Multigenerational Family & Group Travel Specialist

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Helen Skipper, Travel Agent in Saint Augustine, FL

Helen Skipper

Saint Augustine, FL Travel Agent
Super Agent

Helen Skipper

Saint Augustine, FL · 13 Years of Experience

Dandy Time Vacations, an independent agent with Cruises & Tours, Unlimited, a Travel Leaders Network Affiliate Agency
5.0
(22)
100% Recommended
Always available and willing to solve any issue as quickly as possible. We were never on our own to figure things out. Read More >
About
Reviews
My Places
Client Testimonials

Areas of expertise

Destinations:

England, Italy, Ireland

Interests:

Family Vacations, Villas, Yacht Charter, Celebration Travel

Suppliers:

G Adventures, Beaches Resorts by Sandals, Adventures By Disney , Delta Vacations, Kensington

About Me

Villa in St Lucia
Villa in St Lucia

Multigenerational and group travel can be the best kind of luxury—because time together is the whole point. I specialize in elevated family and friends trips that feel smooth, thoughtful, and easy for everyone, from toddlers and teens to adults in their 20s through 40s, parents managing a million moving parts, and grandparents who want comfort without chaos.

This is personal for me. I’m part of a family of five, and we travel often with grandparents, cousins, and close friends who are family. I understand the real-world challenges that come with groups: different budgets, different energy levels, different priorities, mobility needs, room configurations, dining expectations, and making sure the plan feels fair and enjoyable for every generation.

I design high-touch group trips across luxury cruises and small-ship sailings, private villa stays, and tailored land itineraries. That can look like securing the right cabin mix on a cruise, arranging a villa with the space and services you need, or building a custom itinerary with private transfers, private guides, and well-paced touring that keeps the group connected without feeling over-scheduled. I can also coordinate escorted tours when that’s the best fit, especially when the group wants built-in structure with the ease of having everything handled.

My clients lean on me to get the details right—adjoining rooms, multi-room suites, family-friendly yet refined resorts, celebration dinners, logistics for arrival days, and experiences that work across ages. I also help keep group planning organized with clear options, timelines, and simple communication, so everyone knows what’s happening and the trip stays enjoyable long before departure.

If you want a multigenerational or group trip that feels elevated, well-managed, and genuinely relaxing, I’m the person who can pull it together—beautifully.

REVIEWS

Rating: 5.0
22 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 22 reviews

Balanced: Fun and Rest
Reviewed By Jen - Saint Augustine, FL | Traveled to Croatia ~ Europe
Always available and willing to solve any issue as quickly as possible. We were never on our own to figure things out.
Helen Skipper responded
"SO excited you were able to get away ,Thank you."
I would recommend this agent to my family and friends.
4 of 4 people found this review helpful. Was this review helpful to you?YES|NO
Fabulous Last Minute southern Caribbean Cruise
Reviewed By Dancingcgal - St Augustine, FL | Traveled to Caribbean
Obtained info for my immediately for last minute cruise! Answered questions promptly & offered excellent advice. Very thorough. Very easy to contact and personable even though we’d never met in person. She contacted cruise line for more info even if I hadn’t asked her to.
I would recommend this agent to my family and friends.
4 of 6 people found this review helpful. Was this review helpful to you?YES|NO
Mother Daughter Getaway
Reviewed By Cheri and Alissa - Durham, North Carolina | Traveled to Dominican Republic ~ Caribbean
Helen Skipper helped us plan a mother/daughter getaway to Punta Cana in the Dominican Republic . We were very happy with the complete holiday package including flights, accommodations and transfers Helen put together for us. She made it effortless to book, managed everything to the last detail, provided great recommendations, took time to answer all our questions, and made sure we had everything we needed. Unfortunately, we had to cancel our trip at the last minute and Helen was right there to help us with that, too! She was instrumental in securing a refund and even went so far as to ensure we could rebook for the same rate, which made canceling a little less painful. We can’t thank her enough for her patience, hard work and quick responses. We’ll definitely use Helen to book our next trip and the one after that!
I would recommend this agent to my family and friends.
2 of 3 people found this review helpful. Was this review helpful to you?YES|NO
Fun last minute trip
Reviewed By Lyn - Saint Johns | Traveled to Cozumel ~ Quintana Roo ~ Mexico
Helen is very attentive and accommodating.
Helen Skipper responded
"Thank you ! Your patience and tenacity with some of the challenges we have encountered makes us a great team!"
I would recommend this agent to my family and friends.
2 of 3 people found this review helpful. Was this review helpful to you?YES|NO
She’s the best!
Reviewed By Hope Klusmeier - Jacksonville, Fl | Traveled to Mexico
Helen was a great communicator! She always made sure we were in the loop if anything changed about our trip. Helen made our trip so easy, we didn’t have to do a thing. This is our second time using Helen, and we will definitely use her in the future as well.
Helen Skipper responded
"Thank you Hope! So happy you had a wonderful trip, I look forward to helping you with your future vacation plans!"
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.

Client Testimonials

Multiple Trips Nationally and Internationally
Helen is the best! She can hook up anything, anywhere, and is awesome at responding quickly!!! She has helped us on numerous vacations now, both internationally and within the U.S.! HIGHLY RECOMMEND!!
Summer N, Ponte Vedra FL
MultiGenerational Trip Exploring in Asia
Helen Skipper at Dandy Time Vacations is a 5 star Travel Travel Consultant. We have always found her to give excellent advice and assistance on our travel. She stays plugged in the entire time and makes sure we have a wonderful experience whether at home or abroad. Wouldn't want to have anyone else to help plan and execute our travel. Thank You Helen for our wonderful travel experiences!
Patsy H, NC
Anniversay Trip to Italy!
From the start of the planning of my trip to Italy to the execution of the plan and even during the trip Dandy Time and Helen was with us all the way. There were frequent touchpoint, thorough run throughs, details on what to expect, what to be aware of - good, bad, otherwise. Helen ensured to set appropriate expectations and answered my multiple questions (some asked more than once...lol). She was very patient and catered the vacation to my needs. We were able to do and see a lot in Italy while feeling special - she was able to arrange for transfer car services, gave me instructions to work with the hotel, intervened as needed and we were also able to communicate while I was there. Anyone planning a trip? I say consider Dandy Time - it is worth not having the headache, just think about packing your bags, paying and following instructions...no kidding. Thanks again Helen and team, you made our first trip to Italy memorable and smooth.
Christine D, Mount Holly NC
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