Answer: Great question! Yes — the Duval Loop in Key West is still operating, but there are a few important updates to know.

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: 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: Hi Lisa,

Answer: Both La Jolla and Kona Kai are excellent options for a base in the Florida Keys, but each has its unique offerings. Since you’re an active couple with a fishing-enthusiastic son, and you want to explore the water, snorkel, and paddle, here’s a breakdown of what each location has to offer, helping you decide the best place to stay for your trip:

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: For tours around Key West, both sandbar trips and visits to Dry Tortugas National Park are popular options, offering very different experiences. Planning ahead is essential, especially for Dry Tortugas, as trips can sell out quickly.

Answer: Islamorada, known as the "Sportfishing Capital of the World," offers numerous charter options for both full-day and half-day fishing trips. If you’re looking to join a shared charter on November 28th, 29th, or 30th, there are several approaches and companies you can consider to find fellow anglers and secure a spot.

Answer: Welcome to the Florida Keys! Staying on 6th Avenue Ocean gives you a fantastic base for exploring the Keys with easy access to beaches, fishing, and local dining. With a week to explore, you can balance relaxation at your home with day trips to some of the Keys’ best attractions.

Answer: Stock Island offers a distinctly different vibe from Key West’s bustling Old Town. While it is close to Key West, it’s more laid-back, less touristy, and has a local, working-island feel. The area is known for marinas, fishing operations, artist studios, and a few standout restaurants like Hogfish Grill, which is popular for its fresh seafood and casual waterfront setting.

Answer: It sounds like you have an exciting trip to Key West planned for August! The Gardens Hotel is a fantastic choice, offering a charming and relaxing atmosphere right in the heart of Old Town Key West. It's a beautiful, boutique hotel with lush gardens and a tranquil vibe, perfect for unwinding after exploring the island.

Answer: Key West is renowned for its vibrant live music scene, ranging from laid-back acoustic performances to full-on jazz, blues, and rock acts. With a week on the island, you’ll have plenty of opportunities to catch both local favorites and traveling acts.

Answer: The Key West Cooking School and Bar is a new addition to Mallory Square, opening in March. As it is very recent, there aren’t many reviews yet, but here’s what you can expect based on the concept and location.

Answer: The Florida Keys are known for their stunning resorts that offer a perfect mix of luxury, relaxation, and beautiful water access. For a big birthday celebration, you'll want a resort that provides not only a great pool and beach access but also top-notch amenities and a special atmosphere. Here are a few top recommendations for resorts in the Keys that would make for an unforgettable experience:

Answer: It sounds like you're looking for a relaxed, upscale sunset sailing experience with drinks and appetizers included. Both the Danger's Wind and Wine sail and the Argo Navis are excellent choices, but there are a few other options in Key West that could offer a comparable or even enhanced experience, depending on your preferences. Here’s a breakdown of your options:

Answer: Driving from Miami to Key West is a beautiful journey along the Overseas Highway (US-1), covering approximately 160 miles. In May, traffic is generally moderate, and the drive usually takes about 4 to 4.5 hours without extended stops. However, if you want to enjoy the scenic views, stop at keys along the way, or take photos, it can easily take 6 hours or more.

Answer: Key West has several beachfront hotels and condos that provide direct access to the water, giving you that classic tropical “stay on the beach” experience. While Key West doesn’t have extensive sandy public beaches like the Gulf Coast, there are resorts and condos with private or semi-private beachfront areas.

Answer: Visiting Key West for the first time is a real treat! With 7 days, you have plenty of time to experience both the iconic spots and some quieter corners of the island. Since you’re traveling with your mother, I’ll focus on options that are enjoyable without requiring too much strenuous activity, while still letting you experience the best of Key West.

Answer: Great idea — snorkeling around John Pennekamp Coral Reef State Park in Key Largo is one of the top experiences in the Keys. There are several highly rated tour companies, depending on what exactly you want: two reef stops, private vs group, more time in the water, etc.

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: Good eye — yes, the Southernmost Point buoy in Key West *is* currently under renovation, and locals have some good updates on what’s happening. Here’s the latest:

Answer: It looks like you had a delicious and varied sampling of sandwiches across the Florida Keys during your five-day trip! Your ranking gives a clear sense of which spots really stood out and which were more underwhelming.

