We've found that apparently there is NO END to the many things you can do and see in and around Key West. We keep trying to get to them all but we haven't yet! Of course, there are annual events that we have not attended yet but are on our to-do list when it works out to be in Key West at the right time.
Any time of the year you can go fishing, kayaking, snorkeling, diving or jet-skiing. My family has snorkeled and dived in December but wet-suits were required. By January I think the water is too cool and it's too windy for water-based fun, but that's just me. I've seen jet-ski groups out on the Gulf side in the winter so I know it can be done! Lazy Dog kayak and paddleboard rentals and tours are just 2 miles from our house at the Hurricane Hole. We've rented kayaks and gone out ourselves to the Salt Ponds near the airport. It's an easy trip across Cow Key Channel and down Riviera Canal. Someone once pointed out a house on Riviera Canal and said Jimmy Buffett lived there but I've never been able to recognize it again! All of the houses on Riviera Canal are beautiful and it's fun to look at them as you paddle by. You have to watch for the signs to enter the Salt Ponds; it's not really obvious. No worries about getting lost though-you can always tell where you are. Watch out for the low-hanging mangroves! It's easy to get stuck in them. We have not rented jet-skis but see tours leaving all the time from Ibis Bay Resort. The jet-skis are in front of the Stoned Crab restaurant. There are several places that rent boats for the day on Stock Island, including a company at the Hurricane Hole. That's the closest to the house and also gives you the quickest access to either the Gulf or the Atlantic. Of course, there are several charter fishing boats located at the Hurricane Hole as well.
I've mentioned the Dry Tortugas seaplane trip and I'll recommend it again. We loved this trip and thought it to be well worth the money. Fort Jefferson is beautiful and fun to explore. The snorkeling around the walls in excellent. There are two small beaches and restrooms/changing areas. We recommend that you wear your swimsuit and bring a bag with a change of clothes. The tour company allows you to bring a small cooler or they will provide one for you. You can also purchase soft drinks and they'll give you bottled water. We packed our own cooler with koozies and brought a small bag with a towel and dry clothes as well as sunscreen. There is no place to lock up your bag while you snorkel; we left ours under a tree by one of the beaches and it was fine. The tour boat that visits the island has a bar onboard that they open about an hour before they leave-I had an excellent painkiller while I could. We had to dodge thunderstorms on the way back to Key West in the seaplane but the view from the air was still spectacular.
Last November we were fortunate enough to plan our trip to coincide with "Boat Week". This is actually the World Championship Super Boat Off Shore Race. It begins with a parade of the off shore boats down Duval Street and finishes on Saturday morning with the Finals after a week of qualifiers. The boats start in front of Mallory Square, race just north and have a tight turn just off Christmas Island so that they race back in front of the entire waterfront and then out just past Fort Zachary, where they have a nice wide turn that brings them back right alongside the waterfront and Mallory Square. You can try to find a spot on the waterfront to watch but go early and be prepared to stay late if you want a seat with a view. We watched from our boat. The Coast Guard had designated areas for watching from a boat. The anchoring in these areas is quite poor. It took us multiple attempts to get the anchor to catch and we watched more boats take even longer than we did so be prepared. It was a great place to watch-even with the crowd of other boats. The people watching out in the boats was great too! There was significant downtime between each race. We didn't see any crashes but there had been one on Friday that was apparently quite spectacular. Thankfully no one was hurt. There is also an ongoing boat show at the Historic Seaport. Go in the evening, after dinner, when the boats have all their LED lights on. It's quite a sight to see! Theses boats are all for sale so if you're in the market for a high-speed boat, bring your checkbook. There were also some large RV's on display, a Porsche and some crazy looking off-road vehicles. It was really an entertaining evening.
There was another "Race Week" in Key West-the Quantum Key West Race Week for racing sailboats. Sizes ranged from quite small to quite large. There were off-shore races held each day and several divisions were racing at the same time just in different locations. This was another race were we able to watch from our little boat (even in January!). We also watched the boats come in at the end of the day from a waterfront table at the Sunset Pier. We were in town for 3 Race Weeks and unknowingly saw the last one in 2017. We hope that the races will be reinstated some day. We always enjoyed meeting the sailors and their crews out and about downtown.
Still on our to-do list: the Parrot Head Convention, which is held the week before the boat races (and the week after Fantasy Fest). You do have to be a member of an official Parrot Head Club to attend the events (and have any hope of actually seeing Jimmy Buffett). We are members of an official Club so we will get to that convention one day!