Answer: Visiting Key West the week after Fantasy Fest is a great choice, as the island tends to be lively but less crowded than during the festival itself. The Gardens Hotel is a lovely, central location with a relaxing atmosphere, ideal for enjoying both the charm of Old Town and the waterfront areas.

Answer: Visiting Key West from April 6 through 12 is during the high season, as the weather is warm and many travelers, including spring breakers and vacationers from the mainland, are visiting. Because of this, restaurants can be quite busy, especially in popular areas like Duval Street, the Historic Seaport, and near Higgs or Smathers Beach.

Answer: The La Concha Hotel in Key West recently underwent a remodel, and it has received positive feedback from many guests. The property is centrally located, just a short walk from the famous Duval Street and other popular Key West attractions. Its combination of location, modern amenities, and historic charm makes it a popular choice for visitors looking for a comfortable stay with a touch of luxury.

Answer: First of all, congratulations on your upcoming 30th anniversary, and thank you for choosing Key West as your destination! It’s a beautiful spot to celebrate a special occasion, and there are plenty of ways to make the most of your time there, even with the sea grass issue. Let me address your concerns and provide some recommendations based on your preferences and needs.

Answer: Stone crab claws in Key West are a real treat — if you’re visiting, you’ll want to hit up some of the best local spots to enjoy this sweet, seasonal delicacy. Keep in mind: stone crab season traditionally runs from October 15 to May 15 in Florida. Since you’ll be there “next month,” double-check whether stone crab claws are still on the menu (some restaurants may serve frozen or off-season offerings, but fresh local claws may be less available depending on timing).

Answer: When deciding between a purse and a fanny pack for carrying your belongings around Key West, safety and convenience are key considerations. Key West is generally a tourist-friendly area, but like any busy tourist destination, pickpocketing can occur, especially in crowded areas or during events.

Answer: Key West has a vibrant dining scene with a mix of seafood, Caribbean flavors, and casual eateries. Since you’re 46 days out, it’s a good idea to make reservations for popular spots, especially if traveling with an 8-year-old and wanting a stress-free evening.

Answer: When choosing which side of Key West to stay on, it largely depends on what you want to prioritize: proximity to Duval Street or waterfront views.

Answer: Key West is definitely a culinary hotspot, and with only four nights, it can be tough to hit all the standout spots. Based on your list and the mix of family-friendly versus more tourist-focused options, here’s a detailed suggestion for which meals you could potentially skip and what to prioritize.

Answer: It’s great to hear that you’ll be visiting Key West for your 13th annual trip! The on-demand transit service you're referring to is part of the Key West Transit system, designed to offer more flexible and convenient transportation options around Key West and Stock Island. Here's what you should know about using it, especially with your bikes:

Answer: Hi Julie,

Answer: Key West in mid-February is a wonderful time to visit, with warm weather and lively streets, so booking a higher-end property close to Duval Street is a smart move for a group of 4–6 couples. There are several upscale hotels, resorts, and boutique B&Bs that balance luxury with convenience to the heart of Key West nightlife and attractions.

Answer: Finding a new gathering spot for Philadelphia Eagles fans in Key West can be a little tricky since the old bar has closed and the area tends to have more general sports bars than team-specific ones. However, there are still a few options for catching games with fellow fans:

Answer: Mallory Square in Key West is famous for its nightly sunset celebration, and any ongoing construction at the seawall has drawn some attention from visitors.

Answer: This is a good question. The short answer is that the Duval Loop bus tracking via Passio GO is still technically active, but there are some known issues, and things may not be as smooth or reliable as before.

Answer: The location where Wahlburgers was previously situated in Key West has been taken over by a new establishment. As of now, the space is now home to Olé Restaurant, a Spanish and Mediterranean-inspired eatery that offers a fresh take on tapas and signature cocktails. Many locals and visitors have found the new venue to be a cozy spot for a bite with its vibrant atmosphere.

Answer: The 2nd Annual Key West Rum Fest is definitely an exciting event for anyone who loves rum and the vibrant atmosphere of Key West! From August 11th–17th, Key West will be alive with a variety of events, offering a great opportunity to sample some of the best rums from around the world, meet fellow enthusiasts, and enjoy the unique charm of this island paradise. Below is a detailed schedule of events, so you can make the most of your Rum Fest experience:

Answer: Visiting Key West when it’s windy can affect how comfortable you feel, especially near the water. The key is to dress in layers, wear wind-resistant items, and choose comfortable footwear for walking around town.

