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
Share
Save
Review Highlights
Fun Overnight

My wife and I recently did an overnight stay on the Woodwind Schooner, the B&B, boat and breakfast... read more

Reviewed 5 days ago
mss12078
,
Gloversville, New York
Evening on schooner Woodwind

Obviously grand weather enhances the experience, but rest assured that the crew of Woodwind will... read more

Reviewed 6 days ago
mhowar17
,
Annapolis, Maryland
via mobile
Read all 254 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!
  • Excellent83%
  • Very good11%
  • Average2%
  • Poor1%
  • Terrible3%
Travellers talk about
“sunset cruise” (32 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
Write a ReviewReviews (254)
Traveller rating
Traveller type
Time of year
Language
All reviews
"sunset cruise"
in 32 reviews
"captain and crew"
in 26 reviews
"hour sail"
in 14 reviews
"beer and wine"
in 9 reviews
"chesapeake bay"
in 24 reviews
"wedding crashers"
in 7 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
"visiting annapolis"
in 5 reviews
"severn river"
in 6 reviews
Filter

1 - 10 of 252 reviews

Reviewed 5 days 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
Reviewed 6 days ago via mobile

Obviously grand weather enhances the experience, but rest assured that the crew of Woodwind will optimize your enjoyment. You are allowed—- and encouraged to take the helm for a few minutes, if so inclined. The views of Annapolis, the Naval Academy, and the Bay Bridge...More

Thank mhowar17
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 6 days ago via mobile

I had a wonderful sail with Captain Jen. Not only did we get close to the Bay Bridge but Captain Jen was a font of information about Annapolis and the Naval Academy. I highly recommend this fun adventure!

Thank nikkius2016
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
See more reviews
Reviewed 6 days ago via mobile

We always have a great time when we’re sailing with the Woodwind crew. It’s a great opportunity to get some beautiful photos, too!

Thank Vanessa F
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 11 May 2018

Picture a hot spring afternoon, reasonable winds and a fabulous schooner with a friendly crew then add two couples whose ladies both shared a birthday. What a fabulous experience, sailing out of Annapolis to the Bay bridge and back achieving 10.2 knots under full sail....More

Thank bedonboy
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 22 January 2018 via mobile

I had the opportunity to partake in two sailings with two groups of visiting friends. One was the Wednesday night race where not only did you participate in the two attraction schooners racing but also got to view the Wednesday night races of the Annapolis...More

Thank kevin12400
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 26 December 2017 via mobile

Lovely Cruise! We were looking for a way to get out on the water while visiting Annapolis for the first time as a USNA family. This was perfect for us! The younger boys loved getting to steer the boat and the peace and quiet of...More

Thank Kim D
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 25 October 2017

We took the 1230-230 cruise on a sunny autumn day. Captain and crew were friendly, experienced and knowledgeable. About 40 guests onboard---all ages. Beverages and snacks provided.

Thank LSD11
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 10 October 2017

This was a great trip. I was thrilled that we were able to book so short notice. I called and left a voicemail around 9am. They called me back at 10am and were able to fit us in that afternoon (and during the sailboat show...More

1  Thank mquest
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 26 September 2017 via mobile

I am a seasoned boater and this was a first for myself and fiancé. What a wonderfully relaxing afternoon. We did the 3 pm tour and there was about 10 of us and crew was personable and knowledgeable. I got to steer the boat and...More

Thank Lisa B
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
431 reviews
.01 km away
Historic Inns of Annapolis
1,228 reviews
.51 km away
Loews Annapolis Hotel
1,361 reviews
1.10 km away
Hilton Garden Inn Annapolis Downtown
17 reviews
1.27 km away
Nearby Restaurants
Sofi's Crepes
193 reviews
.19 km away
Iron Rooster
1,123 reviews
.27 km away
Kilwins
181 reviews
.32 km away
Dock Street Bar & Grill
316 reviews
.23 km away
Nearby Attractions
Annapolis Historic District
1,063 reviews
.29 km away
William Paca Garden
219 reviews
.46 km away
St. Mary's Church
79 reviews
.19 km away
Ego Alley
318 reviews
.11 km away
Ask a question
Questions & Answers
Grady J
20 June 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
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
;