Wine, Ski or Sea for 6+

Choose your perfect escape between Tuscany, Whitefish, Punta Cana, or St. Martin.

Are the sprawling vineyards of Tuscany on your bucket list? Does the idea of the outdoor paradise of Montana get your heart racing? Or are pristine Caribbean beaches and tropical breezes calling your name? This package is for you! You choose your destination and then leave the rest to your dedicated concierge team! Your group of six to eight (depending on destination) will spend four to seven nights (depending on destination) on a vacation you’ll remember forever.

Choose Italy and spend eight days, seven nights in a beautiful and traditional three-bedroom, two-bathroom Tuscan villa. Indulge in la dolce vita with a stay in an authentic Tuscan villa perched over the rolling hills of Tuscany. Experience true Tuscan living with alfresco lounging and dining, outdoor stone oven, and private pool with sweeping views. Discover the best of the region with Cortona less than 30 minutes away and optional wine tasting or Florence day trip.

Escape to northern Montana's coveted Whitefish for a luxurious five-day, four-night retreat. This upscale residence features three bedrooms and three bathrooms—two with king beds and one with a twin-over-king bunk—plus a versatile sleeping loft with two twin-over-twin bunk beds, accommodating up to 11 guests in comfort. Perfectly situated to explore Whitefish's many attractions, this modern home boasts a generous deck, private hot tub, and alfresco dining area with a BBQ grill. Revel in the breathtaking beauty of Glacier National Park, indulge in a variety of mountain and water activities, and savor award-winning cuisine and vibrant nightlife. Your Whitefish adventure awaits.

Answer the call of the Caribbean with two distinct luxury villa experiences. In Punta Cana, Dominican Republic, spend five nights for up to eight guests in a spacious four-bedroom, four-bathroom private villa located within an exclusive resort. Relax with a private pool and hot tub, daily housekeeping, breakfast service, and your own golf cart to explore the resort. Enjoy access to pristine beaches, championship golf courses, tennis courts, beach clubs, and gourmet dining.

Or escape to the chic island of St. Martin for a sophisticated Caribbean retreat. Enjoy a five-night stay for up to eight guests in an elegant four-bedroom private villa located in the exclusive Terres Basses neighborhood. This beautifully designed residence offers seamless indoor-outdoor living, a private pool, expansive terrace, and serene tropical surroundings just moments from the island’s best beaches. Known for its unique blend of French and Dutch culture, St. Martin invites you to indulge in world-class dining, vibrant beach clubs, and laid-back island luxury.

Experience Includes (Winner Chooses One)

TUSCAN BEAUTY

• 8 days, 7 nights
• 3-bedroom, 2-bathroom villa for 6 people
• Private chef dinner for 6*
• Private pool and gardens overlooking the rolling hills and valley

Bedroom Configuration:

• Master Bedroom: Double bed, private bathroom
• Second Bedroom: Double bed, shared bathroom
• Third Bedroom: 2 Twin beds, shared bathroom

WONDERFUL WHITEFISH MONTANA

• 5 days, 4 nights
• 3-bedroom, 3-bathroom newly constructed condo for 6 people
• Unwind and indulge in the private hot tub
• Whitefish Ski Resort is a 15-20 minute drive away
• 30 minutes from Glacier National Park and minutes from downtown Whitefish
• Access to shared neighborhood amenities including fire pits, a playground, and dock access

Bedroom Configuration:

• Primary Bedroom: King bed, private bathroom with shower
• Guest Bedroom: King bed, private bathroom with shower/tub combination
• Guest Bedroom: Twin-over-King bunk beds, private bathroom with shower
• Other Sleeping Area/Sleeping Loft: 2 Twin-over-Twin bunk beds

PALMS OF PUNTA CANA

• 6 days, 5 nights
• 4-bedroom, 4-bathroom private resort villa for up to 8 guests
• Located inside the exclusive Punta Cana Resort & Club
• Private pool, hot tub, and shaded outdoor dining terrace
• Daily housekeeping and breakfast service included*
• Complimentary golf cart for exploring the resort
• Access to beach clubs, world-class golf, tennis courts, restaurants, and bars
• Short drive to pristine beaches, marina, and Puntacana Village

Bedroom Configuration:

• Bedroom 1: King bed, en-suite bathroom, walk-in shower, soaking tub, A/C
• Bedroom 2: King bed, en-suite bathroom, walk-in shower, soaking tub, A/C
• Bedroom 3: Queen bed, en-suite bathroom, walk-in shower, A/C
• Bedroom 4: 2 Double beds, en-suite bathroom, walk-in shower, A/C

TERRES BASSES POOL VILLA (ST. MARTIN)

• 6 days, 5 nights
• 4-bedroom private villa for up to 8 guests
• Located in the exclusive Terres Basses community
• Private pool and expansive outdoor living spaces
• Seamless indoor-outdoor design with covered terraces and lounge areas
• Close proximity to Baie Rouge, Plum Bay, and Long Bay beaches
• Short drive to world-renowned dining, beach clubs, and nightlife

Bedroom Configuration

• Bedroom 1: King bed, en-suite bathroom, A/C, ocean view
• Bedroom 2: King bed, en-suite bathroom, A/C, ocean view
• Bedroom 3: King bed, en-suite bathroom, A/C, ocean view
• Bedroom 4: 2 Twin beds, en-suite bathroom, A/C, ocean view

Details

• Winner has 12 months to book and 24 months to use. If the booking window has expired, the trip is too.
• This package is non-refundable and non-transferable. Subject to availability.
• Nights must be used during one stay.
• Primary guests must be at least 25 years of age.
• Winner is responsible for a refundable damage deposit due at redemption.
• If property, activity, or service is no longer available at the requested time of stay, a substitute property, activity, or service of equal or greater value will be provided.
• The provider is not liable for providing alternative accommodations if the preferred travel dates are unavailable.
• If an included activity or service is no longer available at the time of your requested stay, the provider reserves the right to amend or substitute the inclusion.
• If you choose to book and travel within 14 days of arrival, the provider cannot guarantee availability or trip planning services.
• Tuscany: Travel Saturday to Saturday year-round with the exception of Christmas and New Year weeks. Blackout dates are the weeks of Christmas and New Years. *Food and beverages at extra cost, cost of groceries is not included.
• Montana: Bookable between August 14 - June 26. Blackout dates are President's Week, June 27 - August 15, Thanksgiving, Christmas & NYE.
• Punta Cana: Bookable between May 1 and December 19 with the exception of Thanksgiving week. Please inquire for details. *Please note, breakfast service does not include the cost of groceries, which will be charged additionally. Use of resort facilities including golf courses, tennis courts, and the fitness center may incur additional fees.
• St. Martin: Blackout dates are April 15 - December 15 and major holidays. Daily housekeeping services included (except on Sundays & public holidays). Staff gratuity is not included.