Vacation packages
Your Personal Vacation Planner & Travel Bestie
Ready to plan the kind of vacation that actually feels like a vacation? As a boutique travel agency specializing in luxury travel and custom itineraries, we design unforgettable getaways for couples, families, and groups. From the Caribbean to Europe and beyond, we’re your go-to travel bestie for trips that are anything but ordinary.
From Daydream to departure
We believe every traveler has a story to tell
Every unforgettable trip starts with a spark—an idea, a feeling, a place calling your name. Whether it’s daydreaming over dinner or a destination you’ve had pinned for years, that moment deserves to be nurtured.
As your personal travel planner and boutique travel agency, I’m here to turn those daydreams into real-world adventures, without the stress, the guesswork, or the generic itineraries. From luxury honeymoons in the Caribbean to multigenerational vacations and everything in between, each trip we plan is crafted with care, built around your story, and designed to feel effortless from the time you say “let’s do it!” to the departure and return.
Because the best travel isn’t just about the destination. It’s about how you feel when you finally get there.
Two paths to paradise
Whether you’re dreaming of a no-stress, all-inclusive vacation in Mexico or the Caribbean or craving a custom journey full of off-the-beaten-path magic, I’ve got you. As a boutique travel agency specializing in both Caribbean escapes and globe-spanning getaways, I’ll help you choose the path that fits your vibe, and handle every detail so all you have to do is pack your bags.
Custom trip planning
Crafted just for you
No two travelers are alike. And your vacation shouldn't be either! This service is ideal for those looking for a personalized itinerary crafted with care, insight, and plenty of thoughtful touches. Whether you're dreaming of Tuscany, Tanzania, or Tokyo, I’ll bring your vision to life with the perfect mix of logistics and magic.
What’s Included:
✓ Curated itinerary planning with destination expertise, including tours & experiences tailored to your vision
✓ Coordination & Booking of all travel components (airfare, transportation, hotels, trains, tours & more)
✓ Pre-travel emails with travel tips & a wrap-up call
✓ Digital & mailed travel documents and itinerary so you can quickly access your itinerary and confirmations on the go during your trip
✓ During-travel support (because I’ve got your back!)
Custom Trip Planning Fee Starting At:
$349
"I’ve worked with Dana many times over the years, and each time she makes it so easy. "
Her suggestions are always on point, her knowledge and resources are expansive, and she’s just a really great, fun human. Take the stress out of planning and ensure your time and money are well spent by using Dana’s expertise on your next trip. You’ll be so glad you did!
- Whitney + Dustin
"It was our first time in Europe and Dana made it so easy, memorable and kept within our budget."
The itinerary she sent was detailed and we never had to worry about anything because she took care of every detail. Dana is my go to travel agent and will recommend her always, thank you for making our family Italy vacation a dream come true!
- Amber & family
"I would like to give Dana 10 stars (5 is not enough)!"
We had some crazy things happen with our flights/tours (all out of our control) and Dana was such an amazing support. She even woke up at crazy hours of the night to help us with our airline/baggage issues so we could enjoy our trip. She exceeded our expectations by even booking us a photoshoot when one of our scheduled tours was cancelled. It turned out to be one of the highlights of our trip,
- Sabrina & Tommy
All-inclusive vacations
Everything taken care of
Sun, sand, and zero stress—just how vacation should be. With a strong expertise of resorts in Mexico and the Caribbean, I match you with the destination and resort that best fits exactly what you need. From there, I take care of the logistics and little touches, so all you have to do is pack your bags and count down the days. It’s travel planning made personal, easy, and totally you.
What’s Included:
✓ Expert guidance to pick the right destination & resort for your budget, dates, trip occasion, and more
✓ Booking of resort stay, flights, transportation, tours & travel insurance
✓ Pre-travel emails with travel tips & a wrap-up call
✓ Digital travel documents via mobile app for easy access right from your phone
✓ During-travel support if anything comes up
All-Inclusive Trip Planning Fee Starting At:
$249
Vacation planning process
Think of us as your one-stop expert shop for stress-free vacation planning with zero guesswork and all the good vibes.
Consultation call
We’ll kick things off with a call to chat about your travel style, must-haves, and dream destinations. This is your time to spill the travel tea. Tell us what you like, and we’ll take it from there.
planning
Based on everything you share, we’ll curate options tailored to your preferences, timeline, and budget. You’ll get personalized resort or itinerary picks (no overwhelm, just “oh wow!”).
Final reveal
Cue the confetti! Once your trip is set in stone, you’ll receive expert pre-departure tips and a snazzy travel itinerary app. All you have to do? Pack your bags and get ready to relax.
"Dana is the absolute BEST for trip planning!"
We are celebrating our 10 year wedding anniversary and way overdue honeymoon. With lots of sudden life changes recently, we did not have the time or mind space to plan & hassle with planning everything. She went above & beyond to give us great details for resorts to review, leaving the final decision up to us. Great communication and always available! Her assistant Sam is great as well!
- Jamie + Dylan
"Dana did amazing job with our friends trip to Dominican Republic."
Highly recommend her services for a stress free vacation. Cheers to our next trip, can’t wait to start planning another with Dana!
- Leslie & friends
"Dana completely took the stress of honeymoon travel bookings out of my hands!"
I gave her an idea of what I wanted and she presented to us several options(with LOTS of details) of different price points. We selected our choice and she had great communication for every detail and during our travels if we had any hiccups or needed her in anyway she would be there to help us. Not only did she book out Honeymoon, we booked and went on an NYC group trip. She knows her stuff! We had two great trips planned with her. Simply amazing and sweet as can be!
- Lora & Adam
"We have used DWD Travel for more trips than I can remember!"
She has saved us from being in a pickle with cancelled flights, and had special surprises waiting at our destinations. We refer her to all of our friends, and they all agree and use her again & again. Do yourself a favor, and hire Dana!
- Lora & Adam
Frequently Asked Questions
You’ll find our most frequently asked questions below, but if you don’t see your questions - contact us!
