Absolutely. Beyond just a reservation, we provide a "VIP layer" you can’t get on your own. On average, our clients receive $500 in daily value through complimentary breakfasts, $100 resort credits, and room upgrades. But the real "worth" is our personal connection to the General Manager which means that your name is at the top of the upgrade list before you even arrive.

While credit cards offer great points, they are a call center; we are a partnership. When you work with Pineapple7, you're working with someone who knows YOU and will be accessible to you for every step of your journey. We are able to provide customized itineraries and experiences. We know your specific travel style such as your preference for a quiet room away from the elevator, your child's food sensitivities, or your love for local vintage wines. Because we work directly with property managers, we can often request and confirm upgrades and special amenities that automated card portals simply can’t access.

American Express is in the credit card business and offers amazing card member benefits. Many of the amenities are similar to Virtuoso. However, AMEX does not contact the hotels to request for upgrades or confirm amenities. When you book your travel investment with a call center, they work differently than we do.

Your time is your most valuable asset. Pineapple7's design fee covers the hours of deep research, price comparisons, and the vetting of local suppliers that we perform on your behalf. Think of it as an insurance policy for your vacation; we handle the logistics, the "what-ifs," and the fine print, so your only job is to show up and enjoy.

We have access to the same (if not better) pricing available online and can offer exclusive VIP perks, amenities, upgrades, and access that you can't get on your own.

Special perks such as complimentary breakfast, room upgrades, and resort credits can value up to $500 per day.

To escape the summer heatwaves, we are currently designing incredible "coolcations" to Iceland, Norway, Alaska, Peru, New Zealand, and the Swiss Alps. Travelers are trading crowded beaches for private yacht charters through the Norwegian fjords or wellness retreats in the Dolomites. It’s about fresh air, sustainable luxury, and finding serenity in the "cool."

We’re seeing a shift toward holistic restoration. This means longer stays in one location, private "bio-hacking" wellness programs in the Maldives, and deep-immersion cultural tours in Japan. We focus on "soul-enriching" travel. It's not just about where you go, but how you feel when you return.

Celebrations are our specialty! Whether it’s a 50th birthday villa takeover in Tuscany or a multi-generational safari in Tanzania and Kenya, a private catamaran charter around the British Virgin Islands or a destination wedding in France, we manage the complexities of group travel. From coordinating different flight arrivals to securing the "hottest" table in town for a private dinner, we ensure every guest feels like the VIP.

In 2026, we’ve moved past the "where" and into the "why." A Whycation is travel driven by an emotional goal. Whether you need to reconnect with your partner, find a creative reset, or celebrate a hard-won personal milestone. At Pineapple7, we don't start with a destination, we always start your intention for traveling. We then curate a "meaning-first" itinerary. Maybe it's a silent retreat in the Canadian Rockies for mental clarity or a private villa stay in the Greek Isles for deep family bonding. This ensures that you'll return home feeling exactly how you intended.

The world is "open" and demand is at an all-time high. For high-demand destinations like Japan, Sicily, or the Galapagos, we recommend booking 9 to 12 months in advance. However, our in-country connections around the globe often allow us to find space or last-minute openings that appear unavailable online.

Yes, and these are some of the most profound trips that we design. As "Heritage" or "Roots Tourism" takes center stage in 2026, we help clients trace their family through immersive, multi-generational pilgrimages. In France, we hired a private genealogist to help a nephew trace the footsteps of his uncle who fought and died in WWII. In Sicily, we secured a local historian to walk through a family's roots in the village where his Mama and her four sisters grew up. In Germany, for a college graduation gift, a Mother-Son visited the town that he grandfather spent his earliest years before heading to the US. We handle the sensitive logistics. We ensure that while you're uncovering your past, you're doing so with the comfort and seamlessness that defines Pineapple7's experience.

No. While we're known for our "white glove" luxury partnerships, our true specialty is high-value travel. Whether you're looking for an entry-level Virtuoso property with VIP or a private villa takeover for your Friendcation, our goal is to ensure your investment -- regardless of size -- is protected. We work with clients at various stages of their travel journey, focusing on properties and experiences that meet our rigorous standards for service and "soul."

Cruising continues to evolve! Today, it’s about ultra-luxe small ships that feel like floating boutique hotels and expedition vessels that take you to the heart of Antarctica or the Galápagos in total comfort. At Pineapple7, we act as your compass. We help you distinguish between a classic Mediterranean river cruise and a rugged-yet-refined Arctic expedition. Because we're Certified with "Virtuoso Voyages," our clients often receive exclusive benefits like private shipboard receptions, dedicated onboard hosts, and specialized shore excursions that aren't available to the general public.

When you're ready to begin, simply fill out this brief travel questionnaire and schedule a quick discovery call. We look forward to crafting an adventure you'll never forget!