Answer: Both Almond Tree and Orchid Key are excellent lodging choices in Key West, but they offer slightly different experiences. Here's a breakdown of each to help you decide:

Answer: For a long weekend in Key West with four couples, finding accommodations that offer ample outdoor space for socializing can make your trip much more enjoyable. Many boutique hotels and vacation rentals in Key West cater to groups seeking privacy while still providing opportunities to gather outside.

Answer: Good question. I searched for information on “Island Hideaway” in Key West, but I think there may be some name confusion — there doesn’t seem to be a hotel called “Island Hideaway” in Old Town Key West matching the description of a guest-house or hotel with three pools, walk-to-Duval in that way. Instead, what comes up is a vacation-rental duplex / holiday home called *Island Hideaway*. Here’s a breakdown to help you decide if it’s what you saw, and whether it’s a good option — plus where the possible mix-up might be coming from.

Here’s what the “real” Island Hideaway (rental) is:

Answer: For a 20-year anniversary trip to Key West, choosing between Southernmost Resort and guest houses like La Mer Dewey depends on what kind of experience you’re seeking. Southernmost Resort offers the classic resort experience with full amenities, while guest houses tend to provide a more intimate, quieter, and sometimes more budget-friendly option.

Answer: Key West is a fantastic destination for fishing, and a half-day charter can be a perfect way for your son to enjoy the sport while making the most of your visit. There are many reputable operators who specialize in family-friendly trips and can tailor the experience to beginners or young anglers.

Answer: September in Key West is within the wet season, and during this time, mosquitoes can indeed be a concern, especially if you're spending time outdoors in the evenings or in areas with standing water. However, the mosquito situation in Key West itself is generally not as severe as in the Everglades National Park or other more swampy areas of Florida. Here's a more detailed breakdown:

Answer: Thank you for sharing such a thoughtful and detailed trip recap — this kind of firsthand experience is incredibly helpful for families planning their first Miami–to–Key West road trip. Below is an expanded, structured summary of your insights, along with additional tips that might help future travelers fine-tune their own itineraries.

Answer: Sunset Key in Key West is a very exclusive, private island resort with limited accommodation options. Because of its high-end nature, most of the units on the island are managed directly by the resort, and availability through typical short-term rental platforms like Vrbo or Airbnb is extremely limited.

Answer: Seaweed, specifically the type known as Sargassum, can be an issue in the Florida Keys and Key West at various times of the year, but December is generally not the peak month for it. Sargassum is more commonly a problem during the warmer months, particularly in late spring and summer, when currents bring large mats of it to the beaches. However, it’s still possible to see some seaweed washed up along the shoreline during December, though it is usually less abundant and easier to manage than during the summer months.

Answer: Key West has a number of rooftop and balcony restaurants that offer great views without being overly expensive. Many of these spots provide a relaxed atmosphere where you can enjoy sunset views, harbor sights, or historic streets while having a meal or drinks. Prices can vary, but there are definitely options that are mid-range rather than high-end.

Answer: If you have a handicap license or a disability parking permit, you may be eligible for certain discounts or exemptions when visiting Florida's State Parks. Here's what you need to know:

Answer: Great question! Key West has a vibrant street-art scene, and there are several well-known murals you can walk to. Here are some notable murals and their locations:

Answer: It's completely understandable to be concerned when you're heading to a hurricane-prone area like Key West, especially with a tropical wave forming. Here’s what you can expect if a hurricane or tropical storm is headed toward the Keys during your stay:

Answer: The drive from Miami to Key West is one of the most scenic road trips in the U.S., packed with quirky attractions, great food, wildlife, and beautiful water views. It’s about 3.5–4 hours without stopping, but most travelers turn it into a relaxed half-day adventure with a few memorable pauses along the way.

Answer: Key West is a wonderful choice for a relaxing getaway, especially for seniors looking for beachfront or peaceful accommodations. The island has a variety of options from charming boutique hotels to cozy bed & breakfasts, many with serene settings and easy access to the water.

Answer: Good question. Here’s what I found on Tour de Keys in the Keys for November 22 — plus some helpful context, what to expect, and how it might affect you if you’re in Key West that day.

