After living in Key West for nearly a decade, I’m still not considered a “local”(Im considered a Freshwater Conch), but I do know my way around the place! This little island packs in a lot to do in just a few square miles.
In the years that I have photographed weddings in the Florida Keys & Key West, I’ve often acted as an “unofficial tour guide” for my couples and their friends and family coming here to get married, helping them find cool things to do here.
Let me give it to you straight, Key West is so much more than Duval St. Sure, that can be fun and I’d never begrudge someone grabbing a tasty beverage at Sloppy Joe’s to take in the local scenery.
I’m going to share some Eco-friendly, locally owned businesses that you don’t want to miss when you are in Key West for your wedding. Any of these activities would be great to do with a wedding party or to suggest to guests who are coming to Key West for your wedding and want to have a real “Key West” experience that isn’t bogged down by touristy trends.
Time and technology moves a little slower in Key West. My best advice is to reach out to these companies directly by going old school and picking up the phone.
While some will have online forms to book and ways to reach them via email, people here don’t live their lives on their devices; we’re too busy getting out and enjoying what this island has to offer.
Also, you’ll often get the best advice and rates by calling them rather than an online booking.
You absolutely do not need a car here in Key West! Even if you arrive at an airport on the mainland such as Ft Lauderdale or Miami, you can easily grab a shuttle down to Key West.
Parking is, let me put it bluntly, a real pain here, especially during high tourist season. You can get around just fine on a bike, taking a Taxi or Uber, or taking the Key West Transit bus. I’m a fan of biking! You can get around quickly and easily, there’s plenty of places to park them and it’s just a great way to see the island.
Get your beach cruiser on, and ride like a local! Even if you haven’t been on a bike in years, you’ll have no trouble with a beach cruiser. No gears, just hop on and pedal, and brake by pedaling backward.
I like this company because the bikes have big wide seats, sturdy tires and they only rent bike shop quality beach cruisers that they keep well maintained. Helmets, locks, lights, and baskets are included in your rental fee. They have also been the ONLY shop I have used in 10 years of living here. They are located at:
1110 Truman Ave, Key West FL, 33040. Their phone is 305-294-1073 and email firstname.lastname@example.org
Bike Rental Rates- $12.00-24 hour day / $60.00 per week / $180.00 per month
The backcountry islands in Key West are a natural wonder that you do not want to miss. These lush waterways are filled with calm azure waters, uninhabited islands with mangrove trees, and shallow water zones where you can hang out on a sandbar when the tide is right.
As you can imagine, the backcountry is an amazing place for snorkeling, fishing, or boating and you can see an abundance of wildlife on any adventure you choose.
It never fails to make me smile when I’m out on a boat and a dolphin starts racing along doing jumps and dives. If you have never had a chance to see these majestic jokers in their element, do yourself a favor and book a Dolphin Safari with Captain Gary. He’s a treasure trove of information on dolphins and the marine animals you will see! Tours generally go out just before sunset from the Perry Hotel on nearby Stock Island. You can snorkel right off the boat and you won’t even have to share the view of the sunset as you cruise around looking for pods of dolphins and learn about the other marine life. They offer 3 trips daily and each one is 6 or less people.
Rates depend on season and number of passengers, generally, around $99/adult and private charters are available for $575+. They are located at 7001 Shrimp Road, Stock Island FL 33040. Their phone number is (305) 747-0453 or you can email them at email@example.com. As a bonus there is Free Parking on the left side of the hotel
If you want to disconnect and connect with nature then I highly recommend getting off the island and getting out on the water with this premier watersports operation. No touristy hype aboard, just great trips to beautiful places with knowledgeable captains. You can choose from tours as short as a few hours to a 4 hour trip to the Key West National Wildlife refuge or Snipe Point, which is a huge sandbar with a great beach area. They also have some paddleboard tours and kayaking tours if that is your thing, including a killer night time paddleboard/kayak adventure.
They also have an awesome night LED paddle trip. Here is the info straight from Capt Pawel:
“If you want an immersive and out of this world experience, join us after the sun goes down for our Night Kayaking. The LED lights will light up under the clear bottomed kayak to guide your way and it really feels like you’re in your own personal aquarium. If you prefer the idea of paddleboarding, you can combine with friends so some of you are paddling along as people kayak. We have something for everyone! Our guides know these islands like no one else, and they can guide you through the calm waters of Key West through mangrove tunnels where you will see amazing aquatic life. We know that this experience will be one of the best experiences you have here in Key West because people tell us that every single day”
These tours book up fast because they are privately chartered and have no set time, so book them before you plan to arrive so you are not disappointed.
Tours start at $350 per trip and they can be reached at (305) 304-4800 or via email at firstname.lastname@example.org. They are located at Hurricane Hole Marina, 5130 Overseas Hwy, Key West, FL 33040. Tell Capt. Pawel that I sent you! He always takes care of my couples and friends.
