Sailing Comparison: Key West Edition

Key West is a water lover’s paradise. Pretty much anything you want to do on the water, you can do here; snorkeling, paragliding, sailing, dolphin watching, jet skiing, kayaking and anything else you can imagine. Whether you grew up sailing or have never been on a boat before, Key West is the perfect place to stretch your sea legs.

I had the to opportunity to give several of the top Water Adventure companies in Key West a spin – Classic Harbor Line, Dolphin Safari Charters, Danger Charters and Fury Water Adventures. What I found is that nearly all genuinely try to make your experience special and memorable.

So how did they stack up? Let the Smackdown begin!

Classic Harbor Line

(Sails from 202 Williams Street – behind Schooner’s Wharf)

The Skinny: The Adirondack III is an impressive 80-foot vessel and unlike other “sailing” experiences on the island that really only use the motor, this thing actually, well, sails!

Their hour and half Morning Mimosa Sail runs $35/per person and while it’s called a Mimosa Sail, they also serve beer, beer wine and straight champagne (if you can’t be bothered with the orange juice) for $1 per drink. The staff was friendly, engaging and very knowledgeable about the vessel and Key West in general.

Kudos: Adirondack III is one of the larger/more impressive sailboats out there. Dollar drinks, a laid-back vibe and actual sailing round out the experience.

Thumbs Down: The 11am start time for the “morning” sail means that the sun is already high in the sky and it’s toasty. Drinks aren’t included in the ticket price like many other sails. Depending on where you’re staying in Key West, Schooner’s Wharf might be a bit out of the way.

Know Before You Go: Bring and wear sunscreen! You will bake otherwise. Don’t be afraid to move around onboard and ask questions, the crew is very accommodating. Bring cash for those dollar drinks! AND as with any sailing experience, bring cash to tip your crew!

Rating: 9 of 10 – great bang for your buck and one of the more budget friendly sailing experiences in Key West.

Dolphin Safari Charters

(Sails from Banana Bay Resort Marina at 2319 N. Roosevelt)

The Skinny: Groups of six (max) head out in speedboats for dolphin watching. Obviously the company can’t guarantee that you’ll see dolphins, but there were about a dozen swimming around during our tour. I’d never seen dolphins in the wild before! After we got our fill of the playful sea mammals, we traveled to the southeast side of Key West (near Fort Zackary Taylor State Park) for snorkeling on the reefs just before sunset.

Kudos: Small groups made it an intimate experience and our guide was extremely knowledgeable both about dolphins and other sea life we saw on the reefs. Soft drinks, water and pre-packaged snacks (think crackers and rice crispy treats) were provided. Perfect duration to fit in all activities, plus we got to see sunset on the ride back to the marina.

Thumbs Down: Banana Bay Marina is a hike away from the main part of Key West. Plan on a 40+ minute walk to get there or catch a cab. The boats only go out if they’re full, so there’s a chance that even if you have a reservation, they might cancel your trip the day of.

Know Before You Go: The “bathroom” onboard is really tiny (not kidding) so be sure to use the facilities at the marina before you go. Shoes are not allowed onboard (you leave then in a box on the dock) so be sure to wear something that’s easy to take off.

Rating: 7.5 of 10 – There was nothing wrong with this excursion; we got to see lots of dolphins plus tons of fish, lobsters and crabs on the reefs. But something felt lacking and I wasn’t blown away. Even thinking back on the experience makes me feel lethargic for some reason.

Danger Charters

(Sails from the Front Street Marina)

The Skinny: Their three hour Wind & Wine Sunset Sail gets you out on the water for the best view of Key West’s glorious sunsets over the Gulf of Mexico. The crew serves hors d’oeuvres and provides a full wine tasting – Champagnoise, 3 whites and 4 reds – describing each and suggesting a tasting order. You can follow their suggestions or jump around on your own and have as much of whatever you want. They’ve also got beer onboard.

Kudos: Personable staff, great snacks, lots of wine choices and very flexible about orders/refills. It was a perfect sunset view with a bit more of a formal vibe than other sails, but not stuffy by any means. The Captain will let you steer if you ask!

Thumbs Down: It might have been a lack of wind, but even though the sails were up, we weren’t really sailing; the motor was moving us the entire time. That said, we were in an ideal spot for sunset. The price tag is a bit steep if you’re on a budget ($89/per person), but you do get lots of hors d’oeuvres, desert and pretty much unlimited wine and beer.

Know Before You Go: Most people onboard were fairly dressed up (for Key West standards) but don’t feel out of place if you’re not. If you have any dietary restrictions, just let them know and they’ll be sure to take care of you.

Ladies, don’t wear heels. This seems like common sense, but there were several women in heels, tottering around awkwardly – don’t be one of them. Don’t be embarrassed if you spill your drink, it will happen to everyone before the night is over.

Rating: 9.5 of 10 – I honestly had trouble coming up with downsides to this sail. It was wonderful from start to finish and the three hours flew by. The staff was exceedingly pleasant and there’s really no better way to see the sunset.

Fury Water Adventures

(Sails from Front Street and Duval)

The Skinny: As the largest water sport company in North America, they offer seemingly endless options for excursions on the water.

Kudos: Anything you want to do on the water, they can accommodate. They’re located literally in the middle of everything so you’ll have no problem finding them and getting out on the water.

Thumbs Down: Full disclosure – I didn’t end up trying any of their water activities. Why? Because I was completely overwhelmed by the volume of choices! When I called to ask for suggestions on what to try, I was simply told that everything was good and then was placed on hold for over 15 minutes. In the end, trying to figure out departure times and durations of the various activities became a chore and I threw in the towel.

Know Before You Go: Take time before you get to Key West to check out their website and decide exactly what you want to do so its not as overwhelming.

Rating: Can’t rate as I didn’t actually try them out.

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And the Winner is…Danger Charters! (with Classic Harbor Line Schooner a close second).

Danger does everything right – they make you feel at home onboard, are helpful, knowledgable and accommodating. By the end of the sail, you kindof just want to just go grab dinner with the crew. Its an upscale experience that manages to be laid-back, homey and a lot of fun all at the same time.