Classic Key West Schooner Sunset Sail with Full Open Bar

Recommended by 98% of travelers

Badge of Excellence

Key West, USA

Popular pick

Booked 5+ times last week!

2 hours (approx.)
Mobile ticket
Offered in: English

Why travelers loved this

4.9

· Brett_R ·

Feb 2026

Great outing. Service and experience were at the center of everything Captain Josh and Christina did. Safe loading of passengers, a ‘to the point’ safety overview, almost immediate serving of tasty cocktails/water/etc, and tasty treats (shrimp cocktail, key lime tart, smoked fish with crackers). The boat was nice having padded seating, toilet below deck, and large cool sails. Highly recommend!

· Richard_B ·

Jan 2026

So much fun! Josh (our captain) and Molly were fantastic! So much fun! Highly recommend! Open bar and food. Great service and so much fun!

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Overview

What's Included

Alcoholic Beverages

Full open bar with cocktails, premium beer, wine and champagne for guests >21 years of age
Soda/Pop
Bottled water
In-person Guide: English

Gratuity

Meeting and Pickup

Meeting point

200 William St, Key West, FL 33040, USA
Check-in is located at the far end of William Street, just to the right of the Western Union sign. From Elizabeth Street, keep the water on your left and follow Lazy Way Lane past the shops. The Marker Resort on your right, and the Schooner Wharf Bar on your left. The booth will be on your left.

End point

This activity ends back at the meeting point.

Itinerary

Key West Historic Seaport (Pass By)

Mallory Square (Pass By)

Sunset Key (Pass By)

Fort Zachary Taylor Historic State Park (Pass By)

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Near public transportation
Infants must sit on laps

Most travelers can participate
Total sailing time is 2 hours. There are no stops.
This tour/activity will have a maximum of 22 travelers

Supplied by

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Ralph_B

We booked this because we heard good things about it! It was fantastic! Captain Marris & first mate Christina did a great job with everything, including drinks, hors d’oeuvres and a “battle” with the Jolly Rover! The sunset was great and it was an overall hit!

Reviews

4.9

based on 225 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Great sailing experience

Amy_K, Feb 2026

Expert Captain and First Mate; great service at a leisurely pace. Will go on this schooner sail experience again!

Response from Host, Mar 2026

So glad you enjoyed your time aboard! Our expert Captain and First Mate will be thrilled to hear you felt well taken care of at a relaxed pace. We can’t wait to welcome you back for another schooner sail soon ⛵🌴

Key West Sunset Sail

Ralph_B, Feb 2026

Response from Host, Mar 2026

So glad you had a fantastic time! Captain Mareson and First Mate Cristina will love hearing this, and we’re thrilled the drinks, hors d’oeuvres, and even the Jolly Rover “battle” added to the fun. Nothing beats a Key West sunset to top it all off—can’t wait to see you back on board ⛵🌅

Great boat, service, drinks and food!

Brett_R, Feb 2026

Response from Host, Feb 2026

Thank you so much for sharing such a thoughtful review! We’re thrilled to hear that Captain Josh and Cristina helped make your outing so enjoyable and that the service, safety, and overall experience stood out to you from start to finish. It’s great to know you appreciated the comfortable seating, onboard amenities, and of course the tasty treats and refreshments — those details really help make the sail special. We truly appreciate your recommendation and hope to welcome you back aboard again soon for another fantastic day on the water!

Awesome! So much fun!

Richard_B, Jan 2026

So much fun! Josh (our captain) and Molly were fantastic! So much fun! Highly recommend! Open bar and food. Great service and so much fun!

Response from Host, Jan 2026

Thank you so much for the enthusiastic review! We’re thrilled to hear you had such a fun time and that Captain Josh and Molly made the experience fantastic. Great service, an open bar, good food, and lots of fun are exactly what we aim for! We truly appreciate your recommendation and hope to welcome you back aboard again soon for another amazing sail!

Great sunset cruise

Deborah_M, Jan 2026

Great captain and crew. Throughly enjoyed it. Drinks and snacks were very good. The sunset view was magnificent

Response from Host, Jan 2026

Thank you for the great review! We’re so happy to hear you thoroughly enjoyed the trip and that our captain and crew made it a memorable experience. Glad you loved the drinks and snacks—and that magnificent Key West sunset never disappoints! We’d love to have you sail with us again soon. 🌅⛵

Wonderful

Michele_G, Dec 2025

It was relaxing and enjoyable, and educational. The hordueves were great! We loved the gun fire and cannons from the other vessels.

