The 30 Best City trips in Islamorada, Florida

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Blackwater Fishing Charters is a family-run business located in Islamorada, Florida, offering the best inshore fishing experience in the Florida Keys. Captain Eric Scoble, a fifth-generation Conch and expert backcountry fishing guide, leads the charters with over 25 years of personal experience. With a focus on light tackle fishing and using live bait, Captain Eric ensures a memorable and successful fishing trip for all guests. Whether you choose to explore the calm waters of Florida Bay or venture into the Gulf of Mexico, Blackwater Charters guarantees a day filled with action and beautiful sights. From catching Yellowtail Snapper to Tarpon and Redfish, the possibilities are endless with Captain Eric at the helm. The Gulf Wreck trip and Spanish Mackerel trip are also popular options for those seeking a variety of fish species. With Captain Eric's extensive knowledge of the local waters and dedication to providing a top-notch fishing experience, Blackwater Fishing Charters is the ultimate destination for anglers of all levels. Book your trip today and create lasting memories on the waters of Islamorada!

Topsiders Resort is a charming lodging establishment located at 75500 Overseas Highway in the picturesque town of Islamorada, Florida. This tropical oasis offers guests a relaxing and comfortable stay in the heart of the Florida Keys. The resort features spacious and well-appointed rooms, a sparkling swimming pool, and stunning views of the surrounding landscape. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Topsiders Resort is the perfect destination for your next trip to paradise. With its convenient location and top-notch amenities, this resort is sure to provide a memorable and enjoyable experience for all guests.

Anglers Reef Vacation Rental is a premier real estate and travel agency located at 109 Anglers Way in Islamorada, Florida. Our vacation rentals offer luxurious accommodations in a picturesque setting, perfect for those looking to escape and unwind in the beautiful Florida Keys. From cozy beachfront cottages to spacious waterfront villas, we have a variety of options to suit every traveler's needs. Our friendly and knowledgeable staff is dedicated to providing top-notch service and ensuring a memorable stay for all our guests. Experience the ultimate tropical getaway at Anglers Reef Vacation Rental.

Anchors Away Boat Rentals is a tourist attraction located in Tavernier, Florida, United States. Serving Islamorada, Key Largo, Tavernier, and Marathon, they offer the perfect solution for experiencing all that the Florida Keys has to offer by getting out on the water. Special discounted rates are available for Military, Law Enforcement, and Fire Fighters. To enhance your experience, they offer rental add-ons such as fishing poles and a GoPro Hero 9 with an 8gb SD card that you get to keep. All boats are equipped with brand new Garmin navigation systems to ensure you can easily navigate to your favorite spots.

The Beach House at Tarpon Point is a luxurious oceanfront home located at 77521 Overseas Highway in Islamorada, Florida. This stunning property offers amazing ocean views, a sandy beach, pool, and an observation pier perfect for watching sunrises and sunsets. As a real estate and travel agency, The Beach House provides top-notch amenities and furnishings to ensure a relaxing and memorable vacation experience for all guests. Whether you're looking for a peaceful retreat or a fun-filled getaway, The Beach House at Tarpon Point is the perfect destination for your next trip to the beautiful Florida Keys.

Florida Keys Vacation Rentals Inc. is a premier real estate and travel agency located at 85996 Overseas Highway in Islamorada, Florida. Specializing in vacation rentals in the beautiful Florida Keys, our team is dedicated to helping clients find the perfect property for their getaway. Whether you're looking for a cozy beachfront cottage or a luxurious waterfront villa, we have a wide range of options to choose from. Let us help you make your dream vacation a reality in this tropical paradise. Contact us today to start planning your unforgettable trip to the Florida Keys.

I Can See CLEAR Kayaking is a unique travel agency located at 96 Madeira Road in Islamorada, Florida, United States. Specializing in clear kayaking adventures, they offer a one-of-a-kind experience where guests can explore the crystal-clear waters of the Florida Keys while paddling through mangrove forests and coral reefs. With knowledgeable guides and top-of-the-line equipment, I Can See CLEAR Kayaking provides a safe and unforgettable journey for nature lovers and adventure seekers alike. Join them for a truly immersive and mesmerizing kayaking experience unlike any other.

Gulf Coast Tiki Tours & Yacht Charters is a premier tourist attraction and travel agency located at 450 Harbor Court in Fort Myers Beach, Florida, United States. Captain Tracy Newsam, with over 40 years of experience and a USCG 100 Ton Masters License, will take you on a memorable journey through the waters of Southwest Florida. Explore iconic maritime sites such as the Sanibel Lighthouse, Estero Bay, Mound Key, and Lover's Key while enjoying the refreshing sea breeze on one of our daily tours for up to six people. Witness the breathtaking Southwest Florida sunsets from the water on our evening sunset tours departing from our private marina.

Allergic to Land Charters is a travel agency located at 84371 Overseas Highway in Islamorada, Florida, United States. Led by Captain Sue DuBon, a seasoned mariner with over 40 years of experience, this agency offers exclusive aquatic adventures in the heart of the Florida Keys. Whether you're interested in snorkeling at vibrant coral reefs, enjoying serene sunset cruises, or exploring eco-friendly tours, Allergic to Land Charters promises unforgettable experiences on the water. With a spacious 22′ Twin Vee Catamaran, Captain Sue provides personalized tours tailored to your interests, ensuring a memorable journey every time. From snorkeling adventures to eco-tours and private excursions, each trip is designed to showcase the natural beauty of the Florida Keys. With over 300 5-star reviews, guests rave about the incredible experiences they've had with Captain Sue and her team. Whether you're a family looking for a fun day out or an enthusiast eager to explore the sea, Allergic to Land Charters offers the perfect adventure for everyone. Book your tour today and discover the wonders of the Florida Keys with Captain Sue DuBon at the helm.

Wild Dolphin Tours is a travel agency located at 80001 Overseas Highway in Islamorada, Florida, offering a variety of boat tours for your enjoyment. Take advantage of our SPRING SALE PRICING and choose from options such as Islamorada Sandbar, Snorkel, Eco Tours, Sightseeing Tours, and more. We also offer Go Pro Camera & Wet Suit Rentals for your convenience. Our Large Group Boat Charter can accommodate 7 to 12 passengers on our 2 boats, providing a more intimate experience compared to larger boats. Explore the beautiful coral reefs of Islamorada and spot tropical fish like angelfish, damselfish, and parrot fish during our Snorkel & Sandbar Charters. Depending on sea conditions, we may visit Alligator Lighthouse, Cheeca Rocks, or Hen & Chickens for snorkeling.

Island Adventures is a premier travel agency located at 80500 Overseas Highway in Islamorada, Florida. Specializing in creating unforgettable island getaways, our dedicated team of travel experts can help you plan the perfect vacation to tropical destinations around the world. From luxurious beach resorts to thrilling outdoor excursions, Island Adventures offers a wide range of travel options to suit every traveler's preferences. Let us help you turn your dream island getaway into a reality. Book your next adventure with Island Adventures today!

Easy Keys Charters is a premier private charter service located at 80460 Overseas Highway in Islamorada, Florida. As a top travel agency in the area, we specialize in providing unforgettable experiences on the water. Whether you're looking to go fishing, snorkeling, or simply enjoy a relaxing cruise, our experienced team is here to make your trip a memorable one. Book your next adventure with Easy Keys Charters online or give us a call at (305) 509-3075.

Happy Cat Snorkel Boat is a travel agency located at 77522 Overseas Highway in Islamorada, Florida. If you're looking for the best snorkeling experience in the Florida Keys, look no further than Robbie's Marina. Come aboard the Blue Heaven with Sundance Watersports for an unforgettable adventure you'll cherish for a lifetime. With two daily snorkel excursions and sunset cruises available, there's something for everyone to enjoy. During your two and a half-hour snorkel trip, you'll have plenty of time to swim with local marine life and explore the diverse underwater ecosystem. Gear rentals are available for your convenience, and the boat is equipped with outdoor showers and a full-sized bathroom/changing room. Whether you're planning a private party, corporate retreat, or wedding party, Happy Cat Snorkel Boat can accommodate your needs.

Blu Dog Charters is a travel agency located at 96 Madeira Road in Islamorada, Florida, United States. Specializing in private charters, they offer a variety of tours including snorkeling, sandbar trips, sunsets, BBQ excursions, sightseeing, lobster hunting, fishing, eco tours, and bar hopping adventures. Captain Steve, a seasoned mariner with experience in the United States Coast Guard and Merchant Marines, leads the trips and is known for his love of the ocean and bad jokes. The newest addition to their fleet, Serenity Blu, is now available for bookings.

Lightly Salted Charters is a top-quality travel agency located at 80500 Overseas Highway in Islamorada, Florida. Embark on the Ultimate Florida Keys Adventure on our 2015, 26′ Twin Vee with Captain Zander. From Flats to Offshore Fishing, Snorkeling Tours, Sandbar Getaways & Mesmerizing Sunsets, we offer fully custom trips for every angler. Experience the magic of sunset tours, snorkeling, sandbar & sunset tours, and fishing all in one unforgettable journey. Our all-inclusive Islamorada sandbar tour takes you to the world-famous Islamorada Sandbar for an unforgettable vacation. With our expert snorkel guide, enjoy 5-star private snorkeling tours through the fabulous coral reefs. Our boat can accommodate a maximum of six passengers, but we can add more boats to accommodate larger groups. Book a trip with Lightly Salted Charters and create memories that will last a lifetime. Schedule your private charter boat tour with us today at (305)205-3500.

