I know…it feels like we just wrapped up summer vacations! But planning ahead has big advantages:

• Spring Break: These weeks book up faster than anything else. If you want the best options, please reach out to plan ASAP.

• Summer Travel: Planning now means better rates, wider availability, and first pick of room categories.

• Non-peak times: Even if you’re traveling during shoulder seasons, there is no harm in planning ahead and booking with flexible rates.

Every year, I see a surge of new requests right after the holidays. This year, we’re implementing a cap on how many new trip requests we’ll take per week. That means the sooner you reach out, the sooner we can secure your trip. If you wait until January, your planning timeline will likely stretch longer.

And if 2025 is any indication, demand isn’t slowing down - so planning early is the best way to secure the experiences you really want.

Bottom line: Get on our calendar now and get ahead of the crowd.

2025 Travel in the Meantime

If you’re looking for something closer on the horizon, I’m here for:

• Fall getaways

• Quick weekend trips

• Overnight escapes

A reminder: hotel-only bookings are always complimentary and include perks like:

• Daily breakfast

• Resort credits

• Priority for upgrades, early check-in, and late check-out

You can book directly through our self-booking portal if you prefer, but never feel like you’re “bothering me” with a hotel-only request; I can turn those around quickly. And if you already have something on the books, reach out! In many cases, I can still add perks on the backend.

So when my son, Thomas, told me he wanted to go to NYC for his 10th birthday, I was all in. It’s a place I know well, one full of memories I could share with him - and, let’s be honest, logistically easy too :)

We stayed at The New York EDITION, which I love for its location and calming interiors. It’s such a peaceful retreat after the buzz of the city, and the ability to connect rooms worked perfectly for our family of 4. I knew we’d be bouncing between Central Park and downtown, so being central was key.

Travel tip: If you haven’t been to NYC, make location a top priority when choosing your hotel. Manhattan is amazing but getting up and down can be a pain. For first-timers especially, you’ll likely be all over the map, so staying somewhere central - like Flatiron or Midtown - makes life easier.

Since this trip was all about Thomas, we did all the classics - and then some:

• RiseNY - This immersive experience walks you through New York’s cultural history, but the real showstopper is the flying theater ride at the end. Think Soarin’ at Disneyland but through NYC. The kids loved it, and it was a nice break from the heat and humidity outside.

• The Lion King – a classic for a reason. The costumes, the music, the wow factor - perfect for a first Broadway show.

• FAO Schwarz – we let the kids run wild in this iconic toy store. It’s touristy and SO crowded, but it was a top request for the kids.

• M&M World + Times Square – our area is free of billboards and advertising (which we love!), so the kids were in awe with all the bright lights.

• Empire State Building at Sunset – still one of the best views in the world

• Sloomoo Institute - my kids still love slime. This was an easy and fun ~60ish min stop.

• Rubirosa - Pizza is Thomas’ favorite food, so of course we revolved our lunch res around it on his actual bday…just a few blocks from Sloomoo.

• Endless treats – can’t take a kid to NYC without stopping at Serendipity (fun fact: also one of my favorite movies of all time)

• Statue of Liberty - hadn’t been there since 8th grade, but this was not my favorite - the lines are insane, and I’d be happy to see it from a boat next time :)

This trip reminded me just how fun it is to see New York through a child’s eyes - the scale, the lights, the energy, the constant sense of wow.

If you're planning a city trip with kids, NYC delivers at every age and stage. Just bring comfy shoes (and maybe a portable fan if you're visiting in summer - it's hot!).

P.S. Did you know that many of the luxury hotels in NYC offer a laundry credit? Love this - especially in the humid summer!

Here are some of my other hotel picks:

• Crosby Street Hotel

• The Mercer Hotel

• The Surrey

• The Lowell

Each hotel has its own personality, and I would choose all of them depending on who I was traveling with and what our plans were. Let me match the right hotel for your next NYC stay…and extend those amazing perks as well.

