Classic Harbor Line Boston

This review is for the Adirondack III
Such a fun time. Super sail, nice crew. We had a super time!

OVERVIEW: I live in Boston, and I love being a tourist I my own city. I had a Friday afternoon off and it was a gorgeous summer day so I decided I should spend it on a sailboat! I had a great time sailing on the 3pm tour on the Adirondack III 80′ schooler.
COST: I found a discount code online, so what would have been a $ 45 ticket cost me $ 38.
DURATION AND COURSE: The sail was 2 hours long, and went out towards the Boston Harbor Islands and back.
BEVERAGES AND BATHROOM: They serve water and sodas for free, and beer and wine for $ 5. There is a head (bathroom) on the boat, which is nice since it’s 2 hours and you might be drinking.
CROWD: There were about 25 people on my tour so it was a good crowd but not too packed; the boat can hold up to 41 guests.
ATTIRE: I wish I had known this before boarding since I wasn’t sure what to wear or bring, but you can definitely wear whatever you want, from at short, shorts, and sneakers to a dress and sandals. They say to wear shoes that are easy to get around on a boat in, but once you get on board, you’ll probably be sitting in the same spot for the duration. And you don’t really have to worry about the wind blowing up your skirt since you’ll be sitting! Also, you can definitely bring a bag or purse– there’s room to set it down at your feet. I would recommend bringing a layer so you won’t be chilly when it gets cooler out on the ocean or when the sun ducks behind a cloud.
TOUR ASPECT: My only disappointment was that I thought by sitting close to the captain at the wheel I would get a bit of a verbal tour of where we were sailing, but the captain was training another captain, so when the new guy was at the helm, the Old Salt captain was up by the bow with guests, giving THEM the juicy details! But I’m sure I could have relocated if I had chosen to, and I’m sure it was just a matter of the dual captains.
CONCLUSION: I would definitely do this tour again. My favorite part was when they raised the sails and then turned off the engine– SO serene!

The cruise is really fun! We took the harbor island cruise and we were not disappointed. The weather was great and it didn’t even feel like 2 hours had passed. Very enjoyable ride!

What’s the best place to go shopping on the ocean? Answer: a Sailboat!
My friends got me this sailing trip as my birthday surprise. In fact, they gave me this riddle above to guess what it was. After a few hints… I finally got it! Blame it on the Martinis…
I can’t express how much I love my experience sailing with Adirondack III!
The crew was courteous, knowledgeable and very responsible. I didn’t know what to expect as I never sailed before. The boat was a lot bigger than I thought. The Adirondack III can hold approximately 25 – 30 ppl and we sailed from the Boston Harbor. It was a gorgeous day and it felt so incredibly refreshing and breezy onboard. The boat was very steady, to my surprise. And since Logan airport is right by the bay, you see flights landing every 2 minutes! I would recommend not wearing flip-​flops or sandals because you will be flipping from side to side at times. Also, hold on to your phone and purses!
The ticket includes free beverages (water & soda). Beers and wine are $ 5. My trip took about 2hrs.

We took a Day Sail yesterday because we had a few hours between a conference ending and our flight back home. Our crew was friendly and accommodating with questions from the onset. It was clear that they enjoy what they do and are about providing the best customer service possible. A perfect sunny and breezy afternoon rounded out a perfect sail.

What a lovely evening aboard this beautiful schooner! Captain Peter and the crew, Brennan and Abby, were friendly, funny, welcoming, and clearly experienced. The views of Boston just before sunset are stunning and classic, even on a slightly cloudy day. I strongly recommend this activity to anyone who loves the ocean, is a romantic at heart, or just wants a calming yet exciting way to spend time with loved ones. Well worth the price. Also, be sure to bring cash to tip the crew at the end of the day if they prove to be just as if not more exceptional than I have described — they do this because they LOVE what they do and it shows!

