travel agents in annapolis

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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: [email protected]

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.

Best Connection Travel

GREAT GROUP TRIPS!

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Exploration Awaits Travel

Annapolis family travel agent specializing in Europe, North America, and beyond.

Travel Advisor Services

Travel advisor services provided by a full-service family travel agent – p roviding all your travel needs from “where to” to “welcome home”.

Travel advisor services include:

• Customized itineraries
• Activities and excursions
• Accommodations
• Flights (as part of package)
• Travel insurance
• River Cruises
• Expedition Cruises
• Group vacations (family reunions, class reunions, clubs, etc)
• Escorted Tours
• Travel assistance while you’re underway

Specializing in:

• Family Travel to European Destinations, North America, and beyond

Whether you’re traveling alone, with friends, or as a family,  let me help put together your customized vacation so that you can relax and enjoy your well-deserved, stress-free time off.

What’s it like to work with me? 

It starts with a conversation – I get all of the information I need  to match you and your family/traveling companions with the best vacation possible. Once we nail down all the details and I understand your vision for the trip and your family’s travel styles and special circumstances,  I get to work. I research the best options and reach out to my travel partners to create a customized trip that’s unique to you and your family.  I’ll provide you with a customized, detailed itinerary for your trip. Depending on the trip, there may be a few options to decide on. We can also make tweaks to the itinerary to make sure everything meets your expectations (expect a little back and forth so we can make it perfect for you!). After we settle on the right itinerary and options, you provide your payment authorization and I book your trip through my partners. Easy Peasy! 

But that’s just the beginning – throughout the process we’ll stay in touch as things come up related to your trip. In the background, I’ll make sure everything’s going according to plan, while you look forward to your vacation. And if anything unexpected happens, count on me to be on top of it!

So that’s it folks – tell me your vision and let me do the work instead of sifting through the overwhelming amount of information. Still not sure what’s involved? Feel free to reach out via email or phone (443-607-2857). Ready to start the next steps? Fill out my travel interest form .

My first experience traveling to another country was with an exchange program in high school. It was only three weeks in Germany, but I got to stay with a host family, fully immersed in the culture. That set me on the path for loving travel and experiencing the culture that other countries have to offer, but it also set high standards for my travel expectations. Being a typical tourist in a destination was not enough. My most memorable experiences have been spending a little time off the beaten path and taking time to do things that locals also do – like ice skating at the Hotel de Ville in Paris, biking around a local park, or going to the movies (what better place to see the premier of the last Harry Potter movie than in London?) Now that I’m a mom of two girls, I find it more important than ever to expose them to this way of traveling. But traveling with children comes with its own set of challenges that can be intimidating.

One of my goals as a travel advisor is to help remove the obstacles for families so that they can travel worry-free and have the fulfilling experiences that come along with experiencing another place. I take care of all the details from a-to-z so all that’s left to do is enjoy the trip and spend time with your loved ones.

Contact me   and let’s make your dream vacation a reality.  Or if you’re like me, let’s make the next  in a long line of dream vacations a reality.

Ready to Plan?

Are you ready to start planning your next adventure?  Drop me a line below.

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Travel Agents in Annapolis, MD

• Locations ›
• Annapolis, MD ›
• Severna Park, MD (7 mi)
• Pasadena, MD (10 mi)
• Baltimore, MD (23 mi)
• Essex, MD (23 mi)
• Ellicott City, MD (26 mi)

Best Connection Travel Inc

• Travel Agent
• 2005 West St Annapolis , MD 21401
• Closed ⋅ Opens at 10:00AM
• Location Great
• Ratings Great

Creative Travel

• 177 Defense Hwy Annapolis , MD 21401
• Open 24 hours

Tiffanys Treasures

• Annapolis , MD 21401

Marilyn Malachi

• Annapolis , MD

Travel agent referral in Annapolis , MD

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Annapolis Travel Agents

Heaven sent travel, llc.

We are a full service travel agency, that is ready to work with you one on one to make your Wedding and Honeymoon ... Read more unforgettable!!

STS Vacations

Located in Annapolis, Maryland, STS Vacations is a travel agency specializing in destination weddings. Working in ... Read more collaboration with the easy-to-use All Inclusive Resorts online tool, these specialists delight in jetting their clients off to their dream marital locations. From the golden sands of ...

Other options near Annapolis, MD

Time for travel.

TIME FOR TRAVEL LTD is a full service travel planning corporation specializing in Destination Weddings and Honeymoons, ... Read more located in Davidsonville, Maryland. Whether you’re dreaming of a destination wedding or lavish honeymoon we have the expertise to make your dream a reality. They’ll take the time to ...

Charm City Travel

Charm City Travel is a wedding holiday company in Baltimore, Maryland. Run by a diverse team of travel experts, this ... Read more business works hard to have couples jetting off to the destination of their dreams. Services Offered Charm City Travel boasts an expansive catalog of services for nearlyweds with ...

Good Day Travel

Good Day Travel is a business based in Capitol Heights, Maryland that provides travel agent services for destination ... Read more weddings and honeymoons. Owner and operator Marshe' Edwards is a research scientist with lifelong experience in traveling and loves helping clients to discover other cultures and ...

