The Black Dog Tall Ships

My wife and I took a sunset sail with Black Dog Tall Ships aboard the historic schooner Alabama on June 27, 2025. Alabama is over 100ft long and has been beautifully restored. When you step aboard it’s like stepping back into the 1800s. Captain Jamie and his friendly crew made sure everyone was safe and comfortable. They explained the workings of the ship and even let passengers help hoist the sails and take turns at the wheel. Sailing on the beautiful waters off Martha’s Vineyard was enjoyable and relaxing. We were welcome to help sail the boat or just sit back and enjoy the views of the island and many other classic boats sailing by. Chips, cheese and crackers, water and soda are provided, but you’re welcome to bring your own food and drinks as well. Bring a sweatshirt or light jacket as evenings on the water can be cool. They are located just a 2 minute walk from the Vineyard Haven ferry dock out back of the Black Dog restaurant and shops.

Interesting expierence; really sweet staff. But once you've done it you won't desire again. Three hours on a sailboat is a bit long when the boat doesn't go very far. If you want a water tour of the island, this is not it. Extremely overpriced for the expierence (over $100 per adult). Maybe a great expierence for families with small children. Would not advise for adults looking to have a peaceful sail or for individuals who can't climb a ladder safely backwards. The loading/unloading process takes half an hour plus as a small boat takes groups of 13ish to/from the main sailboat to land. Pro tip- BE SURE TO BRING FOOD, BLANKETS, WINE ETC. with you!

We took the late afternoon cruise and it was a great time. It was fun and informative, and the ship is very impressive. We packed snacks and a bottle of champagne, it couldn't have gotten much better.

Sailing on the Alabama was an unforgettable experience and first-time for me and my best friend. I couldn’t think of a better way to see the 4th of July fireworks show than positioned right up front and seated in a historical vessel that even participated in WWII! We were allowed to bring our own food, and still offered beverages and helpings to a cracker and cheese board, and practically given free range to explore the ship above and below deck including the engine room. You can walk around safely and barefoot, and jump right in to hoist the sails and coil the ropes! The captain and crew are not only handsome and capable, but very safe, friendly and ready to share their sailing knowledge and about their experiences on the open seas. They really make it a wonderful experience! We’d definitely do it again.

We had a wonderful time on our sunset sail out of Vineyard Haven. The staff was terrific, the Alabama is a fascinating vessel, and we met some wonderful people. It was a pleasure to hear from Capt. Jamie about the history of the boat, his family, and the Vineyard. And the crew was wonderful, too. We would definitely recommend a Black Dog sail.

The crew was wonderful, our sailing companions, from all walks of life (from 2 to 70+ yrs) were friendly and social. We will take the sunset sail again in the Alabama when back on MV!

Great sunset cruise on a beautiful 99-year-old sailboat! Crew was friendly and knowledgeable, and they even let us help raise the sails. They allow BYOB and picnics but given that it’s a large (and from a safety perspective, complicated) vessel, I probably wouldn’t recommend bringing anything. They provided still and sparkling water and snacks (chip bags, cheese and crackers) on board. Would recommend for anyone visiting MV!

This was such a wonderful experience! The captain was a skilled professional, and the crew were friendly, accommodating, and personable. The sail around East Chop and West Chop was absolutely gorgeous, and the captain and crew encourage guest participation which adds to the experience. We will be doing this again next year!!

This is a fabulous experience. This was our 4th sale aboard the Alabama. We go annually for our anniversary while staying for a long weekend on the vineyard. The Captain is extremely knowledgeable about the ship, the island and is aware at all times of what is happening on his ship. This is a family run business and the crew is always friendly. This can be an interactive experience so if you want the full experience and be able to pull up the sails to start your journey, they ask for 6 or so volunteers on both sides of the ship to help pull up the sails. We always help out but it's not mandatory and some folks enjoy watching and have a seat and relax. The time on the water is very relaxing and the Captain encourages photo opportunities at the captain's wheel. It's such an amazing experience. They include cheese, crackers and chips, water, seltzer and flavored water in a large on board cooler. Some crew live on the the boat for the summer. The whole sail is really an amazing opportunity and worth the money. There is a marine toilet on board the ship. There are bathrooms you can use on shore before and after you sail as well.

We loved our sunset cruise and listening to the history of the Black Dog franchise. The son of the founder owner of the Black Dog Tavern explained the reason for the establishment of the tavern and the tall ship sailing programs. All proceeds for sailing go to maintaining the tall ship and staffing. I loved it. The crew made it fun they were nice and down to earth. Plus the group was small so it offered a level of intimacy that if fully sold out we wouldn't have experienced. We brought our dinner and drinks, enjoyed to views and sailed on a beautiful tall ship. It was the perfect ending to our Vineyard weekend.

