valueOf() / 1000;
 				const type = date.type;
-				uniqueSpecialDates.push({ specialDateTimestamp, type });
+				const tooltip = date._tooltip;
+				uniqueSpecialDates.push({ specialDateTimestamp, type, tooltip });
 			}
 		});
 
diff --git a/packages/main/src/DayPicker.ts b/packages/main/src/DayPicker.ts
index ac3f4bca945d..196cf8b12f42 100644
--- a/packages/main/src/DayPicker.ts
+++ b/packages/main/src/DayPicker.ts
@@ -72,6 +72,7 @@ type Day = {
 	selected: boolean,
 	_isSecondaryCalendarType: boolean,
 	classes: string,
+	tooltip?: string,
 	ariaLabel: string,
 	ariaSelected: boolean,
 	ariaDisabled: boolean | undefined,
@@ -238,6 +239,8 @@ class DayPicker extends CalendarPart implements ICalendarPicker {
 
 			const specialCalendarDate = specialCalendarDates.find(specialDate => specialDate.specialDateTimestamp === timestamp);
 			const specialDayType = specialCalendarDate ? specialCalendarDate.type : "";
+			const specialDayTooltip = specialCalendarDate ? specialCalendarDate.tooltip : "";
+			const unnamedCalendarTypeLabel = specialDayTooltip && !this._isDefaultCalendarLegendType(specialDayType) ? specialDayTooltip : "";
 
 			const isFocused = tempDate.getMonth() === calendarDate.getMonth() && tempDate.getDate() === calendarDate.getDate();
 			const isSelected = this._isDaySelected(timestamp);
@@ -248,16 +251,20 @@ class DayPicker extends CalendarPart implements ICalendarPicker {
 			const isToday = tempDate.isSame(todayDate);
 			const isFirstDayOfWeek = tempDate.getDay() === firstDayOfWeek;
 
-			const nonWorkingAriaLabel = isWeekend ? `${nonWorkingDayLabel} ` : "";
+			const nonWorkingAriaLabel = (isWeekend || specialDayType === "NonWorking") && specialDayType !== "Working"
+				? `${nonWorkingDayLabel} `
+				: "";
 			const todayAriaLabel = isToday ? `${todayLabel} ` : "";
 
 			const tempSecondDateNumber = tempSecondDate ? tempSecondDate.getDate() : "";
 			const tempSecondYearNumber = tempSecondDate ? tempSecondDate.getYear() : "";
 			const secondaryMonthsNamesString = secondaryMonthsNames.length > 0 ? secondaryMonthsNames[tempSecondDate!.getMonth()] : "";
 
+			const tooltip = `${todayAriaLabel}${nonWorkingAriaLabel}${unnamedCalendarTypeLabel}`;
+
 			const ariaLabel = this.hasSecondaryCalendarType
-				? `${todayAriaLabel}${nonWorkingAriaLabel}${monthsNames[tempDate.getMonth()]} ${tempDate.getDate()}, ${tempDate.getYear()}; ${secondaryMonthsNamesString} ${tempSecondDateNumber}, ${tempSecondYearNumber}`
-				: `${todayAriaLabel}${nonWorkingAriaLabel}${monthsNames[tempDate.getMonth()]} ${tempDate.getDate()}, ${tempDate.getYear()}`;
+				? `${monthsNames[tempDate.getMonth()]} ${tempDate.getDate()}, ${tempDate.getYear()}; ${secondaryMonthsNamesString} ${tempSecondDateNumber}, ${tempSecondYearNumber} ${tooltip} `
+				: `${monthsNames[tempDate.getMonth()]} ${tempDate.getDate()}, ${tempDate.getYear()} ${tooltip}`;
 
 			const day: Day = {
 				timestamp: timestamp.toString(),
@@ -268,6 +275,7 @@ class DayPicker extends CalendarPart implements ICalendarPicker {
 				secondDay: this.hasSecondaryCalendarType ? (tempSecondDate as CalendarDate).getDate() : undefined,
 				_isSecondaryCalendarType: this.hasSecondaryCalendarType,
 				classes: `ui5-dp-item ui5-dp-wday${dayOfTheWeek}`,
+				tooltip,
 				ariaLabel,
 				ariaSelected: isSelected || isSelectedBetween,
 				ariaDisabled: isDisabled || isOtherMonth,
@@ -784,6 +792,10 @@ class DayPicker extends CalendarPart implements ICalendarPicker {
 		return (target.className.indexOf("ui5-dp-item") > -1) || (targetParent && targetParent.classList && targetParent.classList.contains("ui5-dp-item"));
 	}
 
+	_isDefaultCalendarLegendType(type: string): boolean {
+		return ["NonWorking", "Working", "Today", "Selected", "None"].includes(type);
+	}
+
 	_getSecondaryDay(tempDate: CalendarDate): CalendarDate {
 		return new CalendarDate(tempDate, this.secondaryCalendarType);
 	}
diff --git a/packages/main/src/DayPickerTemplate.tsx b/packages/main/src/DayPickerTemplate.tsx
index ade2d29cee59..6e9735d12493 100644
--- a/packages/main/src/DayPickerTemplate.tsx
+++ b/packages/main/src/DayPickerTemplate.tsx
@@ -42,6 +42,7 @@ export default function DayPickerTemplate(this: DayPicker) {
 										data-sap-focus-ref={day.focusRef ? "true" : undefined}
 										data-sap-timestamp={day.timestamp}
 										role="gridcell"
+										title={day.tooltip}
 										aria-selected={day.ariaSelected}
 										aria-label={day.ariaLabel}
 										aria-disabled={day.ariaDisabled}
diff --git a/packages/main/src/SpecialCalendarDate.ts b/packages/main/src/SpecialCalendarDate.ts
index 9aa53478b65c..23450a158f2b 100644
--- a/packages/main/src/SpecialCalendarDate.ts
+++ b/packages/main/src/SpecialCalendarDate.ts
@@ -33,6 +33,14 @@ class SpecialCalendarDate extends UI5Element {
 	 */
 	@property()
 	type: `${CalendarLegendItemType}` = "None";
+
+	/**
+	 * Defines a tooltip text for the special date.
+	 * @default ""
+	 * @private
+	 */
+	@property()
+	_tooltip = "";
 }
 
 SpecialCalendarDate.define();
diff --git a/packages/main/src/themes/DayPicker.css b/packages/main/src/themes/DayPicker.css
index eba1f0617ae7..794ab1b9c9e0 100644
--- a/packages/main/src/themes/DayPicker.css
+++ b/packages/main/src/themes/DayPicker.css
@@ -87,6 +87,7 @@
 	font-size: var(--sapFontSize);
 	border: var(--_ui5_daypicker_item_border);
 	border-radius: var(--_ui5_daypicker_item_border_radius);
+	cursor: pointer;
 }
 
 .ui5-dp-item:hover {