PortsBahamas and CaribbeanTop 5 Things to Do in Key West While on a Cruise

Top 5 Things to Do in Key West While on a Cruise

I recently visited the southern U.S. island while sailing on Royal Caribbean’s Majesty of the Seas. After a fun filled day in Key West, I realized that it is one of my favorite cruise ports, and thought it was time to put together a list of some of my favorite activities. Here they are, in no particular order!

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Bicycle Tour

If you are visiting in the cooler months (November through April), this would be my top choice. Key Lime Bike Tours offer an excellent two and a half to three hour tour around the island for $45. It will bring you to multiple historic stops, including the Southernmost point, Ernest Hemmingway’s house, and the Key West Seaport.

The tour is a great way to see a number of places on the island while being active and keeping to a small budget. I will advise that you may want to avoid this tour in the summer months as the heat can be oppressive.

As a bonus, the tour ends with a slice of key lime pie from the Key West Key Lime Pie Co. It is absolutely delicious!

Jet Ski Rental

On the flip side to my above suggestion. Renting a jet ski can be a great option in the summer months as a way to keep cool and avoid the heat. Most of the rental companies will offer a general hourly rental as well as a guided tour. I’ve done both here, and my suggestion is go with the tour. It is only slightly more expensive than an hour rental and a much better bang for your buck in my opinion.

On my most recent visit I utilized Sunset Watersports Key West for our tour. For $130 the tour includes a shuttle from downtown and there is no additional charge for a second rider. The one and a half hour tour brings you 28 miles around the island, and there is plenty of time to ride at full speed. It is definitely a change in perspective from an inland tour of the island! Sunset WS also offers a number of other water activities if you are looking to extend your day.

Trolley/Train Tour

If low key and low activity are your thing, you’ll want to check out these two providers. The Conch Train Tour is world famous and will take you on a 75 minute loop of Old Town Key West. Tickets can be purchased in advance for $28 for adults and $14 for children. Sit back, relax, and enjoy the sights.

If you are looking to do a little more DIY exploring, the Old Town Trolley Hop On Hop Off might be more up your alley. They offer up a more extended tour with 13 stops for $38. This option gives you the ability to do more than just a drive by at some of the areas of interest. Both offer a great way to see a little bit of everything in Key West on a low budget.

Bar Crawl

It’s Key West, you had to know this one was coming. Duval Street is lined up with drinking establishments. Some of the more popular ones include Sloppy Joe’s, Rick’s, Irish Kevin’s, and Hog’s Breath. String a few together and make your own bar crawl. Most of the bars offer food as well, be sure to fit lunch in between all the drinks.

On my most recent visit I stopped in at Sloppy Joe’s bar for lunch and drinks. I was really impressed with the Frozen Rum Runner, and at $8.75 a piece you can certainly live with having a couple of them. One other great thing about this option is that you can add it on to any of the other activities here, just be sure to make it back to the ship on time!

I’ll leave you with one more piece of advice on doing a bar crawl in Key West, keep in mind some of these establishments have web cams. You might be a few drinks in when a friend sends you a screenshot of yourself at the bar!

Golf Cart Rental

Full disclosure here, I have not yet rented a golf cart in Key West. However, next time I am there, it will be what I am doing. It really mixes the ability to see everything on most of the tours above, with being able to see it at your own pace. Need to perfect that Instagram shot? No worries, the tour isn’t taking off without you.

There’s an area of interest that’s not included in the guided tour? No problem, because you just changed the tour. In addition, you’ll be mostly shaded during your ride versus walking or riding a bicycle. I thought about renting one this last visit after our jet ski tour, but I felt like it was going to be rushed so I decided not to. I vouched it would be a must do on my next visit.


No matter what you decide to do, Key West is a great destination. It has that feel of the Caribbean, yet still feels like home a bit (assuming you live in the US). I know I’ve mentioned it a couple times already, but please be sure to take the summer heat and humidity into consideration when making your choice.

Be sure you grab a slice of key lime pie at some point during your visit. Don’t make the mistake I made on my most recent visit, and remember as you are taking the shuttle back to the ship! I was bummed that I forgot to grab a slice, but it just means I’ll have to get back to Key West soon.

Thanks for reading along and I hope my list will give you some ideas in planning your next visit to the island. Do you have any other favorites in Key West that I missed? I would love to hear about them so I can incorporate into a future visit! As always, if you are looking for more of my cruise content you can find it at CruiseLifeMatt.com and on Instagram @CruiseLifeMatt.

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Matt Theriault
Matt Theriaulthttp://cruiselifematt.com
Matt started cruising in 2004 and has since taken over 50 cruises. When he's not on a cruise, you can find him talking about or planning his next one.
PortsBahamas and CaribbeanTop 5 Things to Do in Key West While on a Cruise


  1. Pop into art galleries & various little shops. Key West is so walkable that comfortable shoes will take you anywhere. Fantasy Fest is always a “festive, unique” time to be there. I’ll miss it this year but will be in KW next Wed.

  2. Great article! Some cruises only give a short amount of time in Key West. Twice I’ve been there and the departure time was 1:00 p.m. Most bars and restaurants do not open till 11:00 a.m. That cuts it pretty close to get back to the ship on time. If you want a taste of old Key West and a cocktail, I would suggest the ‘Schooner Wharf ‘ bar on the waterfront. They open very early. Their happy hour starts at 7:00 a.m.!!! A great cocktail to try is there is a ‘Dark and Stormy’.

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