Your Ultimate 2025 Holiday Getaway: 7 Festive Trips to Book Now

Each week, we handpick Pineapple7 exclusives for you to consider. This week, we have curated several trip ideas for anyone who wants to celebrate the holidays on their own terms, filled with new traditions and special memories. When you book with us, you'll unlock VIP perks and amenities you won't receive on your own. Offers are time-sensitive and have limited availability. Blackout dates and minimum stays may apply.

Casa de Campo, La Romana, Dominican Republic

Casa de Campo, La Romana, Dominican Republic

Celebrate the holidays with your family at this legendary resort, known for its extensive sports facilities and luxurious amenities. During the festive season, the resort comes alive with magical events and dedicated programs like Toddlers ‘N’ Casa and Bonche 4 Teens, ensuring fun for every age. Immerse yourselves in the holiday spirit with a Christmas Tree Lighting Ceremony, holiday markets, and festive beachside parties perfect for creating new family traditions. Enjoy VIP perks including daily breakfast and resort credit. All-Inclusive option is available too.

Gems of Southeast Europe Christmas Markets, AmaWaterways

Cruise through the heart of Europe during the most festive time of year and experience the timeless tradition of its magical Christmas Markets! Colorful market stalls brimming with whimsical handicrafts and the aromas of seasonal delights fill the air. Discover this region's rich history and participate in the festive holiday traditions of Hungary, Croatia, Serbia, Bulgaria and Romania. Celtic fortifications, medieval towns and grand cities await as they burst with traditional holiday cheer. A festive river cruise with AmaWaterways is a delightful way to bring everyone together with the magic of the season.

Hilton Hawaiian Village Waikiki Beach Resort, Oahu, Hawaii

Experience a tropical holiday at this sprawling 22-acre resort on the widest stretch of Waikiki Beach. Hilton Hawaiian Village transforms into a festive wonderland, bringing cherished island traditions to life for the whole family. Celebrate with the spectacular Waikiki Starlight Luau, a dazzling cultural journey that culminates in a thrilling fire knife dance. In addition to holiday-themed hula and caroling, you can immerse your family in authentic Hawaiian culture with daily ukulele lessons and fish feeding at the lagoon. And every Friday night at dusk, over Waikiki Beach, enjoy a spectacular fireworks show from the beach or your balcony.

Fairytale Christmas in the Canadian Rockies by Rail

Escape the ordinary this holiday season and step into a winter fairytale with a 7-day Christmas in the Canadian Rockies Winter Rail Vacation. Stay at the iconic Fairmont Banff Springs Hotel, affectionately known as 'Canada's Castle in the Rockies,' and enjoy a festive wonderland of holiday events. Spend your days on a guided Icewalk through a frozen canyon, snowshoe across a sparkling landscape, and cozy up on a horse-drawn sleigh ride before indulging in a decadent holiday feast. This is a magical journey that promises many unforgettable memories.

Bishop's Lodge, Santa Fe, New Mexico

Escape to the high desert for a curated holiday retreat where every touch is crafted to celebrate the spirit of the season. Bishop's Lodge is ideal for those who want to immerse themselves in unique, regional holiday traditions. From festive pastry sessions to peaceful snow-dusted hikes, each experience invites you to create lasting memories that honor the spirit of the season. Get hands-on with authentic New Mexico holiday traditions like decorating a Farolito Tree, Tamale Making, Cacao Ceremony, and Biscochitos Cookies Decoration. And this wintertime, for those seeking unique holiday "spirits," make sure to step inside Mezcalería Amarás, an intimate mezcalería, created in partnership with Mezcal Amarás. Tucked away in a cozy, candlelit speakeasy, this limited-time experience blends old-world allure with contemporary Mexican design! Your VIP perks include daily breakfast and resort credit.

Silversands Grand Anse, Grenada

Celebrate the holiday season with Nutmeg and Mistletoe, a tropical escape to Silversands Grand Anse, a modern Caribbean resort perfect for families of all ages. While you unwind with a festive cocktail from the special holiday program, kids can enjoy the Kids Club or explore family adventures like snorkeling at the Underwater Sculpture Park. This holiday season, Silversands will offer an artisanal spiced chocolate market (YUM), and in the evenings, you can indulge in s'mores and Grenadian hot cocoa, creating the perfect blend of warmth and island indulgence. With this holiday offer, stay four nights and get your fifth night free to extend your family's time in paradise!

The Sebastian Vail, Vail Colorado

Revel in playful sophistication and family-friendly winter fun at this boutique hotel in the heart of Vail Village. The Sebastian provides the perfect home base for a holiday filled with snow and memorable moments. After a day on the slopes, warm up with the resort’s signature hot chocolate delivered to your outdoor hot tub. Outside the resort, your family can create a classic holiday memory with a cozy horse-drawn sleigh ride. You'll receive VIP perks such as daily breakfast and resort credit.

Ready to Make Holiday Memories?

These exclusive offers won't last forever, and availability is limited. Don't just talk about it—book your perfect family holiday getaway now and create the unforgettable trip you've been dreaming of. Contact us today at travel@pineapple7.com or schedule a quick discovery call to get started.