Answer: Fort Myers, along with many areas on Florida's southwest Gulf Coast, was significantly affected by Hurricane Ian, which hit in September 2022. However, recovery efforts have been ongoing, and many areas have made substantial progress in rebuilding. That said, it’s important to note that some locations may still have lingering effects, especially in terms of infrastructure and certain services.

Answer: Fort Myers Beach in October has generally returned to a relaxed and quieter vibe since the impacts of Hurricane Ian, though some areas are still in recovery and redevelopment. The town has been steadily improving, with many restaurants, shops, and accommodations back in operation, but you’ll notice some areas are still under repair or reconstruction.

Answer: Little Gasparilla Island is a quiet, mostly undeveloped barrier island off the southwest coast of Florida, known for its natural beauty and low-key atmosphere. It is accessible primarily by boat, which helps keep the crowds low and preserves its tranquil vibe.

Answer: For a first-time visit to Florida’s Southwest Gulf Coast with a focus on laid-back beach vibes, shelling, and good seafood, there are several towns that fit your criteria better than Naples, which can feel a bit more urban and busy. Marco Island is a solid choice, but there are a few other smaller towns and barrier islands that might suit your group even more.

Answer: Good question. Short answer: yes, according to recent guest reports, the elevators at Pointe Santo are accessible by wheelchair, with ramps leading up to them — but there are some caveats. Here’s what I found, plus considerations and a few things you may want to double check before your trip.

Answer: If you're looking for art and craft festivals in the Naples area, you're in luck! Southwest Florida is known for its vibrant arts scene, and there are several festivals throughout the year, particularly in the cooler months. While festival dates can vary, here are some popular events that often occur around this time of year or in the coming weeks:

Answer: The Lazy Flamingo is a popular food truck associated with the well-known Lazy Flamingo restaurant on Sanibel Island. It is typically located in the Periwinkle Way area, often in or near a designated parking lot for convenient access. This location is meant to serve visitors looking for a quick, casual bite without entering the main restaurant.

Answer: Both the Compass Hotel and Margaritaville are excellent options, but they offer different experiences depending on what you're looking for. Here's a breakdown of each, plus some thoughts on whether to stay in Naples or Marco Island.

Answer: Marco Island offers several upscale dining options with beautiful water views, perfect for a special night out. Since you’re staying at the JW Marriott and plan to Uber, restaurants within a 15–20 minute drive will be convenient. Memorial Day is a busy holiday, so advance reservations are highly recommended.

Answer: Yes, Fort Myers Beach has several options for catamaran and sailboat excursions that depart directly from the island, so you don’t need to cross over the bridge. These trips vary from daytime sightseeing sails to sunset cruises and even private charters. Most operators focus on small group experiences, snorkeling, and wildlife viewing such as dolphins and manatees.

Answer: If you're looking to rent bikes for riding the Legacy Trail in Sarasota and need the bikes dropped off at the trail, there are several good bike rental options in the area that offer delivery services. Here are a few reputable places to consider:

Answer: Visiting Boca Grande for the first time is exciting, and choosing the right location on the island can make a big difference in convenience and overall experience. The north end of Boca Grande, while quieter and more secluded, does come with trade-offs, especially if you plan to go to the main beach accesses and town frequently.

Answer: Late March on Sanibel Island is typically one of the busiest times of the entire year. This period falls right in the heart of peak season, when weather is warm, humidity is still low, and spring break travelers—families, retirees, and longtime seasonal visitors—are all on the island at once. Historically, accommodations book up months in advance, and beaches, restaurants, and bike paths all see noticeably higher activity.

Answer: Visiting Sanibel Island in late January is a great idea for a quieter, off-season beach experience. However, it’s not safe to assume that all the top hotels have heated pools, as some properties may have outdoor pools that are not heated during the cooler winter months. If swimming is important to you, it’s best to confirm with the hotel directly or check their website for pool heating information.

Answer: Your plan for the return trip from North Captiva Island through Captiva is reasonable and a good way to maximize your day and experience more of the islands. Here’s a detailed breakdown and some suggestions:

Answer: Fort Myers Southwest Florida International Airport (RSW) is relatively quiet compared to major hubs, but it still has a steady flow of travelers, especially on weekends. Late-night Uber or Lyft rides around 11 PM on a Saturday are generally available, though there may be slightly longer wait times than during the day. For a short 15-minute trip, it should be very manageable.

