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    Casco Bay Custom Charters

    5.0 (20 reviews)
    Closed 10:00 am - 5:00 pm

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    Services - Casco Bay Custom Charters

    Boat charters

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    The Hesper
    Valerie J.

    We enjoyed our 2 hours sunset sail on the Hesper. Captain Tom and First Mate Enya were great; answering questions and letting a few of us help set the sails. The Hesper was perfect for our group of 6.

    A wonderful sunset sailing event. The captain and crew were gracious, informative and attentive. The available catered food and drink were top notch and the perfect compliment for the tour. I highly recommend the Hesper for a grand sailing experience!! I hope the exquisite professional level photo I plan share with this review posts successfully. Camille, that is $1.50 for your use of the photo. :)

    Boat and sunset
    Austin S.

    Perfect 100% evening. We went for the sunset cruise in late October and had not only a great sunset but a miraculously well taken care of boat and kind staff. Couldn't recommend more.

    Sunset
    Lucille H.

    I loved Casco Bay Custom Charters! The captain and first mate were amazing, and let me and my family pull the sails. We did the sunset cruise on the Hesper and it was stunning. Ship was so cool and anyone in Portland should try it!

    I can't say enough good things about them! I booked a private charter for 12 people for my birthday and we had the best time! Me and all my friends/family flew from chicago, the South and across the country so I was hoping everything would run smoothly. Our ride was so easy and Luke (the bartender/deck hand) was a great host and so patient and helpful. He made sure our drinks were full and made sure we could play music and relax on the boat. Kate was our captain and she was wonderful and the boat ride was so smooth (thank god because we were all a bit hungover). Highly recommend!!

    Did the mail boat tour, a lot of fun going firm island to island and getting to know more about each one form the captain as we docked. Got to watch them off load and pick up people and mail form each place. It was a little cold but really enjoyable

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    Ask the Community - Casco Bay Custom Charters

    Hi can you accommodate 30 people with drinks and food?

    Hey Michael! Our largest capacity vessel, MARIE L, is able to accommodate up to 16 guests for private charters with food and drinks.

    Don’t See Your Question? Ask Away!

    Review Highlights - Casco Bay Custom Charters

    My husband & I booked a half-day cruise of Casco Bay on board the ship, Hesper.

    Mentioned in 4 reviews

    Read more highlights

    Maine Day Ventures - Wild Maine blueberry crisp gelato

    Maine Day Ventures

    (254 reviews)

    West Bayside

    We came to Maine very VERY early season (March 20th-24th) and were looking for something to do…read more Most of the area is still in full 'pre season' mode, with many restaurants and services closed, especially during the week. We found the walking Food tour on Viator and jumped at it - and boy were we glad that we did! Because of the time of year, my wife and I were alone on the tour and as such got to spend around 3 hours with our guide, Ray Sapirstein. Putting aside Ray's obvious love for Portland and food in general, he was a charming guy - keeping us engaged and entertained with stories about the area for the entire duration of the tour. Ray is a PHD trained historian and, as such, was able to fill in a lot of color about the area, going beyond the 'food' aspects of the tour, describing the 'hilly roads' which were sand dunes were covered up to build out the city. Add to that the fact that he took us to several places that we NEVER would have found via googling for 'best ofs' and would have been a HUGE failure to miss! Andy's Old Port Pub - a neighborhood bar (don't call it a dive, though in my mind it qualifies). Spend some time chatting with Thomas, the owner, and Steve the bartender - and had what I can only describe as the single best haddock taco I've ever had in my life. Do not judge a book by it's cover: this place is AWESOME. Great craft beer tap list, and a warm and friendly environment. If I lived in the area, this would be my regular. From there we went to Gilbert's Chowder house right next door - Ray was again right: don't sleep on the seafood chili - it was RIDICULOUSLY amazing. After that we paid a visit to the Harbor Fish Market where we got to see the recent catches, and as Ray pointed out the 'transparency' of the thing: fish are cleaned and prepped for sale right where the customer can watch, and all fish are labeled as 'fresh' (with VERY few pre-frozen exceptions). This is also the place to go if you want to buy Maine swag. From there we proceeded to Rigby House, an unassuming 'coffee shop and workspace' that Ray promised us had nothing short of the best lobster roll in Maine: I've had some good lobster rolls so I can't quite commit to that, but the bread it was built on was FANTASTIC, baked locally from one of the bakeries rated tops in the nation right in Portland. This stop came with either 2 samplers or 1 full pour from their 20+ menu. Don't miss the blueberry ale. It's a rare treat and again, came from Ray's love of his city. From there, we visited Dean's Sweet shop for a couple of truffles and terrible jokes, and then Fiasco's Gelato to round up our day - try the lobster gelato, it's weird and not something I'd necessarily do again...but glad to have had the experience. The whoopie pie gelato was top notch and the blueberry was one of the best gelatos I've ever had. For a 3 hour tour, with all food included, we were certainly full and happy. The walk was short - I don't think we wandered more than a mile in total - and when we were showing signs of being "Help me I'm not from Maine cold", Ray took us into Grittys, another neighborhood bar just for a warm up.

    Ross took us on a tour of downtown Portland. His encyclopedic knowledge of the city's authentic…read morehistory went far beyond what is taught or commonly studied. Native Portlanders would do well to walk and talk with Ross to gain a deeper knowledge of this spectacular place.