Answer: The Ernest Hemingway Home and Museum in Key West is a popular attraction, and booking a tour is quite simple. Here’s how you can book a tour for the Hemingway House:

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: Key Largo is a more laid-back area compared to Key West, so truly walkable, lively beachfront hotels with nearby restaurants are limited. Most accommodations are either resorts along the Overseas Highway or smaller boutique hotels. While you will find beaches and some evening dining options, a car is usually helpful to fully explore the area.

Answer: It looks like you are correct! If you are checking the cruise ship schedules for Key West, it appears that there are no cruise ships scheduled to dock in Key West from August 15th through 18th, 2025. This could be due to a variety of reasons, such as scheduled maintenance, seasonal changes, or lower traffic during that time of year. However, it's always a good idea to double-check with local port authorities or the cruise lines closer to your travel date to confirm the schedule, as it can sometimes change.

Answer: Using Marathon as a base for exploring the Florida Keys in March 2026 is a practical choice, as it’s centrally located and allows convenient travel north to Key Largo or south to Key West. With a car, you’ll have the flexibility to visit multiple keys during the day and explore attractions at your own pace.

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: Marathon has a relaxed, friendly vibe, and Sunday evenings are perfect for a casual nightcap with some live music. After dinner at Key Fisheries, there are a few great spots where you can enjoy drinks, dessert, and tunes.

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: 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: Good question. Here’s a breakdown of what recent reviews, amenities, and guest feedback say about Creekside Inn in the Florida Keys (Islamorada), along with thoughts on whether your very low rate might raise red flags or be realistic.

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: 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: 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: Choosing between Cheeca Lodge and a two-bedroom condo at Ocean Pointe depends on what type of experience your family values more—resort amenities and beachfront luxury or privacy and convenience for a longer family-style stay.

Answer: Key West is famous for sunsets, nightlife, and ocean views — but it is *not* famous for long, natural, swimmable beaches. Much of the island has rocky shoreline or man-made sea walls, so beachfront hotels with soft sand and good swimming are limited. You aren’t missing anything—true beach resorts in Key West are rare.

Answer: The Florida Keys are famous for their clear waters and coral reefs, and several resorts offer excellent snorkeling directly from the shore. The quality of snorkeling often depends on proximity to coral reefs, seagrass beds, and calm water areas.

Answer: Choosing between Key Largo and Islamorada depends on the type of experience you want in the Florida Keys. Both offer beautiful scenery, access to snorkeling, and opportunities for relaxation, but they have different vibes and amenities.

Answer: Driving the scenic route along US-1 from Key Largo to Key West gives you the opportunity to see several historic lighthouses, though not all are directly accessible by road. Some can be driven up to, while others are visible from certain points along the Overseas Highway.

Answer: For a first-time visit to the Florida Keys with a base in Key Largo, 3 days and 4 nights gives you enough time to experience a mix of sun, water activities, sightseeing, and great local food. Since you don’t mind driving, you can cover several Keys along the way, enjoying a variety of experiences.

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: 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: For groups or multiple families visiting Key West, staying in a single property or resort that accommodates everyone comfortably is ideal. Key West offers a range of options, from historic homes to modern condos and boutique hotels with multiple bedrooms or connected units.

Answer: Good question. I couldn’t find a *publicly available, detailed resort-map* that clearly shows exactly where each timeshare or condo unit is located (by building number) at The Galleon Resort & Marina in Key West. Their official website lists unit types (studios, 1BR, 2BR, and penthouses) but doesn’t provide a labeled schematic or resort-plan map with unit-by-unit placement.

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: 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: 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: Hi!

Answer: Key West Golf Club has definitely changed over the years, and you’re right — recent reviews are mixed. Some players feel it hasn’t kept up with the higher pricing, while others still enjoy it for what it is: a laid-back, tropical, Key West–style golf experience rather than a polished, resort-level course. Below is a detailed breakdown to help you decide whether it’s still worth a round with your son-in-law over New Year’s.

Answer: Yes, the new terminal at Key West International Airport (EYW) is indeed scheduled to open in the near future. The terminal project is part of a larger $100 million renovation and expansion effort aimed at improving passenger experience and airport capacity. The new terminal will have modern amenities, additional space, and enhanced facilities for travelers.

