Window shopping #36
Loyalty perks unlocked, trending destinations to bookmark, and a chic new debut in Milan
This is Window Shopping, a weekly mini-letter from Window Seat—your stylish scroll through what’s new and noteworthy in the world of travel. Each issue blends timely headlines, personal favorites, and design-forward hotels to keep your wanderlust well-fed.
Plot twist: a loyalty program upgrade that actually benefits travelers. Hilton just announced a major evolution of Hilton Honors for 2026, and it is legitimately traveler-friendly. The brand is debuting Diamond Reserve, a new top-tier status with real, premium perks: confirmable upgrades at booking, guaranteed 4 p.m. late checkout, dedicated 24/7 support, and access to Hilton’s Premium Clubs. Even more surprising is that Hilton is lowering the qualification thresholds for Gold and Diamond, making elite status even easier to earn. In a landscape where loyalty updates usually mean cuts or spin, this one is a genuine upgrade that could reshape elite travel next year.
Ten places poised to dominate your 2026 mood boards. Amex Travel released its list of 2026 Trending Destinations, and it’s a fascinating peek into where high-spending travelers are headed next. The data shows a craving for newness and under-the-radar luxury: 89% of travelers say they get more excited about trips to places they have never been, which tracks with picks like the Indian Himalayas, St. Julian’s in Malta, Papagayo Peninsula in Costa Rica, and the Okinawa Islands. This list is both inspiration and insight: these destinations tend to shape hotel development, flight routes, and what becomes “hot” in luxury travel over the next two years. If you like being early rather than late, this is your roadmap.
Black Friday is my Super Bowl, especially when two of my long-time favorites go on sale. If you have been waiting for a sign to upgrade your home atmosphere or finally invest in good bedding, this is it. Below are the deals I’m personally shopping (and gifting) this year.
P.F. Candle Co.’s Hi-Fi Collection: Inspired by listening bars and hotel lounges, it makes sense that these candles have become personal favorites. For Black Friday, the brand is offering 20% off select products on Amazon (now through 12/1) plus up to 50% off the full collection online and in-store (from 11/26–12/1). If you’ve ever wanted to stock up on scent wardrobe staples or put together a chic, under-$40 gift, now is the moment.
Ostermoor’s Down Pillow: If you’ve been here for a while, you know I take my comfort very seriously. This pillow is the closest thing I have found to a five-star hotel pillow at home: supportive, cloudlike, and wildly well-made. For Black Friday, the brand is offering up to 35% off mattresses and up to 30% off bedding and accessories (from 11/24–12/2). If you want to upgrade your sleep setup before winter hibernation hits, start here.
The Carlton — Milan, Italy
Rocco Forte just opened its newest jewel on Via della Spiga, placing The Carlton at the literal center of Milan’s most stylish neighborhood. The hotel feels tailor-made for travelers who care as much about atmosphere as they do about location: 71 rooms and suites dressed in elegant Italian detailing; a serene spa for decompressing after a day in the Quadrilatero; and a culinary program led by Chef Fulvio Pierangelini featuring seasonal, ingredient-forward dishes at Spiga. I am especially taken by Cafe Floretta, a botanical, glass-domed dining room that brings a soft, luminous glow to the heart of the hotel. And when The Carlton Bar debuts in spring 2026, it is set to lean into Milan’s aperitivo culture with drinks by legendary mixologist Salvatore Calabrese. A very chic new reason to visit (or revisit!) Milan.
Tori Simokov is a Travel Writer and Graphic Designer/Strategist based in New York. To get in touch, email tori@v1projects.com. Want more? Check out Instagram, TikTok, or shop her curated favorites.