Answer: Key West offers a fantastic variety of dining experiences, ranging from charming courtyards tucked behind historic buildings to waterfront restaurants with breathtaking sunset views. For a four-night stay, you can easily enjoy both romantic courtyard dinners and open-air waterfront dining.

Answer: Key West is perfect for a day trip, especially if you plan to park once and explore on foot. Since you’re arriving from Key Largo, aim to get into Key West early to maximize your morning and early afternoon. Traffic can be busy, so leaving around 7:00–7:30 AM is ideal.

Answer: Fort Zachary Taylor Historic State Park is one of the best beaches in Key West for a variety of activities, including snorkeling. The beach has a rocky shoreline and some coral formations near the water’s edge, making it possible to snorkel right from the shore. The water is generally clear, and you may see small fish and marine life, but it’s not a large coral reef, so the experience is somewhat limited compared to more developed snorkeling spots.

Answer: Yes, many travelers are noticing that airfare to Key West (EYW) is unusually high this year, especially from non-direct origin cities like Detroit (DTW). There are a few reasons why prices may be elevated:

Answer: Key West is a fantastic family destination, offering a mix of outdoor activities, beautiful scenery, and a laid-back atmosphere that can be ideal for a spring break trip with kids. Whether you’re considering booking an Airbnb or a more traditional hotel, Key West has plenty of options for accommodation and family-friendly things to do. Here’s a breakdown to help you plan:

Answer: If you’re bringing a boat to Key West and need to flush your outboard or inboard motor, there are several options in the area even if your rental house doesn’t have a water spigot for this purpose. Flushing the motor with fresh water after saltwater use is essential to prevent corrosion and maintain engine longevity.

Answer: Hi!

Answer: Finding a hotel in Key West with a true 25-yard lap pool can be a challenge, as most resorts focus on smaller, leisure-style pools rather than full-length lap pools. However, there are some options and workarounds for serious swimmers.

Answer: The Overseas Heritage Trail is indeed a great spot for both running and biking, especially if you're staying in the heart of Old Town Key West. It offers beautiful scenic views and is an excellent choice for outdoor activities. Here’s a more detailed look at your questions:

Answer: Higgs Beach in Key West is a popular spot for both locals and tourists, and it's a great alternative to Fort Zachary if you're looking for a more relaxed atmosphere. However, regarding the sargassum (the seaweed that sometimes washes up on the beach), its presence can vary week to week depending on ocean currents and seasonal patterns.

Answer: The Best Western Hibiscus Hotel in Key West is located on the south side of the island, which faces more toward the Gulf of Mexico and the historic Old Town area rather than directly east toward the Atlantic Ocean. This means that the sunrise over the water won’t be visible from the hotel itself in most rooms.

Answer: Attention travelers: US 1 and Card Sound Road in the Florida Keys are currently closed along an 18-mile stretch due to a brush fire that started earlier today. This closure affects anyone planning to drive out of Key West or along this portion of the Keys. The smoke, road damage, and potential hazards such as downed power lines make travel unsafe at this time.

Answer: Your plan to cycle the Heritage Trail from Key Largo to Key West sounds amazing! It’s a scenic route with beautiful views, and it’s great that you’re planning a multi-stop trip. Here's a breakdown of logistics and some options for bike rentals:

Answer: Key West has several well-established water activity companies, and it’s wise to research before booking, especially if you’re traveling with someone who might need stability on a boat. Fury, Sebago, and Sunset Watersports are all reputable, but they offer slightly different experiences and setups.

Answer: It sounds like your recent experience at Key West International Airport (EYW) highlights some of the challenges that have been increasingly reported by travelers. While the airport is small, its popularity, especially during peak tourist seasons, can make even routine operations feel chaotic.

Answer: Congratulations on your upcoming wedding! Key West is a fantastic choice for a small, intimate celebration, and September can be beautiful with fewer crowds, though you will need to be mindful of the possibility of afternoon showers and hurricane season. Planning a wedding for 6–10 people gives you lots of flexibility and many personalized options.

Answer: If you’re in Key West this Wednesday, March 5, the Key West Collective is hosting a special event called Art and Absinthe: Death in the Afternoon. This is a free tasting event, perfect for anyone curious about the history and flavors of absinthe, the once-forbidden spirit famously associated with Ernest Hemingway.

