Private Key West Vacation Photo Shoot at Your Resort or Beach
Turn your Key West vacation into memories you can actually keep and be in the pictures too! Instead of spending your vacation searching for the perfect photo location, or trying to get everyone to cooperate for a quick phone snapshot, enjoy your relaxed personalized photo session with a professional photographer who will come to your resort or meet you at the beach, or upgrade to the multi-location shoot.
Whether you are traveling as a couple, bringing the whole family, celebrating an anniversary, enjoying a family vacation or simply want beautiful photographs of your time in Key West, we will create images that will feel natural, genuine and uniquely yours.
This is priced for (1) couple or (1) family unit - For family reunions or large groups ask for the upgrade.
Duration: 45 min
- Free cancellation
- Private tour
Six Passenger Golf Cart Rental in Key West - Downtown
Our 6-passenger golf cart rental offers a fun, private, and convenient way for families and groups to explore Key West together. Instead of splitting up or relying on crowded tours, everyone can ride comfortably in one street-legal cart while discovering the island at their own pace.
With easy navigation through Old Town and quick access to popular spots like Duval Street, Mallory Square, and the Southernmost Point Buoy, it’s one of the most enjoyable and flexible ways to see the island.
Spacious seating, reliable performance, and the freedom to stop wherever you like make this a truly memorable Key West adventure!
Duration: 1–30 days
- Free cancellation
Private Vacation Photoshoot with Photographer in Key West
⭐ Top-Rated Vacation Photoshoots 2025
We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip.
In Key West, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here.
We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results
Duration: 1 hour
- Free cancellation
- Private tour
Key West Ultimate Beach Pass with Parasailing
Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass.
Duration: 8 hours
- Free cancellation
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry.
Your day is spent exploring Key West’s uninhabited mangrove islands in the Key West National Wildlife Refuge. Keep an eye out for dolphins, sea turtles, manta rays and many other wildlife that call the Refuge home. Your captain knows where dolphins are frequently seen and will let you know if he spots any.
Upon reaching the mangrove islands, the schooner anchors and your exploration begins. Your day is divided between guided kayaking tours and guided snorkeling tours. The warm, shallow water is calm, sheltered by the uninhabited mangroves, making kayaking a breeze.
After your tours, come back aboard and wash off with our fresh water rinse, and relax on deck. Choose from plenty of complimentary cold drinks – frosty cold beer, wine, homemade sangria, chilled sodas and filtered water. This is the best of laid-back island living.
Duration: 5 hours
- Free cancellation
Small Group Key West Snorkel Adventure
Experience the ultimate in personalized water adventures with our exclusive snorkeling excursions! Dive into the crystal-clear waters for a full two hours of exploration at not just one, but two incredible underwater destinations. Immerse yourself in the captivating world of vibrant sea life like never before! Please call Lost Reef Adventures 24 hours prior to tour date to confirm your reservation.
Duration: 4 hours
- Free cancellation
Marathon to Key West Private Tour of Florida Keys
Visit the one-and-only island city of KEY WEST!
Enjoy a narrated tour on the way down, and island music on the way back.
HIGHLIGHTS
• See the sights in Key West
• Stay for the Key West sunset
• Plenty of Free Time
• Designated Driver
• Narrated Tour
Do what you want in Key West! We're doing the driving!
Sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more!
Sit back & enjoy the scenery as we drive down to Key West. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide.
See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square
It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.
Duration: 8 hours
- Free cancellation
- Private tour
Key West's Locals' Top Sandbar and Sailing Experience
Join us on Sebago's newest trip, designed to allow guests to experience the waters around Key West as so many locals do, visiting little known, breathtakingly beautiful spots with small groups of friends while enjoying great food and drinks in a relaxed and casual environment. No structured activities. Do as much or as little as you want. After all, you're on vacation!
Step aboard Sebago Cubed, a spacious and luxurious sailing catamaran, for a day of sun, sailing and sangria!
Duration: 5 hours
- Free cancellation
Private Key West Fishing & Sandbar or Snorkel Charter
1 Traveler is equivalent to reserving the entire boat. (Up to 6 Guests)
Explore the vibrant waters of Key West on a fully custom private charter designed for up to 6 guests. Enjoy family-friendly bottom fishing, where all bait and equipment are provided, ensuring a fun-filled fishing experience. We will be targeting grouper, barracuda, yellowtail snapper, mangrove snapper, sharks & much more.
After reeling in your catch, choose between relaxing at a stunning sandbar or go on a reef snorkeling adventure in crystal-clear waters with our expert captain guiding you to the best spots. Dive into this unforgettable adventure that caters to families and ocean lovers alike, complete with all necessary gear for both activities.
