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    Chesapeake Windsail Cruises

    5.0 (6 reviews)
    Closed 9:00 am - 6:00 pm

    Services - Chesapeake Windsail Cruises

    Boat charters

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    9 months ago

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    7 years ago

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    8 years ago

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    8 years ago

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    8 years ago

    Friendly and knowledgeable Captain and crew. Nice boat

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    8 years ago

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    Cruisin Tikis Solomons Island - Tiki boat on the dock

    Cruisin Tikis Solomons Island

    (4 reviews)

    We recently did a 2-hour Tiki cruise for my mom's birthday, and had such a great time! The boat…read moredeparts from a bar/restaurant on the water so there's plenty of parking and you can grab a drink or a bite (and use the bathrooms--there's none on the boat) before or after. The boat itself is literally a round, floating tiki bar on the water. It holds up to 6 people plus the captain. You can bring your own drinks (recommend taking a page out of our book and bringing a pitcher of pre-made painkillers with you for the ride!) and snacks, and they provide water and drinking ice. You can also connect to bluetooth speakers to play your own music. Our captain was great, he chatted with us throughout the ride, pointing out wildlife and sharing little tidbits about the landmarks and history of the area as we cruised around. As you'd expect this thing doesn't move very quickly, but it made for a really relaxing ride with plenty of time to check out the views, enjoy a few drinks, and gawk at all the houses and boats along the shore. We went around 6:30pm and it was perfect for beating the heat and catching some sunset. Would totally do this again for a special occasion or with out of town visitors!

    Relaxing and fun! Two hours on the water with a nice breeze, despite the blazing heat, was chill…read moreand just enough time. My husband and I were with two other couples/family and every one of us loved it. The skipper Jim was friendly and knowledgeable about the area. We brought a couple of adult beverages, leis, and snacks, and we had an instant floating luau!

    Rod 'N' Reel Marina - Rod 'N' Reel Marina

    Rod 'N' Reel Marina

    (3 reviews)

    So disappointed with the customer service. We had rented a pontoon weeks ago and made arrangements…read morewith family from out of town. We received a call this morning the boat is not available due to engine failure. Ok these things happen. But the fact that they knew a week ago and only called us a day before our scheduled rental is extremely frustrating. When asked why they waited so long, we were told that they thought someone had told us. Huh, then why did you call us to tell us today if you had thought someone had already told us? It's impossible to get a rental in July on a Saturday the day before, so now our plans are shot. We would have just liked to have been given some consideration when they knew the boat wasn't going to be up and running. We understand that things happen, but advance communication would have been nice and have shown a courteous customer service. We have rented from them once before and the pontoon boat that we rented was very nice. We couldn't take it out on the bay due to a Coast Guard advisory so we took it up and down the creek for a slight discount, which we had to make an argument for. I mean we could walk faster than we sailed the boat and we didn't even use as much gas as we would have...long story short...it was an argument to get a SLIGHT discount and they had an attitude with us as well. All in all, beautiful boats, gorgeous area....but the customer service needs to be worked on and unfortunately that is what is remembered. Just be KIND.

    First and last time season slip holder, brought my boat hear for this season after seeing the…read moreplace.I live 5hrs.away so I come down twice a month. Thought when I came and brought the grandkids they could go to the pool to entertain themselves WRONG. They closed the hotel pool, but they have another pool not in the hotel but they tell us that pool is for hotel guests only. My contact states we have pool access, all there websites state the marina has a pool we just can't use it. Like I said first and last year.

    St. Michaels Sailing Charters - Our guide

    St. Michaels Sailing Charters

    (125 reviews)

    We first sailed with Captain Iris 10 years ago with our children. This year we chose to return for…read morea Monday night for a moonlight cruise. Captain Matt and first mate Mike were top notch. Informative and attentive. Weather was perfect in our eyes, clear with almost full moon. Wasn't much wind, but the Salina II sailed beautifully. Plenty of beverages, great history of a beautiful vessel, and a photograph worthy sunset. Thank you so much for a wonderful night!

    I needed to get away, and saw this excursion via Eric Oranges' wine happenings. Wine tasting and…read moresailing! Right up my alley. I booked and made reservation at Harbour Inn- I love that I stayed at before. Approached by a spry lady, I was asked my name - she turned out to be the granddaughter of this 1926 New England Charter, Capt Iris. Very personable and knowledgable as she pointed out things along St Michaels banks e.g., The Perry Inn and the focal point filming of The wedding crashers. The name Selina, itself had family virtue and significance-pronounced different ways, the one I remember is as in Selena Gomez. We were also quizzed on how many tons the vessel weighed. My guess way low-16 tons!!. We marveled at the woodwork and upkeep of the ship and hours to maintain- not to mention gas cost. We were offered our choice of beverage- I had a tasty Chardonnay, although I'm not sure the brand. The first mate. Was agile at that point coasting in a nice spot to put up the sail, beautiful as the sky was starting to cast its evening glow with the sunset. It was truly relaxing as we made small talk about catfish and enjoyed the ambiance. I then had a second Pinot Noir however the water being a little choppy declined a third- we were Rockin ! a little with wind picking up. It was a very enjoyable outing and I would do it again in a heartbeat! Next time I want to be at the helm lol, if only for a photo shot. Speaking of photos...a picture paints a thousand words...btw the name means 'moonlight'

    Chesapeake Windsail Cruises - boatcharters - Updated May 2026

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