The 3 Best Travel Agencies Around Winchester

In 2023, U.S. travel agencies saw gross bookings surge 28% to $109.7 billion as travelers resumed bucket-list trips and multi-generational getaways. Air ticket sales alone topped $99.2 billion in 2024, marking the highest annual total recorded by ARC and underscoring the enduring value of expert advice in an era of choice overload. Winchester’s readers can turn to three standout agencies that blend deep local knowledge with global reach and personalized service.

Lawler Classic Travel LLC

Founded in 2002 by Cathy Lawler—who began as a consultant in Winchester in 2001—Lawler Classic Travel has guided thousands of couples, families and corporate groups to destinations worldwide. Cathy’s credential as a Certified Sandals & Beaches Specialist and her firsthand experience on more than 40 cruises inform every recommendation, whether planning honeymoons, destination weddings or luxury river cruises. The agency’s team travels extensively, maintaining relationships with resorts and cruise lines to secure the best pricing and perks. From all-inclusive beach escapes to custom European itineraries, Lawler Classic Travel handles every detail so clients can focus on making memories.

Drummonds Travel Service

Beth Drummonds—an Independent Travel Advisor affiliate with Lawler Classic Travel—leverages her background as one of the few female plant managers in her family’s manufacturing business to deliver meticulous planning and budget-savvy solutions. Since launching her practice in 2019, she’s specialized in family and multi-generational vacations, romantic honeymoons, cruisetours, National Parks itineraries and theme-park adventures. Available by appointment seven days a week—either face-to-face or via Zoom—Beth emphasizes a stress-free process that aligns with each client’s interests and financial goals.

Wishes Granted Travel Co. (Rae Lowery)

Rae Lowery’s Wishes Granted Travel Co. brings boutique service to every booking, from curated river-cruise journeys to group retreats and incentive trips. Through her Facebook page, Rae highlights seasonal promotions, destination spotlights and real-client testimonials. She works closely with vendors to arrange exclusive add-ons—think private shore-excursions or suite upgrades—ensuring each itinerary reflects clients’ personal tastes. Whether it’s a coastal escape or a ski-resort getaway, Rae crafts seamless experiences that turn travel dreams into realities.

Thanks, ChatGPT.