Crafting Meaningful, Custom Travel Experiences

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Jaime Crosthwait, CTA, Travel Agent in Middletown, MD

Jaime Crosthwait, CTA

Middletown, MD Travel Agent
Super Agent

Jaime Crosthwait, CTA

Middletown, MD · 3 Years of Experience

Jaime Crosthwait- Terrapin Travel, an independent agent with KHM Travel Group, a Travel Leaders Network Affiliate Agency
5.0
(31)
100% Recommended
I get overwhelmed when traveling and I am not good with apps. Jaime send me color coded copies of everything so I would have all... Read More >
About
Reviews
Certificates & Awards
My Places
Travel Stories & Media
Client Testimonials

Areas of expertise

Destinations:

Europe, Croatia, Antigua & Barbuda, Iceland, Punta Cana

Interests:

Adventure, Solo Travel, Outdoor Activities & Sports, Scuba, Bespoke Travel

Suppliers:

Inclusive Collection – World of Hyatt, Backroads, Virgin Voyages, Intrepid Travel

About Me

Hiking in Sedona
Hiking in Sedona

I’m a Certified Travel Associate through The Travel Institute with specialty certifications in Active & Adventure Travel, Iceland, and Croatia. I also specialize in honeymoon and romance travel, helping couples design stress-free, deeply personal getaways that feel intentional, elevated, and unforgettable. I believe travel has the power to shift our perspectives, build empathy, and create connection — and that’s what I help my clients experience every time they leave home.

As an advisor with Terrapin Travel Co, I craft customized travel experiences for individuals, couples, families, and groups who seek more than just a getaway. My clients value meaningful exploration — whether that means hiking in remote landscapes, discovering a new culture, reconnecting with loved ones, or celebrating a personal milestone in an extraordinary setting.

Specialties:

Active & Adventure Travel: I help travelers of all experience levels plan active adventures, from soft hiking and kayaking to multi-day treks, cycling tours, and winter escapes. Whether you’re looking for a challenge or a scenic escape, I’ll match you with the right destination, pacing, and guides to make your trip inspiring and safe.

Honeymoons & Romance Travel: From secluded, all-inclusive Caribbean resorts to private villas, boutique hotels, exotic adventure honeymoons, and luxury hideaways around the world, I tailor each itinerary to match your vision. I coordinate special touches — private transfers, romantic experiences, upgraded amenities, and personalized surprises — so couples can focus on what matters: celebrating the beginning of a new chapter together.

Group Travel Experiences: I design group trips that bring people together — alumni groups, service organizations, extended families, professional associations, or friends celebrating a milestone. These journeys are fully customizable and can include cruise charters, guided tours, cultural exchanges, or wellness-focused escapes.Celebration & Milestone Travel: I build experiences around birthdays, anniversaries, retirements, graduations, reunions, and other life events. Whether it's an all-inclusive resort in the Caribbean or a European river cruise, I ensure every detail supports the moment you're commemorating.

Destination Expertise:

Iceland Travel Specialist: dramatic landscapes, geothermal wonders, and seasonal experiences like the Northern Lights and midnight sun

Croatia Specialist: coastal cruising, UNESCO heritage sites, local wine and cuisine, and charming old towns

Caribbean & All-Inclusive Resorts: beachfront escapes, couples-friendly luxury, overwater bungalows, and curated cruise itineraries

Cruising & Small Group Tours: partners include Virgin Voyages, Royal Caribbean, Azamara, and luxury small-group tour companies worldwide, with tailored pre/post cruise extensions

My Philosophy: Travel should be intentional, enjoyable, and tailored to your interests, values, and style. Whether you crave cultural immersion, adrenaline, peace and quiet, or meaningful time with loved ones, I approach each trip with thoughtfulness, creativity, and logistical precision. I bring resilience, empathy, and professionalism to my work — helping people turn inspiration into real-world memories that become more than bucket-list items.

Who I Work With:

Couples and families

Honeymooners and romance travelers

Milestone travelers seeking meaningful celebrations

Alumni, nonprofit, and service-based groups

Solo travelers and first-time explorers

Professionals wanting curated, hassle-free escapes

Why Work With Me? If you're looking for a travel advisor who provides destination expertise, personal attention, and integrity throughout the planning process, let’s talk. Whether you're organizing a once-in-a-lifetime honeymoon or a quick, effortless getaway, I’m here to make your travel meaningful, seamless, and unforgettable. Let’s plan your next journey together.

