Small Ship Cruising and Expedition 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
Travel Stories & Media
Client Testimonials

Areas of expertise

Destinations:

Virgin Islands, France, Croatia

Interests:

Global Travel, Luxury Cruises, River Cruises, Small Ship Cruises, Culinary & Foodie

Suppliers:

AmaWaterways, Explora Journeys, HX, Tauck, Windstar Cruises

About Me

If you love travel that feels personal, calm, and immersive, you’re in the right place. I specialize in small ship cruising across rivers, oceans, and expedition routes, and I help clients choose the right ship and itinerary based on how they actually like to travel—not just what looks good on paper.

My recommendations come from real, recent onboard experience. I’ve sailed an Amadeus river cruise, which gave me firsthand insight into how river cruising truly works day to day—cabins, dining, service style, pacing, excursions, and what makes one itinerary feel easier (and better) than another. I’ve also been onboard Windstar and Explora Journeys recently, so I can speak clearly to what the experience feels like in real life: the ship vibe, the flow of the day, the comfort level, the little details that matter, and who each brand fits best. 

Small ships create a different kind of trip. You get better access to ports that larger ships can’t reach, fewer crowds, more attentive service, and an onboard atmosphere that feels relaxed and refined. But every small ship line has its own personality, and the details matter—cabin locations, inclusions, dining style, port times, and the overall pace of the itinerary. That’s where my experience becomes your advantage.

River cruising is one of the easiest ways to explore Europe and beyond because you unpack once and wake up close to the heart of each destination. For small-ship ocean cruising, I match travelers with the itinerary and onboard vibe that fits—whether you’re drawn to scenic sailing days, culturally rich ports, or a quieter, more elevated experience at sea. And for expedition travel, the right ship, right season, and right activity level make all the difference, especially for places like Antarctica, the Galápagos, and the Artic.

Clients choose me because I don’t just book trips—I build travel plans that feel effortless, protect the experience, and fit the traveler. If you’re ready for a river cruise, small-ship ocean sailing, or expedition that’s thoughtfully planned from start to finish, I’m the person to help you get it right.

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.

My Photo Albums and Videos

Explora I Puerto Rico to Miami
View Album

    My Travel Stories

    Ocean Suite 1

    "Ocean State of Mind" with Explora Journeys

    After 13+ years of sending clients on luxury cruises, I finally stepped aboard Explora I to understand what makes this brand different. The answer hit me before we even left San Juan: a 1-to-1 crew-to-passenger ratio that you don’t just notice — you feel. Every corridor, every restaurant, every quiet corner of the ship held a crew member ...
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    Ocean Suite 1

    "Ocean State of Mind" with Explora Journeys

    After 13+ years of sending clients on luxury cruises, I finally stepped aboard Explora I to understand what makes this brand different. The answer hit me before we even left San Juan: a 1-to-1 crew-to-passenger ratio that you don’t just notice—you feel. Every corridor, every restaurant, every quiet corner of the ship held a crew member wh...
    Read more

    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
    BESbswy