Response from Host, Dec 2025

Thank you so much for sailing with us and for sharing your experience! We’re delighted to hear you found the trip relaxing, enjoyable, and educational. We’re also glad you loved the hors d’oeuvres and the fun excitement of the gunfire and cannons from the other vessels — it definitely adds to the adventure! We truly appreciate you joining us and hope to welcome you aboard again soon!

Perfect!

Cathy_T, Nov 2025

Great experience! Captain Joe and Christina did a great job making us feel welcome onboard. Yummy snacks, the best sangria, and beautiful sunsets made for the perfect night! We will be back the next time on Key West!

Response from Host, Nov 2025

Thank you so much for joining us and for sharing your wonderful review! We’re delighted to hear that Captain Joe and Cristina helped make you feel right at home onboard. The snacks, sangria, and sunset are some of our favorite parts of the evening, so it’s great to know they made your night special. We truly appreciate your kind words and can’t wait to welcome you back the next time you’re in Key West!

Sunset Sail

Dan_M, Nov 2025

Great time with a beautiful sunset! Very professional crew! The crew took great care of us the entire time.

Response from Host, Nov 2025

Thank you so much for sailing with us! We’re delighted to hear you had a great time and were able to enjoy such a beautiful sunset. Our crew takes pride in providing professional, attentive service, so it means a lot to know you felt well cared for throughout your trip. We appreciate your kind words and hope to see you aboard again soon!

Truly Delightful

Kathy_S, Nov 2025

This is a gentle sunset sailing cruise on a fine vintage sailing vessel with a competent, friendly and knowledgeable crew. You sit on deck enjoying scenic views and conversation. Includes generous drinks and hors d’oeuvres. Skipper Joe and Christina (?) were awesome hosts!

Response from Host, Nov 2025

Thank you for sharing such a thoughtful review! We’re so glad you enjoyed a gentle and scenic sunset sail aboard our vintage vessel. It’s wonderful to hear that the relaxed views, conversation, and generous drinks and hors d’oeuvres made your experience special. Skipper Joe and Cristina will be thrilled to know they helped make your cruise memorable. We truly appreciate you joining us and hope to welcome you back aboard again!

Very peaceful, crew was...

meaghan_b, Nov 2025

Very peaceful, crew was great and attentive. I would highly recommend this over any of the “party” sunset cruise boats. It was nice to sit have a cocktail, enjoy the weather and sunset with a small group. Being in the sailboat was highly enjoyable.

Response from Host, Nov 2025

Thank you so much for joining us! We’re really glad you enjoyed the peaceful vibe — we like to think of ourselves as the “no loud speakers, just good sunsets” kind of cruise. 😄 Our crew will be thrilled to hear your kind words, and we couldn’t agree more that a small group, a cocktail, and a sailboat make for a pretty unbeatable combo. We truly appreciate the recommendation and would love to have you back aboard anytime! ⛵️✨

Joe and Vitali were great...

Timothy_S, Oct 2025

Joe and Vitali were great hosts. Very nice time. Would highly recommend this excursion if looking for a pleasant relaxing evening.

Response from Host, Oct 2025

Thank you for your kind words! We’re so glad you had a relaxing and enjoyable evening with Joe and Vitali — they’ll be happy to know they made your experience special. We truly appreciate your recommendation and hope to welcome you aboard again soon!

Peaceful Sunset Cruise

Tara_S, Oct 2025

Very fun sunset cruise. The crew were very friendly and accommodating. Very peaceful, a nice way to end the day.

Response from Host, Oct 2025

Thank you for joining us on the sunset cruise! We’re so glad you had a fun and peaceful experience and felt well cared for by our friendly crew. It’s wonderful to hear it was a nice way to end your day. We’d love to welcome you back for another beautiful sail!

Loved the trip. Great...

melissa_F, Oct 2025

Loved the trip. Great experience and would highly recommend. Shout out to Joe and Vitale. Well done!

Response from Host, Oct 2025

Thank you for your kind words! We’re thrilled you loved the trip and appreciated the experience. Joe and Vitale will be delighted to hear your shout-out — they take pride in making every sail enjoyable. We’d love to welcome you back aboard for another great adventure!