Answer: If you're looking for a hotel in Naples with an indoor pool for the kids in case of bad weather, there are a few options that offer great amenities and should fit your needs. While Naples is known for its beautiful outdoor attractions, including beaches and pools, there are some resorts with indoor pools that would provide a good alternative on rainy days.

Answer: Lely Resort is a well-known master-planned community in Naples, located just a few miles from downtown Naples and the Gulf Coast beaches. It’s a popular area for both seasonal visitors and long-term residents, offering a mix of single-family homes, townhomes, and condos for rent. Renting in Lely Resort provides a comfortable, amenity-rich environment with convenient access to golf, shopping, and dining.

Answer: Thanks for the update! Since you have older kids and are comfortable walking with backpacks, that really opens up your options for getting around North Captiva Island and the surrounding areas.

Answer: Good question. Short answer: yes, Captiva (and Sanibel) can be fairly busy in the couple of weeks before Christmas—but “tons of traffic” and restaurant difficulties are less likely than you might fear, especially compared to peak spring/summer season. That said, things are a bit complicated right now (in late 2023 into 2024) due to ongoing recovery. Here’s a detailed breakdown based on recent reports:

Answer: Naples is a great location for both fishing charters and sunset sails, and staying at the Naples Charter Club Resort gives you convenient access to Naples Harbor, where many operators run daily excursions.

Answer: Sanibel Island has long been a cherished destination, and the impact of Hurricane Ian on the local real estate and rental market has indeed shifted pricing dynamics. While it’s understandable that renovation costs, higher insurance premiums, and HOA fees would influence rental rates, whether $7,000 per week becomes the “new reality” depends on several factors, including location, amenities, and seasonality.

Answer: Fort Myers Beach is a popular destination with a vibrant selection of breakfast, brunch, and happy hour spots, especially around the Times Square area. Here's a breakdown of what you can expect:

Answer: The Naples, Bonita Springs, and Fort Myers area has a vibrant live music scene ranging from intimate bars and lounges to larger concert venues. The offerings vary from jazz and blues to rock, pop, and classical performances. Whether you are looking for casual beachside music or a more formal concert experience, there are options to suit a variety of tastes.

Answer: The Sundial Resort on Sanibel Island has been gradually reopening its facilities following renovations and new construction phases. While the main resort pool is fully open and operational, the pools for the Phase IV and V condo buildings (L through T buildings) have experienced some delays, which has caused conflicting reports online.

Answer: Naples is a wonderful place to spend Christmas, and although it’s not a traditional snowy holiday destination, it offers many special seasonal events, festive decorations, and uniquely Floridian celebrations. The city becomes lively with lights, concerts, shopping events, and waterfront holiday activities.

Answer: Choosing between Island Inn on Sanibel and Tween Waters on Captiva really comes down to what kind of vacation vibe you prefer, especially in August when the heat is intense and having a pool can be a nice respite.

Answer: Staying at South Seas Resort on Marco Island in April gives you a beautiful base, but transportation logistics are important to consider. The resort is relatively self-contained, with beachfront access, pools, restaurants, and some amenities onsite, but for groceries, exploring the island, or visiting nearby attractions, you’ll need a plan.

Answer: For a girls’ trip in the Naples/Marco Island/Ft. Myers area focused on lounging by a pool with food and beverage service, several hotels stand out for their pool scenes, ambiance, and proximity to nightlife or fun areas.

Answer: If you are staying at the Best Western Plus in Fort Myers, there are several nearby food markets and grocery options where you can shop for fresh produce, local goods, and everyday essentials. Fort Myers offers a mix of chain supermarkets and smaller local markets, making it convenient for visitors.

Answer: Captiva and neighboring Sanibel offer several resorts and clubs that provide day passes for pools, which can be perfect for families looking to enjoy a little pool time along with the beaches. While most accommodations are resort-based, some allow non-guests to purchase day passes for their pools and facilities.

Answer: Choosing between Davide and Ciao Bella on Marco Island is indeed subjective, as both offer quality Italian dining but with slightly different atmospheres and styles.

