Caribbean Expert
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Penny Ryan
Rocklin, CA Travel Agent· 25+ Years of Experience
The Vacationeer, an independent agent with Travel Leaders Kissimmee, FL
5.0
(17)
100% Recommended
I highly recommend working with Penny for all things travel related. She has booked all types of experiences for us domestically and internationally, from cruises, expos... Read More >
Areas of expertise
Destinations:
Caribbean, Puerto Plata, St. Martin, Virgin Islands, Antigua & BarbudaInterests:
Adult Only, All Inclusive, Cruises, Beach Vacations, GroupsSuppliers:
Adventures By Disney , Beaches Resorts by Sandals, Disney Cruise Line, Royal Caribbean, Sandals and Beaches ResortsAbout Me
Puerto Plata, Dominican Republic
Explore the Caribbean with a Seasoned Cruise & Travel Expert
The Caribbean is sun-soaked, vibrant, and full of unforgettable experiences. From turquoise waters and white-sand beaches to lively ports and island culture, it’s the ultimate destination for relaxation, adventure, and fun.
Having sailed the Caribbean on cruises for many years, I bring firsthand knowledge of the islands, ports, and onboard experiences to every trip.
I design Caribbean itineraries that combine iconic destinations with hidden gems. Whether you’re planning a cruise, resort stay, or a mix of both, every detail from excursions to accommodations is tailored for a seamless, memorable vacation.
Must-See Destinations
- St. Thomas, U.S. Virgin Islands – Stunning beaches, snorkeling, and shopping, perfect for both relaxation and adventure.
- St. Maarten – A lively island split between Dutch and French cultures, known for gorgeous beaches, shopping, and vibrant cuisine.
- St. Kitts & Nevis – Tropical charm, historic sites, and lush landscapes, offering a serene escape for couples and families alike.
- Cozumel, Mexico – Premier snorkeling and diving, combined with rich local culture and scenic beauty.
- Grenada – Known as the “Spice Isle,” with pristine beaches, waterfalls, and vibrant culture, perfect for nature lovers and explorers.
Other favorites include Barbados, Aruba, Antigua, and St. Lucia.
Caribbean Travel Specialties
- Cruises: Expertly planned Caribbean sailings with insider knowledge on ships, cabins, itineraries, and excursions
- All-Inclusive Resorts: Worry-free vacations with accommodations, meals, drinks, and many activities included
- Beach & Water Adventures: Snorkeling, diving, sailing, and island exploration
- Adults-Only & Romantic Escapes: Luxury resorts, boutique stays, and private experiences
- Family-Friendly Travel: Activities for all ages, kid-friendly excursions, and smart pacing
- Culinary & Cultural Experiences: Local cuisine, markets, and authentic island culture
Why Plan Your Caribbean Trip with Me?
Having sailed the Caribbean extensively, I know the best ports, excursions, and cruise experiences to maximize your time and enjoyment. I create customized itineraries that combine iconic highlights with local insights, ensuring stress-free, unforgettable travel for couples, families, or multi-generational groups.
Let me design a journey that captures its magic while handling every detail with care.
Contact me today to start planning your Caribbean escape!
Areas of expertise
Destinations:
Caribbean, Puerto Plata, St. Martin, Virgin Islands, Antigua & BarbudaInterests:
Adult Only, All Inclusive, Cruises, Beach Vacations, GroupsSuppliers:
Adventures By Disney , Beaches Resorts by Sandals, Disney Cruise Line, Royal Caribbean, Sandals and Beaches ResortsREVIEWS
Rating: 5.0
17 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 17 reviews
Great experience all around
Reviewed By Fariba - Sacramento, CA | Traveled to Mexico
I highly recommend working with Penny for all things travel related. She has booked all types of experiences for us domestically and internationally, from cruises, expos to standard vacations that are 1-2 years out or just last minute and it has always been a pleasant experience. She always goes above and beyond. Highly recommend!
✓ I would recommend this agent to my family and friends.