Enlighten Excursions

Enlighten Excursions is a travel agency with travel agents located in Silver Spring, Maryland, and Boston, ... Read more Massachusetts. Specializing in destination weddings and honeymoons, the company has over two decades of experience in the industry. They encourage every couple to take advantage of their team ...

CP Experience & Travel

CP Experience & Travel located in Cheltenham, Maryland, is here to assist with the major wedding planning & other travel ... Read more services you may have! Need a Hotel Room Block? Want to book a honeymoon? Want to plan a bachelor/bachelorette party? I would love to help be a part of your special day! Please ...

Suite Dreamz Travel

Suite Dreamz Travel is a travel agent in Cockeysville, Maryland, with more than two decades of experience in the field. ... Read more Hire them to plan your destination wedding or honeymoon so you can focus on everything else. Suite Dreamz Travel wants to “make your travel dreamz come true” and will do so through ...

Asimina Tours

Asimina Tours is a boutique luxury travel company located in White Plains, Maryland that services destination weddings ... Read more and honeymoons. This company specializes in tailor-made trips to Greece, Italy, and Turkey. These travel professionals are dedicated to giving each client the chance to explore ...

Indian Destination Wedding

Expanding horizons and breaking through borders – that has always been the mission of Indian Destination Wedding. Led by ... Read more seasoned event planner Ateet Ahuja – we’ve always been impassioned by the prospect of helping folks create memorable moments they’ll cherish for a lifetime, and have been planning ...

Booked N Busy Travel

Based in Alexandria, Virginia, Booked N Busy Travel provides premier travel planning services.

Destination-Wedding-Experts

Based in Gaithersburg, Maryland, Destination-Wedding-Experts is a full-service boutique travel agency that specializes ... Read more in planning trips for honeymoons and destination wedding packages. Your travel specialist will work closely with you from the beginning of your trip to the very end. ...

Travel Agents near Annapolis, MD

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• Viewing Travel Agent : Linda Halstead

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About Cruise Planners- Halstead

Cruise Planners has a tremendous reputation for quality, service, and very competitive pricing for ALL of your travel needs. Cruise Planners travel advisors will help you discover exciting adventures around the world. From cruises to land tours and completely packaged vacations, we specialize in all types of travel and will create an unforgettable vacation just for you.

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Centsible Travel & Vacations

Unveil the Extraordinary - Your Adventure Awaits!

Explore incredible vacation packages and tours across the globe!

Welcome to Centsible Travel & Vacations!

Embark on a journey of extraordinary experiences with us. We are a dedicated travel agency committed to curating unforgettable adventures that cater to your unique desires and preferences. From exploring breathtaking destinations to immersing yourself in diverse cultures, we are here to transform your travel dreams into reality.

At Centsible Travel & Vacations, we understand the value of your time and budget. Our expert team combines extensive knowledge and personalized service to design travel itineraries that offer exceptional value without compromising on quality. Whether you seek relaxation, adventure, or a blend of both, we have the perfect options to suit your style.

Our partnerships with renowned travel suppliers allow us to secure exclusive offers, privileged access, and top-notch amenities for our valued clients. From luxurious accommodations to immersive experiences, we take care of every detail, ensuring a seamless and remarkable journey.

With our commitment to transparency, fairness, and customer satisfaction, we strive to exceed your expectations at every turn. Our attentive support team is always available to assist you, providing peace of mind throughout your travels.

Let us be your trusted travel companion, guiding you towards incredible destinations and creating cherished memories. Start your journey of discovery with Centsible Travel & Vacations today!

Why Book with Us?

At Centsible Travel & Vacations, doing things differently. Starting from the belief that travel holds limitless possibilities, we create exceptional experiences for our very special guests. With a global collection of hotels, private residences, yachts and luxury hideaways, we use our local knowledge of worldwide destinations to deliver an unrivalled blend of culture and Centsible luxury for every traveller.

Join Our Upcoming Experiences

Join us on of our many destination experiences. Prices are based on double occupancy and may be reserved with a deposit for travel 90+ days in advance. We also can curate your custom group experience. Simply complete the quote request form or contact us to get started!

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Explore Annapolis , Maryland

Annapolis' roots hark back to 1649 when a group of Puritan families from Virginia established the settlement of Providence on the north bank of the Severn River. Within a year a new county named after Lady Anne Arundel, the late wife of Cecil Calvert, the second Lord of Baltimore, was established. By 1684 Anne Arundel Town was laid out on 100 acres across the Severn from Providence and by 1694 the first royal assembly meeting under Governor Sir Francis Nicholson designated the settlement on the south side of the river the new capital, which was renamed Annapolis in 1695 in honor of Princess Anne, King James II's daughter and future queen of England. Learn More...

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Aladdin Travel Agency

Location & hours.

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2820 Broadview Ter

Annapolis, MD 21401

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I'm pretty offended. My boyfriend and I had him recommended by a co-worker so we decided to check him out. We had a few emails back and forth where he was excited to work with us and we discussed where we were going. However, once we told him what we thought our budget was, he sent us this email: "After reviewing your email, I find I will not be able to assist in your traveling planning. Reasons are many but primarily my current work load is heavy and I can not devote the time neccesary to do a good job." I'm assuming he's upset because of what our hotel budget was ~$150-$200 a night, but we said we'd go higher - that was just our ideal price.

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