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    Nautilus Sailing Company

    5.0 (12 reviews)
    Closed 9:00 am - 8:00 pm

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    Kyle A.

    Sam and Crow were an absolute delight as both our guides and sailing crew, making a memorable experience for my wife and I on our honeymoon. Not only were they very accommodating by offering water and snacks, but they even brought us a few blankets when things got cold. Both Sam and Crow handled the choppy waters well, allowing my wife and I some time taking in the sights of Fort Gorges, and the nearby lighthouses. Both folks were super nice and talkative, as well as knowledgeable of the rich history and fun facts. They were a delightful crew who take pride in what they do here on the shores of Portland Maine. My wife and I highly recommend you take a trip out on the water with Sam and Crow. We hope to come back soon.

    Sailing on the Nautilus

    We had a very pleasant and informative sail on the Nautilus on Casco Bay, Captain Sam and crew Crow were very professional and made the trip a pleasant way to spend the afternoon. I would recommend this trip to anyone who wants to spend a couple of hours exploring Portland harbor on the water.

    She's beautiful!

    What a fabulous way to spend two hours while in Portland!!! Absolutely loved making this memory with our son and his wife. Definitely recommend! Nick and his crew member were awesome.

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    Review Highlights - Nautilus Sailing Company

    Our captain also had an assistant (I think his name was Crow?) and both were beyond friendly and charming.

    Mentioned in 6 reviews

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    Mail run trip. Six islands: Little diamond, Great Diamond, Long, Cliff, Chebeague. The Casco Bay…read moreLines are the premier ferry line for folks getting back and forth to the many islands in and around Portland Maine. Primarily this trip is a working freight/mail ferry trip that they have allowed passengers to join and enjoy the beautiful views while the deckhands work. Super fun and economical way to get out of the city and see Casco bay. We were super satisfied and pleased. Would give my highest recommendation. Staff was phenomenal.

    Eat, Drink, & Be Ferry…read more Ferry service that charters passengers from Portland harbor to one of numerous inhabited islands just off the coast. We chartered a Ferry ride to Peak's Island on a crisp early Autumn day. The Good: *You can load your car on the Ferry *Nice boat with a top view *Staff was friendly enough *Fairly inexpensive at $14/adult & $7/child for round-trip ticket. *They also do scenic boat tours, as well as the Ferry service. Check their website for dates and times. The Meh: *Peak season pricing on autos that can go from Off-Peak Season price of $70-100 (depending on vehicle size) to $150-170 for Peak Season price. The Ugly: *Make sure to plan your day accordingly with the boat schedule. You don't want to get stuck on an island there without a reservation. Conclusion: Even if you just go out to the island and back, it's still worth the $14 of entertainment riding across the ocean.

    Fogg's Water Taxi and Charters

    Fogg's Water Taxi and Charters

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    My friends booked the Casco Bay Cat for my bachelorette party - we had a 2-hour boat ride around…read morePortland on a beautiful Saturday morning in October. The captain and staff were extremely kind and supportive of our group. They were helpful as we got things situated, accommodating our need for ice and getting it for us before we left. Once on the water, we put our music on and had a great time. We brought all our food on and enjoyed brunch, mimosas, and beautiful weather. The boat ride itself was smooth despite some choppy waters. The staff even helped us out by taking some photos of our group - the captain turned the boat and the staff member did a great job getting the lighthouse in the picture. I'd absolutely recommend!

    Heading to meet up with friends to take the Casco Bay Ferry to Great Diamond Island for a friends…read moresurprise birthday dinner. Unfortunately, on the way up the highway, there were two accidents and we knew we would miss the ferry. My spouse searched online (I was driving) and found Fogg's Water Taxi and we called to see if we could schedule a taxi. It was so easy and they were so professional. We determined our arrival time and set it up. We were greeted by the most friendlies people and they offered to sit in the lounge area (A/C) and they had fun beverages for purchase, while you waited. The captain of the taxi vessel was fantastic and professional We arrived just a few minutes late for the reservation and still surprised the birthday boy. Oh, you pay the captain of the vessel when you arrive to your destination and they take cash or card. So easy and really not that expensive. Thank you.

    On the Rocks Cocktail Cruises

    On the Rocks Cocktail Cruises

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    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!

    Nautilus Sailing Company - boattours - Updated August 2026

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