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: When it comes to renting a property in Key West, reliability is key, especially during peak travel seasons. Key West has a mix of local rental agencies and larger national companies, and choosing the right one can make a huge difference in terms of ease of check-in, quality of property, and customer service.

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: The new terminal at Key West International Airport (EYW) serves both arrivals and departures. It was designed to improve the overall passenger experience, streamline check-in, security, and baggage handling, and accommodate increasing traffic.

Answer: The Hemingway Days Festival in Key West, held annually in July, includes a street fair on Duval Street, typically on the Saturday of the festival. This fair celebrates Ernest Hemingway’s life and legacy and is a mix of arts, crafts, food, and live music.

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: Great idea to make the 21st birthday dinner feel special, especially in a place as fun and vibrant as Key West — and since you’ll also have your 19- and 15-year-olds with you, here are some restaurant suggestions and vibes to match.

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: Mid-May is a great time to visit the Florida Keys—warm water, quieter crowds than peak winter, and still before the heavy summer heat. Planning a Mon–Fri itinerary with a Sun arrival works very well, and choosing a car over an RV is wise for most visitors. Parking is extremely limited, especially in Key West, and navigating an RV along US-1 can be stressful rather than relaxing.

Answer: If you're arriving in Key West on a cruise ship and looking to rent bikes for just a few hours, there are several great options available. Most bike rental shops in Key West are flexible with short-term rentals, making it easy for you to rent bikes for around four hours to explore the island. Here are a few options to consider:

Answer: Your December trip from Fort Myers to Key West via Marathon sounds wonderful — it’s a classic Florida Keys drive with plenty of scenic views and things to see along the way. Here’s a detailed guide for your stops, accommodations, dining, and must-see attractions.

Answer: Breeze Airways has recently added new direct flight options to Key West International Airport (EYW), which is great news for travelers looking for more flexibility in planning trips to the Florida Keys.

Answer: Key West has indeed evolved over the decades, shifting from its quirky, offbeat roots to a more commercialized tourist destination. Many travelers looking for that same eccentric, bohemian energy may need to explore lesser-known towns and destinations that retain a local, artistic, and slightly unconventional vibe.

Answer: Key West is famous for its fresh seafood, including lobster and conch, and offers a variety of restaurants ranging from casual to fine dining. For a first-time visit, you’ll want a combination of quality, atmosphere, and local flavor.

Answer: When you arrive in Key West via the Key West Express (from Fort Myers or Marco Island), you’ll dock at the Key West Ferry Terminal, which is about a mile from the heart of Duval Street. Fortunately, there are several convenient ways to reach your Airbnb, depending on your preference for speed, convenience, or cost.

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: There are several convenient ways to get from Key West International Airport (EYW) to either Tranquility Bay Resort or Isla Bella Resort, both of which are located on Big Pine Key. Here's a breakdown of your best options:

Answer: The Key West Bar Card is a convenient option for visitors who plan to enjoy multiple bars in Key West without having to carry cash or pay separately at each location. Here’s what you need to know about obtaining it:

Answer: Thanks for the update! It’s great to hear that The Bali Bar in Key West is welcoming all visitors, even though their website previously suggested it was only for hotel guests. This makes it a fantastic spot for anyone looking to enjoy the Key West atmosphere.

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: 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: 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: Islamorada is known for being more laid-back compared to Key West or Miami, so “party hotels” in the traditional sense are limited. Most resorts cater to couples or families and focus on relaxing, waterfront activities. However, there are a few options that tend to attract a younger crowd looking for a lively atmosphere.

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: Sargassum seaweed is a seasonal issue in the Florida Keys, typically peaking in late spring through summer. Mid-June is often within the window where sargassum can be more noticeable, particularly along Gulf-facing beaches like those on Grassy Key.

Answer: Key West is famous for its fresh seafood, and a classic grouper sandwich is a must-try. Since you're arriving next Thursday, here are some of the top spots known for serving delicious grouper sandwiches, ranging from casual to slightly more refined:

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: 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: Good question! The royal poinciana (Delonix regia), also called the “flame tree,” is indeed planted in Key West and makes for a beautiful tropical photo — but some caveats when it comes to *where* to find them and *when* they bloom.