An enjoyable evening on Vineyard Sound watching the sunset from the deck of a historic schooner.

Invite your friends and family to take the most scenic sunset 3-hour cruise on the island! Arrive early to snag an ideal seat because space is limited! Be sure to pack a snack (cheese, crackers, grapes, and lobster rolls were our choice) and a bottle of wine (don't forget the wine opener) for the adults. Water and juice are ideal for your younger family members! Don't forget to snap pictures of the lovely sunset!

We had an incredible experience on the sunset cruise while on vacation! Captain Jamie and the crew couldn't have any been more accommodating. We loved learning about the history of the ship and our six year-old had so much fun steering. The views and overall experience were top notch and we highly recommend!

went sailing today on the Black Dog sailing trips. we were scheduled for an 11:30am trip. we received a call at 10:45am saying the trip was moved to 11am. we had to take a $20 Uber ride to make it on time for their last minute time change. upon arrival we walked into a group of staff complaining about the scheduling issues. upon arriving on the vessel the captain and staff were initially complaining and arguing about the way the boat was rigged. tension was high between all staff. we could hear the crew complaining for most of the trip. we were also told we would be provided with chips, crackers and cheese. none of this was provided to us. at the end of the trip we could still hear complaining from the crew. overall very dis trip. I have reviewed anything on here but felt this experience deserves to be made known.

We discovered this Cruise last year a d while it was fun there was little wind. This year we had wind and it was a much more enjoyable ride. Both years the Captain and crew were wonderful. A definite recommendation for those looking for something to do on the water

This 2 Mast Scooner is Amazing. .the Alabama is a wonderful, beautiful boat that provided a beautiful evening here in Martha's Vinard. The crew was amazing, we had a beautiful assortment of cheese and crackers on board, we also brought our own beverages and snacks to enjoy our sunset cruise. The entire experience from end to end was superior. We enjoyed ourselves very very much

August 3,2011. This was our first trip to MV with family 6 adults and 2 small kids. We wanted something fun to do in the evening and noticed that there were signs for a special " Black Dog Tall Ship race" in the harbor that afternoon from 4pm-7pm. 3 hours.. Two ships were competing the Alabama and Shenandoah. What a unique and fun thing to do....NOT! We called and made reservations at 11am that morning and arrived for the boarding process. We observed that many families had bottles of wine and snacks as if it was a picnic on the high seas...To our HUGE surprise, we then found out there would not be any food or beverages aboard the boat. For $70 per person and $50 per kid( two 6 year olds). We were horrified at this, and if we had known, would have made food and beverage plans in advance, especially since this is a dry town and alcoholic beverages are not sold retail. We boarded the skiff to take us to the Alabama boat and got a short informational class on the age, history and uniqueness of the ship. The crew was polite and small kids were encouraged to help roll up the ropes to leave port. The captain welcomed us and pointed out the other ship we would be competing against. We finally left and 10 minutes into the sail we DEAD stopped. No wind No race. No attempt to"motor" ( it had a back up motor). Everyone on the boat was eating the food they brought and just sat, and kids walked around making friends and going below deck to the restroom& check out the bunks. If you have not maneuvered up and down a tall narrow ladder, or need any physical accommodations this is not for you. Bathrooms are down,down down. The captain made light of the situation by explaining with (his girlfriend beside him) about the kids summer camp & other Black Dog Tavern history. We were soon hoping to get the "race" started or at lease slowly motor along the shore. We had a 3 hour tour to NOWHERE! After 45 minutes several other passengers were asking the captain what the "plan" was. We were just sitting and doing nothing except looking at the brick building of the local hospital in the bay. This must be how the "Dead-man's Float" got its name. He responded by saying something to the effect that he had no control over the weather but we were on course to get back in at 7pm. The other boat we were competing against was a bit farther back. Shenandoah boat was a kids pirate boat tour which had pizza. After repeated requests to bring the boat in, the captain docked us early reminding everyone at least 3-4x during the sail to "leave a tip" for the crew. My tip to them would be to remind people to bring a lunch or snack, post a sign on the walkway as you enter, and clearly POST it on your web page. We understand that you have no control over the weather conditions, but a little marketing and fun for the kids would go a long way. This event did not deliver on what it had promised, and I would only recommend it to those who have a historical interest in tall ship history and sailing techniques. I hope this is helpful to those who are not familiar. Spend your money elsewhere but not at the Black Dog Tall Ships.

Sailed on the sunset trip (5-8pm) on the Alabama with captain Morgan. The history of the ship is fascinating and we had a wonderful evening and beautiful sunset view over the Vineyard. The crew was great and helpful in answering questions about the ship. Highly recommended!