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.

Guildive Cruises

Closed Now: 10:00 AM - 8:00 PM
Open today: 10:00 AM - 8:00 PM

Guildive Cruises
Booking unavailable on TripAdvisor

Want other options you can book now?
All photos (61)
Full view
Traveler Overview
  • Excellent98%
  • Very good0%
  • Average2%
  • Poor0%
  • Terrible0%
Travelers talk about
“sunset sail”(8 reviews)
“penobscot bay”(13 reviews)
“two hours”(3 reviews)
There's no better way to experience the timeless beauty and history of Penobscot Bay than from the water! The daily 2-hour excursions, Sunset Sails and Specialty charters offer a historic perspective of Castine and Searsport from the water aboard...more
Closed Now
Hours Today: 10:00 AM - 8:00 PM
See all hours
Dennett's Wharf, 15 Sea Street, Castine, ME 04421
+1 207-701-1421
Reviews (50)
Filter reviews
50 results
Traveler rating
Traveler type
Time of year
Show reviews that mention
All reviews sunset sail penobscot bay two hours beautiful scenery great sunset lovely cruise next year sunny day zander kate boat sails captain seals wind passengers hand
Updating list...
1 - 10 of 50 reviews
Reviewed 2 October 2018

Well, our hopes of sailing went by the wayside after stormy weather blew in. We were notified of the cancellation by phone the night before our sail, which I really appreciated since it made a difference to our itinerary for the following day. We couldn't...More

Thank Steffi H
Reviewed 7 September 2018

Having a small group of only 5 (plus 2 crew) made the experience so special. It was a sunset cruise during a lovely evening. So great to have the owner captaining. I highly recommend the Guildive!

Thank Ariella N
Reviewed 16 August 2018 via mobile

Owner operated cruise. Lovingly restored antique wooden boat. We had a beautiful cruise with two other couples Great to see the boats and stunning homes from the water. Then under sail we made a swift run around the point and best of all a slow...More

Thank ClaudiaThatsMe
Reviewed 14 August 2018

We cannot say enough about the lovely people and their fabulous sail boat. A quality experience. Not to be missed. The day we sailed it was very calm and the winds were light, however the professionalism of the Kate and Zander were very impressive. We...More

Thank Bobbie M
Reviewed 9 August 2018 via mobile

The Guildive was absolutely beautiful! My husband and I took the sunset cruise. Our Chief and his First mate Taylor were so welcoming and put me at ease for my first sail! I highly recommend taking this trip you won’t regret it. The views are...More

Thank Carla S
Reviewed 27 July 2018

Zander and his crew provided the best possible experience for our family. We have 3 kids ages 19, 15, and 10. They all had a great time and loved the boat. If you don't do anything else on the Maine coast do this! Castine is...More

Thank joloAtlanta
Reviewed 23 July 2018

This 80 year-old sailing ship is in excellent condition and affords a true sailing experience. The sails are worked by hand as the boat tacks back and forth. If there is a good wind, there is a nice lean or tilt , and if you're...More

1  Thank West L
Reviewed 18 July 2018

My wife and I had a lovely time on our sunset sail. We loved that it is limited to six passengers and feels like you are on your own private sailboat. Fun to bring our own wine and toast to the sunset too! We will...More

Thank S C
Reviewed 17 July 2018

Took our 5 year old and 3.5 year old and it could not have gone any better. Captain Z was awesome with them - let them raise the sails, steer, and a little bit of everything else in between. Everyone in our family is looking...More

Thank Brad G
Reviewed 16 July 2018 via mobile

Captain Jeep and 1st mate Taylor met us at the dock and gave us a warm welcome. We picked a great night for a sunset sail. Castine Harbour and Penobscot Bay have some of the most beautiful views from the water. This is a “must...More

Thank tomcargen
View more reviews
Nearby HotelsSee all nearby hotels
Pentagoet Inn
609 reviews
.15 km away
Bait's Motel
21 reviews
12.04 km away
Yardarm Motel
64 reviews
12.12 km away
Admiral's Ocean Inn
21 reviews
14.31 km away
Nearby RestaurantsSee all 13 nearby restaurants
Pentagoet Inn Restaurant
210 reviews
.15 km away
Markel's Bakehouse
110 reviews
.06 km away
The Wharf at 15 Sea Street
300 reviews
.03 km away
Danny Murphy's
55 reviews
.07 km away
Nearby AttractionsSee all 13 nearby attractions
Wilson Museum
50 reviews
.85 km away
Castine Kayak Adventures
68 reviews
.00 km away
Castine Historical Society
36 reviews
.34 km away
Questions & Answers
Ask a question
12 April 2015|
AnswerShow all 2 answers
Response from Guildive | Property representative |
Hi, thank you for contacting us. Our trips are $45/ person for our day trips and $50/person for the sunset sails. Each trip is 2-hours and we get out into the Penobscot Bay and see where the wind takes us! In terms of... More
9 February 2015|
Response from Guildive | Property representative |
Hello. Thank you for reaching out to us. A 50th wedding anniversary sounds like a wonderful reason to visit Castine. We can accommodate a maximum of 6 passengers per sail. What we have done with larger groups in the past... More