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Easiest Trips Ever
Reviewed By JacobS - WA | Traveled to Disneyland | California | USA
Iv been doing Disney trips for years. I know how to make plans and get everything squared away, but it’s time consuming and stressful. Penny makes it so much easier. No stress! I just tell her what I want and she gets it done, never a problem. I even had a change 2 weeks before the trip that she was able to make, and honestly it felt like she upgraded us. If you’ve never planned a trip before or just want a stress free experience, use Penny.
✓ I would recommend this agent to my family and friends.
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Wonderful cruise
Reviewed By BarbL13 - Marysville, CA | Traveled to Alaska | USA
Thanks to Penny, we had an amazing cruise. She took care of transport from airport to ship and back. She thinks of the little things I don’t and it means so much more.
✓ I would recommend this agent to my family and friends.
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Pat Z
Reviewed By Pat - Lincoln, CA | Traveled to Alaska | USA
The cruises arranged by this agency have been very professional, complete and leaving no loose ends.
Accommodations were top notch.
✓ I would recommend this agent to my family and friends.
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Penny takes care of all of our GROUP CRUISES and we love HER!
Reviewed By Hassi S - Sacramento, CA | Traveled to Europe
Penny has been our trusted travel agent for years, and she is the only one we use. She has expertly organized multiple company group cruises for us, and every experience has been outstanding. From the Caribbean and Mexico to Europe and Alaska, Penny has flawlessly managed travel for our large groups with incredible attention to detail. She is always available to answer our questions, consistently checks in with us, and keeps everyone organized from start to finish. Penny also takes care of arranging port excursions and provides the very best advice, ensuring every destination is experienced to the fullest. For our European cruise, her knowledge was unmatched. She shared fantastic insider tips for each city and even organized our hotels and guided city tours both before and after our cruise. We sailed on a seven-night itinerary from Greece to Italy, ending in Barcelona and every detail was perfectly planned. In Alaska, Penny arranged exceptional port excursions in Skagway, Ketchikan, and Juneau that truly made the trip unforgettable. For our Mexico and Caribbean cruises, she always has the best recommendations for shopping, excursions, and local experiences. Penny’s expertise, responsiveness, and personal touch make every trip seamless and stress-free. We couldn’t imagine planning our travels without her and recommend her without hesitation. We've already booked our next group cruise on Royal Caribbean's Icon of the Seas with her for 2027!
✓ I would recommend this agent to my family and friends.
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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
She is absolutely amazing
Penny Ryan has been our TA for two years and I could not be more happy. She takes care of everything from A-Z for our Disney Cruises and RCL cruises. Finding the right cruise, cabin, ship, time etc. Taking care of transport to and from, gratuities, special occasions, answering my endless list of questions and so much more. Last but not least…on a whim we decided we wanted to go on our cruise not in October but change it to ‘the week after next’. Penny didn’t flinch, sat on the phone for goodness knows how long to turn our 8 day cruise into a back to back which we loved! In other words, she is absolutely amazing!”
Helga H | Waxahachie, TX
Penny is spectacular!
Penny is spectacular! I would not want to book a vacation with anyone else. She is very personable, friendly, and patient. She always makes sure to find answers to any questions we have and will always reply in a timely manner. Since she is a Disney fanatic herself, she always has great suggestions and tips to make our lives easier and less stressful. She knows the best way to get things done because she has already done them with her family. We have a special needs son (Cerebral Palsy) and she makes sure that whatever needs or concerns we may have for him are addressed...from transportation, lodging, parks, meals...his needs are always met. We have planned our own Disney trips before Penny came into our lives and never will try that again!
Pat W | Syracuse, NY
Disneyland
We have booked 2 Disney trips with Penny Ryan and each time she has been extremely friendly, informative, and provided quick customer service! Her knowledge about all things Disney and the surrounding activities, restaurants, travel info, venues, weather, and even traffic is much appreciated!! We will definitely continue working with her on future vacations.
Jene W | Rancho Cordova, CA
Amazing Travel Agent
Penny Ryan has set up two cruises for us with rapid responses to all of our questions during the booking process. Moreover, she offered her insights from her extensive personal travels to assist us in selecting the most reasonably priced options and provided pointers for restaurant and available tours. The experience returned us to a time when local travel agents knew their customers and worked through their expectations to ensure they were met.
Ray S | Basking Ridge, NJ