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: Good question. Unfortunately, Smokin’ Tuna Saloon in Key West is *not currently open* in its original location. According to several sources, the Charles Street spot has closed.

Answer: Key West offers several accessible beaches where you can enjoy snorkelling right from the shore. While the island is better known for boat-based snorkelling trips to coral reefs, there are a few spots where shallow water snorkelling is possible directly from the beach.

Answer: Key Colony Beach and the surrounding Middle Keys have a few great spots for authentic Cuban sandwiches and coffee without needing to drive far. The area is more low-key than Key West, so the best options are small, local cafés or sandwich shops that focus on fresh, flavorful food.

Answer: For a July dive trip in Key Largo, if your main goal is privacy and comfort with a two-room suite, there are a few alternatives to consider that may require a short drive to Rainbow Reef boats but could provide a more relaxing stay than the Courtyard or Marina del Mar.

Answer: Islamorada, in the Florida Keys, is known more for its world-class offshore reefs than for typical sandy beaches with snorkeling right from shore. The coral reefs here are vibrant and offer excellent opportunities to see tropical fish, coral formations, and sometimes even sea turtles. However, because of the steep drop-off and distance of healthy reefs from most beaches, most serious snorkeling is done via boat or guided tours.

Answer: Islamorada has some excellent dining options, and even on a Sunday you can find upscale spots that take reservations. Since Chef Michael’s and Kaiyo are closed that day, here are some alternatives for your first night:

Answer: Conch Republic Days in Key West is one of the island’s signature events, celebrating Key West’s quirky history and independent spirit. It typically draws a large number of visitors, especially when it coincides with Easter week, as in your dates (4/20–4/26). Expect the island to be very lively, crowded, and festive during this period.

Answer: Spending New Year's in the Florida Keys is a wonderful idea, especially for a birthday celebration! Late December is peak season in the Keys, so booking accommodations early is highly recommended. Since you want to avoid Key West for NYE but still be near a beautiful beach with restaurants, consider staying in the Upper or Middle Keys.

Answer: This is a tricky one — I wasn’t able to reliably identify a B&B in Key West that clearly matches *all* of the details you remembered (free bikes, breakfast, happy hour, pool, and Schipperkee dogs). That said, I found a few properties that share *some* of those characteristics, plus some thoughts and follow-up questions — and a few possibilities based on memory and B&B options in Key West.

Answer: If you’re looking for adult-only hotels in Key West that have parking and a pool, here are some highly recommended options, along with key details to help you choose:

Answer: For a first-time trip to the Florida Keys with a large group, Key Largo and Islamorada are both excellent options, especially if you want to stay together in a condo or house with a pool. Both areas offer a more relaxed atmosphere compared to Key West, and they are conveniently located for a day trip to Key West.

Answer: Key West is a fantastic destination for families, especially if you enjoy wildlife and marine life. Here are answers to your questions:

Answer: In Key Largo, finding restaurants or bars that allow swimming directly from their property without purchasing a full day pass can be a bit tricky, as most waterfront locations focus on dining and bar service rather than casual beach or swim access. However, there are a few options and workarounds you might consider.

Answer: Key West is an excellent destination for deep sea fishing, offering a wide variety of fishing charter options to suit all preferences, whether you're a seasoned angler or a beginner. Here are some top-rated fishing charters you might want to consider for your deep sea fishing trip in October:

Answer: It sounds like you're about to have a fantastic trip to Key West! It’s great that your son is excited about a sunset cruise — they’re one of the highlights of Key West. As for your previous experience with Sebago, it’s a popular company, but there are a few other sunset cruise options that might offer a different experience. Here are some recommendations based on local favorites:

Answer: BoatBooker.com is an online platform that connects travelers with private boat captains as well as licensed charter operators. Many users find it convenient for booking private or semi-private experiences, but there are some considerations to keep in mind when comparing it to booking through a traditional licensed charter company.

Answer: Key West is a fantastic destination for snorkeling and half-day excursions, especially in early July when the waters are warm and visibility is generally excellent. There are several options depending on whether you want a relaxed experience near the reef or a more adventurous day on a larger boat.

Answer: If you're looking for unique ways to cook your catch in Key West beyond the usual fried, blackened, or tacos, you're in luck! Several restaurants in Key West offer creative and distinctive preparations for your freshly caught fish. Here are some great options:

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: