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    Chesapeake Sailing Tours

    5.0 (4 reviews)

    Services - Chesapeake Sailing Tours

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    9 years ago

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    12 years ago

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    13 years ago

    Captain Dan was a pleasure during our sail! Very knowledgeable of the area and kept us safe. Definitely would recommend.

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    United States Naval Academy - BANCROFT HALL

    United States Naval Academy

    (109 reviews)

    Annapolis, MD - we toured the Navy Academy as a side trip to DC, as I knew it was an activity that…read morewould interest my dad. You can either check out the visitor center and free museum (a few blocks away) and walk around on your own (after going through security - this is an active naval base so ID is required to enter), or opt for a public guided tour, if you wish learn more about the history, traditions, and campus life of this institution. The 90-minute historical walking tour is the most popular, but I booked a GEM riding tour for my family (in a 5-passenger electric vehicle), since we were traveling with elders and a young child, so wouldn't be able to cover much ground across the sprawling Yard otherwise. The 75-minute tour takes you all around the Yard in comfort and highlights the "gems" of the naval academy. The campus is beautiful and pristinely maintained, and we were expertly entertained and informed by our wonderful tour guide Anne, whose whole family is Navy, and shared additional insights into the life of a midshipman and beyond. Parking: the limited parking near the visitors center is only available to those who hold a military ID. Otherwise you can either park at a garage or try metered street parking which is limited to 2 hours.

    I walked around the campus of the U.S. Naval Academy two weeks ago, when my husband and his family…read morevisiting us from out of town explored Annapolis for a few hours. I wish we'd had time for a guided tour (the other reviewers have really sold me on that experience, and I look forward to doing it in the future), but we had a great time exploring on our own. We arrived in the late afternoon. When you arrive, you need to enter through the Armel-Leftwich Visitor Center (even if you're going to the chapel or the museum, navigate your walking directions here to avoid wasting time - Google Maps doesn't know you need to enter at this particular gate), where you'll show ID and put your things through a metal detector, but that was very quick. The highlights of our walk around campus included the walk down Porter Road (the houses on this street looked like I was on the set of Top Gun), the U.S. Naval Academy Museum, and the Naval Academy Chapel. Both the museum and the chapel were easy to find, because the campus has very good signage. The museum is located in Preble Hall and is two floors of naval and U.S. Navy history and a collection of model warships. It's definitely worth a visit (it has its own Yelp page, so you can read reviews specific to the museum there). The chapel really blew me away. It was built in 1904-1908 but underwent extension remodeling in 1940. It's large (it seats 2,500), with a copper dome (the cupola is 193 feet above the main altar area). It's very beautiful, and you should definitely stop in for a look if you're exploring campus. The campus is beautiful and a unique space in Annapolis. I'd been to Annapolis dozens of times (mostly for work before) visiting the Naval Academy! I wish I'd explored it sooner.

    Annapolis Ghost Tours & Crawls

    Annapolis Ghost Tours & Crawls

    (46 reviews)

    $$

    5/5 -- Incredible Halloween Ghost Tour with Kasey!…read more We had an amazing experience on the Annapolis Ghost Tour with Kasey on Halloween night! Her storytelling was absolutely captivating -- she brought every tale to life with incredible detail, fun facts, and just the right touch of spooky flair. You could tell she really loves what she does, and that made the whole evening so engaging. We also loved that our tour included stops at three fantastic bars, each with its own private room where we could relax, enjoy a drink, and listen to more stories -- it made the night feel extra special and intimate. The highlight for us was the basement of the Maryland Inn -- that space was simply picture-perfect and full of atmosphere! If you're looking for a fun, fascinating, and slightly spooky night out in Annapolis, we can't recommend Kasey enough. She made our Halloween unforgettable!

    I've been in the surrounding Annapolis area for nearly 9-years and never done a ghost tour!…read more Surprisingly, tickets were only $20/person, $18 with military identification and it was beyond worth it! There were at least 10 stories told of Annapolis facts and stories from earlier decades and it was informative, spooky, and most of all... interesting. The best night to go would more than likely be Halloween, but I lucked up and got tickets for the night before Halloween and had the best time! Our guide was great and I would love to go again to say hi to Charles! ;)

    Annapolis Food Tours - Raw Oyster Shooter with a Natty Boh Chaser at Middleton Tavern

    Annapolis Food Tours

    (7 reviews)

    We took the history and food walking tour of Annapolis this past Saturday, and had a great time…read more Our tour guide, Carolyn, was knowledgeable and enthusiastic. Her love of Annapolis was obvious. Food was varied, excellent, and plentiful; neither one of us was hungry for dinner that night!Will certainly return to a couple of the restaurants we visited and tour some of the buildings she talked about. A great way to get a sense of Annapolis and a lot of good food.

    Started 7 minutes late due to other patrons being late (they were looking for parking), so don't…read morefret if you are running a little bit late. Our tour guide was an energetic, knowledgable young woman named Sam. Historic stops included: St. Anne's Parish, Maryland State House, Shiplap House, Maryland State Capitol Building, and some other random street corners where the tour guide pointed out some notable buildings/historic sites. We stood outside while Sam discussed some interesting history and culture of the town and each attraction. The tour guide discussed and recommended other establishments around the area (she pointed them out along the route) that were not on the tour, including places to eat, drink, and buy souvenirs. I really appreciated that aspect of the tour. See the pictures for the food stops and menu. The food was really great, with the exception of the tacos. The cream of crab soup at the Federal House was FANTASTIC. This was a pretty incredible way to experience and learn about Annapolis, and just a great afternoon outing. I highly recommend it.