Skins and Fins Charters is a premier tourist attraction and travel agency located at 81924 Overseas Highway in Islamorada, Florida. Specializing in fishing charters and guides in the Florida Keys, Skins and Fins offers a unique experience for anglers of all levels. Captain Ted Benbow, a skilled fisherman and Florida Keys native, has over 20 years of experience fishing the waters of Key Largo, Islamorada, Marathon, and the Everglades. With a focus on families and trips with kids, Captain Ted provides stress-free instructions and tips for both novice and experienced anglers. Targeting a variety of species including tarpon, redfish, snook, shark, and bonefish, guests are guaranteed an enjoyable and fun day on the water. Father and son fishing team, Captain Donnie, is a second-generation captain with a lifelong passion for fishing. With over ten years of experience as a licensed captain, Captain Donnie offers a unique and educational fishing experience for guests of all ages. Whether you're looking for your first catch or a dream fishing adventure, Captain Donnie will go above and beyond to ensure a memorable experience on the water.

Easy Livin Charter is a renowned travel agency located at 81576 Overseas Highway in Islamorada, Florida, United States. Led by the world famous Captain Augie, who is a local legend in the community, Easy Livin Charter offers custom boat tours that are sure to create lasting memories for all who embark on them. With over two decades of experience in offshore fishing and a deep knowledge of the area, Captain Augie is more than just a tour guide - he is a source of fun and entertainment for all guests. His sense of humor and larger than life personality are guaranteed to put a smile on your face as you explore the beautiful waters of Islamorada.

Pirates For Hire Charters is a travel agency located at 81576 Overseas Highway in Islamorada, Florida. Captain Ron Brack, a third generation professional fisherman, offers Back Country Fishing Charters in the Fabulous Florida Keys, Florida Bay, and Everglades. Choose from full days, half days, night fishing, Ecotours, and Sunset tours, targeting a variety of fish including Tarpon, Snook, Trout, Redfish, Permit, and Spanish Mackerel. To book your trip, a deposit is required to reserve your date. Payment can be made with Visa, Master Card, or American Express. Cancellations must be made at least 48 hours in advance to receive a refund. Captain Ron's vessel, a 247 Sportsman Masters bay boat, is clean and equipped with a 250 four stroke Yamaha engine, Garmin GPS/Fishfinder, JL Audio sound system, Standard Horizon VHF, and more. The boat can accommodate up to four people comfortably.

Family Fun Boat Tours is a premier travel agency located at 85920 Overseas Highway in Islamorada, Florida. We specialize in providing unforgettable boat tours that are perfect for families looking to explore the beautiful waters of Florida. Our experienced guides will take you on a thrilling adventure where you can enjoy snorkeling, fishing, and wildlife watching. Whether you are looking for a relaxing day on the water or an exciting excursion, Family Fun Boat Tours has something for everyone. Book your tour today and create lasting memories with your loved ones.

Key Largo Adventures is a top-rated travel agency located at 85501 Overseas Highway in Islamorada, Florida. Offering Multi-Activity Charters to the Sandbar, guests can enjoy snorkeling at the reef, stand-up paddle boarding at the Islamorada Sandbar, relaxing on floats, and dancing to bluetooth stereo. Visitors can bring their own lunch, snacks, and drinks or upgrade to a boat with a BBQ grill. Customize your Key Largo Adventure boat tour with amenities such as snorkeling, fishing, and exploring the flats. Full-day, half-day, and customized tours are available for an all-inclusive price. Captain Charlie Filpes and his crew provide five-star service aboard the TIKI TIKI, a 25-foot open fisherman. Guests can expect a fun-filled day on the water with paddle boarding, boat trips, snorkeling, and more. Customers rave about their experiences with Key Largo Adventures, praising Captain Charlie for his knowledge, service, and attention to detail. Don't miss out on the opportunity to book your own private, all-inclusive adventure with Key Largo Adventures in the beautiful Florida Keys.

Solfinis Sunset Cruise is a premier travel agency located at 84001 Overseas Highway in Islamorada, Florida. Specializing in unforgettable sunset cruises, we offer a luxurious and relaxing experience on the beautiful waters of the Florida Keys. Our expert staff will ensure that every detail of your cruise is perfect, from the stunning views to the delicious cocktails served on board. Whether you're looking for a romantic evening with your loved one or a fun outing with friends, Solfinis Sunset Cruise is the perfect choice for a memorable experience on the water. Book your cruise today and prepare for an unforgettable journey into the sunset.

Blackbeard Private Charters is a premier travel agency located at 85920 Overseas Highway in Islamorada, Florida. Specializing in private custom boat charters, Blackbeard Charters offers a unique opportunity to experience the Florida Keys like a local. Whether you're looking to relax at the Islamorada Sandbar or explore the vibrant reefs in the upper Keys, our experienced team is dedicated to providing you with the trip of a lifetime. Swim among tropical fish, soak up the sun, and create unforgettable memories with Blackbeard Private Charters.

