Casco Bay Custom Charters
Casco Bay Custom Charters
5
8:30 AM - 9:00 PM
Monday
8:30 AM - 9:00 PM
Tuesday
8:30 AM - 9:00 PM
Wednesday
8:30 AM - 9:00 PM
Thursday
8:30 AM - 9:00 PM
Friday
8:30 AM - 9:00 PM
Saturday
8:30 AM - 9:00 PM
Sunday
8:00 AM - 9:00 PM
About
Casco Bay Custom Charters is Portland, Maine's, most exclusive boat tour operator. We are the only private charter operator on Casco Bay that uses a vintage wooden lobster boat, and we are the only company to include a tour guide on EVERY charter. Bring your friends, family, or just that special someone and join us in viewing southern Maine's best coastal sights in the relaxed comfort that only a private charter can provide. Whether you want a 2-hour sightseeing or sunset cruise, an evening-long private dinner cruise with our onboard chef, or a half- or full-day adventure around the bay, your family or small group will get an authentic Maine experience that most people only dream of.
Portland, Maine

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Tours and Tickets by Casco Bay Custom Charters
Travelers talk about
(29 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles146 reviews
Excellent
143
Very good
2
Average
1
Poor
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Terrible
0

James Dean
1 contribution
5.0 of 5 bubbles
Oct 2020 • Couples
The Sunset cruise was easily the most memorable part of our trip to Portland. Captain Nick was impeccable with his timing to provide a lovely view of the Sun setting while also allowing enough time during our 4 hour cruise to explore the surrounding area of Portland. Chris’ hospitality during our charter was amazing. He provided a wealth of knowledge and interesting information about the seaside town of Portland. We had the honor to experience Chef Paul’s 5 course dinner during our voyage and to say the cuisine was immaculate would be an understatement. Chef Paul does not make a meal twice and to experience this once in a lifetime opportunity will forever be a fond memory. The vessel was perfect. The trip consisted of me and my wife and we had a comfy booth along with enough pillows and blankets to support the chilly Portland seas. The sunset was breathtaking and we felt we had the view to ourselves during its captivating departure. The crew excused themselves to below deck or the front of the vessel to make the experience that much more private. Each crew member had their individual tasks and excelled at their craft.
Written October 15, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Chelsey D
Phoenix, AZ1 contribution
5.0 of 5 bubbles
Aug 2020 • Friends
Booked Marie L. for my party of 7. Jim was very attentive from the start by replying to all my emails right away with any questions I had. They provided great detailed information beforehand and especially where we could find them at their second dock. The trip was a blast, Matt was fantastic with getting our drinks and explaining anything we were curious on with sightseeing. It was the highlight of our weekend! I highly recommend, and can’t wait to visit again and book them in the future!
Written August 25, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Valerie J
Prague, Czech Republic21 contributions
5.0 of 5 bubbles
Jul 2021 • Solo
We did a private sunset tour aboard the Hesper to celebrate a birthday with four people total. It’s safe to say this was the absolute highlight of our trip. Enya and the Captain were so kind and answered all of our questions about the Portland area. It was truly a one of kind experience having the boat to ourselves and being able to participate in raising the sails! As visitors of Portland we would consider coming back to the city just to take this tour again.
Written July 25, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Brianne T
Nashua, NH9 contributions
5.0 of 5 bubbles
Aug 2020 • Friends
Planned this for a Portland bachelorette event! We were taken on a relaxing, 2-hour private boat ride with all of the drinks included (local beers, wine, hard seltzer’s and non-alcoholic beverages). I was blown away at how accommodating the staff was as well as how reasonably priced the trip was. The girls were ecstatic to have the boat all to ourselves. We were able to bring our own snacks and cheeseboard which was amazing, though they did offer us an option to have food provided for us. Our crew was incredibly fun and knowledgeable about the area (pointing out sights as well as sea wildlife- pointed out a puffin and a seal!). They were quick to get us refills on drinks, provided us plates for our snacks and were utterly hospitable. Couldn’t have had a better time :) thank you Casco Bay Custom Charters for providing a great time for our bride and the rest of the “I Do Crew”!
Written August 17, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Joshua T
1 contribution
5.0 of 5 bubbles
Jun 2021
I chartered the private sunset sailing cruise with Tom and his crew. I let Jim and Tom know that I was planning to propose to my girlfriend during the cruise.

