Key West: Sunset Sail with Champagne & Harbor Views

Summary

Key West harbor cruise at sunset with drinks and local color

You’ll sail through Key West Harbor with a small group as evening falls, sipping champagne or local craft beer while your guide points out historic sights and passing boats. Watch Mallory Square’s Sunset Celebration from a peaceful spot on the water, and maybe catch that legendary green flash if you’re lucky.

What’s the experience like?

We stepped onto the Floridays just as the last heat of the day was starting to fade — you know that sticky feeling on your skin in Key West, where even the breeze feels like it’s been out in the sun too long? Our captain (I think his name was Mike, but honestly I was already distracted by all the boats bobbing around us) handed me a glass of something cold and fizzy. It tasted like relief after a hot afternoon. The harbor was busy, but somehow our little group felt tucked away from it all.

As we sailed out, our guide pointed out some of the old buildings along the Key West Historic District — I caught a whiff of salt and sunscreen every time someone shifted on deck. There were other boats out there too, some packed tight with people waving or singing along to music. We drifted past them toward open water, everyone sort of quiet for a minute when the sky started changing colors. Someone said something about watching for the green flash at sunset; I didn’t really believe it until everyone stopped talking at once when the sun hit the horizon. Didn’t see it myself, but maybe next time.

The best part might’ve been catching glimpses of Mallory Square’s Sunset Celebration from out on the water — you could hear bits of laughter and music drifting over, even though we were far enough away that everything felt softer. A couple on board toasted with margaritas (which were actually pretty good), and I tried a local craft beer just because it felt right. There was this moment where nobody said anything at all, just watching that last bit of light slip away behind all those sails. I still think about that view sometimes, especially when I hear seagulls back home.

Step-by-step itinerary

Day 1 — Sunset sail and celebration viewing

• Sail through Key West Harbor
• Watch boats and enjoy sunset
• See Sunset Celebration from water
• Watch street performers and revelers

Top questions

What drinks are included on the Key West sunset sail?

The tour includes champagne, white wine, margaritas, craft beers, and non-alcoholic beverages.

Is there a restroom onboard during the sunset cruise?

Yes, there is a restroom available onboard for guests’ convenience.

Does this Key West sunset sail include pickup?

No hotel pickup is included; guests meet at the departure point near public transportation.

Are service animals allowed on this sunset cruise?

Yes, service animals are allowed on board during the cruise.

How crowded is this Key West sunset cruise?

The cruise is known for being uncrowded compared to other options in Key West.

Can I bring children or older family members?

The tour is suitable for all physical fitness levels and ages.

What’s included

Your evening includes sailing through Key West Harbor with a small group, all beverages (champagne, white wine, margaritas, craft beers, plus non-alcoholic options), and access to an onboard restroom before returning after sunset.