Just had my second OTR cocktail cruise (I went last year with a Yelp group), and I'm so glad to…read morehave gone out on the Kismet again! This time two friends and I joined the sunset cruise, and we had only two other people with us on the boat. On the Rocks isn't fancy; it's a laid-back local vibe and a great alternative to a giant party boat. Before boarding you have a choice of beverages you can take along, both alcoholic and non; they put them in a cooler, and off you go! You can bring your own snacks on board if you want to. Tours are an hour and a half and that feels leisurely. The route might vary: last summer we cruised over toward Cape Elizabeth, but this time we wound our way through the islands scattered around the bay: Peaks, Cushing, Long Island, Cliff, and the Diamonds. I loved this route for the the glimpses at the back-island views--and then we sailed back toward the port with a gorgeous sunset lighting the way, lights twinkling on all around. Practicalities: it's a bit hard to find the launch point; there wasn't a sign for OTR and they've moved from where I'd caught it last time. Fortunately the first mate eventually wandered down the pier and found me looking around. If you're driving, give yourself plenty of time to park and walk--Old Port is crazy busy in the summer. Money: any drinks you buy and consume will be charged to the card of whoever made the reservations, so no need to fuss with Venmo on board (I recommend bringing some cash to tip afterward, though). And that's really all you'll need to navigate: once you're on board just relax, settle in, and enjoy being out on the Casco Bay!

Sandy and team were able to accommodate my sunset cruise last minute as my other company cancelled…read moreon me a few hours before sailing. Our captain Sandy was very kind and made sure we always had a drink or snack in hand! The sunset was stunning and for $65/pp and a 1.5 hour sailing, I could not have asked for more! Only downside is no BYOB, but drink options are extensive!

We really enjoyed our sailing trip with Captain Bob and his mate (Jake I believe). They were very…read moreknowledgeable and great story tellers. We would definitely do this trip again!

Our family had a great time with Shawn! Awesome experience and he gave us some tourist tips on…read morewhere to find the best lobster roll!

Great charter, captain Ben is a super down to earth guy with lots of experience and knows how to…read morerun a boat. Had an absolute blast out on the water!

Called, emailed, and called again.. Crickets.. sorry if u…read moreguys aren't open anymore??!!

My wife and I, on a whim, booked a tour with the Nautilus Sailing Company while touring Maine's…read morecost. The two hour tour was absolutely perfect. Enough time on the water without being too short or too long. We were met at the Marina entrance by our Captain who walked us to the boat. The first mate was already working on the rigging and it seemed the process of getting underway ran like clockwork. The Sail around the bay was amazing and the Captain and her staff were perfectly knowledgeable about all of the points of interest. We genuinely appreciate the amazing experience, how safe we felt, the funny anecdotes, and for a life long memories!

The weather gods smiled upon this past weekend as rain was looming repeatedly, but not during this…read moreboat trip! Our captain (who I feel bad for not remembering his name :( ) met us out front on the marina dock and we were able to use the bathrooms before boarding the boat. We lucked out - we were the only two passengers on the boat that day. Pretty sweet deal for an anniversary getaway. Our captain also had an assistant (I think his name was Crow?) and both were beyond friendly and charming. They told us some history, pointed out landmarks, and even pointed out a little seal in the water. We got to shoot the breeze a bit as well which made for a very enjoyable trip. The boat ride itself was very smooth - not a very windy day so they had to use the motor here and there, but thankfully that also meant we weren't keeling from side to side and getting splashed (not very fun, from experience). The boat ride was about 2 hours in beautiful weather. Saw some cool old war forts, lighthouses, and islands. Would completely recommend the Nautilus for a pleasant and fun boat ride around Portland.

We had a great time. Jim and Katie were knowledgeable and answered all of our questions about the…read morearea and sailing. We booked in March for a sail with 5 people in June. We were scheduled for 4 PM when we booked. We ended up getting bumped to an earlier sail due to some impending inclement weather. I was happy that they were able to bump us up to an earlier sail instead of cancelling us completely. Although the sea was calm before the storm, I wish the sun had been out! Get there early so that you can get the seat of your choice!

My wife and I had a lovely 90 minute cruise on the Pineapple. The boat captain was skilled and…read morekept any motion to a minimum. The deck hand was knowledgable and did an amazing job of sharing information about almost everything we saw. A very worthwhile and pleasant 90 minutes. I would highly recommend.

Cruise company cancelled cruise and did not provide refund. Called multiple times with no response.read more

Tour was ok, but a little boring for the kids - lots of "dad, can we please get off soon?"…read more We booked for an easy tour, but in retrospect would definitely go with a smaller boat and more unique tour. Would probably be 2-3 stars, but bumped further down to 1 for the very rude tour guide.

We are staying at Sandy Pines Campground and they have a sign up for kayak rentals. We rented a…read moretandem (2 person) kayak for 3 hours this afternoon (you can only make reservations a during high tide hours). We had a BLAST. It's less than 25 minutes to get to a white sand beach to dock / swim / walk. The water was crystal clear and not too deep! I don't know the gentleman's name who delivers and picks up the kayaks but he was super knowledgeable about the area and gave great directions! Super fun activity right from the campground for under $100!

Amazing trip! We had so much fun paddling the outer harbor by Biddeford Pool. We booked in advance…read moreand they met us right on time. The man we spoke to recommended we go in the afternoon because of the tides, so that's what we did. It was a perfect afternoon! We got a few tandem kayaks and the parents, grandparents and kids all had fun! We paddled to a few little islands and Wood Island, and had a nice walk out to the lighthouse. All in all a beautiful Maine afternoon. Highly recommend this activity- would definitely go again!

What a amazing experience. My wife and I went to Portland to visit Maine (we fell in love with it…read morea few years ago and wanted to check out Portland). She searched for things to do and found this tour and I am sure glad she did. We did the biking tour with Don and it was wonderful. Was able to taste some local mead, beer, and rum and see parts of Portland. He was extremely friendly, fun, and informative. I am not going to lie...I was a little bummed when my wife said she booked this tour instead of the earlier biking brewery tour (visit 3 local brewery's as opposed to our scheduled mead, beer, and rum tour). But it didn't matter, it was a amazing experience. In fact, our guide pointed out man local establishments on the tour that we tried the next day (cough..cough..Forage Market) and was amazed; it truly added to our Portland experience. And we have a tour for the next time we come. All in all...6 out of 5 stars for this organization. I wish I was able to post some pictures, but to be honest, I didn't think about it as I was immersed in the moment and enjoying every second of it. So when in Portland...book your tour, you won't be sorry.

best 21+ cruise/ tour in the greater portland area by far. Both Joe and Pete have been fantastic,…read moreesp after bad trips with other companies. It was refreshing to have professional knowledge in a comforting setting!