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Schooner Woodwind

80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
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Review Highlights
THE BEST CAPTAIN ON THE CHESAPEAKE!

If you are going to be in Annapolis, a must is taking the Schooner Woodwind out on the Chesapeake... read more

Reviewed yesterday
Donna P
,
Wexford, PA
An amazing July 4th!

Captain Jen and her crew were fantastic! Very knowledgeable, fun and engaging. We lucked out with... read more

Reviewed 1 week ago
jahk2015
,
Bowie, Maryland
via mobile
Read all 263 reviews
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Overview
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The classic, wooden 74' Schooner Woodwind sails multiple cruises daily (in season) for public and private charters. Up to 48 passengers on each of our twin schooners. Whether a couple, family, party or corporate, we can accommodate you. We also have a Boat & Breakfast available (in season) on Saturdays. Come Sail Away!
  • Excellent83%
  • Very good11%
  • Average2%
  • Poor1%
  • Terrible3%
Travelers talk about
“sunset cruise” (33 reviews)
“hour sail” (14 reviews)
Open Now
Hours
Hours Today: 10:00 AM - 6:30 PM
LOCATION
80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
CONTACT
Website
+1 410-263-7837
Write a ReviewReviews (263)
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All reviews
"sunset cruise"
in 33 reviews
"captain and crew"
in 26 reviews
"hour sail"
in 14 reviews
"bay bridge"
in 22 reviews
"wedding crashers"
in 7 reviews
"beer and wine"
in 9 reviews
"bag of chips"
in 4 reviews
"amazing ride"
in 3 reviews
"two hours"
in 15 reviews
"wednesday night"
in 7 reviews
"relaxing afternoon"
in 4 reviews
"great sailing"
in 6 reviews
"sailing experience"
in 5 reviews
"perfect weather"
in 4 reviews
"lots of fun"
in 4 reviews
"naval academy"
in 15 reviews
"visiting annapolis"
in 5 reviews
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1 - 10 of 261 reviews

Reviewed yesterday

If you are going to be in Annapolis, a must is taking the Schooner Woodwind out on the Chesapeake! Captain Jenn and her crew were just the best! Hwe knowledge about the waterways was amazing and you felt confident in her abilities at all times!...More

Thank Donna P
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 1 week ago via mobile

Captain Jen and her crew were fantastic! Very knowledgeable, fun and engaging. We lucked out with the weather...cloud cover but no rain and enough wind for all the sails to be raised. A lovely time and a stunning view of the fireworks.

Thank jahk2015
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 1 week ago via mobile

We took the sunset cruise on the schooner woodwind out of downtown Annapolis on a warm Saturday evening. Thankfully there were good winds and the sails went up as soon as we cleared the harbor. It was a fabulous night out on the water —peaceful...More

Thank Cyndi C
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
See more reviews
Reviewed 1 week ago

My husband and I celebrated our 33rd wedding anniversary by taking a sunset cruise. The crew made it known to everyone it was our anniversary. It was very special and we had a lot of fun. Highly recommend going for a special date or with...More

Thank 925Pamela
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 1 week ago via mobile

This whole experience was awesome! We did the sunset cruise, which included a snack and a pop with the ticket price and then you could buy beer and wine. The prices were reasonable ($4 domestic and $6 craft beer). This is definitely something that couples,...More

Thank littlecourt3
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 2 weeks ago via mobile

My husband and I were celebrating our 45th Wedding Anniversary and wanted to do something different. This was so much fun, my hubby even got to steer the boat for about 1/2 hr. The crew was great too. They brought us bags of snacks and...More

Thank Robin W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 2 weeks ago

This was our first time on a sailboat cruise and it was amazing. The crew was funny and very informative.

Thank William C
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 2 weeks ago via mobile

We took the public cruise. For our first vacation in the Annapolis area. It was great fun. The skipper was entertaining and very informative. You can get as personally involved in the sailing as you do or do not want. Be sure to bring your...More

Thank Stephen H
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 3 weeks ago

The public sailing option is fantastic! My husband and I took some family members about a month ago and had so much fun that we took some different family members this past weekend. The crew is excellent and quick to assist (one in our group...More

Thank Heather C
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 4 weeks ago

My wife and I recently did an overnight stay on the Woodwind Schooner, the B&B, boat and breakfast and we had a very enjoyable time. We boarded around 6pm for a 6:30 sailing, which included folks that were just doing the two hour cruise as...More

Thank mss12078
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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Ask a question
Questions & Answers
Grady J
June 20, 2018|
Answer
Response from nikkius2016 | Reviewed this property |
You must be able to take a step up or down once on board. There are lots of crew members to help you!
0
Votes
Kimbercat S
June 5, 2016|
AnswerShow all 2 answers
Response from Bill M | Property representative |
Guests have the opportunity to help raise the sails, steer the schooner, and ask questions. You also can just sit back and relax! Captain may have suggestions of where best to take a lesson locally. Weight is not an issue... More
0
Votes