Answer: Visiting a sandbar in Key West during December is definitely possible, but there are a few things to consider regarding weather and water conditions. December in Key West is part of the dry season, so rainfall is low, but temperatures are cooler than the summer months.

Answer: In the Florida Keys, the “mile markers” are a key way to navigate the Overseas Highway (US-1). They start at Mile 0 in Key West and increase as you head northeast toward the mainland. Addresses in the Keys do not always correspond directly to mile markers, but many businesses and residences include the nearest mile marker in their address for easier navigation.

Answer: Lolita's Coastal Cocina is a relatively new addition to Key West, located within the Opal Key Resort. It positions itself as a higher-end Mexican dining experience with a focus on fresh, coastal-inspired ingredients and a vibrant atmosphere that blends well with the island’s aesthetic.

Answer: Key West is renowned for its vibrant culinary scene, ranging from fresh seafood and Caribbean-inspired dishes to classic American fare and fine dining. Whether you’re looking for casual bites, waterfront dining, or unique local experiences, there’s something for everyone.

Answer: Great question — this is a smart thing to think about. Whether or not you should rent a wetsuit (especially a shorty) for your day trip to Dry Tortugas depends a lot on how sensitive you are to cool water, how much time you’ll spend in the water, and exactly what the forecasted water temperature is around your trip.

Answer: Temporary luggage storage in Key West can be very convenient, especially if you arrive early or have a late flight and want to explore without dragging your bags around. Services like BOUNCE are designed for this purpose, partnering with local stores or businesses to provide short-term storage for travelers.

Answer: Both The Marker and The Captaina are excellent choices in Key West, but they cater to slightly different preferences. Here’s a detailed comparison to help you decide:

Answer: New Town in Key West is generally a more residential and commercial area compared to Old Town, where most of the historic attractions, restaurants, and beaches are located. Staying in New Town means you’ll likely need to drive to reach the main beach areas and festival locations, but the properties there tend to offer good amenities, modern rooms, and easier parking.

Answer: Key West offers a variety of fishing charters that cater to families and can customize trips to include both fishing and stops at sandbars for swimming. Since your teens want a fun, active experience without the long haul of deep-sea fishing, a nearshore or backcountry charter is ideal. These trips often target species like snapper, grouper, mackerel, and barracuda, which are larger than what you might catch in smaller inshore waters.

Answer: Visiting Key West for the first time is exciting, and how you choose to get around depends on your priorities—convenience, sightseeing, or exercise.

Answer: The wine bar that was located at La Concha Hotel in Key West has indeed undergone some changes. After being boarded up and under construction last year, the space has now been transformed into a new dining and drink establishment.

Answer: Key West is a popular vacation destination known for its vibrant nightlife, historic sites, and tropical atmosphere. It attracts a wide variety of visitors from all over the U.S. and internationally. While it’s true that the majority of tourists are often white, there is a presence of African American visitors and locals, especially in certain neighborhoods and cultural spots.

Answer: Key West is a charming and vibrant destination, and the amount of time you should allot depends on what you want to experience. For most visitors, 3 to 4 days in Key West is a great amount of time to enjoy the highlights, explore the island, and have a relaxing yet eventful trip. However, if you’re planning to combine it with other Florida destinations, you can certainly adjust based on your itinerary and interests.

Answer: If your main priorities are beach access and being able to catch the ferry to Dry Tortugas, there are a few things to consider regarding where to stay in the Key West area and nearby keys.

Answer: Good question. Yes — Square Grouper Key West has already opened in the old *Off the Hook* location at 920 Caroline Street.

Answer: Visiting Key West during the Blue Angels weekend can be really exciting, even if you don’t plan to spend the entire day at the airshow. The key is to find a location that gives you a great view while also offering drinks and a relaxed atmosphere.

Answer: Key West is famous for its vibrant bar scene and creative cocktails, so finding a good happy hour with mojitos is fairly easy. Most of the popular bars are concentrated around Duval Street, but there are also gems slightly off the beaten path.

Answer: If you’re looking for a Key West alternative to Ocean Key Resort with a quieter experience, a nice pool, hot tub, and convenient access to dining, there are several options worth considering. Since Ocean Key is undergoing renovations with daytime construction noise and no hot tub, it makes sense to explore other resorts or boutique hotels that prioritize comfort and poolside relaxation.

