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Dan Calabretta

Agent TIp
  • One thing I always emphasize with my clients is the importance of securing reservations in advance—especially for those must-do experiences like popular restaurants, museums, and beach clubs. When you’re traveling somewhere special, you’ve likely been looking forward to certain moments for weeks or even months. The last thing you want is to arrive and find out that a place you were so excited about is fully booked.

With an insatiable passion for uncovering the world’s most lavish accommodations and crafting unforgettable experiences, Dan Calabretta is your go-to travel advisor for indulgent escapes.

Specializing in luxury hotels and magical encounters across North America, Scandinavia, the Caribbean, Latin America, Europe, Japan, and Southeast Asia, Dan has an innate knack for discovering hidden gems and iconic destinations alike. Whether it’s a secluded hotel nestled in the lush forests of Scandinavia or an opulent beachfront retreat in the Caribbean, Dan ensures every detail of your stay exceeds expectations.

What truly sets Dan apart is his expertise in tailoring journeys for every occasion. From multi-generational adventures and soul-searching solo trips to ultra-luxury getaways, meticulously planned corporate events, romantic honeymoons, and LGBT travel, Dan creates bespoke itineraries that speak to each traveler’s unique desires.

Based in Long Island, Dan shares his love of exploration and storytelling with his husband and their spirited young daughter. As both a travel expert and a devoted family man, Dan understands the importance of creating meaningful moments—whether you’re traveling the world or making memories close to home. With Dan as your guide, prepare to embark on a journey where luxury knows no bounds and every moment is a testament to the extraordinary. Let him turn your travel dreams into reality, one impeccable experience at a time.

How do you prepare for your trips?

I like to think that the planning is half the fun. When I prepare for a trip, I dive into researching the destination from every angle. I read up on local neighborhoods, talk to people who’ve been there, and look beyond the typical tourist spots to find unique experiences.

One thing I really focus on is food. I love researching restaurants; everything from local favorites and hidden gems to buzzy new openings. I check menus, follow local food blogs, and look for places that feel authentic to the destination. Whether it’s a casual spot perfect for families or a special dinner with a view, I want to know what makes each place special. I also think about how the trip will flow and what’s realistic, what’s relaxing, and how to make it all feel effortless. Every detail counts, and I always plan with the mindset of creating something I’d be excited to experience myself.

Which destinations or hotels do you go back to again and again?

California just keeps calling me back. No matter how many times I visit, there’s always something new to experience. It’s one of those rare places where every region has its own personality—one trip you’re wine tasting in the rolling hills of Napa, and the next you’re soaking up the sun in Santa Barbara or hiking above the cliffs in Big Sur.

I’m drawn to the variety. The hotels are incredible—from cozy coastal hideaways to ultra-luxury resorts with world-class spas. You can find adventure, beach time, beautiful drives, amazing food, and total relaxation all in one state. Whether I’m exploring a new boutique hotel in Palm Springs, walking the streets of San Francisco, or just enjoying the Pacific views in Laguna, California, never gets old. It’s a destination that truly has it all—and that’s why I keep going back.

Travel Tip

  • A well-planned trip should feel seamless, not stressful. Whether it’s a hard-to-get dinner reservation, timed museum entry, or a coveted cabana at a beach club, I make it a priority to lock in those details early so you can truly relax and enjoy the experience once you’re there. Planning ahead doesn’t take away the spontaneity—it actually creates more space for it, because the key pieces are already in place.