Vitalik and Cpt. Joe are awesome

Pabel_M, Sep 2025

My family and I had a great time with Vitalik and Cpt. Joe! Very professional, welcoming and engaging. Even dealt with drunk customers like true professionals

Response from Host, Sep 2025

Thank you for sailing with us! We’re so glad you and your family had a wonderful time with Vitali and Captain Joe. They’ll be happy to know their professionalism and warm welcome made your trip memorable—and yes, they handle all kinds of situations like true pros. We hope to see you all back on board for another smooth sail soon!

First Sunset Cruise

Dana_D, Sep 2025

Great experience!! Staff and captain were wonderful!!! Plan to do again!! This cruise was great due to small number of people.

Response from Host, Sep 2025

Thank you so much for your kind words! We’re delighted to hear you had a great experience and enjoyed the smaller group setting—it really does make the cruise feel special. We’ll be sure to share your compliments with the captain and crew, and we look forward to welcoming you back on board again!

Just don't

Georgia_S, Aug 2025

Sadly it sucked! maybe if ur 97 years old and half dead you would like it slow and drab. capt killed engen w no wind. the food n drinks maybe get a 5 out of 10. 1st mate was ok. Highlight was the rain, no joke. would not pay over 15.00 but even for free we would not go back!

Response from Host, Aug 2025

I usually try and respond professionally, however: this review does not merit that so. We’re honestly glad you won’t be coming back—because we wouldn’t have you back if you paid us. Your review is not only rude, but it’s also disrespectful to our hardworking crew who put in every effort to give guests a safe and enjoyable trip. Sailing depends on wind and weather, and anyone with a shred of common sense would understand that. Insulting our guests with comments like “97 years old and half dead” is tasteless and unnecessary. We have no interest in hosting people who show up with such negativity and disrespect.

Beautiful sunset, nice...

Cheryl_G, Aug 2025

Beautiful sunset, nice schooner. Great service (drinks and snacks). The parking was tough, so leave early. I have done a KW sunset tour before and enjoyed the captain pointing out a few landmarks. We did not have that this time. A bit of soft music would have been nice, too. Right as we jockeyed into place as the sun was about to go down, another schooner crossed in front of us and blocked our view. There seemed to be some sort of banter between the two ships and they fired a 'cannon' shot at us, just about ruining the sunset. It seems there would be some sort of etiquette to respect passengers' viewpoint. It was beautiful, we enjoyed it, but I sensed some flaws.

Response from Host, Aug 2025

Thank you for sharing such thoughtful feedback. We’re happy to hear you enjoyed the sunset, the schooner, and the service, and we truly appreciate your honesty about what could have made the experience even better. We’ll be sure to share your comments with the team so we can keep improving and make future sails as smooth and memorable as possible. We’re so glad you joined us and hope to welcome you aboard again for an even more perfect sunset. 🌅⛵

Unhappy sunset cruise

Donna_M, Aug 2025

First we called the company to find out if trio was cancelled because it said in description has to have good weather, it was pouring so we called the guy was rude saying in a rude manner “we will call if it’s cancelled!” So we went still it was very overcast, description said open but it was just coolers with. Very limited drinks. There wasn’t any wind so we just went out in the middle of the water and pretty much just sat there, and because it was so overcast we didn’t even get to see the sunset. Trip should have been cancelled it wasn’t cheap definately didn’t get moneys worth! But the captain and crew were awesome and they tried to make the best of it,

Response from Host, Aug 2025

Thank you for taking the time to share your feedback. While we’re glad to hear that you found our captain and crew to be awesome and attentive, we’re truly sorry that your overall experience did not meet expectations. We understand how disappointing it can be when weather conditions don’t cooperate—especially on a sunset sail. Our policy is to sail as long as it’s safe, as many guests still enjoy the experience even on overcast days, but we regret that the conditions didn’t allow for the views you were hoping for. We’re also concerned to hear about your interaction over the phone, as our team should always be courteous and helpful. Please know we’ll be reviewing this to ensure it doesn’t happen again. We appreciate your feedback on the beverage options as well, and we’ll take this into account as we continue working to improve the experience for our guests. Thank you again for sharing your thoughts, and we do hope you’ll consider giving us another chance in the future under clearer skies.

Joe, Colin and Christine...

Todd_B, Jul 2025

Joe, Colin and Christine were amazing. It was a beautiful evening sailing. The smaller intimate setting on this boat added to the experience. Highly recommend.