Answer: If you're craving sushi in Sarasota, you're in luck! The city has some excellent options for sushi lovers, whether you're looking for a casual spot or a more upscale dining experience. Since you're staying near Lido Key, here are a few places you can try for great sushi:

Answer: Sarasota and the surrounding Southwest Gulf Coast offer some unique and adventurous activities beyond typical museums and beach outings. Since you’re looking for unusual experiences similar to bungee-type exercises, ocean horseback riding, and e-bike sunset tours, here are several options that could be fun and memorable for you, your daughter, and granddaughter:

Answer: Naples is a fantastic destination for a long weekend over Memorial Day, especially if you enjoy art, music, beaches, and local culture. Staying near downtown gives you easy access to many attractions and activities without needing to drive far.

Answer: This detailed trip report from a first-time visitor to North Captiva Island (NC) provides a comprehensive overview for anyone planning a similar vacation. The experience covered flights, taxis, grocery logistics, accommodations, restaurants, local stores, and boating, highlighting both what worked well and potential considerations for future visitors.

Answer: Turner Beach, located near Blind Pass on Sanibel Island, experienced significant sand displacement and parking lot damage from Hurricane Milton. As of mid-January, local updates indicate that while some sand removal and repair work has been completed, the lot may still be partially restricted. Access conditions can change quickly depending on ongoing maintenance, so it’s advisable to check the City of Sanibel or Sanibel Island official beach access pages for real-time updates just before your visit.

Answer: Great question. I found some credible reports that suggest White Cap Cottages on Sanibel Island did not fully survive Hurricane Ian in their original form.

Answer: If you’re looking for an experience similar to the old Mote Marine and Sarasota Bay Explorers sandbar tours, there are a few options in the Sarasota area, though none are exact replicas. Many local eco-tour companies focus on hands-on marine life experiences, shallow-water exploration, and sandbar trips where guests can see and sometimes interact with marine life in a controlled and safe way.

Answer: Happy hours are still very much a thing on Sanibel Island, though they tend to be more laid-back and focused on the local resort and waterfront dining scene rather than high-energy bar scenes. Most restaurants and bars on the island offer early evening specials, typically between 4:00 PM and 6:30 PM, with discounted drinks and small plates.

Answer: Great question. It’s very reasonable to be thinking carefully about hurricane recovery *and* water-quality issues like red tide before planning a girls’ trip to Siesta Key or Naples in May. Here’s an up-to-date look (as of 2025), plus my suggestions for which area might be “best” for you, given your concerns.

Answer: Naples and North Naples both offer plenty of charm, but they each have their own unique feel and attractions. Whether it's worth driving from North Naples to downtown Naples for an afternoon depends on what you're looking for. Here's a breakdown of what to expect in both areas:

Answer: Several beloved Sanibel Island businesses have recently relocated to the Village Shops on Periwinkle Way. This move comes after these establishments faced significant challenges from flood damage caused by past storms. By moving to higher ground, they aim to protect their operations from future flooding and continue serving both locals and visitors.

Answer: Venice, Florida, and the surrounding Southwest Gulf Coast towns offer a variety of early dining deals and happy hours, especially in April when the season is still popular with snowbirds and tourists. Many restaurants provide discounted appetizers, drinks, or prix-fixe menus before typical dinner hours.

Answer: Staying at the Hilton Marco Island Beach Resort gives you easy access to several casual spots for a simple, light breakfast within walking distance. While the hotel itself offers breakfast options, exploring nearby local cafés can give you a more relaxed, local vibe and lighter fare.

Answer: Great news for visitors and locals on Sanibel and Captiva! Two popular dining spots have recently reopened, giving everyone more options for casual and delicious meals on the islands.

Answer: Spending Christmas Eve and Christmas Day in Naples or Marco Island can be a relaxed and festive experience, though it’s important to plan ahead because many businesses and restaurants operate on limited hours or close entirely on December 25th.

Answer: Great news for guests of the Sundial Resort on Sanibel Island! The West pool is now open and available for guests to enjoy. Along with the main pool, this provides an excellent spot for relaxation and swimming while staying at the resort. If you’ve been waiting for the pools to open, you can now make the most of the West pool during your visit.

Answer: Marco Island has some excellent waterfront happy hour spots, perfect for sunset watching, tropical cocktails, and relaxed island vibes. Whether you prefer something lively, upscale, or casual, the island offers a great mix of choices right on the water.

Answer: Sarasota and the surrounding Gulf Coast area offer some excellent waterfront bars and tiki-style spots perfect for enjoying sunset drinks. Since you have a car, you have flexibility to explore options both in Sarasota and a short drive to Siesta Key or Lido Key for prime sunset views.

Answer: When choosing between the Compass Hotel Margaritaville on Anna Maria Sound and Zota Beach Resort near Bradenton, it’s important to consider the type of experience you’re looking for, as both properties cater to slightly different preferences.

Answer: If you need a hotel in Fort Myers for just one night with an early morning shuttle to Southwest Florida International Airport (RSW), there are several convenient options. Many hotels near the airport cater to travelers with early flights and provide 24-hour or scheduled shuttle service.

Answer: Visiting Sanibel Island for the first time at the end of June can be a wonderful experience, especially with young adults. The island is known for its beautiful beaches, shelling, biking paths, and laid-back atmosphere. Pointe Santo provides a convenient base to explore both the natural beauty and local attractions.

Answer: For a large group of 15 traveling from Punta Gorda to Captiva, you’ll want breakfast spots that can accommodate bigger parties and have a good variety of options. Here are some excellent choices along your route:

Answer: Both the Capri Inn and Margaritaville Beach Hotel in Naples offer convenient stays, but they cater to slightly different preferences and locations, especially if you won’t have a car.

Answer: The area around Estero Beach and Tennis Club has seen quite a bit of development over the past few years, with some beachfront properties undergoing renovations or new construction. Typically, larger projects like pool updates or building additions are done during the off-season or spread out over several months, but this can vary depending on the property owner and contractor schedules.

Answer: Staying at Lido Beach Resort is a great base — St. Armands Circle (lots of restaurants and a short, pleasant walk) is very close, and a short rideshare or taxi will get you to popular fine-dining spots around Siesta Key and downtown Sarasota. Because you’re arriving on Mother’s Day afternoon and staying four nights, I strongly recommend booking reservations early (Mother’s Day fills quickly) and checking each restaurant for special Mother’s Day brunch or prix-fix menus.

Answer: For a group of 13 staying at the JW Marco Island and looking to enjoy shelling and fishing, a private charter boat is an ideal option. Marco Island and the surrounding Ten Thousand Islands offer excellent shallow-water shelling spots, calm waters for kids, and good fishing opportunities for both beginners and experienced anglers.

Answer: The recent demolition of the West Wind Island Resort on Sanibel Island marks a significant change for the community and for visitors who remember it as an iconic lodging option. The resort had been a mainstay on the island for decades, and its removal underscores the lasting impact of Hurricane Ian, which caused widespread destruction along West Gulf Drive.

Answer: Venice, Florida offers some wonderful options for a special Valentine's Day celebration, especially if you want to treat your aunt to a memorable night of great food and experiences. Given your description, a mix of fine dining and a unique activity would be ideal.

Answer: Good question. As of the most recent updates, here’s what is known about the Stickney Point Bridge construction (the “south drawbridge” to Siesta Key) and whether it’s passable for pedestrians — and what to expect if you’re trying to cross from the south side near Avenue A.

Answer: Sarasota is a convenient and enjoyable stopover when driving from northern Florida down to Marco Island. Late November tends to be a quieter time, with pleasant weather and fewer tourists.

Answer: Good question. Here’s a breakdown of current (or recent) information on weekly golf cart rentals for North Captiva Island:

Answer: Marco Island is a great spot for family-friendly dining, offering a mix of relaxed and more upscale options that everyone will enjoy. Here are some great places to try during your stay with your daughter:

Answer: Good question. Short answer: yes, the south end of Fort Myers Beach (on Estero Island) is generally open, but there are some important caveats. Here’s what the latest information shows as of now, and what to expect during your January ‘26 stay.

Answer: Naples offers a variety of casual dining options that cater to all tastes, from seafood to international cuisine. Many restaurants have outdoor seating and relaxed atmospheres, perfect for a two-week stay exploring the local food scene.

Answer: Good question — your concern is totally valid: the Hyatt Regency Sarasota is indeed closing permanently. Here’s the most up-to-date information and what to expect for your stay June 14–21:

Answer: Marco Island is a fantastic destination for a variety of outdoor activities, from fishing to island excursions and relaxing beach experiences. Here’s a breakdown of reputable and highly rated companies for each of your interests:

Answer: Sanibel Island is a wonderful choice for a relaxing, upscale beachfront getaway, especially for couples. The island is known for its shell-filled beaches, calm waters, and laid-back vibe, so the best accommodations tend to be resorts or boutique hotels with private beach access and high-end amenities.

Answer: If you're looking for some old-school Florida restaurants in Naples that serve hearty seafood platters without the upscale prices, there are definitely some great options to consider. While Naples can be a bit on the fancy side, there are still places that give you that laid-back, local vibe with generous portions of fresh seafood. Here are a few recommendations:

Answer: Sanibel Island is a popular destination on Florida’s Southwest Gulf Coast, known for its beaches, wildlife refuges, and relaxed island atmosphere. When planning lodging for a first-time visit, especially with a 19-year-old, the main considerations are location, amenities, and how much of the island is currently open or under repair due to recent construction or storm recovery.

Answer: Hi there,

Answer: Yes — Marco Island (Collier County) has had red tide issues recently, though the situation is improving according to local health officials. Here’s a detailed breakdown of the current and recent red tide conditions, what was happening, and what to watch for: 

Answer: Sanibel’s noseeums (biting midges) have always been part of island life, but many long-time visitors — especially those returning post-Hurricane Ian — have noticed changes. Your timing (mid-November) is actually one of the better periods for managing them, but conditions can vary year to year based on wind, humidity, and rainfall. Below is the clearest, most practical summary of what’s happening recently and what you can expect for a Sanibel return trip.

Answer: Good question. Yes — there used to be pretty bad waits for rental cars at SRQ (Sarasota-Bradenton International Airport), but things have improved somewhat. That said, there are still potential bottlenecks, depending on the time of day and how busy the airport is.

Answer: Sarasota and the surrounding areas, including Lido Key and Longboat Key, have been actively recovering from the recent hurricane season. As of now, most of the major beaches and public spaces have been cleared and are open to visitors, and local businesses have resumed operations. That said, some beach access points or small local establishments may still be undergoing repairs or minor renovations.

Answer: Rainy days in Naples can still offer plenty of enjoyable activities, even if the weather isn’t perfect for outdoor fun. Since you've already explored places like Tin City and The Best of Everything, here are some indoor options to consider for a rainy day:

Answer: The Eight Lakes area in Cape Coral is well-known for its extensive canal system, which provides excellent opportunities for freshwater fishing, including catfish. For anglers targeting catfish specifically, the area generally performs better than the standard residential canals, thanks to deeper waters and larger fish populations.

Answer: Shell Island Beach Club on Sanibel Island is a popular beachfront resort offering a relaxed, tropical getaway on Florida’s Gulf Coast. The property is known for its casual, family-friendly atmosphere and easy access to Sanibel’s renowned beaches.

Answer: Santini Plaza in Fort Myers Beach is primarily a shopping and dining area, and its parking is intended for customers of the businesses there. While some people do park there early in the morning before stores open, this is technically not permitted, and there is a risk of receiving a parking ticket.

Answer: It sounds like you’ve planned a wonderful trip to Southwest Florida, and Naples is a fantastic base for your adventures, especially for exploring the Everglades and the Overseas Highway. Your concern about the beaches is valid, as both St. Pete and Clearwater are known for their iconic, powdery white sands. That said, Naples has some beautiful beaches too, and you’re not sacrificing too much by staying there instead of driving farther for those beaches.

Answer: Visiting Fort Myers in February is perfect for enjoying pleasant weather and waterfront dining. If you’re looking for restaurants with sea or river views but want to avoid the crowds at Fort Myers Beach, there are several excellent options along the Caloosahatchee River, Estero Bay, or on nearby islands.

Answer: Great question. Yes, there has been a lot of progress in Fort Myers Beach since Hurricane Ian (2022), but some parts are still recovering as of mid-2025. Here’s a breakdown of where things stand now, which resorts are open, and some limo/transport options to consider.

Answer: The Kimball Lodge on Sanibel Island is a well-known property, but it's always a good idea to check the current condition of any vacation rental, especially after events like storms or renovations. As of the last updates, Kimball Lodge is still a popular choice for those looking for more space, particularly when compared to smaller hotel rooms or condos.

Answer: Great question — there are several very good private boat or pontoon-style tour options out of Cape Coral (or nearby) that run for 4-6 hours (and even longer) which are well-suited to a family of 6 adults + 2 children. Here are some top picks and what you can expect, plus tips for booking and planning.

Answer: Both the JW Marriott Marco Island and the Hilton Marco Island Beach Resort are excellent beachfront properties, but they offer slightly different experiences depending on your priorities for beach, pool, food, and activities. Here’s a detailed comparison:

Answer: Sanibel Island has largely recovered from the hurricane as of early January 2025. Visitors report that most of the infrastructure, beaches, and accommodations are fully operational, with very few visible signs of recent storm damage.

Answer: For seniors looking to explore Southwest Florida, choosing a base that balances convenience, comfort, and proximity to attractions is key. Naples and Bonita Springs are both excellent options depending on your priorities.

Answer: Hello — great questions. Here’s the most up-to-date info (as of mid-2025) on the status of South Seas Resort on Captiva, especially regarding its dining and what to expect in spring. Then I’ll cover what other restaurant options are nearby on Captiva and Sanibel.

Answer: It’s always a little disappointing when a beloved spot like Duck Donuts closes, but don’t worry, Naples still has some excellent places to satisfy your donut cravings! Here are a few spots where you can find some delicious donuts while visiting the area:

Answer: Good question. Yes — “no-see-ums” (biting midges) are a real thing in Southwest Florida, including Marco Island, and they can be annoying. But there are ways to prepare so they don’t ruin your trip. Here’s a detailed breakdown of what to expect, when they’re most active, and how to minimize their impact.

Answer: Naples on the Southwest Gulf Coast is fantastic for both sunset cruises and shelling excursions. The area offers a mix of calm waters, scenic coastline, and abundant marine life, making it ideal for both relaxing and active experiences.

Answer: Marco Island offers several public beach access points beyond the very busy South Beach, so you can enjoy sand and surf without the huge crowds. Most of the public accesses have parking lots, restrooms, and easy pathways to the beach, though some are smaller and less crowded than others.

Answer: For a stay in Sarasota without a car, choosing a centrally located hotel with shuttle service is key. Downtown Sarasota is the best area for walking access to restaurants, galleries, and some attractions, and several hotels offer airport shuttles as well as optional local shuttles.

Answer: Sanibel Island is known for its laid-back, low-rise vacation rentals and smaller condo complexes rather than large hotels. For a visit in March, which is peak season, it’s best to book early as options fill quickly. You’ll find smaller oceanfront or beachfront condo complexes that cater to a quieter, “old Florida” vibe.

Answer: Great question. Yes — there *are* a number of restaurants on Sanibel (and nearby Captiva) that are typically open on Thanksgiving Day, though options may be more limited than a regular day. Based on recent and historical information, here are some good places to consider, plus tips for making your plans.

Answer: Sanibel Island has been gradually recovering from recent storms and hurricanes, and while the beaches themselves remain beautiful and sandy, the foliage in some areas has taken longer to return to its lush, tropical state. Most of the public beach areas and preserves, like Bowman's Beach and the J.N. "Ding" Darling National Wildlife Refuge, are open and accessible, and many trees and plants have regrown, though some areas may still show signs of damage or slower regrowth.

Answer: If you're looking for a great spot to watch the USA vs. Canada game in Naples, there are several great casual places where you can enjoy the game with good food and drinks. Here are a few recommendations:

Answer: Driving to Anna Maria Island on April 26 from Bradenton will be affected by the Desoto Parade, but it won’t make it impossible to get there. Most of the closures are localized around downtown Bradenton along the parade route.

Answer: Short answer: yes — there is still active redevelopment work connected with the South Seas property, but the resort and much of the island are open to visitors. The resort has re-opened a number of amenities and is marketing a new “Captiva Landing” area that is slated to open in late December 2025, while larger rezoning/permit approvals for the full redevelopment were only finalized in mid-2025 and major hotel/residential construction is expected to be phased in over the next few years.