Why work with us
A travel partner, not just a booking service.
When you book with Generations Getaways, you're not another transaction. You become part of our travel family - with a dedicated advisor who learns what matters to you and builds your trip around it.
Expert guidance
Insider knowledge, exclusive access, and up-to-date advice to get your trip right.
Personal connection
Your advisor takes time to understand your preferences, expectations, and travel dreams.
Real value
Same or better pricing than online - with no added fees and a professional in your corner.
Peace of mind
We handle the logistics. If anything comes up before or during your trip, we're here.
Our specialty experiences
Deeper expertise for distinct journeys.
Within the Generations Getaways family, two specialty brands offer focused, custom-designed experiences for travelers seeking something more specific.
Italy by Rail & Sea
Italy made easy
by rail & sea.
Custom Italy itineraries built around the rhythm of train travel and Mediterranean cruising. Every journey is designed from scratch - no packages, no shortcuts, no compromise.
Ideal for travelers who want to experience Italy deeply, on their own terms, with an advisor who understands that rail is at the heart of Italy.
Lunara Journeys
Intentional travel
for a new chapter.
Thoughtfully designed journeys for women 50+ who are seeking something more meaningful than a traditional vacation - slower, more intentional, and more enriching.
Small groups, beautifully paced itineraries, and curated experiences deeply rooted in connection, reflection, and personal discovery.
A word from our clients
Memories made.
"I have been able to save money and get tons of helpful tips from my travel agents from Generations Getaways. I have booked tons of cruises but now choose to do all my booking through GG because it is a simple and fast way of doing it. Also, I have been able to save money on a few of my trips!"
- Jennifer A.
"My wife and I liked to travel. There are those who know more than we do about the intricacies of the travel process. For that we need a guide. We chose Ray from Generations Getaways to be our advisor. He has listened to what we want to do, then helped us form the trips that we want to accomplish. If we have a problem or a question Ray is always willing to help. We have greatly appreciated how Ray and Generations Getaway and their app. have enhanced our travel experience."
- Craig A.
"Ray is the best agent! Fought to the end to help remedy a situation with a rental car that was not up to par. Thank you, Ray, for all you did to make this an easy process and helping to follow through on everything!"
- Robyn C.
"Well another cruise on the books thanks to the dedicated work by Generations Getways!! Cruising the world with the help and knowledge of Generations Getaways is as simple as making a phone call. Just say the word and they take all the work away from you. The only thing to do is call them again and again!! Thank you!"
- Doreen T.
"I just want to thank Ray & Suzanne of “Generations Getaways” for their knowledge and expertise of all the questions me and my new wife we had about our Honeymoon. And a big thank you for setting us up on our tours and questions about COVID testing which was a difference maker."
- Jose D.
"Ray and Suzanne were a pleasure to work with. Very helpful with planning this memorable trip. They made great suggestions and answered any questions. Responded promptly. I would recommend them to friends and family for future traveling needs! Thank you both for your time and attention in making this trip something we will never truly never forget."
- Sarah S.
How we work
Simple from start to finish.
Initial consultation
We learn about your travel preferences, budget, and destination ideas - in person, by phone, or virtually.
Itinerary proposal
We research and present curated options. Off-the-shelf options in 1-2 days; custom itineraries in 3-4.
Booking & confirmation
Once you approve, we book everything and deliver a complete digital itinerary - or printed documents if you prefer
Ongoing support
Our service doesn't stop at booking. We're available before, during, and after your trip for anything you need.
Ready to start?
Let's plan something worth remembering.
Whether you're dreaming of a Caribbean cruise, an all-inclusive escape, or something completely custom - Generations Getaways is ready to make it happen.
Tell us where you want to go - or let us help you figure that out too.