Schooner Cruises – The Key West Guide https://thekeywestguide.com Sat, 06 Jun 2026 22:40:06 +0000 en-US hourly 1 https://wordpress.org/?v=7.0.1 https://thekeywestguide.com/wp-content/uploads/2026/05/tkw_favicon_for_wp.png Schooner Cruises – The Key West Guide https://thekeywestguide.com 32 32 Key West Schooner Sunset Sail with Bar & Hors d’oeuvres https://thekeywestguide.com/key-west-schooner-sunset-sail-with-bar-hors-doeuvres/ Sun, 24 May 2026 12:16:31 +0000 https://thekeywestguide.com/?p=430

2.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★ 5.0

Key West sunset on America 2.0: beer, wine, champagne, and plated hors d’oeuvres as you pass Fort Zachary and Mallory Square.

“Captain Janet and crew were fantastic. Great experience. The food and drinks were great. We also had a spectacular sunset.”

804 reviews2 hours (approx.)From $122.59by Classic Harbor Line

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]]> Key West: Schooner Sunset Sail with Food & Drinks https://thekeywestguide.com/key-west-schooner-sunset-sail-with-food-drinks/ Sun, 24 May 2026 12:16:41 +0000 https://thekeywestguide.com/?p=124

4.Key West: Schooner Sunset Sail with Food & Drinks

★ 4.9

Sail Key West on a classic schooner at sunset with drinks, hors d’oeuvres, dolphin sightings, and a shot at the Green Flash.

“Fantastic sunset experience on a real sailing trip with cool drinks and even some really nice snacks! Very much recommended!”

318 reviews2 hoursFrom $122by Classic Harbor Line - Key West

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]]> Key West Sunset Sail Aboard Legendary Schooner Appledore https://thekeywestguide.com/key-west-sunset-sail-aboard-legendary-schooner-appledore/ Sun, 24 May 2026 12:16:45 +0000 https://thekeywestguide.com/?p=429

6.Key West Sunset Sail Aboard Legendary Schooner Appledore

★ 5.0

Sail Key West at sunset on the classic Schooner Appledore: real sailing, small group vibes, and drinks plus hors d’oeuvres included.

“It was an absolutely fantastic experience and the crew (Christina and Ryan) and captain Josh were great. We enjoyed three tasty apps and a mini key lime pie as a desert. Note that there is a premium upcharge for some cocktails but "basic" stuff is included and I was very happy with my G&T. Note:…”

251 reviews2 hours (approx.)by Key West Schooners

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]]> Classic Key West Schooner Sunset Sail with Full Open Bar https://thekeywestguide.com/classic-key-west-schooner-sunset-sail-with-full-open-bar/ Sun, 24 May 2026 12:16:47 +0000 https://thekeywestguide.com/?p=202

8.Classic Key West Schooner Sunset Sail with Full Open Bar

★ 5.0

Small-group Key West schooner sunset sail with full open bar, tasty hors d’oeuvres, and iconic bay views.

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

213 reviews2 hours (approx.)by Key West Schooners

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]]> Key West Day Sail on Schooner America 2.0 with 2 Drinks https://thekeywestguide.com/key-west-day-sail-on-schooner-america-2-0-with-2-drinks/ Sun, 24 May 2026 12:16:48 +0000 https://thekeywestguide.com/?p=200

10.Key West Day Sail on Schooner America 2.0 with 2 Drinks

★ 5.0

Sail Key West aboard America 2.0, a classic schooner-style day sail with Fort Zachary and Mallory Square views, plus two drinks included.

“Great relaxing experience! Although the wind was too calm to properly sail, we enjoyed a nice relaxing ride. It helped that there weren't many people on the boat. Great crew!”

198 reviews1 hour 30 minutes (approx.)From $73.10by Classic Harbor Line

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