My wife and I are headed to Key West in April to celebrate our anniversary. We're familiar with all the bars and museums, but have yet to do any water sports. Has anyone done any of the sunset sailboat cruises or kayak tours and if so, do you have a specific one you would recommend? Any other fun activities?

Restaurant recommendations always appreciated as well.

Thanks!

It's been years but we did a sailing, kayaking, and snorkeling tour with Danger Charters and loved it. Active and educational... We even came across a horseshoe crab which was very cool.

We've done the sunset sail booze cruise as well. Different objective obviously but fun in it's own context.

Cheap: Go see Cat Man and his Flying Cats at Mallory Square or any of the other odd performances.

Not Cheap: If you like National Parks take a seaplane to Dry Tortuga National Park.

These aren't water sports but are a lot of fun.

Lloyd's Bike Tours

Lloyd is a trip and his tours are a unique perspective.

Drag Queen Bingo
Sundays at 801 Bourbon Bar (upstairs). This isn't all of the drag brunch crap in the headlines. it is an absolute blast. All walks of life attend and there are a lot of locals. Cheap strong drinks and a hell of a lot of laughs.

BO's Fishwagon for fish sandwiches

Garrelli 5000 said:

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These aren't water sports but are a lot of fun.

Lloyd's Bike Tours

Lloyd is a trip and his tours are a unique perspective.

Drag Queen Bingo
Sundays at 801 Bourbon Bar (upstairs). This isn't all of the drag brunch crap in the headlines. it is an absolute blast. All walks of life attend and there are a lot of locals. Cheap strong drinks and a hell of a lot of laughs.

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Lloyd's Bike Tour sounds awesome. Think we'll do that. Thanks!

hds said:

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Cheap: Go see Cat Man and his Flying Cats at Mallory Square or any of the other odd performances.

Not Cheap: If you like National Parks take a seaplane to Dry Tortuga National Park.

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Seaplane is sold out for the dates we'll be there. Definitely doing this if we go back though.

TulaneAg said:

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It's been years but we did a sailing, kayaking, and snorkeling tour with Danger Charters and loved it. Active and educational... We even came across a horseshoe crab which was very cool.

We've done the sunset sail booze cruise as well. Different objective obviously but fun in it's own context.

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Just booked the sunset wine sail with Danger. Looks great. Thanks!

Boat Shoes said:

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hds said:

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Cheap: Go see Cat Man and his Flying Cats at Mallory Square or any of the other odd performances.

Not Cheap: If you like National Parks take a seaplane to Dry Tortuga National Park.

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Seaplane is sold out for the dates we'll be there. Definitely doing this if we go back though.

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Dry Tortuga is very cool for history buffs. Take the seaplane ride; it's a long boat ride, especially if your spouse is prone to seasickness.

Kayak through the mangrove forest was awesome. Ended in a jellyfish spawning pool, millions of them. Sorry don't remember the tour name.

Bump. A couple weeks out. Getting real excited.

Boat Shoes said:

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Bump. A couple weeks out. Getting real excited.

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Your wife will like the indoor butterfly sanctuary.

Also, the author Judy Blume (most wives read her books as kids) has a bookstore in Key West and she works in the store regularly. Take your wife there if she was a fan growing up.

I did a kayak trip through the mangroves and to a secluded beach at Snipe Point which was amazing, it was with Reelax Charters out of I think Sugarloaf Key. 10/10, would highly recommend

Also did a large group snorkeling trip from Key West with I think Fury charters. It was pretty good but the seas were rough that day so it could be tough if anyone in your group is a weak swimmer

I'm going to piggy back on this thread.

I'm planning on going mid may with my gf. Can someone recommend a good beach hotel with excellent service? Also, can I get around without a car?

I'm planning on flying directly into key west via delta.

you are fine without a car, actually maybe better off because parking is tough there. beaches are virtually non-existent however. I think there were a couple of resorts on the north side of the island with very tiny private beaches. if you want a better beach you will need a car or take a charter boat out to one of the other keys.

My wife and I were just there and had a great time. If you want to fish it was amazing and we used All IN fishing guide and Garrett was awesome. Brought home 25 pounds of snapper filets. We stayed at Casa Marina and was pretty good but they are closing for 5 months for renovations. You do not need a car at all. We just got bikes and were able to get everywhere easy and on date just used Uber. Scooters were fun but dangerous as the pedestrian come out on streets at random times. Highly suggest Moondogs for great sangria, burgers and best key lime pie there. Blue Heaven was great for brunch. Better than sex was great dessert place(dont eat dinner that day just late lunch) but need reservations. There were some really nice places on tank island just across key west and quick ferry ride that looked like had a nice beach to use. We ate at Latitudes which had awesome views of sunset but definitely need early reservations.

Thanks a bunch.

Barefoot Billy's at Casa Marina has a great jet ski tour around the whole island. Lasts a couple hours and super reasonable on the price.

Strongly recommend renting bicycles. The first time we visited we spent 1.5 days hoofing it and finally rented bikes. Vacation changed instantly. You can get to anywhere you want to be in a few minutes, and you make your own A/C (KW is hot and humid).

We were nervous at first due to the vehicle traffic, but you quickly adjust and the cars are used to people on bikes. And drunk people on bikes.

Make sure you stop in at Garden of Eden, on Duval, for a drink.

We booked a trip at the end of the month. Staying at the Marquesa but this time we're trying their 'newer' rooms across the street from the main house.

Already mapping out my food and beverage checklist. Always wanted to try Santiago's Bodega (tapas restaurant) so grabbed a reservation there one night. I'd also like to try a cuban burger at Frita's - a co-worker said it was so good he went twice. We always go to El Siboney for a meal (their ropa vieja is killer) but not sure we'll squeeze it in this trip. Garbo's Grill will be visited a couple of times. Once for a mango dog, again for another mango dog or an umami burger.

Drag queen bingo on Sunday afternoon, visit the Hemingway House since our first visit we had to rush through to meet up with friends. Beers to be drank at the Green Parrot, Captain Tony's, etc. Rum drinks at Tiki House and The Rum Bar.

Evenings will be spent watching live music. We'll make sure to watch the Marshall Morlock band at least once, maybe 2 nights in a row. Cover band that has regular weekly gigs at various spots. His dad is the bass player and will play keyboards with his right hand while hammering out the bass lines on the bass w/his left hand. Morgan is an absolute stud guitar player and has a great voice.

Last time there my wife one a bingo game at the Green Parrot, so we ended up w/a $50 gift card to Fausto's grocery store. When we get to our hotel we'll walk over there and get some snacks/pool side beverages.

Much time will be spent cruising aroudn on our Key West Hogs (rented bicycles), drink in hand, ringing the bell on the handlebars at anyone who looks like they might step out in front of me. We'll ride around, grab a drink, share a small bite to eat, pop in some art stores or whatnot, look at vacation or retirement second homes we can't afford but will if we win the lottery, repeat. Then we can eat/drink a lot of different places but never overindulge on anything at one time. It's the NOLA/French Quarter method to survive and prosper.

I wanted to take the sea plane to Dry Tortuga but she said we'll do it another time when we're in town longer. Only going to be 3 full days on the island, staying 4 nights.