The difference between a good trip and a great trip

Custom itineraries, seamless booking, and concierge-level planning for trips that feel as good as they look.

travel better

Stop sweating the small stuff

Planning shouldn’t get in the way of pleasure. Whether it’s your honeymoon, a milestone celebration, or an overdue escape, Ciao Bennett handles the how so you can focus on the why. Good taste, great perks, and the kind of vacation that permanently raises your standards. 

how it works

reach out

Fill out a quick inquiry form with the basics like where you’re headed, who’s coming, and what kind of trip you’re dreaming about. 

Tell me everything

We’ll hop on a call to talk out your wishlist, non-negotiables, and vacay personality. This is the part where I get to know you so your trip feels like you, too.

do nothing!

Seriously. While you’re living your life, I’m over here booking the flights, locking in suites, and scoring reservations. Every detail handled, every box checked.

have it all

It’s go time. Welcome champagne? Already chilling. Late checkout? Handled. Your perks are waiting and your trip is ready to impress. 

planning packages

How spoiled are we talking?

The Essential

For the confident traveler who knows what they want and just wants the perks

  • Hotel booking with VIP perks!


* Complimentary if you know the hotel you'd like to book! If you'd like a few options, we can provide a hotel look book tailored to you for a fee.

The Classic

For the decisive traveler who’s ready to delegate

  • Complimentary consultation call

  • 1 custom trip proposal based on your style

  • 1 round of complimentary revisions based on feedback

  • Bookings and management of all hotel, tours, and transfers

  • Optional pre-departure call

  • In destination travel support

The Full Escape

For the luxury lover who wants zero stress and all the extras

  • Complimentary consultation call

  • 1 custom trip proposal based on your style

  • Unlimited rounds of complimentary revisions based on feedback

  • Bookings and management of all hotel, tours, and transfers

  • Booking of flights (premium-class and higher) and luxury private airport transfers

  • Concierge-level planning (dinner reservations, down time recommendations, exclusive experiences, etc)

  • Optional pre-departure call

  • In destination travel support

A La Carte

Want a little bit of this and a little bit of that? We can still help!

  • Premium class and higher flight bookings

  • Destination guides and local recommendations

  • Hotel look books (3 custom tailored options)

  • Airport transfers

  • All-inclusive resort bookings

  • Group trips!

  • Restaurant recommendations and bookings

let’s go somewhere

◉

let’s go somewhere ◉

your trip’s best friend

meet elena

Ciao! I’m Elena, founder of Ciao Bennett and the travel-obsessed bestie you didn’t know you needed.

After years in healthcare (where my only vacation views were computer screensavers), I traded scrubs for suitcases and turned my love of travel into a full-time job. I’m a big-picture thinker and a total detail nerd, turning my client’s Pinterest boards and random iPhone notes into trips that strike the perfect balance between adventure and indulgence. 



I bring the same energy to clients that I give to my closest friends: thoughtful, creative, and always going the extra mile to make you feel heard. Just give me a dream and a budget—I’ll take it from there.

love letters

  • hr

    Switzerland Family Trip

    "OBSESSED!!!!! Seriously the fact that I threw a whole family trip that would please everyone AND for it to be in Switzerland I am not sure how Elena did it. It was the most well planned and beautiful trip. Every single activity she sent us on was so amazing and made the trip 100000x better. We saw seriously the most amazing views and the most amazing places I am SURE in the world. She was more than helpful throughout this entire process and made sure to answer every single one of my questions and concerns (most of which were insane). The itinerary she provided literally guided us through the whole trip and made it so enjoyable and seamless to see what we needed to see everywhere we went. She decided to have us stay in Lucerne for majority of the time which was super easy to get to all of the mountains that she had planned. I have not stopped yapping about her abilities to plan this trip and how every single person should absolutely 10000000% use her for literally any type of trip, including whole family!!!!!!!! 10000/10 stars"

    - Haley

  • british virgin islands honeymoon

    “Elena was nothing short of amazing - she was so attentive to all of our requests, quick to respond, and extremely patient when we decided to completely re-plan our entire honeymoon. She is super accommodating and knowledgeable and I would recommend her to anyone that is looking to book a trip! She also managed to save us hundreds of dollars by getting us a free breakfast package, which was a huge plus.”

