Explore the World Your Way
Welcome to Fair Winds Travel
Let us plan your perfect getaway and create unforgettable memories.
Fair Winds Travel is a boutique travel agency based in Annapolis, Maryland, focusing on truly bespoke travel. With our extensive knowledge and expertise in the travel industry, we are dedicated to providing exceptional, fully customized travel experiences to our valued clients. Our experienced owner and senior travel advisor is committed to delivering personalized service and creating unforgettable journeys tailored to meet each individual’s unique preferences and needs. Whether you’re planning a relaxing beach getaway, an adventurous hiking trip, or a luxurious cruise, we are here to make your travel dreams a reality. Trust Fair Winds Travel to handle all aspects of your travel arrangements with professionalism, attention to detail, and a genuine passion for creating lifelong memories.
Our Services
Fair Winds Travel specializes in curating fully customizable, multi-destination, and culturally immersive vacation experiences. Our history, knowledge, and expertise delivers big-box travel knowledge into a one-on-one partnership with our clients. Our primary destination is Central Europe, but in sending thousands of travelers to more than 100 different countries, we have the contacts and knowledge base to pair you with your ideal vacation, regardless of destination.
Flight/Land Packages
If you’re looking for a quick getaway to Mexico or the Caribbean, we’ll work with you to maximize the value of your trip and pair you with an awesome flight-hotel combination.
Epic Cruises
Whether a short cruise to Mexico or the Caribbean or a more exotic cruise to Alaska, Europe, Asia or any of the other seven continents (yes, even Antarctica!), we’ve got the right cruise for your needs and tastes.
Organized Tours
Whether large groups or small ones, on conventional tour buses or more locally-flavored transport, touristy or adventurous, we’ll pair you with a like-minded tour group to ensure an awesome adventure.
Fully Customized Trips
These are the trips we live to pull off: multi-destination, two weeks or more, and culturally immersive. We’ll provide you with a mix of enriching activities and downtime to explore your destinations like a local.
Past Projects
Munich, Prague, Vienna; city, food, historical tours; day trips to Kutna Hora, Neuschwanstein, Bratislava; 4-star lodging
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Florence, Rome, Amalfi; Museums; Tuscan Cooking Class; Wine Tasting at Vesuvius; Cinque Terre Hiking; Motorcycle Drive
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Vienna, Salzburg, and Paris; Spanish Riding School, Sound of Music Tour, Normandy Tour, Eiffel Tower; family hotel
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We Love Our Clients, and Our Clients Love Us!
California Seller of Travel Registration Number: 2089491-50. Registration as a seller of travel does not constitute approval by the State of California. Florida Seller of Travel Reference Number: ST37113. Washington Seller of Travel Number: UBI#602775122. Hawaii Seller of Travel Number: TAR 7231.