    Annapolis Electric Boat Rentals

    Annapolis Electric Boat Rentals

    (41 reviews)

    On April 5, 2026, I made online reservation for a boat at 10 AM April 6, and was charged $423 at…read morethat time. At 8 AM the following day, I received a voicemail, an email, and a text message from the company stating that they were closed Monday and I should not have been allowed to make a reservation via their own website,. Obviously there would be a full refund, and they were very apologetic. I never received the refund and contacted them twice more during the next six days. Today I received an email from Benjamin. Tiederman stating that I would only be refunded 50%, which would not be received for another five days. This is fraud and theft, Along with basic incompetence and lack of ethics. I had to eventually submit a charge back to my credit card company, which will cost them extra money in fines instead of doing what they stated they would do. I've never left a negative review on any site so congratulations Annapolis electric boat rentals.

    This was a great opportunity from start to finish. Reserving was easy, and during the process I…read moremade a change due to the weather and that was easy. Driving an electric boat was a first and it was easy. I've been boating since 2012 and driving this boat was not only easy but fun...and but the way despite sailing since 2012 I'm still slightly step above a novice. The Captain/owner is a great guy, professional, and thorough. I didn't think this was a thing for me where I would want to come back and do it again but I feel like I'll be back this summer. I highly recommend it! Great experience and the perfect way to celebrate a birthday.

    Watermark - Thomas Point Lighthouse Cruise

    Watermark

    (29 reviews)

    This is a perfect go to event if you have out of town guests to show around. The 40 minutes is a…read moreperfect amount of time to get a glimpse of the beautiful Severn River feeding into the Chesapeake Bay. The trip is narrated so your guests get a blast of history particularly focused on the Navel Academy. Snacks and drinks are served. Seating is inside and out side on the upper deck. Great time!

    TL;DR: Don't do business with this company! Horrible experience inside and out, wasted money, lies,…read moreand no concern for customer care. Worst Wedding Experience. Details: We recently got married and thought it would be an awesome idea to get married with Watermark while sailing on one of their boats. From day one we asked several questions about things we wished to have on our wedding night. Watermark ensured us that our desires/wishes were manageable and doable. As we got later in the process, several promises they made to us early on became untrue. There seemed to be a massive communication gap between the sales team and the operation team. A communication gap that ultimately cost us thousands of dollars. A few examples: From the day we took the tour we asked if we could bring our own chairs (rent from another company), place those chairs on the third deck for our ceremony, then have them moved downstairs for dinner. We were told this wouldn't be an issue. Come to find out roughly a month before the wedding we were told this cannot be done because furniture cannot be moved once the boat is moving. This wouldn't have been an issue if we were told from the beginning, but being we had paid for chairs, now we had to scramble to come up with different ideas for the top deck, ultimately renting couches so we wouldn't overcrowd the third deck (where we wanted to dance after the ceremony). This was a several thousand dollar last minute change due to incompetence. Furthermore, we discussed several times wanting to bring our own chairs, but the sales team waited until the very end of the process letting us know the price would be $1,000 fee. This felt like extremely dirty business as you knew the price the whole time, but failed to tell us until we had no choice but to pay it. Every contract they sent us with quotes didn't have the fee on there, even though we discussed it several times. If you would have been up front in the beginning we could have planned around this. Another communication gap between sales and operations is when the sales team told us we could have an Ice luge, so we purchased one. Only for them to come back days later saying we are not allowed. I had to push back on this and eventually they let us, but it was still very frustrating. If we weren't confrontational with them on this, it would have cost us another $750 dollars. Additionally, we paid for the unlimited drink package and specifically asked not to leave a tip jar on the counters because we didn't like how it looked. We were told this wouldn't be an issue, however when we got on the boat each bar had a tip jar on it. Throughout the course of the night, all the lights on the boat kept flickering on and off to the point where several guests started making jokes that the boat was going to lose power and we would be stuck out on the water. The sales team also tried personally reaching out to our vendors, telling them they need to bring more staff to set things up, yet again trying to cost us last minute additional charges. These vendors billed us properly from the start based on their understanding and the conversation we had with those individuals. Why would Watermark try to contact them and tell them they need more people to set up? I have several more examples where I could go on and on about the issues we had with Watermark, but ultimately it comes down to how sneaky it felt. All these hidden charges at the end, telling us we can do one thing, then later telling us we can't. At no point was working with Watermark pleasant and I truly in no good faith will ever recommend anyone doing business with them. For us, we spent a lot of money just for several things to go wrong, our food to be ice cold. At no point did anyone seem like they cared about our business from Watermark. Every interaction with them they treated us like nobodies, we were just a transaction to them. Watermark made it clear that it was simply a business transaction and they didn't care about our wedding day. We truly regret sailing with Watermark.

    Chesapeake Sailing Tours - boating - Updated May 2026

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