Key West: Sunset Dolphin Sail with Tapas & Wine Pairing

Summary

Sail from Key West for dolphins, sunset colors, wine & chef’s tapas

You’ll sail from Key West as dolphins surface nearby, then unwind with boutique wines and chef-made tapas while the sun sets over open water. Your captain shares local stories as you drift past famous landmarks—expect laughter, fresh sea air, and that feeling you get when time slows down for a while.

What’s the experience like?

I didn’t expect the sky to look so pink before we even left the dock at Key West’s Historic Seaport. There was this buzz in the air — not loud, but you could hear people chatting quietly as we stepped onto the catamaran. Our captain (I think her name was Maria?) gave a quick wave and said something about “dolphin luck” today. I just grinned and hoped she was right. The salt in the air mixed with someone’s sunscreen; it felt like vacation already.

We glided past Mallory Square and Sunset Key — both looked different from the water, somehow less crowded. Maria pointed out Fort Zachary Taylor off to our left, and then everyone sort of fell quiet watching for dolphins. I heard a splash before I saw anything, and then there they were — maybe six or seven dolphins weaving through the wake. Someone next to me gasped (I might’ve too). It wasn’t a showy thing; just these quick flashes of grey backs and that little puffing sound they make when they breathe.

After that, things slowed down in a good way. The crew brought out trays of shrimp cocktail and these little bites with goat cheese — honestly, I lost count after my third glass of wine (they kept topping it up). The sun started dipping lower, turning everything gold. People started talking more again — stories about where they were from, someone laughing about trying to pronounce “catamaran” after champagne. That light on the water… I still think about it sometimes when I’m stuck in traffic back home.

Step-by-step itinerary

Day 1 — Sunset sail with dolphin watching

• Depart from Key West Historic Seaport
• View Key West landmarks while sailing
• Spot dolphin pods in open water
• Enjoy tapas and drinks onboard
• Watch famous Key West sunset

Top questions

How long is the Key West sunset dolphin sail?

The tour lasts approximately 2.5 hours from departure to return.

Are drinks included on this dolphin watching cruise?

Yes, premium wine, beer, champagne, soda, and pop are all included in your tour price.

Is food served during the sunset sail?

A chef’s selection of tapas including shrimp cocktail is served during the cruise.

Does this Key West tour include dolphin watching?

Yes, dolphin watching is a main highlight before relaxing with food and drinks at sunset.

Is there pickup included for this sunset sailing tour?

No hotel pickup is mentioned; tours depart from Key West’s Historic Seaport.

Can infants or small children join this dolphin sail?

Yes, infants and small children can ride in a pram or stroller on board.

What landmarks will we see during the cruise?

You’ll pass Mallory Square, Sunset Key, and Fort Zachary Taylor along the route.

What’s included

Your evening includes all premium drinks—wine, beer, champagne—and a chef’s selection of hors d’oeuvres like shrimp cocktail served on board as you sail with a local guide past iconic Key West landmarks before returning to port after sunset.