Key West Sunset Schooner Sail & Open Bar from Historic Seaport

Summary

Key West sunset sail with open bar and historic seaport vibes

You’ll board a classic schooner at Key West Historic Seaport for a sunset sail with an open bar and local guide. Sip cocktails as you pass Mallory Square and catch glimpses of Fort Zachary Taylor while warm breezes and laughter fill the air. There’s time for stories, music, and unexpected moments—leaving you with that salty-sweet feeling only Key West can give.

What’s the experience like?

I’ll admit, we almost missed the boat—literally. My friend forgot her sunglasses in the car and sprinted back just as they were untying the ropes at the Key West Historic Seaport. The crew just laughed, said it happens all the time. That set the tone: nothing rushed, no one judging. The wood deck felt warm under bare feet, and someone handed me a cold drink before I even realized I needed one. Our captain—can’t remember if it was Mike or Mark—pointed out Mallory Square as we slid past, already packed with people waiting for sunset but honestly, it felt better to be floating away from the crowd.

The wind picked up a bit after we passed Sunset Key, making the sails snap overhead. There’s something about that sound—it’s sharp but comforting. I tried their “Schooner Bloody Mary” (spicy enough to make me cough once), and Li behind the bar grinned like she’d seen it happen before. She told us stories about old rum runners and how you can sometimes spot dolphins if you’re lucky (we weren’t). The light started changing fast—first gold, then this weird pink that made everyone’s faces look softer. Someone spilled their beer but nobody cared; saltwater dries quick anyway.

We drifted close to Fort Zachary Taylor just as the sun hit that line where sea meets sky. It wasn’t quiet—there was music playing somewhere near the bow—but there was this hush among us for a minute or two. I leaned against the rail and let my hand trail over the wood, sticky from spilled soda or maybe just humidity. The whole thing lasted about two hours but felt shorter; maybe that’s what happens when you’re not checking your phone every five minutes. On the way back into Key West Historic District, a couple started dancing near the mast—not well, but nobody minded.

Step-by-step itinerary

Day 1 — Key West waterfront and sunset sail

• Explore Key West Historic Seaport
• Visit Mallory Square waterfront
• See Sunset Key island views
• Pass by Fort Zachary Taylor
• Board schooner for sunset sail
• Enjoy full open bar on sail
• Watch Key West sunset from deck
• Sail back to Key West harbor

Top questions

How long does the Key West sunset schooner sail last?

The total sailing time is 2 hours with no stops during the cruise.

Is there an open bar included on this Key West schooner tour?

Yes, there’s a full open bar with cocktails, premium beer, wine, champagne for guests over 21.

Where does the sunset sail depart from in Key West?

The schooner departs from Key West Historic Seaport along the waterfront.

Are children allowed on this sunset cruise?

Yes, but infants must sit on an adult’s lap during the tour.

Does this tour include hotel pickup?

No hotel pickup is included but public transportation options are nearby.

What landmarks will I see during this sunset sail?

You’ll pass Mallory Square, Sunset Key, and see Fort Zachary Taylor from the water.

Is food provided on board during this cruise?

No meals are included; only drinks like soda, water, cocktails are served.

What’s included

Your evening includes a two-hour schooner cruise departing from Key West Historic Seaport with an English-speaking guide onboard. You’ll enjoy unlimited cocktails (plus premium beer, wine or champagne if you’re over 21), soft drinks and bottled water—all while soaking in coastal views before returning to port after sunset.