There’s no “best” side of Maui—just the one that fits your travel style. On a recent trip, I spent time in both Kāʻanapali (where we stayed at the Westin Maui) and Wailea (at the Fairmont Kea Lani), and also visited Kapalua, exploring the Montage and the Ritz-Carlton properties (my daughter has become an expert site visitor like her mama!). Each area has its own personality, pace, and perks, and all are great in their own ways. Here’s a breakdown to help you figure out which one might be the best fit for your next Maui vacation.🌴

Kāʻanapali: Energetic, Convenient, and Walkable

If you're looking for convenience and access to everything, Kāʻanapali is tough to beat. The hotels here line one long, wide, beautiful beach. It’s a very walkable stretch—you can stroll from hotel to hotel, hop on a snorkel cruise directly from the beach, or walk to Whalers Village, which is great for quick market stops (extra sunscreen, pool toys, snacks, or even a bite to eat).

The Westin Maui is especially great for families. The waterslides and splash zones were a hit with our kids, and the beach is just steps from the pool. It's definitely more active and a bit more crowded, but in a fun, buzzy way. Many of the properties here are larger, branded resorts—Marriott, Hyatt, etc.—so it feels familiar and full-service. Highly recommend a club level room here just because the hotels are so much larger.

Wailea: Laid-back Luxury and Scenic Beauty

Wailea offers a more serene and polished experience. The Fairmont Kea Lani is all-suite (plenty of space for families) and has its own beach that's calm, uncrowded, and ideal for swimming and boogie boarding. Each hotel in Wailea has its own beach or shares with just one other, so you won’t find the same “one big beach” vibe, but it feels more private and peaceful.

While the Wailea beach path is still paved and safe, it winds along the cliffs and coastline rather than being a straight shot. It’s stunning and scenic, and you’ll pass some of Maui’s most luxurious properties: Four Seasons, Grand Wailea, Andaz…

There’s a small shopping village with a market (yes, you can still grab snacks and toys here!), and all the major hotels offer courtesy cars to take you around Wailea. Dining options are excellent—both at the hotels and nearby.

Kapalua: Quiet, Luxe, and a Bit More Remote

If you're looking for something even more peaceful and tucked away, Kapalua is a beautiful, serene option. While I didn’t stay here this time, I visited both the Montage Kapalua Bay and Ritz-Carlton Kapalua—and they’re both stunning in very different ways.

Kapalua has a more remote feel, with dramatic coastline, lush greenery, and a quieter pace. It’s the kind of place where you unplug and settle into a slower rhythm. Montage is perfect for families or groups looking for spacious residences with kitchens, and it’s perched right above a swimmable bay. The Ritz feels more classic and resort-like, surrounded by golf courses and tropical forest. Highly recommend the firepit rooms here.

There’s less walkability here than in Kāʻanapali or Wailea—Kapalua is more spread out and less commercial—but the tradeoff is total tranquility. There are a few nearby restaurants here as well.

Final Thoughts

Each part of Maui offers something unique:

• Kāʻanapali: Lively, very walkable, action-packed

• Wailea: Upscale, scenic, polished

• Kapalua: Quiet, lush, and luxurious

There’s no wrong choice—just the right match for how you want to vacation. Let me know if you’re trying to decide between them—I love helping clients pick their perfect fit.

Like many of my clients, I often focus on the next international destination. But there’s so much to explore right here in the U.S. I wasn’t all that familiar with Big Sky, and I’m so glad I spent a few days experiencing what this incredible part of the country has to offer.

Why Montage Big Sky impressed me — and why it’s worth considering for your next getaway:

• Easy to reach: Just over an hour’s drive from Bozeman (which is under two hours by air from SFO, with connections through Dallas, Chicago, and other major hubs). Even in winter, the logistics are seamless — Montana knows how to handle snow, and the roads are well maintained. You don’t need to worry about closed roads.