Highlights
- Private 4-hour charter for up to 6 guests
- Family-friendly bottom fishing with included bait and equipment
- Choose between a beautiful sandbar experience with lily pad float or snorkeling
- All snorkeling gear provided for your convenience
Duration: 4 hours
- Free cancellation
- Private tour
Dinghy Drinking Tour through Key West Waters
On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to 5. An experienced licensed boat captain who knows the waters will lead your tour. Dinghies can go through narrow tunnels in the mangrove trees that bigger boats cannot get through. Be ready to duck under branches. We will stop at waterfront bars. 2 or 3 stops depending on your preferences. If your group is larger, we will arrange additional boats. You can get in the water to swim or wade at any time. You will see lots of fish and sea creatures. Most of our guests bring beer, water or other beverages along for the tour. We have coolers to keep them chilled.
Duration: 3 hours
- Free cancellation
Key West: 3hr Snorkeling Experience with Unlimited Drinks
Highlights:
Explore the world's 3rd largest coral reef, teaming with life
Receive expert snorkel instruction, with all gear provided
Perfect for beginners and experienced snorkelers
Morning trip includes breakfast and unlimited mimosas
Afternoon trip features unlimited beer, margaritas, wine and mixed drinks
Duration: 3 hours
- Likely to sell out
- Free cancellation
Key West Dolphin Watch and Sunset Sail on Catamaran
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unobstructed view of the surrounding seascape.
We will search for our resident Atlantic Bottlenose Dolphins and then head to the best seat in the house to witness a world-famous Key West sunset. Watch as the sky erupts in a spectacle of color from the peaceful vantage point of the water.
Organic fruit and filtered water will be provided to keep you refreshed, and you're welcome to bring your own adult beverages to toast to a successful day.
Join us for a relaxing and memorable evening that celebrates the serenity of sailing, the wonder of marine life, and the breathtaking beauty of a Key West sunset.
Duration: 3 hours
- Free cancellation
Key West Private Charter: Sandbar and Snorkeling
This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you to create your own adventure.
Connect with Key West's abundant wildlife as you cruise the waters in search of our resident coastal dolphins. From there, we'll head to a secluded sandbar, a pristine shallow-water oasis where you can unwind and enjoy the tranquility.
This tour is ideal for those who prefer to relax and socialize. Spend your time floating, swimming, or simply lounging with a cold beverage in hand. While snorkeling is an option, it is not a guided activity on this trip, making it perfect for guests who are more interested in a leisurely day on the water than a structured snorkel excursion.
We'll provide a snack of fresh, organic fruit from Date & Thyme, and the trip is BYOB so you can bring your favorite drinks.
Duration: 4 hours
- Private tour
Tropical Drift - A Key West Sunset Cruise
Private 2-Hour Key West Sunset Cruise | Luxury Manitou Pontoon | Up to 10 Guests
Leave the crowds behind and experience the magic of a Key West sunset from the water on your own private 2-hour cruise aboard a brand-new Manitou luxury pontoon. Departing from the tranquil Cow Key Channel, you'll enjoy a relaxed and intimate journey through hidden backchannels and open waters — all with a front-row seat to one of nature’s most unforgettable shows.
Cruise in comfort with up to 10 guests, guided by a licensed local captain, and take in stunning views of the sunset-drenched coastline, including iconic sights near Mallory Square — without ever getting caught in the crowd.
Whether you're planning a romantic evening, a family outing, or a fun get-together with friends, this cruise offers the perfect mix of laid-back luxury and scenic beauty.
Reserve your sunset escape now — and experience Key West the way locals love it: peaceful, personal, and absolutely stunning.
Duration: 2 hours
- Free cancellation
- Private tour
Boat Excursion in Florida Keys with Snorkeling Equipment
Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the Lower Keys really well. So there are a few different areas to choose from on where to go and we can decide based on weather, wind, etc. There is the option to bring up to 2 kayaks ($25 rental fee per kayak). Snorkel equipment available (just let us know in advance sizes). The guide would be glad to hop in and point things out just let him know ahead of time. Possibility of seeing dolphins. We love the ocean and have a passion for being on or under the water! Also we are kid friendly!
Duration: 4 hours
- Free cancellation
- Private tour
Deep Sea Fishing-Key West Since 1965-45 FT Cowgirl-Cold AC-4 Hrs
Get ready for an exhilarating adventure on the vibrant waters of Key West with our private deep sea fishing charters. Led by the skilled and experienced Captain, our team is dedicated to making your fishing trip unforgettable.
Target a Diverse Catch: Reel in the fight of a lifetime as you battle magnificent mahi, king mackerel, sailfish, and more. Our knowledgeable captain and mate will guide you to the sharky hotspots and employ various techniques, including trolling and bottom fishing, to maximize your chances of landing a trophy catch.
Personalized for You: We believe in providing personalized service. Whether you're a seasoned angler or a curious first-timer, we'll tailor the experience to your skill level and preferences. Choose from our flexible charter options, with half-day, full-day, and multi-day trips available.
