Key West: Sunset Sail on Schooner Appledore with Drinks & Hors d'Oeuvres

Summary

Sail past key west’s historic seaport as the sun dips low and laughter drifts across the deck

You’ll watch Key West glow from the deck of a classic schooner as sails fill above you and locals wave from Mallory Square. With chef’s hors d’oeuvres in hand and your choice of boutique wine or cocktails, you’ll catch glimpses of Fort Zachary Taylor and Sunset Key before drifting back under a sky that lingers long after the last light fades.

What’s the experience like?

The first thing I noticed was the sound — not engines, but canvas snapping overhead and that low hum of people settling in, shoes off, drinks in hand. We’d barely left Key West Historic Seaport when our captain (I think her name was Jamie?) grinned and asked if anyone wanted to help with the sails. I tried — arms awkward, rope rough in my palms — and this older couple from Ohio cheered me on like I’d just run a marathon. The sky was still pale blue but you could already feel that slow shift toward gold, you know?

We drifted past Mallory Square where crowds were gathering for their own sunset celebration — street performers tossing fire, kids chasing after bubbles. Someone pointed out Fort Zachary Taylor off to the right, its old stone half-shadowed. The crew kept appearing with trays of shrimp and these tiny little bites (I still don’t know what one of them was — something smoky and salty). My glass never seemed empty for long; I went for the white wine first but ended up trying a local beer too. There was a moment when everyone got quiet at once, just watching the sun drop behind Sunset Key. It felt almost private, even though we were all strangers.

I kept thinking how different it felt to be on an old schooner instead of one of those big party boats — there was space to move around but it never felt crowded. The wood underfoot had this worn-smooth feel, and every so often a bit of sea spray would catch your face if you leaned out too far (which I did, obviously). One of the crew told us stories about Appledore’s trips around the world; apparently she’s circumnavigated the globe more than once. That stuck with me for some reason — made everything feel bigger than just a two-hour sunset sail.

Step-by-step itinerary

Day 1 — Sunset sail and Key West sights

• Board the schooner at Historic Seaport
• Help crew hoist the sails
• Take a turn at the ship's wheel
• Sail past Key West Historic Seaport
• View Mallory Square Sunset Celebration
• Pass Navy Mole and Fort Zachary Taylor
• Enjoy drinks from full cocktail bar
• Watch sunset over the Gulf of Mexico

Top questions

How long does the Key West sunset sail last?

Total sailing time is 2 hours with no stops.

Are drinks included on the Appledore sunset cruise?

Yes, premium beer, boutique wine, champagne, cocktails, soft drinks are included for guests over 21.

Is food served during the sunset sail?

Yes, chef’s selection of hors d’oeuvres and cocktail shrimp are served onboard.

Can children join this Key West sunset cruise?

Yes, suitable for all fitness levels; infants must sit on an adult's lap.

Does this tour include hotel pickup?

No hotel pickup is mentioned; tour departs from Key West Historic Seaport.

Is there live commentary or guidance during the cruise?

The crew shares stories about the ship and local sights naturally during sailing.

Will I see Mallory Square during this sunset cruise?

Yes, you’ll sail past Mallory Square’s famous Sunset Celebration.

Are service animals allowed on board?

Yes, service animals are allowed on this tour.

What’s included

Your evening includes a two-hour sunset sail aboard classic wooden Schooner Appledore—she’s sailed around the world—with premium beer, boutique wine, champagne or cocktails for adults over 21 years old. Chef’s hors d’oeuvres (including cocktail shrimp) are served throughout as you glide past Key West Historic Seaport and iconic waterfront sights before returning to shore together.