• Accommodations for every group: From King rooms with sofabeds (and connecting options) to 6-bedroom mountain homes (some with bunk rooms for kids). The interiors are beautiful, and the residences have top-tier appliances — great for entertaining, having a place to gather after kids go to bed, or bringing in a chef for a celebratory dinner.

• A skier’s paradise: Big Sky offers something for everyone — from first-timers to experts. About a third of the mountain is beginner-friendly, and 18% is dedicated to advanced terrain. It’s home to the largest ski school in the U.S. (with over 500 instructors!) and the most high-tech lifts (heated seats, bubble covers, and space for 6–8 people). And it’s never overcrowded — this past winter, the longest lift line was about 12 minutes, with more than an acre per skier.

• More than just skiing: Snowmobiling, sleigh rides, and other winter adventures abound. In summer, you’re only an hour from Yellowstone National Park. Right in Big Sky, you can go hiking, fly fishing, rafting, stroll farmer’s markets, see live music, and head on guided e-bike tours.

• Perfect for families and groups: Whether it’s a small family or multigenerational trip, a guys’ golf getaway (saw MANY of those), or a ladies’ weekend of hiking and spa treatments, Montage Big Sky has something for everyone. Dining options both on property and in town are easy to access, with complimentary shuttles every half hour or so provided by Montage.

Big Sky delivers that small-town charm with just enough to do — plus the most luxurious accommodations. Whether you visit in summer or winter, especially if your group includes both skiers and non-skiers, this hotel really checks all the boxes.

I’ve been quiet on Substack the last couple of weeks—not because I’ve disappeared, but because I’ve been deep in the details of summer travel for so many amazing couples and families. Flights are being booked, final itineraries are being polished, and I’ve lost count of how many dinner reservations we’ve made.

This time of year always feels like controlled chaos—but the good kind. The kind where I get to help clients get excited for their vacations, smooth out the stress, and make sure they actually get to relax once they’re on the ground.

Where DR Luxury Travel clients are headed this summer:
One of my families of six is kicking things off in Morocco and Rome before the parents sneak away for an anniversary celebration on the Amalfi Coast—staying at Casa Angelina in Praiano and Capri Tiberio Palace, with a dreamy boat day and lunch at Lo Scoglio along the way.

A family of five is headed to Mexico City and San Miguel de Allende to eat their way through the local food scene and explore the sights on an e-bike tour through the city’s iconic landmarks.

Another family of four is celebrating mom’s milestone birthday with a Rome + Puglia itinerary—complete with a mozzarella farm visit, cooking classes, and boat days near Borgo Egnazia.

A couple is enjoying a kid-free adventure through Rome and Croatia before meeting up with their own parents at a seaside rental for some much-needed relaxation and family time.

One multigenerational crew—grandmas included—is heading to London and Paris for the kids’ first-ever trip to Europe (what a way to start!).

Another couple is marking their anniversary with a full-blown Italian dream tour, staying at some of my favorite properties: Grand Hotel Tremezzo, Borgo Pignano, and Masseria San Domenico.

A big family spread across the U.S. is reuniting in London, staying at the lovely Corinthia and soaking up every moment of quality time together.

And a special multigen birthday celebration is taking place at Montage Los Cabos—complete with ocean views and plenty of poolside memories for Grandpa’s big day.

And that’s just June….and not including the many hotel-only bookings and shorter trips.

As for me, we’re keeping things domestic and low-stress next month. I’m heading to Hawaii solo with my kids for a few days in June—part mom-and-kid adventure, part property scouting for future client trips. We’ll be linking up with my colleague and her kids for some beach time, cocktails, and family time.

Here’s to summer—whether you’re hopping across the globe or just crossing a few state lines. I’ll be back soon with more updates and inspiration when things settle down a bit.

Today felt like the perfect time to introduce—or reintroduce—someone many of you already know: Carly Daniels. Carly has been deeply involved in the day-to-day planning here at DR Luxury Travel for over a year now, and if you've worked with us recently, chances are you've had the pleasure of interacting with her.