This charter is Key West fun in the sun done right. Rent this spacious 24-foot boat with up to 6 people to go out for a few hours all day. Hang out on sandbars, sun yourself and swim all around the Back country, they will design a cruise based on what you like to do.
Very family-friendly, and you can bring your own food and drink. You may even see a dolphin or two. Get away from the crowds and explore the Keys. Their sunset cruises are popular, so book early!
Half day: 4 hours $600 for 6 guests or $99 per guest from 2-5 people
Full day: 6 hours $800
Sunset: Private charter only for $300 for 2 hours. Up to 6 people
7009 Shrimp Rd
Key West, FL 33040
I’m an avid fisherman, so the places I recommend are all companies that do it right in the Keys. While the seas are generally calm here in Key West, you don’t want to be out in the changing channels with someone who doesn’t know what they are doing and doesn’t understand the tidal flows here. These companies are all reputable, have great safety records and understand and respect the islands. Most provide all that you need for a great day on the water, from licenses to rods and bait, but be sure to check out their sites and ask questions if you have your own gear or needs.
A day with Captain Pepe on the water is a good day. Known for his Tarpon fishing tours on his 27 foot Conch boat, you can charter him for various fishing tours for half, three quarters, or full-day tours. He offers both channel fishing and offshore fishing depending on the time of the year.
My best advice is to talk to him directly and take his advice about the best tour to take, he knows his stuff and won’t steer you wrong. You might even run into me, due to both of us keeping our boats at the same marina. You can reach Pepe at (305) 304-0983 or email him at email@example.com. Garrison Bight Marina is located at 711 Eisenhower Dr, Key West, FL 33040
If you want a great day of fishing offshore with all the amenities, this sportfishing tour is well respected and great for up to 6 people. The boats are tricked out with a V berth for a nap, bathrooms, and they’ll send you home with your catch filleted and bagged.
They can also get you onto a smaller Flats Skiff tour or Light Tackle tour, or you can split a charter with other people who want to go out for the day. If you’ve got the time to spend, you can really make it an adventure and do their Dry Tortugas Overnight Fishing Adventure which is a fishing vacation as far away from civilization as you can get. Prices start at $250 per person for a split charter (with other people not in your group) and private Charters start at $1000 for a 1/2 day. They keep the Premium Time and Reel Deal at A&B Marina, located at 700 Front St, Key West, FL 33040. To book at charter call (305) 432-0046 or email them at firstname.lastname@example.org
If you’re looking to catch some big fish, Double Down offers an excellent sportfishing experience. Run by Captain Brice and Captain Ryan Barr who are brothers and serious anglers. They specialize in hands-on fishing with light tackle and also use live bait to target fish. I honestly think Captain Brice is part sailfish, due to always flying multiple flags (some days 17 others 23) for each one they caught. Capt Brice is a personal friend and many captains strive to be as good as him.
It is best to call them directly to book as they have a lot of repeat customers and they book up quickly. Rates vary by time of the year and the number of people on the boat. Contact Capt Brice at (305)304-2314 or email email@example.com. You can also visit the boat at Historic Charter Boat Row which is located at 1801 N Roosevelt Blvd Slip #14, Key West, FL 33040
If you want to get away from it all and see some pretty scenery while you catch some fish, this backcountry charter with Captain John and Capt Justin will take you where you want to be. You’ll get to see a part of Florida unchanged by time, and there’s no doubt you’ll see a variety of wildlife. The low and stable boats are shaded and can hold up to 4 anglers and include all rods, reels, tackles, lures and bait. Charters can be commissioned for half-day or full-day and range from $600-800. They have 2 boats one being located at A&B Marina Slip #3, and the other at Garrison Bight Marina. You can call them at (305) 587-7669 or email firstname.lastname@example.org
Captain Aaron is your guy if you are looking to do some spearfishing in the Keys. An experienced angler, he’s passionate about fishing and what’s biting. He also offers wrecks and reef fishing, offshore fishing, and low key and relaxing sandbar fishing. Rates vary, but you can go out for as little as 4 hours or all day, and he handles all licensing requirements for all passengers. Aaron has a great location at Hogfish Marina which is 6810 Front St, Key West, Florida. You can get your catch cooked right as you step off the boat. His email is email@example.com, or call him at (305) 842-1048.
Key West is a tiny little island surrounded by some of the prettiest water in the US. If you don’t spend some time out on it while you are here, my feelings are you are missing the heart and soul of this island.
The best part of watersports are that you can find the one that fits your personality, and the vibe you are seeking. From paddle boarding along the channels to kiteboarding, there is something for everyone to do on the water.
