Tuscany, Italy

Tuscany in winter transforms into a magical landscape, blending breathtaking scenery, rich history, and delectable cuisine. During your stay, you'll find a variety of winter activities and attractions to explore. Cozy up with a glass of exquisite wine during a tasting tour in the renowned Chianti region, or admire iconic landmarks like the Duomo and the Uffizi Gallery in Florence and Siena, where the crowds thin and the holiday lights sparkle. Wander through the festive streets and shops of hilltop towns like Cortona and Montepulciano, where local markets offer seasonal treats and crafts. For the more adventurous, explore the Tuscan countryside on a winter hike or enjoy a day of truffle hunting, followed by a warm and hearty Tuscan meal.

The Residence

Experience an unforgettable winter escape in Tuscany at this exquisite five-bedroom villa, nestled in the breathtaking countryside of Cortona. The villa features three queen-size beds, two single beds, and a bunk bed, providing a cozy retreat for up to 10 guests (8 adults comfortably). With three and a half baths, guests can unwind in style and comfort. Spend your days exploring the local food and wine scene or taking in the stunning panoramic views of the hilltop town, all while enjoying the serene beauty of Tuscany in winter.

Includes

• 7-nights in a 5 bedroom and 3 ½ bathroom villa in Italy
• Bedroom Configuration
• Bedroom #1: two single beds
• Bedroom #2: queen bed
• Bedroom #3: queen bed
• Bedroom #4: bunk beds
• Bedroom #5: queen bed
• Booking and concierge services by Raise Away

Notes

• Nights must be used consecutively in one trip
• At least one person staying at the residence must be 25 years of age
• Winners have 2 years to travel from date of purchase
• A cleaning fee of $500 is required at the time of booking
• Property subject to availability; this property is available exclusively during the winter months, from December through February
• Please note that check-in and check-out is Friday to Friday
• Blackout dates include: the months of March through November; New years and Christmas available for upgrade and subject to availability
• Additional fees and taxes may apply due to local ordinances

Havana Cuba

The Havana neighborhood is a must-see for any traveler. This area is home to some of Havana's most popular attractions including the Capitol Building, Grand Theatre, and National Museum. The architecture in Havana is simply stunning, and you can't help but be captivated by the beauty of it all. The locals are friendly and welcoming, always willing to help show you around. Another great area to explore is Old Havana, or Habana Vieja. This is the historic center of Havana and a UNESCO World Heritage Site. The streets are lined with beautiful Spanish colonial buildings, and there are plenty of museums, churches, and other landmarks to visit. You can easily spend a day or two exploring all that Havana has to offer. No matter what your interests are, you're sure to find something to love in Havana. With its rich culture, diverse neighborhoods, and friendly locals, Havana is a truly unique destination. Whether you're interested in soaking up the sun on the beach, exploring Cuban history and culture, or simply enjoying the nightlife, Havana is the perfect place for you.

The Residence

This newly restored apartment offers 4 bedrooms with en-suite bathrooms, two of which have balconies overlooking the square. Situated in the heart of Havana, it is just a short walk from major attractions like Plaza Vieja, in a genuine neighborhood away from typical tourist areas. The open layout includes a fully equipped kitchen and an adjacent common area with a dining room, living room, and office.

Includes

• 4-night stay in a newly renovated apartment in Havana, Cuba
• Residence is 4 bedroom / 4 bathroom
• Accommodates 4 guests
• Booking & Concierge provided by Raise Away

Notes

• Nights must be used consecutively in one trip
• At least one person staying at the residence must be 25 years of age
• Winners have 2 years to travel from date of purchase
• Property subject to availability
• Blackout dates include: Thanksgiving week, Christmas week, and New Years week

Additional fees and taxes may apply due to local ordinances

Puerto Plata in the Dominican Republic, Puerto Morelos, Riviera Maya, Mazatlán, or Cozumel in Mexico

Escape to paradise on a dreamy all-inclusive getaway designed for just you and your special someone. Choose from five exquisite destinations: Puerto Plata in the Dominican Republic, Puerto Morelos, Riviera Maya, Mazatlán, or Cozumel in Mexico, and revel in a five-night escape that promises unforgettable moments. Indulge in a diverse range of activities that cater to your every whim. Dive into the mesmerizing underwater world with thrilling snorkeling adventures or unwind together at the rooftop bar, savoring your favorite drinks while enjoying live entertainment. For the daring at heart, embark on a thrilling round of golf or indulge in a romantic horseback riding escapade. The all-inclusive package ensures your culinary desires are met with delectable meals and a variety of beverages, including alcoholic options.