We first met back in 2021 at our daughters’ dance class. Both of our girls were named Emmy (mine short for Emery, hers legally Emmy), and they were both confident, fearless, and totally at home on stage. They partnered up for their dances—two tiny three-year-olds with zero stage fright and total confidence.

But today is also about celebrating our role as working mothers. We work hard—not just for our clients, but for our families. We pour our hearts into curating incredible travel experiences, while also juggling afterschool activities, early dismissals, sick days, and dentist appointments. It’s not always a perfect balance, but it’s one we’re figuring out, day by day.

To our clients: thank you for inviting us into your family memories and for giving us the space to be present for our own. We're grateful that this work allows us the flexibility to do both.

To the moms reading this—should we go ahead and plan your Mother’s Day 2026? You deserve the trip.

For our family trip, we chose to stay at the Rosewood.

Rosewood struck the perfect balance for our family of four (my kids are 9 and 7). It was incredibly kid-friendly without ever sacrificing that feeling of luxury. It felt calm, beautiful, and well-paced, which is not always the case in large resorts like this. Once we passed through the gate that separates Rosewood from the rest of the complex, it felt like a true retreat.

What We Loved About Rosewood

• The atmosphere: peaceful, elevated, and quiet. After a day at the water park, I visibly felt my shoulders drop the second we walked back through those gates.

• The rooms and shared spaces: beautifully designed, comfortable, and not overly crowded. We never had a problem getting 8 loungers together at the Rosewood pool at any time of day during a very high occupancy week (Spring Break).

• Dining: The food at Rosewood was phenomenal. I’m still thinking about the sea bass and soft-shell crab at Café Boulud. The Manor Bar also became our go-to in the evenings—a lively place to unwind while the kids were happily at the kids' club. We especially loved the live music and craft cocktails.

Highlights from the Baha Mar Complex
While we loved the Rosewood, I also want to give credit to the larger Baha Mar complex, especially the water park. It’s clean, easy to walk around, and has something for every age: big thrill slides, a wave pool, and toddler-friendly splash areas. Even during spring break, the lines were manageable. In fact, I’d recommend going between 2–5 p.m.—when many people are taking a break or heading back to their rooms—because we had zero lines during that window.

We also loved mini golf, the arcade (nice and clean here as well!!), and the basketball court. There are so many places to stay active with the kids. While our husbands would have loved to fit in a round of golf, and my friend and I would have enjoyed a morning of tennis, we weren’t able to fit it in. There is just so much to do; we could have definitely stayed a few more days.

We did, however, take a catamaran out to another island to snorkel, see a few turtles, and feed the pigs. While it was a bit stinkier than I anticipated, the kids loved the little pigs and snorkeling in the open water.

Dining Notes Across the Resort
I don’t recommend eating at Fi’lia, but were pleasantly surprised by Pizza Lab—the pizza was genuinely great, and the salad was fresh, filling, and perfect for an easy lunch with the kids. That said, food and beverage can add up quickly across the resort. There isn’t a grocery store or market within Baha Mar to stock up on snacks or basics (there may be options outside the complex, but we didn’t leave during our stay), so be prepared to dine on property. Don’t forget—you get daily complimentary breakfast for 2 and resort credits—a huge value—when you book through DR Luxury Travel.

Our favorite restaurants for dinner were Costa, Katsuya, and Cafe Boulud (where we saw Tom Brady! Fun sighting)

Evening Tips for Parents
Definitely take advantage of the Baha Mar Explorers Kids Club, which offers an evening session until 10:30 p.m. You can order dinner for your kids to eat there, they get to enjoy fun programming and a movie night, and you can head out for a much-deserved date night. I’d recommend dinner at Marcus, Carna, or Katsuya, followed by live music at the jazz club, cocktails at the Manor Bar, or even a nightcap at the cigar bar.

If you book at Rosewood, their kids club is complimentary (better for little ones), but it doesn’t run in the evenings. Again—huge value when traveling with little kids.