Well long story short, due to a cancelled flight and having to drive 12 hours to Portland, we ended up being pretty late for the cruise. However, Jim and Tom were extremely patient and understanding and made a very stressful situation more calm and reassured me multiple times that everything will be fine.

We showed up to a food spread and drinks on deck and Tom and his crew were very accommodating to the situation. I was able to propose (she said yes!) and we were able to experience the incredible sailing due to Tom generosity by keeping us out a little past the ending time of the cruise. Tom and his crew then packed up all of the food (we weren't able to eat because we got there late) and gave us some bottles to take home to celebrate.

I cannot say enough wonderful things about Jim, and Tom and his crew. I would HIGHLY recommend this experience for anyone who is interested, and we will absolutely be going back to Portland and doing another cruise in the future.

Thank you Casco Bay Custom Charters Team!
Written July 8, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Tracy M
Albany, NY3 contributions
5.0 of 5 bubbles
Jun 2021 • Family
What an amazing time sailing Portland harbor and Casco bay aboard Hesper! We went out for a sunset sail with my brother in law and family for a birthday celebration and it truly was the perfect night. First time on a sailboat, but it did not disappoint! Hesper is beautiful, and We loved hearing about the history of the boat, but also the work that went into it!

We enjoyed the private aspect of the trip and it was fun to watch. Chris (?) go back and forth working the ropes. Both the captain and crew work hard and you can tell there’s a lot going on, but they communicate seamlessly and make it look easy! I believe there is an option for all inclusive but we choose to purchase on board. They had a variety of hard seltzer’s, craft beer and wine.

The only thing that was less than ideal was parking, but it’s a city so it was to be expected
Written June 15, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

pfem22
Northern Virginia, VA13 contributions
5.0 of 5 bubbles
Jul 2021 • Family
We did a private sunset tour for 8 people ages 6 to 82. It was fantastic. Our crew was very knowledgeable and took us to sights we were interested in. We saw several light houses, forts, birds and seals. And we saw a fantastic sunset. The ride was smooth and even included drinks. We highly recommend this tour.
Written July 21, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Sarah B
New York City, NY6 contributions
5.0 of 5 bubbles
Aug 2021 • Family
Our multigenerational family (ages 4 to 86) had a great time on the Hesper. The two hour sail was perfect for our group and we all loved snacking on the charcuterie plate. Captain Tom and mate Jessie were amazing! As we sailed they answered all sorts of questions about the history of the bay and the Hesper. Thanks for a terrific afternoon. We can’t wait to come back next summer.
Written August 27, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Kathryn A
Charlotte, NC75 contributions
5.0 of 5 bubbles
Jul 2021
We really enjoyed our trip on the HESPER with Captain Tom Cutter and first mate Camille! This is a GREAT option for a family or friends activity while in Portland. We had the boat completely to ourselves as a party of 6 with plenty of space. We even got to help raise the sails. We went all around the bay and Captain Tom answered all of our questions and pointed out landmarks, but it didn’t feel like we were constantly being talked at. The whole crew was very knowledgeable. We enjoyed drinks on board and they had a great selection of wine, beers, and seltzers. It was overcast the day we went on our trip, and we really appreciated that Captain Tom called us and made sure we were okay planning to go today, and even offered to move our trip one day back to July 4th if we were more comfortable. We decided to go for it and the rain held out! They were super considerate and communicative. If you are in Portland, I highly recommended booking with this family run business for a great experience!
Written July 4, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Suzie B
3 contributions
5.0 of 5 bubbles
Jun 2021 • Friends
We had a fantastic time on our cruise around the bay! The weather was beautiful and Lauren was fantastic! She was friendly, professional, fun and made our experience beyond enjoyable! Captain Rick did a wonderful job motoring us around the bay and was also very professional and friendly.
We would totally recommend this excursion and look forward to doing it again in a future visit. We did the 2 hour private charter-the “booze cruise”, as we called it. Thank you Lauren and Captain Rick!
Written June 13, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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Casco Bay Custom Charters - All You Need to Know BEFORE You Go (2024)

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