I went on both the sunset tour and the Boston Harbor Island Tour. The staff is very friendly and accommodating. I particularly liked the sunset sail as we were on a actual sail boat. It was a windy day, so the sail was quite an adventure. I never knew the boats could cut through water at such a steep angle! It was exciting! I highly recommend the sunset tour as a fun way to see Boston from the water. The staff was really great at helping to take awesome photos, too!

Great experience. Took my fiancé for the sunset sail. It was a little cold but luckily they provide blankets.
It’s a great way to see Boston from a rare vantage point. The crew was very friendly and knowledgable.
They also serve alcohol on board so remember to bring some cash. $ 5 for beer or wine. Great way to start the night.
Only complaint is we couldn’t hear the crew very well (read: «at all») when they were giving us history lessons. So, you (yes, you!) sit close to the captain of you can and problem solved!

What a unique and enriching experience! My boyfriend surprised me with a three-​hour sail through Boston Harbor for my birthday. The sail included lunch and an informative guide (the captain) who talked about the history of the Harbor Islands, lighthouses, etc. There were also two staff on the boat who answered questions, served the food and offered beer and wine for purchase. It was a fantastic time!
It was a bit chilly on the water in October, but we wore our winter coats and were fine. The way out was colder because we were on the shade-​side, but on the way back we were pretty warm from the sun (not to mention the beer, wine and hot apple cider!)
Extras: There are two bathrooms on the boat, blankets for when it gets cold and you can walk around to get different views of the skyline, harbor, boat, etc.

While on vacation in Boston we were lucky enough to do a sunset sail with Classic Harbor Line. This was definitely the best part of our trip. Drinks served on board were great and reasonably priced. The crew was knowledgeable and very friendly. Most of all, the view was incredible. Couldn’t have enjoyed this more!

I was lucky enough to enjoy all three separate day cruises aboard CHL’s delightful motor yacht Beacon. Be sure and check which trip you’re on because they’re unique throughout the day: Charles River, Boston Harbor, or Inner Harbor Sunset cruise. I was impressed how their brochure lists these and shows the route of each. Each cruise shows a different aspect of the Boston waterways and were equally interesting and enjoyable. My favorite had to be the sunset cruise however, particularly because they had planned the route to coincide with the USS Constitution’s lowering of the American flag, which features a live cannon fire that even as you expected it you weren’t quite prepared for. The sunset was also gorgeous against the skyline of downtown Boston as we continued the sail.
Beacon smoothly cuts through the choppy harbor as the mate kept our experience smooth. A great deal to get a nice Italian Prosecco at $ 5 for a healthy glass, and free water or soda. Also I liked the focus on customer comfort as right away fuzzy blankets were passed out once we hit the cool open sea breeze. Far from an ordinary tour boat operator, I think CHL is a true customer experience company.
Each of the three cruises was skippered by Captain Ruth, who provided entertaining and informative narration — without over-​doing it. On the evening sunset cruise, the mood shifted and light jazz replaced the more touristy narrative.
The only thing I would suggest to make this even better is perhaps a light snack offering. It’s great you can bring your own food, but even some chips or a meat/​cheese tray (especially in the evening cruise) would really go far to pampering the guests. Nothing fancy, event airline-​style bags of snacks would be an extra bonus touch!

We did the Schooner Adirondack III on a Saturday afternoon as the kickoff to my friend’s Bachelorette Party. We had GORGEOUS weather and the crew was very friendly & helpful. The man at the check-​in counter was VERY patient with us, as 3 of our friends were running late.
I didn’t pay TOO much attention to the gorgeous views, as we were busy chatting, eating (you can bring your own food) and partaking in the $ 5 Prosecco (although the first round was flat). For $ 5, you get a very generous poor — much larger than expected.
Overall, this is a great experience and totally worth the money (which is not too expensive).