The Residence

Indulge in an unforgettable vacation experience with a luxurious stay in a standard suite at our exquisite beachfront resorts in Puerto Plata, Puerto Morelos, Riviera Maya, Mazatlán, or Cozumel. Each location offers spacious and comfortable accommodations, a refreshing pool, and easy access to the best attractions and activities in your chosen destination. Immerse yourself in the perfect blend of relaxation and adventure during your stay in these tropical paradises.

Includes

• 5-night stay in a beach resort
• Choice of destination: Puerto Plata, Puerto Morelos, Riviera Maya, Mazatlán, or Cozumel (subject to availability)
• All food and beverages (alcohol included)
• Accommodates 2 adults
• Booking assistance provided by Raise Away

Notes

• Nights must be used consecutively in one trip
• Winners have 2 years to travel from date of purchase
• Property subject to availability
• Resort fee $100-$250 total (not per day) and varies by location
• Blackout dates include: Thanksgiving week, Christmas week, and New Years week
• Additional fees and taxes may apply due to local ordinances

SEVILLE SPAIN

Seville Spain

Ranked #1 travel destination according to Lonely Planet. The city is known for its rich history, stunning architecture, and authentic culture that includes plenty of tapas tasting and Flamenco dancing. Must-sees include Seville's Central Cathedral, the largest gothic cathedral in the world, and Alcázar Palace and Gardens, which were built over a 100-year span (and made a Game Of Thrones appearance in season five).

One thing when visiting Seville that can't be missed is the Southern Spanish food of tapas. Take a tapas tour or dine in one of the many local restaurants that the city has to offer. Take a night out to grab drinks and watch a Flamenco dancing show, another absolute must-do in Seville.

The Residence

Located in downtown Seville, this vibrant property features two bedrooms and two bathrooms, comfortably sleeping four adult travelers. Being centrally located, this residence is ideal for an easy stroll downtown to one of the many local wine bars or culinary masterpieces Seville has to offer.

Includes

• 4-nights
• Private residence, 2 bedrooms & 2 bathrooms
• Raise Away booking & concierge service
• The property sleeps up to 4 people

Notes

• Nights must be used consecutively in one trip
• At least one person staying at the residence must be 25 years of age
• Winning bidders have 2 years to complete travel from date of purchase
• Property subject to availability
• Blackout dates include; Thanksgiving Week, Christmas Week, New Years' week, and Easter Week.

Additional fees and taxes may apply due to local ordinances

Sonoma Valley, CA

Sonoma Valley is a great destination for family fun, romantic getaways and active adventures. You can explore the local farmers markets for fresh ingredients to create a delicious meal, or take part in one of the many cooking classes offered. Golfers can play on courses ranked among the best in California, while nature lovers can explore breathtaking trails and gardens. Spend an afternoon wine tasting or take a Segway tour of the vineyards, and cap off your day with some live music or theater at one of the many Sonoma Valley venues. Whether you're looking for leisurely outdoor activities, cultural attractions, world-class wineries or simply breathtaking scenery, Sonoma Valley is sure to have something special for you to enjoy. Come and explore the endless possibilities in this beautiful destination!

The Residence

This 2 bedroom 2 bathroom residence in Sonoma Valley is the perfect location for a romantic getaway or an unforgettable family vacation. With its close proximity to the downtown plaza, you won't have to travel far for great shopping, restaurants, and entertainment. The fully stocked kitchen includes all the amenities you'll need to create a delicious home-cooked meal. Relax on the balcony and enjoy a glass of wine as you take in the stunning views.