Florida Keys Dive Center, located at 84001 Overseas Highway in Islamorada, Florida, is a premier ocean adventure paradise. As part of the Scuba Town USA family, we offer a wide range of activities for the whole family, including scuba diving charters, scuba courses, snorkeling, spearfishing, shark encounters, and more. Our experienced and friendly staff go above and beyond to ensure that your vacation in the Keys is unforgettable. With amazing dive sites and top-notch service, Florida Keys Dive Center is a favorite among visitors. Our team, led by Captain Allison and dive guide Kyle, provides a safe and enjoyable diving experience. Whether you're a beginner or an experienced diver, our staff will make sure you have a fantastic time exploring the underwater world.

Casa Morada Tours is a premier travel agency located in Islamorada, Florida. Situated at 136 Madeira Road, this institution specializes in creating unforgettable travel experiences for its clients. From arranging luxurious accommodations to organizing exciting excursions, Casa Morada Tours is dedicated to providing top-notch service and ensuring that every trip is tailored to meet the unique needs and preferences of each traveler. Whether you're seeking a relaxing beach getaway or an adventurous outdoor expedition, Casa Morada Tours has the expertise and resources to make your dream vacation a reality. Experience the beauty and charm of Islamorada and beyond with Casa Morada Tours as your trusted travel partner.

Got Fishues is a premier travel agency located in Islamorada, Florida, United States. Specializing in fishing excursions, our experienced team is dedicated to providing unforgettable experiences for anglers of all levels. Whether you are a seasoned pro looking for the ultimate challenge or a beginner wanting to learn the ropes, we have the perfect trip for you. Situated at 84001 Overseas Highway, our convenient location makes it easy to access some of the best fishing spots in the area. Let Got Fishues help you plan your next fishing adventure and reel in the big one!

True Island Adventures is a premier travel agency located in the heart of Islamorada, Florida. Our team of experienced professionals is dedicated to providing unforgettable experiences for those seeking the ultimate island adventure. Whether you're looking to explore the crystal-clear waters of the Florida Keys, encounter exotic wildlife, or simply relax on pristine beaches, True Island Adventures has you covered. With a wide range of customizable tour packages and expert guides, we ensure that every trip is tailored to your individual preferences and interests. Come and discover the true beauty of the islands with True Island Adventures.

Dean Rabb Expeditions, LLC is a premier travel agency located in Islamorada, Florida. Situated at 85920 Overseas Highway, this institution offers unforgettable expeditions and adventures for all travel enthusiasts. With a focus on providing unique and personalized experiences, Dean Rabb Expeditions, LLC is dedicated to creating memories that will last a lifetime. Whether you're looking to explore the beautiful landscapes of Florida or embark on a thrilling adventure abroad, this travel agency has got you covered. Book your next expedition with Dean Rabb Expeditions, LLC and get ready to embark on the journey of a lifetime.

Sand Hopper Adventure Tours LLC is a premier adventure tour company located at 76777 Overseas Highway in Islamorada, Florida. We offer a variety of exciting experiences for the whole family, including Florida Keys family fishing, visits to the Islamorada sandbar, snorkeling at the Alligator Reef Lighthouse, boat tours, custom tours, and more! Book your private charter today with Sand Hopper Adventures and experience the beauty of Islamorada and Key Largo in Florida. Contact Captain Rob directly for an immediate response and start planning your unforgettable adventure on the water.

Bluewater Adventure is a premier institution located at 81576 Overseas Highway in Islamorada, Florida, United States. Specializing in boat rentals, sandbar trips, and sunset tours, Bluewater Adventure offers a luxurious and pampering experience for all guests. Step aboard your chartered vessel and enjoy the freedom to bring your favorite food and beverages on board. With amenities such as a bar area and Bluetooth connectivity, you can set the soundtrack for your adventure and relax while cruising along the azure waters. Whether you prefer lively beats or tranquil melodies, the music is yours to control, creating the perfect ambiance for your voyage. Visit Bluewater Adventure at Shelter Cove Marina in Hilton Head Island, SC for an unforgettable experience on the water.

Captain Perry is a renowned fishing institution located at 79851 Overseas Highway in Islamorada, Florida, United States. The institution is run by Captain Perry Scuderi, who has been fishing the backcountry and flats of the Florida Keys since 1977. With 25 years of experience as a professional guide, Captain Perry is dedicated to catching you the fish of a lifetime. Whether you are a first-timer or an expert angler, Captain Perry welcomes all to experience the beauty of the fish and backcountry in the Florida Keys. Fishing in the Everglades National Park, known for its abundant marine life, you may encounter various marine animals such as Porpoise, Manatee, Sea Turtle, Shark, and native birds.