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 Jolly II Rover

Greene and Elizabeth Streets, Conch Republic Seafood Company Docks, Key West, FL 33041
+1 305-304-2235
Website
Share
Save
Review Highlights
Fun and Beautiful Sunset Cruise

We had originally booked with another company, but after a misunderstanding about locations (we are... read more

Reviewed 1 week ago
Heather E
via mobile
Great Time!!

Wow, it was my husband and I and another couple AND the Jolly II Rover took us out! We had a great... read more

Reviewed 1 week ago
CindyC3696
,
Stuart, FL
Read all 876 reviews
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
  • Excellent93%
  • Very good4%
  • Average1%
  • Poor1%
  • Terrible1%
Travelers talk about
“captain rio” (118 reviews)
“red sails” (53 reviews)
“sunset sail” (126 reviews)
LOCATION
Greene and Elizabeth Streets, Conch Republic Seafood Company Docks, Key West, FL 33041
CONTACT
Website
+1 305-304-2235
Write a ReviewReviews (876)
Traveler rating
Traveler type
Time of year
Language
All reviews
"captain rio"
in 118 reviews
"red sails"
in 53 reviews
"sunset sail"
in 126 reviews
"captain and crew"
in 80 reviews
"great sunset"
in 47 reviews
"beautiful ship"
in 20 reviews
"sailing experience"
in 25 reviews
"green flash"
in 17 reviews
"key west sunset"
in 29 reviews
"crackers"
in 18 reviews
"hour cruise"
in 11 reviews
"two hours"
in 24 reviews
"a lot of fun"
in 21 reviews
"mallory square"
in 31 reviews
"highlight of our trip"
in 11 reviews
"laid back"
in 12 reviews
"great trip"
in 15 reviews
Filter

1 - 10 of 866 reviews

Reviewed 1 week ago via mobile

We had originally booked with another company, but after a misunderstanding about locations (we are not in Massachusetts, we’re in Key West!) we had to cancel and rebook with someone else. We are SOOOOOO glad we rebooked with Jolly II. What a great sunset cruise....More

Thank Heather E
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 1 week ago

Wow, it was my husband and I and another couple AND the Jolly II Rover took us out! We had a great time! We cut in between islands to catch another schooner out sailing. We caught her and fired our cannons at her. And they...More

Thank CindyC3696
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 4 weeks ago

I had a great time! It was a perfect little sailing escapade. Chill and fun vibes from all - great crew, great guests, cannons to shoot off with gunpowder, plus the kids (and anyone else - kids or sailors at heart I guess) got to...More

Thank Mae A
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
See more reviews
Reviewed May 22, 2018 via mobile

We’ve been out on the Jolly II Rover sunset cruise five times now and the captain and crew never disappoint! Always a fun, relaxing, and entertaining sail. The owner is extremely nice, easy to talk to, and really makes the effort to get to know...More

Thank HuskerFaithful
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 15, 2018

An inexpensive way to see a beautiful sunset on a beautiful ship! No frills and extra fluff but an amazing adventure awaits you! Expect an extra "blast" to go along with a knowledgeable crew and Captain. The owner personally sat and talked with all of...More

Thank kkress2018
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 14, 2018

We went on this with our daughter and son in law and our 5 year old and 7 year old grandsons. It was so fun and the weather was great. The crew was awesome especially with the kids. A great memory

Thank bsmith88dj
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 10, 2018

My wife and I booked at the last minute after talking with the owner and a tour of his ship. We bought a bottle of wine nearby and enjoyed on our 2 hour sunset sail. The winds were perfect and enjoyed a beautiful sunset. Everyone...More

Thank peytonstorm
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 8, 2018 via mobile

Awesome! Awesome! This is a must do when visiting Key West. The captain and crew are very skilled at what they do. Also, they make every passenger a part of the journey and sailing. It’s an adventure not to be missed

Thank Wayne T
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 7, 2018 via mobile

What an awesome experience. Great crew and unbelievable view of the sunset, and the island. The two hours were two of the most piece full and best views since we have been in Key West

Thank kentucky_travelor
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 6, 2018 via mobile

The Jolly Roger II, red sailed schooner, is a most pleasant way to spend an evening sunset in Key West. This is not a booze and cruise, but a very relaxing experience. BYOB for added enjoyment. As an added treat, the crew discharges a replica...More

Thank md3333
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Nearby
Nearby HotelsSee all 51 hotels in Key West
Marquesa Hotel
1,099 reviews
.09 miles away
The Gardens Hotel
1,913 reviews
.16 miles away
Pegasus International Hotel
757 reviews
.18 miles away
Simonton Court Historic Inn and Cottages
736 reviews
.21 miles away
Nearby Restaurants
Keys Coffee Co.
195 reviews
.17 miles away
The Cafe, A Mostly Vegetarian Place
1,361 reviews
.16 miles away
Date & Thyme
400 reviews
.18 miles away
Mr Z's
749 reviews
.18 miles away
Nearby Attractions
Nancy Forrester's Secret Garden
424 reviews
.03 miles away
Key West Distilling
76 reviews
.12 miles away
Wyland Galleries
84 reviews
.18 miles away
KEPart Studio-Gallery
17 reviews
.12 miles away
Ask a question
Questions & Answers
Celia R
June 26, 2017|
AnswerShow all 2 answers
Response from Bobby B | Property representative |
The Jolly II Rover lets the Boy Scouts use the ship 5 days a week during the months of June, July, and August. We offer Sunset sails on Friday and Saturday nights only, up till the last week of August.
1
Vote
Rachel S
March 26, 2017|
AnswerShow all 3 answers
Response from Bobby B | Property representative |
We provide a lite snack of assorted crackers and cheese, fruit and veggies, and bottled water. You are free to bring anything you want to eat or drink. BYOB. We supply the cups, ice, coolers, and corkscrews.
0
Votes
Alaskalover2006
February 18, 2017|
Answer
Response from Fred111 | Reviewed this property |
We got there about an hour early and sat at the bar next to the dock.
0
Votes