A Few More Observations

• The Hyatt pools get crowded—if you plan to spend time there, I recommend claiming loungers early.

• The property is large, but it’s very walkable and easy to navigate.

• The casino has a high-end feel—similar to the Wynn—and while you do pass through it often, it’s not smoky.

• The location is a big win: only a 15-minute drive from the airport. Even better, you can pre-clear U.S. customs before your flight home, so you land in the U.S. in the domestic terminal—making arrival fast and easy.

Let me know if you want help deciding which part of Baha Mar would be the best fit for your family or trip—I’ve now seen the difference firsthand. I know we will be back.

I remember being pretty young—under 10—when my dad took my siblings and me to the bank, which wasn’t anything out of the ordinary. But one time, he got each of us a zippered leather bank pouch and told us we were to use them to save money for Europe. Some kids got piggy banks for toys—we got bank pouches to save for travel.

We had already traveled quite a bit within the U.S., but Europe was the next big goal.

I didn’t actually make it to Europe until I was a teenager. It took a few years to save those bucks, but eventually, my parents took my sister and me on a two-week trip across Europe. When they had to head home for work, my sister and I stayed behind for another week or so on our own. It was such a fun adventure, and even back then, I remember being excited by the details—finding the right train, reading paper maps (no iPhones back then!), and planning where to go next.

One of the cities we visited as a family was Florence. I loved it so much that I decided to study abroad there in college. Living in a city where beauty, history, and everyday life are so intertwined changed how I thought about travel. It wasn’t about checking places off a list—it was about being immersed in a place and learning how other people live.

That experience lit a fire in me that hasn’t gone out since. I still feel it every time I land somewhere new. It’s exciting, grounding, and invigorating in a way that’s hard to put into words. But I know you probably know the feeling—or you wouldn’t be here.

Over the years, my “why” has evolved. Now it’s about helping others access that same feeling—whether it’s through a dreamy anniversary trip, a multigenerational getaway to a fabulous resort, or a long weekend that feels like a full reset. Every itinerary I build is personal, thoughtful, and designed with care.

I hope my trip planning helps people experience more joy, more connection, and more presence. I also hope that by taking it off their plates, they get to focus on the fun parts of travel—the anticipation, the excitement, the memories—not the stress of navigating options or sorting logistics.

That’s why I travel.
And it’s why I do what I do.

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Why I’m starting Inside the Itinerary

I’ve never been much of a newsletter person. That format always felt a little too… polished. A little too salesy. And that’s just not how I want to show up here or ever to my clients. And Instagram has felt overwhelming - the constant need to post.

So, I’m trying something new: Substack. It’s what I’ve been drawn to lately and where I have been consuming content.

This space is a bit of an experiment—but one I’m genuinely excited about. I don’t love posting on Instagram, but I’ve always loved writing the captions, especially when I get to share travel stories or spotlight a hotel I’m obsessed with. But lately, I’ve been craving something a little more open-ended. Less algorithm, more intention.

What to Expect

I’m a business owner and luxury travel advisor, and this is where I’ll be sharing the behind-the-scenes of what that actually means. You can expect:

• Trips I’m designing for clients

• Hotels and destinations I’m genuinely excited about

• Notes from my own travels and industry events (a bit of ‘behind the scenes’)

• Client feedback, learning moments, and what’s trending in travel

• Special promos that land in my inbox (only the good ones!)

• …and more! As I come up with content..

This is just… me, sharing thoughts, updates, and inspiration from inside the world of curated travel planning.

How Often Will I Post?

Great question—I’m figuring that out too. My clients come first, always. So the cadence here may be irregular to start. But when I do post, I promise it’ll be thoughtful, useful, or at least interesting.

And if you’re reading this, thank you. Whether you’re a current client, a future traveler, or just someone who loves the travel world as much as I do—I’m glad you’re here.

Let’s see where this goes. ✈️

Dainee Ross
Owner + Luxury Travel Advisor, DR Luxury Travel

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