And there’s no two ways about it; the best place to watch an iconic Key West sunset is on the water. Don’t get me wrong, Mallory Square is fun a time or two, but to see that sun drop into the ocean from an unobstructed view is something you don’t want to miss.
Sunset Sail Key West
As the name implies, sunsets are their thing. With three vintage charter boats you can pick the one that is right for you and your crew to go out and spend the day on the boat and watch the sun drop, or you can do a shorter 2 hour tour
Unlike other companies, Sunset Sail doesn’t crowd their boats. Bring up to 12 friends and some adult beverages of your choice and take it all in. It’s a really fantastic way to see the islands. They also have several different kinds of swim tours, snorkel tours and proposal sunset sails. They have boats at two different locations, but provide a free shuttle. Reach out to them at (305) 587-4488 or email them at firstname.lastname@example.org
Don’t be fooled by the name, the only danger is that you’ll overindulge in their gourmet wines and cheeses aboard. This Schooner charter is loved by foodies, because they serve the good stuff on their tours! Along with sunset cruises, they also do snorkel tours, kayaking and weddings and special events for up to 30 people. They are highly rated, so book early! This knowledgeable crew will take you out and even if you have never sailed, kayaked or snorkeled they will hook you up. They have an office location on Whitehead Street or you can check out the boats at Margaritaville Marina which is located at 255 Front Street, Key West, FL 33040. Their phone is (305) 304-7999 or you can visit their site here: Email/Contact
If you’re looking for a challenge and something different, then kiteboarding is an absolute blast. This company does it right, taking you out into the pristine waters to clear, flat shallow knee-deep water to show you how it’s done. If you’ve never kiteboardinging before, an instructor will show you the ropes. It’s not as hard as it looks, but it does take some skill learning how to position yourself, and it’s fun as hell to learn. Rates begin at $150. They are also located at Garrison Bight Marina (Park by the Thia Island Restaurant) which is located at 711 Eisenhower Drive, Key West, FL 33040. Call, text or WhatsApp Skot: (305) 432-1355 email@example.com
Family owned company that will take you and your friends out on the water for a fantastic experience. They have both traditional paddleboards that you stand up on and also clear bottom kayaking. One of their signature tours is their after dark LED illuminated glass bottom kayak tour that makes you feel like you are paddling around a vast aquarium. You’ll get to cruise through silent mangrove forests at night, which is just amazing.
Each boat holds two people, but they are happy to accommodate groups as well. Rates are $59.95 per person, and they are located at Marriott Beachside Hotel. firstname.lastname@example.org
A paddleboard and kayak outfit that does lots of fun things on the water including paddleboard yoga in the mangroves and snorkeling. As the name suggests, dogs are welcome! Paddleboarding is great for people of all ages, and if you’ve never done it before you’ll get a quick lesson before you leave the dock. Cruise through the shallow waters in the mangrove creeks and learn about the marine and tropical birds of Key West. If you prefer, you can kayak instead of paddleboarding. The team at Lazy Dog are always willing to help and customize things for you, and make your experience great. They are located at Hurricane Hole Marina which is 5411 Overseas HWY, Key West, FL 33050. You can call them at (305) 295-9898.
This Key West institution has been around for over 40 years, so if you want to do some diving while you are here,they are the people you want to call. Their instructors are super knowledgeable about marine life and are tuned in to the best places to snorkel and dive around the changing coral reefs in the area, and Dive Key West was instrumental in helping Key West become a National Marine Sanctuary. As well as dive trips, they also provide rental, repair and air for divers. Rates depend on time of year and the charter you choose. Stop by their shop at 3128 N. Roosevelt Blvd, Key West, FL 33040. You can also call (305)296-3823 ~ (800)426-0707 or email info@DiveKeyWest.com
If you have time to get out of Key West for a day, then I highly recommend a trip to the Dry Tortugas.
This day trip to the southernmost national park takes about 9 hours, 4 hours of it is spent on the island. You can do a tour of Fort Jefferson and find out some interesting information about the people who were kept there, or if you prefer birding or snorkeling it cannot be beat.
It’s a world away from everything, with a tropical ecosystem that has thousands of species of fish and wildlife you won’t find anywhere else in the US. Bush Key, which is sometimes accessible by a sandbar that connects it, is a rookery to thousands of birds and is open during select times of the year to protect nesting birds.
You can fish, camp, hike, swim and just take it all in and relax at The Dry Tortugas, but don’t expect touristy amenities here. If you’re a lover of nature, the water and history, this place will hit all your buttons.
If you’re considering getting married in Key West, I’d love to talk to you about your plans! I’m happy to talk to you more about what you can expect here, and to help you find the right vendors for your wedding.
Key West is an amazing place to start your life together,and I have no doubt you’re going to love it here if you have never been. I’ve helped hundreds of couples with meaningful, storytelling images, and I’d love to help tell your story. Let’s connect!