Response from Host, Jul 2025

Thank you for your kind words! We're so glad you enjoyed your evening sail and that the intimate setting made it even more special. Joe, Colin, and Cristina will be thrilled to hear they helped create such a memorable experience. We truly appreciate the recommendation and hope to welcome you back aboard soon!

Good value and well done!

Kenneth_T, Jul 2025

Crew was fantastic! Great sail out and around the Key with incredibly beautiful views. Very friendly with drinks and snacks.

Response from Host, Jul 2025

Thank you for the great review! We're so glad you enjoyed the sail around the Key and had a chance to soak in those beautiful views. It’s always wonderful to hear that the crew’s friendliness and hospitality made your experience even better. We’ll be sure to pass along your kind words — and we hope to see you aboard again soon for another memorable trip!

Great experience! The...

PAULINE_L, Jun 2025

Great experience! The crew was very knowledgeable and attentive. Yummy drinks and hors d'oeuvres! Beautiful sunset and great company.

Response from Host, Jul 2025

Thank you for the wonderful review! We're so glad to hear you had a great experience with our knowledgeable and attentive crew. It’s always a joy to know the drinks, hors d'oeuvres, and sunset made the evening special — and great company makes it even better. We hope to welcome you aboard again soon! 🌅⛵

Sunset cruise on the...

troy_W, Jun 2025

Sunset cruise on the smaller schooner was much more intimate than trips we had taken in the past. Captain and first mate were terrific and did everything possible to make our trip special. Much more enjoyable than the bigger party boats.

Response from Host, Jun 2025

Thank you so much for sailing with us and for sharing your experience! We're thrilled to hear you enjoyed the more intimate feel of our schooner — it's something we take great pride in. The crew will be so happy to know they helped make your cruise special. We're glad this trip stood out from past excursions, and we’d love to welcome you aboard again anytime!

If you are looking for a...

Leigh_M, May 2025

If you are looking for a nice quiet ride in the ocean to enjoy the Sunset this is the trip. Was happy to no have all the drinking young people and loud music🍷🍷

Response from Host, Jun 2025

Thank you so much for your thoughtful review! 🌅 We’re so glad you enjoyed the peaceful atmosphere and the quiet beauty of the sunset sail. It’s wonderful to hear that the relaxed vibe and smaller group made the experience just what you were looking for. We aim to offer a serene escape on the water — and we’re so happy it hit the mark for you. Cheers to more sunsets and smooth sailing! 🍷⛵

Beautiful Sunset Views but the rest fell short

Lesley_W, Apr 2025

The sunset views on the Appledore Star were beautiful! However, we expected a crew who would proactively share relevant historical or current day facts / stories. When questions were asked by people on the vessel, they were answered but that was pretty much the extent of it. The most unsolicited communication given by the Captain was at the end when he asked people to write positive online reviews and also to give the crew tips. Michael, the deck hand, did a very good job with giving people drinks and appetizers. Again, the sunset views were amazing, but the rest of the 2 hour voyage was a bit dull in our opinion.

Very nice professional...

Anne_K, Apr 2025

Very nice professional staff. Fun ride and really liked that only a limited number of people can be on the boat. Did not feel crowded.

The Best Sunset Experience

Eric_M, Mar 2025

It was everything I expected and more. This was my first sunset experience on a schooner and well worth it. Captain Joe and 1st Mate, Michael were great! It was cool to see them open the sails. They were both so attentive to everyone’s needs. The cocktails and appetizers were great. It’s a FULL bar just as advertised. Captain Joe took the boat where there wasn’t another boat between you and the perfect sunset where we were fortunate enough to see the green flash off the water at the sun disappeared. I will take this sunset experience again the next time I’m in town. By far the best sunset cruise I’ve been on. I wasn’t disappointed, not even a single bit. Don’t miss the opportunity to have the best sunset experience, either by yourself or with the ones you love

Worth it!

Natalie_C, Dec 2024

We had a great time on the Schooner Sunset Cruise. The three young gentlemen running the show did a phenomenal job on all fronts. I highly recommend this excursion. We will definitely be making this a tradition! Thank you for the memories!!

Response from Host, Dec 2024

"Thank you for your fantastic review! We're so glad you had a great time on the Schooner Sunset Cruise and that our crew made the experience so memorable. It’s an honor to hear that you plan to make this a tradition—we can’t wait to welcome you back aboard for many more unforgettable sails. Thank you for choosing us and for sharing your kind words!"

Likely to Sell Out