Includes

• 4-night stay in a luxury 2 bedroom 2 bathroom residence
• Accommodates up to 4 guests
• Conveniently located near the Downtown Plaza
• Concierge & booking services provided by Raise Away

Notes

• Nights must be used consecutively in one trip
• At least one person staying at the residence must be 25 years of age
• Winners have 2 years to travel from date of purchase
• Property subject to availability
• Blackout dates include: Thanksgiving week, Christmas week, and New Years week
• Additional fees and taxes may apply due to local ordinances

Colorado

If you're looking for the perfect mountain getaway, look no further than Colorado. With some of the best ski towns in the country, you'll be spoilt for choice. Choose your destination from classic Vail, beautiful Beaver Creek, or amazing Breckenridge. Each town offers something unique so you can find the perfect place to stay and hit the slopes. After a long day of skiing or snowboarding, relax in one of the area's signature restaurants. Whether you're hitting the slopes or enjoying the après-ski scene, there's something for everyone. And with our luxury mountain home, you'll be able to relax in style after a long day on the mountain.

The Residence

Colorado is the perfect place to spend a winter vacation. Enjoy 4 nights in a luxury mountain home, complete with 2 bedrooms and 2 bathrooms, with all the amenities you need. The residence is conveniently located next to the slopes so you can hit the ground running each day. With plenty of room to entertain, this home is the perfect place to enjoy quality time with family and friends. Our team of concierges will be on hand to take care of all your needs, so you can focus on enjoying your holiday.

Includes

• 4-nights in a 2 bedroom 2 bathroom gorgeous mountain home
• Destination of choice: Beaver Creek, Vail, or Breckenridge
• Ski-in ski-out lodging (varies by location and subject to availability)
• Accommodates up to 4 guests
• Conveniently located near the slopes
• Concierge services offered by Raise Away

Notes

• Nights must be used consecutively in one trip
• At least one person staying at the residence must be 25 years of age
• Winners have 2 years to travel from date of purchase
• Property subject to availability
• Blackout dates include: US Holidays, March 1st - April 15th
• Additional fees and taxes may apply due to local ordinances

Tuscany, Italy

Tuscany in winter transforms into a magical landscape, blending breathtaking scenery, rich history, and delectable cuisine. During your stay, you'll find a variety of winter activities and attractions to explore. Cozy up with a glass of exquisite wine during a tasting tour in the renowned Chianti region, or admire iconic landmarks like the Duomo and the Uffizi Gallery in Florence and Siena, where the crowds thin and the holiday lights sparkle. Wander through the festive streets and shops of hilltop towns like Cortona and Montepulciano, where local markets offer seasonal treats and crafts. For the more adventurous, explore the Tuscan countryside on a winter hike or enjoy a day of truffle hunting, followed by a warm and hearty Tuscan meal.

The Residence

Experience an unforgettable winter escape in Tuscany at this exquisite five-bedroom villa, nestled in the breathtaking countryside of Cortona. The villa features three queen-size beds, two single beds, and a bunk bed, providing a cozy retreat for up to 10 guests (8 adults comfortably). With three and a half baths, guests can unwind in style and comfort. Spend your days exploring the local food and wine scene or taking in the stunning panoramic views of the hilltop town, all while enjoying the serene beauty of Tuscany in winter.

Includes

• 7-nights in a 5 bedroom and 3 ½ bathroom villa in Italy
• Bedroom Configuration
• Bedroom #1: two single beds
• Bedroom #2: queen bed
• Bedroom #3: queen bed
• Bedroom #4: bunk beds
• Bedroom #5: queen bed
• Booking and concierge services by Raise Away

Notes

• Nights must be used consecutively in one trip
• At least one person staying at the residence must be 25 years of age
• Winners have 2 years to travel from date of purchase
• A cleaning fee of $500 is required at the time of booking
• Property subject to availability; this property is available exclusively during the winter months, from December through February
• Please note that check-in and check-out is Friday to Friday
• Blackout dates include: the months of March through November; New years and Christmas available for upgrade and subject to availability
• Additional fees and taxes may apply due to local ordinances