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

Whether a weekend getaway with plane tickets or hotel, a scheduled escorted tour or cruise, or a bucket-list multi-stop family vacation, we have the experience and the connections to make your vacation the best it can be.

Flight/Land Packages

If you’re looking for a quick getaway within the US or to 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 Antartica!), 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

All of our vacations are customized to your needs and tastes, but for those looking to tackle larger multi-stop dream trips, you’ve come to the right place: these are the types of trips we live to pull off.

Past Projects

Holy Land Cruise-Tour: Roundtrip flights, 11-night cruise Rome-Jerusalem, 4 nights Jerusalem, 3 private tours

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Iguazu Falls Excursion: Roundtrip flights from Buenos Aires, full-day Iguazu Falls experience with private guide

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Vienna, Salzburg, and Paris, with Spanish Riding School, Sound of Music Tour, Normandy Tour, Eiffel Tower, all hotels

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We Love Our Clients, and Our Clients Love Us!

“David put me and my fiance at ease by developing a few different itineraries based on our interests. I highly recommend David, as he is highly responsive and will take away any anxieties you have of planning a major trip!”

Sara H., Maryland (Italy)

“David arranged an amazing trip for me within some tight logistical constraints. He was professional, responsive, and he listened to my requests. Will definitely use Fair Winds again!”

Sarah J., Maryland (Argentina)

David presented options, listened to our feedback, and finalized the details we chose. Help at the end of the trip with a slight change to itinerary was priceless. We would recommend Fair Winds Travel because of the ease, the quality of service, and David’s friendliness, knowledge, and attention to detail.”

Margaret F., Alaska (Wales)

The World is Waiting for You

Ready to get going? Reach out today!

Phone: (410) 212-5088

Email: info@fairwindstravelagency.com

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.