Comfort & Safety First: We offer well-equipped vessels, clean facilities, and essential safety gear for a smooth journey
Duration: 4 hours
- Free cancellation
- Private tour
Key West: Water Sports Adventure includes Jetski, Parasail, Snorkel & Waterpark
A fun full day of water activities and fun. On the do it all adventure you will enjoy 12 different watersport activities including jetskis, parasailing, snorkeling, banana boat rides, grilled lunch, drinks and unlimited draft beer on the ride back in.
Duration: 6 hours
- Free cancellation
Hemingway Tour
You will begin this 65 minute nighttime guided walking tour by meeting your tour guide at Capt. Tony's Saloon outside front doors (428 Greene Street). You will then be taken to several of Ernest Hemingway's haunts around Old Town where he worked and played. You'll hear incredible stories of history and lore about Hemingway and Key West.
Duration: 1 hr 5 min
- Free cancellation
Dolphin Watch, Snorkel, Open Bar & 1 Day Hop-On Hop-Off
This is the best 1 day combo where you will enjoy the water and land in Key West. Get to Hop On Hop off the conch train, one of Florida's most popular attractions, going to Truval Village: Steps away from the Ernest Hemingway Home and Museum, the Key West Lighthouse, the Southernmost Point and Key West Butterfly and Nature Conservatory. Start the day with a Catamaran adventure going Delphine watching and then snorkeling in 1 of the worlds largest reefs. We may even see sea turtle and other exotic fish.
On the return enjoy and open bar that includes well mixed drinks, draft beer, margaritas, rum runners and a great selection of wine & champagne.
As an added benefit join us at the Sails and rails museum to learn our history.
Duration: 1 day
- Free cancellation
Parasailing Experience in Key West
Soar up to 300ft above Key West for stunning panoramic views
Enjoying a thrilling 10-15 minute parasailing experience
Parasail with friends with the double, or triple flight options
Safe and fun for ages 6 and up.
Choose between two departure locations in Key West
Duration: 1 hour
Explore the Waters of Key West
Explore the vibrant & diverse underwater world of the Florida Keys with Salty Paws' Reef Snorkel Trip! Our experienced & knowledgeable crew will take you on a journey to the best snorkeling sites in the area, where you will witness breathtaking views of colorful coral reefs, tropical fish, and other marine life all of which call the reef home.
Our Reef Snorkel Trip is perfect for both beginners & experienced snorkelers. Our crew will provide you with snorkeling gear and give you a safety briefing before entering the water. You'll be amazed at the sights you'll see and the memories you'll make during this once in a lifetime experience.
During the trip, our experienced captains will take you to some of the most stunning locations around the reef where you can snorkel among the vibrant coral formations and observe an incredible range of marine creatures, including colorful fish, sea turtles, and even dolphins. All of which call the reef home.
Duration: 4 hours
- Free cancellation
- Private tour
Key West Private Full-Day Marquesas Keys Eco Charter
The Marquesas Keys offer one of the most remote private boat experiences available from Key West. This full-day charter gives your group time to prioritize snorkeling, beaches, sandbars, paddleboarding, wildlife viewing, photography, or relaxation. Unlike a fixed group tour, the preferred itinerary is tailored to your interests while the captain determines the safest route for the day’s conditions.
Duration: 8 hours
- Free cancellation
- Private tour
Key West Custom Charter: Snorkel, Sandbar Sightseeing
The Experience: Don't miss your chance to experience a luxury charter in the Florida Keys, versatile enough for any on-water activity you can envision. Whether you're interested in snorkeling, light tackle fishing, sandbar hopping, sunset cruises, dolphin watching, sightseeing, trips to the intercostal from key west to miami, we do it all! Fun for the entire family! We also offer poker runs, with our 36 Contender powered by triples give us a whopping 1,050 hp
YOUR day, YOUR way: Probably the best thing about our boat service is we don't do cookie-cutter trips. Every trip is personalized to who and what is important to you. As a bareboat/demise charter, this vessel offers ultimate freedom—the itinerary is entirely up to you. With endless possibilities in the Keys, our seasoned team, in conjunction with the captain you choose, will tailor the journey to your dream day's desires. We'll provide you with a curated list of recommended captains, ensuring a seamless, expert-guided adventure.
Duration: 4 hours
- Free cancellation
- Private tour
38' Private Luxury Sunset Charter w. Music & Drinks, up to 13 ppl
Ready to explore Sunset Charter with drinks and Music? aboard a luxurious private boat charter, accommodating up to 13 guests. Sailing aboard a 38’ private charter a smoother ride with plenty of deck space, and you’ll see 20s of things do from boat can do photography and get a explanation from caption cum guide
Duration: 2–4 hours
- Free cancellation
- Private tour