Additional Languages
Signed English

REVIEWS

Rating: 5.0
31 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 31 reviews

Stress-free travel
Reviewed By Reluctant traveler - Myrtle beach, sc | Traveled to Bermuda ~ Caribbean
I get overwhelmed when traveling and I am not good with apps. Jaime send me color coded copies of everything so I would have all info and know what to expect. She is very organized and communicates well. She even had my favorite wine waiting for me in my room so that I was sure to have a relaxed, stress free trip.
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
Amazing Getaway thanks to Jaime!
Reviewed By Jennie M. - New York, NY | Traveled to Bermuda ~ Caribbean
The best in thoroughness, communication, and professionalism - would not plan a trip through anyone else! Jaime planned a beautiful trip for myself and my mother and I couldn’t be more thankful for her attention to detail, reminders, and overall thoughtfulness. I’ve never met a travel agent who takes it to the next level like Jaime does. Moving forward I will ONLY book trips through her! Truly setting the bar and made our trip beyond enjoyable and seamless. Thank you Jaime! Can’t wait for the next one :) I would absolutely recommend Jaime to anyone looking to plan a trip without hesitation.
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
Best and most carefree trip I’ve ever taken
Reviewed By Happy traveler - Frederick md | Traveled to Bermuda ~ Caribbean
She made the entire booking and travel process easy
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
Great Experiences
Reviewed By Jack Putnam - Frederick, MD | Traveled to Europe
I went on two trips with Jaime. She was organized and we were able to see a lot of sites I would not have seen otherwise. She was thorough with planning and communication. I would highly recommend using Jaime to organize any trip.
Jaime Crosthwait, CTA responded
"Thanks Jack- Let me know anytime you are ready to cross something else off your bucket list."
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
Great trip and money SAVED!
Reviewed By Papa Bruce - Houston, TX | Traveled to Nashville ~ Tennessee ~ USA
Jaime handled every aspect of my travel exceptionally. From airline flight, to rental car, to hotel, she made everything EASY for me. Her suggestions were right on as she listened to all my concerns and delivered across the board.
Jaime Crosthwait, CTA responded
"Thanks so much Bruce- it was a pleasure to work with you."
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

Certifications & Awards

ASTA is the leading global advocate for travel agents, the travel industry and the traveling public.It is the world's largest association of travel professionals.Our members include travel agents and the companies whose products they sell such as tours, cruises, hotels, car rentals, etc.Expand your world. Go with the pros.
Certified Active & Adventure Travel Specialist: During this certification program Travel Agents study several components including: Understanding the Active & Adventure Travel Customer, Destination Knowledge, Active & Adventure Travel Experiences, ATTA Travel Resources, Active & Adventure Preferred Suppliers, Case Studies and a Marketing Plan. This is a two-year study program.
Trusted Travel Advisor: A Trusted Travel Advisor credentials, resources and global connections translates to today’s consumer in respectful interactions, confidentiality, knowledge, and client advocacy of travel services provided in parallel with building long lasting client relationships that builds with each interaction.  A Trusted Travel Advisor knows their client better than the client may know themselves and puts those polishing touches on each travel collaboration.
AMResorts Master Agent
AMResorts Master Agent
Celebrity Learning Certification
Celebrity Learning Certification
NCL University - PHD Degree
NCL University - PHD Degree
Royal Caribbean University - Master of Adventure
Royal Caribbean University - Master of Adventure
Seabourn Academy Graduate
Seabourn Academy Graduate
Seacademy - Gold Certification
Seacademy - Gold Certification
Windstar Star Specialist
Windstar Star Specialist
World Azamara Academy
World Azamara Academy
Antigua Specialist
Croatia Specialist
Iceland Specialist

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 Travel Stories

Why Iceland Is the Ultimate Destination

If you're the kind of traveler who prefers hiking boots over heels and finds joy in chasing waterfalls instead of cocktails at the bar (though Iceland has those, too), let me introduce you to your new adventure soulmate: Iceland. This otherworldly destination isn’t just beautiful — it’s wild, raw, and made for movement. As a certified Iceland sp...
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Ahoy!

Why Virgin Voyages Is My Favorite Cruise Line

Let’s be honest: cruising has changed a lot over the years. And so have we. As a Gen X traveler, I’ve outgrown the giant water slides, the crowded buffets, the forced group photos at every turn. I want to travel in a way that feels grown-up, fun, indulgent, but also relaxed — and that’s exactly what Virgin Voyages delivers. After sailing ...
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Your Ultimate Pickleball Getaway

I’ll be honest — the first time I started thinking about planning a pickleball vacation, I pictured exactly what we all dream of: ?? Sun-soaked courts ?? Ocean breeze while playing ??A tropical drink waiting after the game ????? Relaxed afternoons by the pool And, it sounded perfect. But once I started mapping ...
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Farm Stay in Tuscany

Agritourismo: A Growing Trend in Active and Advent

In recent years, agritourismo has gained popularity as a unique and immersive way to travel, combining cultural exploration with outdoor activities and a connection to the land. For those seeking authentic experiences that go beyond the typical tourist routes, agritourismo presents an opportunity to engage deeply with rural landscapes, local tra...
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South Shore Beach Trail

South Shore Beach Trail- Bermuda

The South Shore Beach Trail in Bermuda promises adventure and stunning scenery, blending stunning coastal vistas, rugged terrain, hidden beaches and the refreshing embrace of the ocean. This trail that spans from Horseshoe Bay Beach to Warwick Long Bay Beach is only a little over one mile long, but is considered one of the most beautiful trails ...
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Client Testimonials

The BEST trip EVER!!
Knowledgeable, detail oriented, great communication, all around amazing experience!
Kristie F- Frederick, MD
Best and most carefree trip I’ve ever taken!
She made the entire booking and travel process easy.
Marion C- Frederick, MD
Amazing Getaway
The best in thoroughness, communication, and professionalism - would not plan a trip through anyone else! Jaime planned a beautiful trip for myself and my mother and I couldn’t be more thankful for her attention to detail, reminders, and overall thoughtfulness. I’ve never met a travel agent who takes it to the next level like Jaime does. Moving forward I will ONLY book trips through her! Truly setting the bar and made our trip beyond enjoyable and seamless. Thank you Jaime! Can’t wait for the next one :) I would absolutely recommend Jaime to anyone looking to plan a trip without hesitation.
Jennie M- New York
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