We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Bufflehead Sailing Charters

Windjammer Wharf - Captain Spear Drive, 50 Tillson Ave (GPS), Rockland, ME
+1 207-691-5407
Review Highlights
Wonderful Day Long Sail

Highly recommend Bufflehead Sailing Charters. Capt. Daniel is a engaging and enjoyable host, always... read more

Reviewed 2 days ago
Columbus, Ohio
Private Sailing

Two of us called at the last minute for a sailing tour. Captain Daniel provided a private two hour... read more

Reviewed 3 weeks ago
Memphis, Tennessee
via mobile
Read all 104 reviews
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Bufflehead is a 32 foot wooden gaff sloop, a classic boat, built in 1964. She is a very pretty boat, superbly swift, comfortable and safe. Captain Daniel Bennett sailed around the Pacific Ocean on a tall ship, and twice across the Atlantic (and back and forth to the Caribbean) on his own small boat.
  • Excellent99%
  • Very good1%
  • Average0%
  • Poor0%
  • Terrible0%
Travellers talk about
“hour sail” (9 reviews)
Closed Now
All hours
Hours Today: 08:00 - 23:30
Windjammer Wharf - Captain Spear Drive, 50 Tillson Ave (GPS), Rockland, ME
+1 207-691-5407
Write a Review
Reviews (104)
Traveller rating
Traveller type
Time of year

1 - 10 of 104 reviews

Reviewed 2 days ago

Highly recommend Bufflehead Sailing Charters. Capt. Daniel is a engaging and enjoyable host, always ready with an interesting story and a quick witted joke. The day of our sail his young daughter helped crew the shipped and she impressed everyone with her ability and intelligence....More

Thank robdorans
Reviewed 3 weeks ago via mobile

Two of us called at the last minute for a sailing tour. Captain Daniel provided a private two hour tour that was truly beautiful. We learned a lot as well!

Thank skb2426
Reviewed 20 October 2016 via mobile

Captain Daniel does a fabulous job of navigating and narrating Penobscot Bay. He possesses a wealth of historical and nautical information of the area, excellent sailing skills, and the most engaging personality! Loved our time on the Bufflehead!

Thank LaurieCooper
Reviewed 16 October 2016

Bufflehead is fantastic! Captian Daniel provides a relaxing (& informative!) tour. We were in the area for just one overnight for our anniversary. Our sail was 3 hours but beautiful scenery and tranquility on the water made us feel like we'd been gone longer... what...More

Thank tednsadie
Reviewed 12 October 2016

My husband and I took a three hour sail with Captain Dan this afternoon. The whole experience was wonderful, from the initial booking, change of plans because of weather, casual, friendly atmosphere, and, of course the beautiful relaxing sail. Captain Dan makes you feel completely...More

Thank annA1660VV
Reviewed 10 October 2016 via mobile

We were able to book the last two seats on the Bufflehead by text (so easy!) with Captain Dan with just two hours' notice following our spur of the moment decision to get out sailing on a beautiful fall afternoon. Over the two-hour tour, we...More

Thank SMBYoung
Reviewed 25 September 2016 via mobile

Sailing on the Bufflehead (love that name!) with Captain Daniel has been one of the highlights of our trip to Maine.He is very accommodating and the motto on the ship is "Do what you want". My mother and I wanted to sail on a smaller...More

Thank Lyda M
A TripAdvisor Member
Reviewed 15 September 2016 via mobile

Well I see that Captain Daniel has straight A's for this experience. It is unique and I have to add my two cents. I have a long sailing background but I have to say sailing with the captain Daniel on the Buffelhead was one of...More

Thank A TripAdvisor Member
Reviewed 14 September 2016

Whether you charter the boat privately or join a public sailing this is a must do if you're in the Rockland area. Captain Dan and his assistants are welcoming, knowledgeable and overall great hosts (hostesses). I surprised my husband for his birthday with a private...More

Thank gertsown
Reviewed 9 September 2016

There are almost a hundred reasons to sail on Bufflehead! So far, there are 93 - Ninety-three happy, glowing, cheering reviews for Bufflehead Sailing Charters! The stability and charm of the classic wooden Bufflehead, plus the warm charm and cool knowledge of Daniel Bennett cannot...More

Thank Seeqer
Nearby Restaurants
Cafe Miranda
710 reviews
.37 km away
316 reviews
.34 km away
In Good Company
309 reviews
.17 km away
Atlantic Baking Co.
189 reviews
.29 km away
Nearby Attractions
Farnsworth Art Museum
631 reviews
.28 km away
Maine Lighthouse Museum
165 reviews
.40 km away
Project Puffin Visitor Center
127 reviews
.36 km away
Maine State Ferry Service
56 reviews
.18 km away
Questions & AnswersAsk a question
Kevin M
My wife and I are staying in Owls Head for two weeks. 9-16 to 9-30. What would be the cost for a private sail. Half day. Thinking of 4 hours late afternoon-early evening with traditional lobster dinner. Maybe timed to see sunset? Thanks. Our schedule is flexible. Thanks. Kevin McHugh. We are 63 yrs old, decent shape. Happy to help with the sailing duties.
6 September 2016|
Answer Show all 2 answers
Response from Bufflehead S | Property representative |
Hi, Kevin, Thank you for your interest in sailing with me aboard Bufflehead. A four hour private charter runs 475. To get to an island, and cook up the lobsters and corn ashore as well as sail back into Rockland (into the... More