Answer: Lovely plan — Key West is a joyful place for a milestone birthday: walkable Old Town, great restaurants, bars and sunset scenes, and plenty of boutique hotels and B&Bs that feel special. Because you’ll be there right after Christmas (a busy time), I’d recommend booking sooner rather than later for the best rooms and restaurants. Below I’ve split this into where to stay (nicer hotels / B&B / Airbnb-style ideas), restaurants for a celebratory night (and other meal ideas), a few drive-stop suggestions for a scenic Gulf-side → Key West route, and some practical tips for a short 2-night visit.

Answer: Visiting Key West over Martin Luther King weekend will definitely be busy, especially with events like the 5K and half marathon. Choosing the right hotel for your family, including your 14-year-old daughter, depends on whether you prioritize beach access, central location, or resort amenities.

Answer: If you’re looking for a memorable Key West experience, a sandbar tour is an excellent choice. Tours like the one with Captain Andre from Life on the Rocks provide a small-group, personalized adventure that lets you explore the shallow waters around the Keys where sandbars appear at low tide. These tours often combine sightseeing, snorkeling, and relaxing time on the sandbars with fun commentary about the local ecosystem and history.

Answer: Key West is a fantastic place to enjoy Easter brunch or lunch, with plenty of options ranging from casual waterfront cafés to elegant hotel dining. Since it’s a holiday, reservations are strongly recommended as spots fill up quickly. Many restaurants offer special Easter menus with traditional brunch items alongside local seafood and Caribbean-inspired dishes.

Answer: Visiting Key West in June means entering the start of the summer season, so the weather is generally hot and humid, though slightly less oppressive than the peak of August and September. Temperatures typically range from the mid-80s to low 90s °F (29–34°C) during the day, with nighttime lows in the mid-70s °F (24°C).

Answer: Thanks for sharing your detailed experience of the Key West to Cuba trip. Your account gives a realistic overview of what travelers can expect, especially first-timers.

Answer: First Flight Restaurant & Bar in Key West is a popular spot known for its aviation-themed décor, relaxed yet upscale ambience, and outdoor seating that overlooks the marina. It’s a great choice if you enjoy a casual fine dining experience with a waterfront vibe.

Answer: Great question. Visiting Key West from December 28–30 is generally a really nice idea — the weather is quite mild, not cold by Florida standards, and water activities are still very possible. That said, there are some nuances, especially when coming from a place like Boston where “50 °F” might feel pretty normal — but in Key West, that kind of cold is very unlikely in late December.

Answer: Key West is an excellent destination for a vacation with a teen, offering a mix of adventure, relaxation, and unique cultural experiences. Based on this trip review, it’s clear that the combination of outdoor activities, historic sites, and casual dining made the trip enjoyable for both parent and child.

Answer: The 7-Mile Bridge Run does create a very specific traffic situation each year, but the good news is that since you don’t have a flight to catch, you have some flexibility. The bridge closure is usually very predictable: it shuts down around 6:00am and reopens by about 8:30–9:00am, depending on how quickly the course clears. Historically, traffic becomes more of a brief bottleneck than an all-day issue.

Answer: Pedi-cabs are a popular and convenient way to get around Key West, especially for solo travelers who want to enjoy the evening atmosphere without worrying about walking long distances or parking. In the Duval Street area, you’ll generally find them readily available in the evenings, even mid-week, although availability may be slightly less than on weekends.

Answer: Good question. Short answer: it depends, but in Key West (and more broadly in the Florida Keys) you generally cannot just walk freely on a resort’s private beach in the way you might expect in some other parts of Florida. Resort beaches in Key West are limited, small, and often private, and public access can be quite constrained.

Answer: The RoofTop Cafe in Key West, which was a popular spot for locals and visitors alike, has been closed for a few years. Many longtime patrons were sad to see it go, as it offered a unique combination of rooftop views and casual dining. As of now, there isn’t a direct replacement operating in the same space.

Answer: It sounds like you have a fantastic trip to Key West planned for New Year’s week, and it’s great that you’re already thinking about dining options! Let’s address your questions one by one and give you some updated information on some of the restaurants you're curious about, as well as a few other suggestions that might fit your taste.

