Answer: Key Largo offers several family-friendly restaurants that are perfect for children, especially with younger kids like 4 and 1-year-olds. Many of these spots provide casual atmospheres, kid menus, and outdoor seating which is great in February’s mild weather.

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

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: Congratulations on your 30th anniversary! Planning a Florida Keys and Miami trip for June can be exciting, especially for first-timers to Key West. Here’s a detailed approach for your itinerary and suggestions based on your interests.

Answer: Great question. Choosing between Three Waters Resort & Marina in Islamorada and Baker’s Cay Resort in Key Largo really comes down to what “beach” and pool vibe you prefer. Here’s a detailed comparison based on their beaches, pools, and overall feel — plus my take on which might be “better” depending on what you’re looking for.

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: Noseeums, also known as biting midges, are very small insects common in the Florida Keys, particularly in areas like Marathon. They are notorious for leaving multiple itchy bites, often in clusters, and can be quite bothersome for those sensitive to insect bites.

Answer: Key West is a compact island, and staying in Old Town is ideal if your goal is to experience the heart of the city, walk to restaurants, shops, and attractions, and soak in the historic charm. Old Town can be pricier, but there are some options that might fit your requirements if you book early and are flexible on amenities.

Answer: Hi!

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: 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: Driving from Miami to the Florida Keys in a single day is possible, but it’s important to be realistic about the distance, sightseeing stops, and time constraints. The drive to Key West, the southernmost point, is about 160 miles one way, which takes roughly 3.5–4 hours without stops. With sightseeing, meals, and traffic, a full round trip could easily take 10–12 hours or more.

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: Great question. Both are solid Marriott-brand options in Key West, but they offer very different experiences. Here’s a breakdown to help you decide which fits you best as a Platinum member.

Answer: Both Crane Point and Curry Hammock are excellent nature-focused destinations in the Marathon area of the Florida Keys, but they offer different experiences depending on what you are looking for.

Answer: Mid-February is part of the peak winter season in the Florida Keys, including Marathon. This period coincides with the “snowbird” season when many visitors from colder northern states come to Florida to enjoy the warm weather. As a result, the town tends to be noticeably busier than during the summer months, though it is generally less crowded than Key West.

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: Good question. There’s a lot of circulation (especially in forums like Reddit) about Smokin’ Tuna Saloon in Key West relocating — here’s a rundown of what seems to be going on, what’s confirmed, and what’s still unclear:

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: With your timeframe of Friday arrival through Wednesday afternoon departure, spending the first two nights in Fort Lauderdale and then heading to the Florida Keys (likely Key West) from Sunday to Wednesday is feasible for a relaxing, food-and-drinks-focused trip. Since your focus is on unwinding, eating well, enjoying drinks, and lounging by a pool with a great view, you can design a balanced itinerary that mixes some scenic drives with plenty of relaxation.

Answer: Key West has a surprisingly vibrant contemporary art scene, beyond the typical touristy crafts and beach-themed art. While many galleries in Key West do feature souvenir-style work, there are several spaces dedicated to original and innovative contemporary pieces. The Old Town area, particularly around Duval Street and the surrounding side streets, is the hub for art galleries.

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: Visiting Key Largo for the first time with a group of young adults is a fantastic choice! The area offers beautiful beaches, water activities, and great restaurants, all set in a more relaxed environment compared to Miami. Flying into Miami is the most common and convenient option, as it’s only about a 1–1.5 hour drive to Key Largo. You could also consider Fort Lauderdale-Hollywood International Airport, but Miami is generally more convenient for this itinerary.

Answer: Hi!

Answer: La Te Da in Key West is a well-known restaurant and cabaret that offers a charming and upscale dining experience. Yes, you can request outdoor seating here, and many guests enjoy dining on their patio, which provides a relaxed yet elegant atmosphere, perfect for people-watching or enjoying the evening breeze. It’s advisable to make your outdoor seating request when you make a reservation, as it can fill up quickly, especially during peak tourist season.

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: 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 Largo is a great stopover for a few nights on a Miami to Key West trip, especially if you want water activities and a relaxing atmosphere. For late April, the weather is typically warm and sunny, ideal for pool and beach activities.

Answer: Taking a sandbar excursion in Key West, such as the one near Jewfish Key, can be a very enjoyable experience, especially if you’re looking for a mix of relaxation, sightseeing, and unique water experiences. These trips typically combine cruising through the shallow, crystal-clear waters of the Keys, stopping at sandbars to swim, snorkel, or just hang out, and sometimes include additional activities like spotting dolphins or enjoying drinks on the water.

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: For a 2-night stay after Key West, your base choice really depends on how you want to structure your driving and activities. Since you have a car and want to explore snorkel spots, the Turtle Hospital, and John Pennekamp Coral Reef State Park, here are some considerations:

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: Hi!

Answer: Visiting the Florida Keys for the first time in March is a fantastic idea—weather is usually warm, water is clear, and crowds are moderate. Based on your itinerary and questions, here’s a detailed breakdown of recommendations for snorkeling, coffee, and sandwiches.

Answer: If you are staying on Louisa Street in Key West and are looking for walkable grocery options, there are a few convenient choices nearby. Louisa Street is in the Old Town area, which is more residential and historic, so grocery stores are somewhat limited compared to larger commercial areas.

Answer: Great question. Finding an affordable, water-view place in the Florida Keys that’s roughly halfway between Miami and Key West (i.e., in the Upper or Middle Keys) for under $200/night can be a little tricky — but there *are* some solid budget options that come close or might dip under $200 depending on the season and current deals.

Answer: Visiting the Florida Keys for the first time is exciting — it’s a unique blend of laid-back island vibes, beautiful beaches, boating, and incredible seafood. Flying into Miami is a solid choice, as it gives you the option to either spend a night in Miami before heading down the Keys or drive straight to Key Largo (about 1.5–2 hours) to begin your island adventure.

Answer: Key West has long been known as a vibrant LGBTQ+ destination, but the scene has evolved significantly since the 1990s. While it may feel different if you haven’t visited in decades, the gay community is still very present, though there are several factors that have changed the atmosphere.

Answer: Grassy Flats Resort is located in Marathon, right in the heart of the Florida Keys, which gives you several convenient options for watching the Super Bowl locally. While the Keys don’t have huge sports bars like in major cities, there are a few spots that cater to sports fans and typically show NFL games, including the Super Bowl.

Answer: Key West doesn’t have as many “big” birthday freebies as large cities, but there are still several places—restaurants, dessert shops, and occasional excursions—that offer specials if you sign up for reward programs or visit on your birthday. Many of the older promos from years ago (like certain boat tours) no longer run the same offers, but there are still a handful of worthwhile options. Most require joining an email list or rewards app before your trip.

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: Visiting the Florida Keys with a child who has severe cognitive impairments requires careful planning, but it is definitely doable. Safety near water is a primary concern, especially with jetties, docks, and open beaches.

Answer: Key Largo has some excellent dining options for fresh seafood and a more refined menu than the typical tourist bar fare. Since you already have C & C’s planned, here are a few other standout options to consider during your two-day stay:

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: For a fun-loving couple in your mid-50s visiting Key West in February, a half-day sandbar trip can be a perfect mix of relaxation, scenery, and casual socializing. Since you prefer not to charter a private boat or be in a group dominated by families or younger crowds, the key is choosing operators that cater to an adult-oriented crowd and offer a chill, laid-back vibe.

Answer: Both the Bayside Inn and Hampton Inn in Key Largo are solid options, but they cater to slightly different experiences depending on what you want from your stay.

Answer: Key West offers a variety of resorts and boutique hotels that are within walking distance of Duval Street and have either ocean views or attractive pool areas. Since you enjoyed Santa Maria Suites last year, you might appreciate options that blend charm with a central location and scenic views. Traveling in May with two 20-year-olds, you may want a lively atmosphere but also relaxing spaces to unwind.

Answer: Staying at Grassy Flats in Marathon in March gives you access to a number of excellent local restaurants, many of which offer outdoor seating with waterfront views. March is a great time in the Keys for dining outdoors because the weather is warm but not unbearably hot, and the humidity is lower than in summer.

Answer: The Florida Keys offer some excellent spots for beginner-friendly snorkeling right from the beach, which is ideal for those who are not experienced swimmers. Many of these areas are shallow and calm, allowing snorkelers to stay near the bottom and feel more secure.

Answer: Good question. Short answer: the Higgs Beach playground has been a bit up and down, but there is some encouraging news — mixed as it may be.

Answer: Happy New Year! If you’re having second thoughts about Oceans Edge Resort for your Key West trip with your 8-year-old, there are definitely alternatives that are more kid-friendly, have great pools, and offer on-site dining and bars. Key West and the surrounding areas have several resorts that cater well to families and make it easy to enjoy the island without being restricted to downtown Key West.

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: Your plan for the Florida Keys sounds reasonable for a relaxed family trip with teens, especially since you’re prioritizing quality time over packing in every activity. Mid-June is warm and tropical, so finding a resort with good beach access for the kids is ideal. For your two nights in the middle Keys—Marathon or nearby—there are a few oceanfront resorts that combine a tropical feel, beach access, and family-friendly amenities, often close to your budget of around $400/night.

Answer: For a small Australian Labradoodle visiting Key Largo, there are a few dog daycare and boarding options that cater to social, playful dogs. While Key Largo is relatively small, there are reputable facilities both on the island and nearby in the Upper Keys.

Answer: For a romantic anniversary weekend in the Florida Keys, both Isla Bella Resort (in Marathon) and Tranquility Bay Resort (in Marathon) are excellent options, but they cater slightly differently depending on the experience you want.

Answer: Both the Southernmost Guest House (often listed as Southernmost Point / Guest House properties near the Southernmost Point) and the Best Western Hibiscus are solid choices in Old Town Key West — but they offer different vibes. The Guest House leans into a small, historic/quirky, resort-like experience near the very southern tip and beach access, while the Best Western Hibiscus is a dependable, budget-friendly motel in an excellent Old Town location with straightforward amenities (pool, free breakfast, free parking).

Answer: For a week-long Florida Keys trip focused on diving, sightseeing, and a relaxed pace rather than nightlife, limiting your stay to two main hotels is often the most practical approach. This reduces frequent packing and moving while still allowing you to explore multiple parts of the Keys.