Karen Wiswall

Boston has some great luxury hotels, but Raffles feels different in the best way. It has that polished, elevated feel you’d expect from the brand, but it still feels warm, relaxed, and very livable instead of overly formal. The location in Back Bay is ideal, and the hotel itself feels like a true escape from the city once you walk inside. I honestly think it’s the best luxury staycation spot in Boston right now.

Beaches Turks & Caicos is one of those trips where you can truly shut your brain off and just enjoy being on vacation. From the moment you arrive, everything is taken care of, which makes it feel easy in a way that a lot of trips don’t. What I love most is how it’s designed for families to relax, not just keep the kids busy. It’s fun, beautiful, and completely seamless from start to finish.

There is truly nothing like sailing with Disney Cruise Line, and our voyage aboard the Disney Fantasy reminded me why so many families return again and again. From the moment you step on board, everything feels thoughtfully designed for both kids and adults to have an incredible vacation. Between Broadway-quality shows, incredible dining, and the famous Disney service, it’s a seamless and magical experience. If you love Disney—or simply want a cruise where every detail is handled—this is one trip I recommend to clients again and again.

There’s something special about pairing a few days at Walt Disney World Resort with a Disney Cruise—it truly feels like extending the magic. On our last trip, we spent a short stay exploring two parks, EPCOT and Disney’s Animal Kingdom, before boarding the Disney Fantasy. Even with limited time, these parks delivered incredible food, immersive storytelling, and unforgettable experiences for both kids and adults. If you can swing it, I always recommend visiting all four parks—but this quick Disney fix was the perfect start to our cruise vacation.

New York City is one of those destinations that never feels the same twice—and that’s exactly what makes it so special. Whether it’s your first visit or your fifteenth, the city has a way of reinventing itself through neighborhoods, dining, culture, and energy. This trip reminded me how effortlessly NYC can balance iconic experiences with quieter, elevated moments when you choose the right hotel and pace. From seamless train travel to standout dining and world-class entertainment, this was a classic New York stay done right.

Portland, Maine is one of those destinations that immediately wraps you in charm—an effortless mix of coastal beauty, award-winning cuisine, and a walkable, historic downtown. I love how the city feels both elevated and hometown-cozy at the same time, perfect for travelers who want incredible food without the fuss. Every time I visit, I’m reminded of how easy it is to build a weekend here that feels indulgent, restorative, and full of personality. It’s a place that surprises people in the best way, and that’s why I love sending clients here.

Sailing on the Disney Wish is like stepping into a floating fairytale. It’s an incredible getaway for families looking to make magical memories — whether you’re chasing character meet-and-greets, lounging in luxury or indulging in next-level dining. From the whimsical staterooms to the jaw-dropping entertainment, the Wish blends Disney storytelling with cruise ship elegance in the most enchanting way. Sailing with a preschooler? This dreamy three- or four-night cruise is the perfect intro to Disney Cruise Line magic!

Sailing on the Disney Treasure is an unforgettable adventure filled with magic, relaxation and excitement for everyone! It’s the perfect vacation for families with diverse interests. Want to soak up the sun by the pool all day? Amazing! Prefer thrilling waterslides and immersive entertainment? There’s plenty to keep you busy! Looking to indulge in world-class dining and Broadway-caliber shows? You won’t be disappointed. Rather unwind in the adults-only areas while the kids have a blast in the youth clubs? You’ll have the best of both worlds! Sailing on the Disney Treasure with little ones? This 7-day itinerary is for you!