    - Claudia

  • Tokyo and Osaka

    “Elena went above and beyond with everything when planning this trip. She was clear when it came to why she chose specific locations and consistent with reminders of upcoming bookings. She made sure we had everything we needed and checked in / was available for recommendations throughout. This trip couldn’t have happened without her!”

    - Clark

  • hr

    Mexico Anniversary Trip

    “Elena was absolutely incredible. She made sure everything ran smoothly from the time we landed in Mexico to the time we landed back in the US. She set us up with welcome drinks and custom drink making ingredients in our room. We were able to even pick details down to our pillow preference to make for a totally customizable experience. She made sure we always had all of the information we needed in regards to activities, excursions, dinner reservations and more. We cannot recommend Elena enough as a travel agent! She truly went above and beyond and made the experience 10/10 from start to finish.”

    - Erin

  • hr

    Cannes + Paris Honeymoon

    Elena was absolutely FANTASTIC! From our very first conversation, she took the time to understand my preferences, budget, and travel style. The itinerary couldn't have been better, and Elena was super on top of ensuring all private transfers were on time and completed as well as communicating with different companies if we wanted to change or cancel a reservation. She even was reaching out to check in on how things were going on her own wedding week AND honeymoon. Throughout the trip, I appreciated the little touches she included such as welcome drinks at each hotel along with a note and upgraded rooms! We truly had the time of our lives on our honeymoon thanks to Elena.

    - Jessica

  • hr

    South of france honeymoon

    “Elena truly understood exactly what we wanted for our honeymoon, both personally and professionally. We knew nothing about the South of France when we first started working with her, but she magically took our survey answers and created an incredible, detailed itinerary that hit every single thing we were hoping for—and she did it so fast! We wanted to relax on a beach while having a comfortable home base to explore from, and the research she put into this trip left us in awe. It's rare to not have to worry about planning a European vacation, but Elena made that possible! I've told all my friends about her—whether they're planning a weekend getaway or a big milestone trip. She even stepped in quickly when we had to make last-minute changes to our trip. We couldn’t have done it without her!”

    - Emily

  • Sicily, Italy

    “Elena was fabulous! She was so helpful with our hotel and excursions. The hotel was perfect- 5 star all the way. Our excursions were exactly what we wanted. Drivers top notch and our private guides were amazing. Highly recommend Elena Williams!! Thank you for a wonderful holiday!”

    - Edward

  • Punta Cana Honeymoon

    “Elena has been absolutely amazing during the whole planning, booking, and trip experience. We were very indecisive when it came to our honeymoon and Elena laid out options in detail and when we picked our destination she made it so easy to make it official. When we decided we wanted to take a catamaran ride she booked a great experience and handled all logistics. We cannot recommend or thank her enough for her expertise, her patience, and for making our honeymoon the best trip we’ve ever taken!!”

    - Zoe

faqs

  • My trip-planning packages range from completely free to $400+, depending on the level of support you’re looking for. These prices are designed to cover the time, research, and energy I put into crafting each itinerary, while still staying accessible thanks to the commission I receive from hotels and tour partners. In other words, you get hours of dedicated planning and insider expertise at a lower rate than if my business relied on fees alone.

  • I don’t have a strict budget minimum, but I work best with travelers who value thoughtful planning, want a more elevated experience, and are open to recommendations that make the most of their time and money. If you’re someone who wants to skip the hours of research and still feel confident you’re getting something special, you’re in the right place.

  • The earlier the better, especially for popular destinations or peak seasons! That said, I’ve worked magic on a deadline before, so don’t be shy if your dates are coming up soon. I’ll always do my best to make it happen.

  • You won’t be stuck on hold with a 1-800 number, I promise! If anything comes up (flight delays, hotel hiccups, weather drama), I’ll be there to troubleshoot and get things on track as smoothly as possible.

  • Yep! For full-service trips, I’ll build out your itinerary and handle the bookings for great food, local gems, and fun experiences that match your vibe. If you’ve got travel plans covered and just want more niche support, check out my a la carte offerings. 

  • When you book on your own, you get a room. When you book through me, you get a room plus perks (think upgrades, daily breakfast, late checkout, depending on the property), personalized recommendations, and a real human keeping tabs on all the moving pieces. I handle the research, bookings, and back-and-forth emails so you can have your time back and leave the administrative hat at home. 

our favorite spots*

*so far!

  • Sicily

  • Thailand

  • Portugal