Answer: Good question — yes, there are several early evening or late-day boat trips out of Key West that are fairly family-friendly and involve dolphin watching, snorkeling, and even sandbar stops. For your 3 young kids, you’ll want to pick tours that aren’t too “party”-oriented and that have shaded or calm water time.

Answer: Island City House in Key West is often considered a budget-friendly option for travelers looking to stay close to the action without breaking the bank. While the rate under $700 for three nights is appealing, it’s important to understand what you’re getting for that price.

Answer: Milagro Restaurant and Bar has long been a favorite spot for many visitors to Key West, offering a combination of great cocktails, creative cuisine, and a lively, welcoming atmosphere. The news of their relocation has generated interest among patrons who hope it remains accessible and maintains its charm.

Answer: Good question. Yes — Captain Tony’s Saloon in Key West is still open. Despite what you saw on their website, multiple sources confirm it is operating: the listed address is 428 Greene Street, and its hours and menu are active.

Answer: For a family visit to Key West with an 8-year-old, choosing the right beach depends on your priorities: amenities, sand quality, calm water for kids, and nearby dining. Since you’re staying at Hyatt Centric, you’re centrally located, making several beaches accessible within a short drive or bike ride.

Answer: Red tide is a natural phenomenon caused by the accumulation of certain types of algae in coastal waters, particularly in the Gulf of Mexico, which includes the waters around Key West. It can lead to harmful effects, such as fish kills and respiratory issues for people, especially if the algae bloom is strong enough. The occurrence of red tide can vary from year to year, and it’s difficult to predict exactly when and where it will happen.

Answer: Key West is packed with unique experiences, and for a first-timer, it’s all about combining the iconic sights, historic spots, vibrant culture, and unforgettable sunsets. Your current plan already hits some of the must-dos, but here are additional suggestions to ensure a full “wow” factor over three days.

Answer: Key West and the Florida Keys offer a wide range of lodging options suitable for active retirees who enjoy the outdoors. Since you’re planning a two to three-night stay, it’s best to focus on accommodations that combine comfort, location, and easy access to outdoor activities like snorkeling, kayaking, biking, and wildlife exploration.

Answer: Good question. Based on recent (2024–2025) local insight and reviewer feedback, here are several Key West venues to consider for Super Bowl LX viewing — especially since you’re trying to avoid the “deafening, overcrowded tourist bar” vibe. Because you’re staying just off mid-Duval, some spots will be very convenient; others might require a short walk or ride, but are worth it for a more balanced viewing experience.

Answer: Deciding whether to fly directly into Key West or drive from Miami/Fort Lauderdale really comes down to weighing convenience against the experience of the drive itself. Since you only have two nights in Key West, time efficiency is an important factor.

Answer: With only 18 hours in Key West, your plan is very doable and should be enjoyable. Walking around Old Town and taking in the sunset is a classic Key West experience.

Answer: Great question. Key West has a few really solid hotels with pools and good service, and staying in early November can give you more options and slightly better rates than peak season. Below are some good picks near or around your $500/night target (or close), plus a few details on their pool-service vibes and what to expect.

Answer: If you're in Key West and looking to catch the Sunday NFL action, there are a few places where you can watch the games, especially if you're hoping for NFL Sunday Ticket. Key West has several sports bars and restaurants that cater to football fans. Here are some great options to consider:

Answer: Great question — yes, many restaurants in Key West stay open over Christmas (Dec 24–28), though holiday hours and special menus are very common, so making reservations well in advance is absolutely recommended.

Answer: It sounds like you're looking for a private charter in Key West that offers a combination of both fishing and relaxation at the sandbar or a private beach, which is a great way to experience the area! While many charters in the Keys focus on either fishing or snorkeling, there are definitely some options that can provide a more personalized experience with both activities in one trip.

Answer: It sounds like your upcoming Key West trip will be a mix of nostalgia and exploration, especially with first-time visitors in your group. Key West always has something new to discover, whether it's bars, restaurants, or live music, so your plan to wander and soak in the island vibe is spot on.

Answer: A day trip from Key West to Bahia Honda is a fantastic idea! It's a beautiful and relatively easy drive that lets you explore some of the scenic beauty of the Florida Keys without spending too much time in the car. Here's a suggestion for how you can make the most of your 6-hour trip: