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.

Schooner Woodwind

80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Website
Share
Save
Review Highlights
Not a golliwobbler!

The skipper on our cruise started sailing when she was four years old. Her confidence, knowledge... read more

Reviewed 1 week ago
Russell R
,
Annapolis, Maryland
Beautiful sunset and an incredible crew

My fiancé and I travelled to Annapolis for a few days just to enjoy the food, scenery, and bars. We... read more

Reviewed 1 week ago
brogalb
,
Lititz, Pennsylvania
via mobile
Read all 267 reviews
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
More
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!
  • Excellent84%
  • Very good11%
  • Average2%
  • Poor1%
  • Terrible2%
Travelers talk about
“sunset cruise” (34 reviews)
“hour sail” (14 reviews)
Closed 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 (267)
Traveler rating
Traveler type
Time of year
Language
All reviews
"sunset cruise"
in 34 reviews
"captain and crew"
in 27 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
"perfect weather"
in 4 reviews
"sailing experience"
in 5 reviews
"lots of fun"
in 4 reviews
"naval academy"
in 15 reviews
"visiting annapolis"
in 5 reviews
Filter

1 - 10 of 265 reviews

Reviewed 1 week ago

The skipper on our cruise started sailing when she was four years old. Her confidence, knowledge, and respect from the three-person crew show it. The paying guests get to help raise the sails, but the crew run the vessel, trim the sails, and "answer up"...More

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

My fiancé and I travelled to Annapolis for a few days just to enjoy the food, scenery, and bars. We had planned the trip prior to our engagement but there could not have been a better way to celebrate than this sunset cruise. We went...More

Thank brogalb
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 3 weeks ago via mobile

Planned an afternoon sail/tour, the boat conveniently leaves from the center of town located next to dinning, pubs. All within walking distance of the academy. Captain and crew do a great job making an tour fun and a bit adventurist, drinks and craft beers offered...More

Thank David J
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
See more reviews
A TripAdvisor Member
51
Reviewed 4 weeks ago via mobile

We enjoyed our ride on this sailboat. The bay was beautiful. My son was able to steer the boat for a time. Worth our time and reasonable fee.

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

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 11 July 2018 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 11 July 2018 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.
Reviewed 9 July 2018

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 9 July 2018 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 6 July 2018 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.
Nearby
Nearby HotelsSee all 22 hotels in Annapolis
Annapolis Waterfront Hotel, Autograph Collection
443 reviews
.01 km away
Historic Inns of Annapolis
1,254 reviews
.51 km away
Hotel Annapolis
1,383 reviews
1.10 km away
Hilton Garden Inn Annapolis Downtown
42 reviews
1.27 km away
Nearby Restaurants
Sofi's Crepes
202 reviews
.19 km away
Iron Rooster
1,169 reviews
.27 km away
Kilwins
190 reviews
.32 km away
Dock Street Bar & Grill
324 reviews
.23 km away
Nearby Attractions
Annapolis Historic District
1,096 reviews
.29 km away
William Paca Garden
225 reviews
.46 km away
St. Mary's Church
80 reviews
.19 km away
Ego Alley
328 reviews
.11 km away
Ask a question
Questions & Answers
Grady J
20 June 2018|
AnswerShow all 2 answers
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!
1
Vote
Kimbercat S
6 June 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