    Maine Foodie Tours - Kennebunkport

    Maine Foodie Tours - Kennebunkport

    (6 reviews)

    While visiting the Kennebunks, I decided to book my first ever foodie tour with Maine Day Ventures…read more This three hour tour not only covered delicious eats, but delivered in history. As our tour group visited each restaurant, we got a side of Kennebunkport history and the insider scoop as to where all of the locals dine. Marlene Brooks is an exceptional host and tour guide. She is a 13th generation Mainer and provided such detail about each local spot including the history behind our food. Her professionalism and Maine pride was evident throughout the tour. The ticket price for this experience was around $145. In my opinion, it is well worth the price because it is an opportunity to meet new people, learn more about Maine, and try different restaurants. Marlene took our group to some restaurants that my friend and I didn't know existed. Some advice would be to arrive on the tour hungry because you get to try so many delicious plates. By the end, my friend and I were full. Below please find some of the places we visited and the food we enjoyed: 1. Fiafia - mixed berry smoothie 2. Alisson's - lobster roll (you get a choice between three - the original, lemon garlic, or lobster chowder) 3. Federal Jack's - clam chowder with potatoes and a sample of beer 4. Mornings in Paris - whoopie pie and a choice of coffee or select tea 5. The Pilot House - fried haddock bites 6. Bar Harbor Cheesecake - cheesecake sample (can have more than one) This foodie tour encouraged me to try other food tours when traveling to new places. Marlene and Maine Day Ventures left a lasting impression and added great value to my Maine trip. The Kennebunks are filled with a rich history, excellent seafood, and the most friendly people. Thank you for a great experience!

    A gourmet tour this is NOT. There is a world-class lobster roll place on the tour (Clam Shack), but…read morego there yourself and save yourself the rest of the garbage. Mead? Really? Undrinkable. Whoopie Pies? If you happen to like them, buy it yourself and the local grocery store. Our guide, a schoolteacher, treated us like idiots and managed to convey very little information. She couldn't even pronounce macaroon correctly, and she's leading a food tour? Do yourself a favor and skip this; go to one of the fantastic food tours in Portland ME instead.

    Lady Oyster

    Lady Oyster

    (3 reviews)

    Stellar and unique experience at Lady Oyster!…read more Fantastic views, locally sourced and delicious oysters, great wine pairings, and incredible knowledge gained -- cannot say enough positive things about our oyster tasting experience.

    I booked a half day seafood adventure with Lady Oyster while my brothers and sister in law were…read morevisiting Maine from the West Coast. From the second we walked in this felt like a one of a kind experience. The table was set beautifully, Virginia and her team were so welcoming, and she is so incredibly knowledgeable. After the oyster tasting we enjoyed a lobster roll and then hopped on Captain Joe's boat for a tour of an oyster farm and a ride around this beautiful midcoast area. Timing of the tides worked out so that we got to see a bunch of seals. Captain Joe also helped us shuck some oysters while we enjoyed delicious rum punch cocktails he whipped up on the boat. We ended the tour with a beautiful sunset before heading back to the dock. Since moving to Maine seven years ago, it seems like during summertime, all the classic destinations have become so overrun with tourists and certain activities and places that are my go-tos have lost a bit of their charm. I think that's what I loved so much about Lady Oyster. Located in a tiny little peninsula village called West Point, it is off the beaten path, and almost feels like stepping back in time. I would 10/10 recommend Lady Oyster to anyone looking for a true hidden Maine gem. I hope to come back this winter for one of her dinners!

    Maine Day Ventures-Kennebunk

    Maine Day Ventures-Kennebunk

    (1 review)

    We took a day trip down to Kennebunkport from Portland and wanted to get the most our of our time…read morethere. We decided the 2pm history tour would be the best way, and it certainly was! Our tour guides Julie and Peter had a wealth of information to share. We were able to go inside a couple of the very old homes we learned about. We happened to book the tour on the 3rd day of the new season, so there were only three of us, which was nice! I highly recommend. Oh, and if you are driving, there is a public pay lot on the right, just as you enter the square by Alisson's Restaurant. It fills up, so get there before lunch and snag a spot.

    From the owner: Maine Day Ventures, formerly known as Maine Foodie Tours, continues to grow its offerings to…read moreKennebunkport, a charming coastal town in Maine. Maine Day Ventures offers a range of exciting walking tours in Kennebunkport, providing visitors with a chance to discover the rich history and culture of this beautiful town. One of the most popular Kennebunk walking tours is the "Walk Through Time" tour, which takes visitors on a journey through the town's fascinating past. This Kennebunk walking tour shares the rich history of the area, including how it became a shipbuilding hub for the country and a destination for travelers. Foodies will enjoy A Tasty Lunchtime Walking Tour of Kennebunkport. The tour features full servings of the town favorites, which include fresh lobster, clam chowder, craft brews and fruit sodas, Maine's favorite dessert -- the iconic whoopie pie -- freshly roasted coffee and more. Maine Day Ventures also offers A Gardening Stroll Through the Historic District that walks visitors to Kennebunkport's sea captain's homes with the most beautiful gardens and green spaces. For dog owners, the Doggy and Me Tour offers a chance to spoil your furry friend with treats throughout town, all to support the Animal Welfare League.

    Casco Bay Custom Charters - boatcharters - Updated May 2026

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