This was a lot of fun. We had a GREAT time on the 3 hour tour (Not on the Minnow). It was a perfect day for a sail on the schooner Adirondack III and the Captain was terrific and full of information about the Boston Harbor. The crew was excellent manning the sailing duties while still catering to the passengers. OK, the picnic was a box lunch but the turkey sandwich I had was very tasty and all the extras like an apple were quite good. We highly recommend this excursion and I’m sure we will go back. The only problem we had was finding where to check in. 60 Rowes Wharf was difficult to find but if you enter the big archway at the Boston Harbor Hotel and walk to the dock on the right side you will see the ferry office.

This was such a nice experience. After living in Boston for a few months it was nice to finally get out on the harbor for a beautiful sunset cruise.
My boyfriend booked this through groupon which offered an amazing deal. The captain and staff were courteous, funny and knowledgeable. The weather was great, we enjoyed a few beers and got a new view of the awesome city we live in.
I recommend bringing snacks (we didn’t) to enjoy with your drinks.
I can’t wait to take friends and family back out on the Adirondack III when they visit.

My boyfriend and I went on the Schooner Adirondack III day sail and really enjoyed it despite it being a bit chilly that day. The captain and other crew members were very friendly and would explain what we were seeing while sailing around the harbor area. There is also free water and soda, and alcoholic beverages for $ 5 if you are interested. You’re allowed to bring your own food on board and they even supplied blankets since it was a bit cold when we went. We really enjoyed the views and he experience of sailing, since we don’t own our own boat! I would recommend as a great trip for couples or even families. I want to bring my grandfather back because he loves sailboats!

I just came from sailing in the Caribbean. So, I didn’t expect to have as much fun as I did sailing in the Boston Harbor with these guys. Full of historic and current facts about the city, the captain and crew were great to talk to. I felt like I was on a private cruise. I would definitely suggest going to all my friends.

A friend and I took the sunset cruise last night and it was amazing! Not only is the boat spectacular but the crew is super friendly and knowledgeable. Captain Tim is fun and very laid back and after a few safety tips he got us right out into the harbor-​and quite smoothly I might add! It was amazing to watch the crew raise those huge sails over our heads and then see them fill with wind as we went along. The boat is very comfortable-​we sat up front so we could get a better view of the city but from what I heard, there really isn’t a bad seat on the boat.
Soda and water are free (where can you get THAT in Boston?!) and beer and wine is only $ 5. There weren’t any snack on board but they said you could bring them with you if you wanted to. Next time, that’s what I’ll do. This would be an amazing date night but was also so much fun with my friend! I highly recommend you book a trip before the end of their season!

Got really excited when the boyfriend told me about this sunset cruise around the Boston harbor. It was a perfect way to spend a Monday, summer night.
Parking was adjacent in the Boston Harbor Hotel. We received the parking validation upon checkin and waited to board. Usually parking is $ 18 – 25 but with validation, only $ 12.
The crew was very helpful and the boat is great! Things to remember to bring on board, include cash for alcoholic drinks, a jacket to stay warm, and snacks to eat on board. Complimentary drinks, water and soda included.
This was a great evening on the water with breath taking views! I would highly recommend to anyone to take the sunset sail.

The perfect way to spend a summer evening!
We took the sunset sail cruise last night and loved it! The crew couldn’t have been nicer. Soda/​water is free, wine/​beer is just $ 5 (cash). You can bring snacks to enjoy during the cruise. The boat left the dock precisely at 6:30PM and returned at 8:30PM.
The boat is in great condition and very comfortable.
Two tips: bring cash (for wine/​beer and tips) and warm clothing (although they have fleece blankets to use as well).

Took a sunset cruise on this boat this past Friday night after work and after an amazing 2 hours I know it certainly won’t be my last. The captain and crew were laid back, fun and made the experience that much better. We happened to catch perfect weather and the views of the city from out in the harbor are perfect — the girlfriend and I could not stop taking pictures of the skyline as the sun started to set.
This is perfect for couples, friends, co-​workers, whatever it may be. Give it a try one evening and you’ll be thinking about your next trip before you hit the dock. We will definitely be taking more harbor cruises on the Adirondack III.