The 10 best-rated travel agencies in Annapolis, MD average 4.9★ on Google across 2,693 reviews. Majestic Global Travel Agency has the top rating (5.0★), and Watermark Tours, Charters, Cruises has the most reviews (892). Updated October 25, 2026.
10 companies that meet our bar: rated 4.5★ or higher on Google, with a meaningful review history (2,693 reviews combined) and currently operating. Request a call back and the company will phone you directly.
“We had the best time on our sailing 9/20/2026. Peggy was amazing! Our kids are 3 and 5 and the younger was a little nervous but the crew was so good to her. We will absolutely sail with them again in the future.” — Google review
“Our trip to Greece was amazing!! The hotel and activities did not disappoint. Tilwanda is an excellent travel agent!! I love that fact that she travels with her groups.” — Google review
“We had a lot of fun cruising around. The boat had a speaker, coolers, and plenty of space for food. It was easy to find, and the crew were great.” — Google review
“We called on the day we were looking for a tour, and Lisa very kind to book one for us that afternoon. Craig our guide took us on a leisurely ride explaining the history of what we were seeing and answering all of…” — Google review
“What a wonderful couple of hours we shared with our tour guide Seamus. He was the most friendly and heartfelt guide to show us around what I would consider “his“ Annapolis and the Naval Academy. This was truly…” — Google review
“This was our 2nd cruise on the Woodwind and it was again just beautiful. The captain and crew were very friendly, and very knowledgeable about the area and, of course sailing. It will always be on our to do list…” — Google review
“Amazing sailing trip with Rick and his first mate Matt. Very experienced and knowledgeable and learned a lot while enjoying the beautiful waters! Highly recommended if you are looking for a sailing trip in Annapolis!” — Google review
“We had a great time on our rental of the Large Group - Private Tour boat! Even though we only had 8 people, we were able to rent the larger boat and it was super fun. The captain and crew were awesome, stopping to…” — Google review
“Had a fabulous time on Uniworld River cruise to Venice and Rome! Grateful for the perfectly orchestrated vacation which included, flights, cruise, hotels and ground transportation. The excursions were top-notch with…” — Google review
“This was my favourite tour on our trip. It was the most relaxing, while also learning so much about the river and other local landmarks. Alexandra couldn't have done enough for us, with food and beverage supplies,…” — Google review
We scan Google Maps for travel agency listings in and around Annapolis, keep only open businesses whose main category matches the service, and require a Google rating of at least 4.5 from at least 20 reviews. Companies are ordered by a confidence-weighted score that balances rating and review volume. We do not accept payment for placement.
Majestic Global Travel Agency has the highest Google rating on our Annapolis list: 5.0 out of 5 from 114 reviews (as of October 25, 2026).
Watermark Tours, Charters, Cruises has the most Google reviews among the companies listed here: 892, with a 4.8★ average.
Only open Annapolis-area businesses whose Google category matches the service, rated at least 4.5★ from at least 20 Google reviews. They are ordered by a confidence-weighted score of rating and review volume. Placement is never paid.