🌅 Key West, Florida
Key West Sunset Cruises
Everyone else is elbowing for space at Mallory Square. You'll be out on the water.
Captain Rio's Charters runs private 2-hour sunset cruises from Hurricane Hole Marina in Key West for $500 flat for up to 6 guests. Boats depart roughly 90 minutes before sunset, and guests are welcome to bring their own food and drinks.
The experience
What the day actually looks like
Key West sunsets are genuinely famous, and there is a reason a few hundred people gather at Mallory Square every single evening to watch one. There's also a much better way to do it: from the deck of a boat, with nobody else on board but the people you came with.
We leave Hurricane Hole Marina about 90 minutes before the sun goes down, which gives us time to get out, find a spot with an uninterrupted western horizon, and settle in. Bring whatever you want to eat and drink — there's a cooler on board and a Bluetooth speaker, so it's your music and your bottle of wine.
It's the trip people book for anniversaries, proposals, birthdays and last nights of a holiday. Rio has been part of more than a few engagements and he's very good at being exactly where he needs to be with the camera at the right moment.
Two hours, $500 flat
For the whole boat, up to 6 guests. Not per person.
BYOB
Bring your own food and drinks. Cooler and Bluetooth speaker on board.
Built for occasions
Anniversaries, proposals, birthdays, bachelorette parties, family reunions.
Make it longer
Stretch to 4 hours and add a sandbar stop, snorkelling or some light fishing first.
The boat
1998 Stamas 32 · Twin Yamaha 250s
One 32-footer, licensed for six, with a shaded cabin and a bathroom on board. Everything you need and nothing you have to share.
What's included
- Private use of the 32 ft boat
- Cabin with seating & shade
- USCG licensed & insured captain
- Bluetooth speaker
- Cooler provided
- Bathroom on board
What to bring
- Whatever you want to eat and drink — the boat is BYOB
- A light layer, it cools off on the water after dark
- A camera. You will want one.
Rates
Flat rate. Never per person.
Whether there are two of you or six, the price is the price. That is the whole idea of a private boat.
All rates are flat per boat for up to 6 guests — never per person. Fuel is not included: consumption is tracked on every trip, and the fuel your charter uses is billed on top of the rate. This applies to every trip, inshore and offshore, with no exceptions. Gratuity is not included.
Questions
Key West Sunset Cruises FAQ
What time does the sunset cruise leave?
About 90 minutes before sunset, which shifts through the year. Captain Rio confirms your exact departure time when you book.
Can we bring our own food and drinks?
Absolutely — you're encouraged to. There's a cooler on board, and you're welcome to bring whatever you'd like to eat and drink.
How much is a private sunset cruise in Key West?
$500 flat for a 2-hour cruise for up to 6 guests. That is the whole boat, not a per-person price.
Is it good for a proposal or an anniversary?
It's one of the best ways to celebrate in Key West, and Rio has helped with plenty of proposals. Mention it when you book and he'll help you set it up.
Can we bring kids?
Yes — families with children are very welcome.
What if it's cloudy?
Key West sunsets are often spectacular even with some cloud cover — cloud is what gives you the colour. If genuinely unsafe weather is coming, Rio will talk to you about moving the trip.
Also aboard
Combine it with something else
Half and full-day charters can mix any of these into one trip. Just tell Rio what your group is after.
Key West Fishing Charters
Reef, wreck, offshore or backcountry — you pick the fight, Rio finds the fish.
See the trip
Key West Spearfishing Trips
Go get it yourself. Rio is a competitive spearo and he'll teach you how.
See the trip
Key West Snorkeling & Sandbar Tours
The only living coral barrier reef in North America, plus a sandbar all to yourselves.
See the trip
Key West Lobstering & Island Exploration
Dive down, tickle him out, net him. Then eat him. Hard to beat.
See the tripKey West Private Group Charters
Your boat, your people, your day. Tell Rio what you're celebrating.
See the tripReady when you are
Let's get you out on the water
Rio answers his own phone. Call or text him about dates, tides, group size, or what's been biting this week.
Departing Hurricane Hole Marina · Key West, FL · 7 days a week