Winter Getaway to Southwest Florida

Being from New England, in the winter months all I can think about is warm breezes, beach sand, sun and ocean water—all things you can’t get up north. To get away from our seasonal depression, my husband and I went for a five-day trip to Naples in Southwest Florida.

Naples is a gorgeous town. It is actually pretty large, however the posh area is located in the downtown region.

We went on this trip to warm up and also start to look for a condo to purchase so we can start to live half the year in Florida and half the year in Connecticut.

We took Southwest Airlines to get to the Fort Myers, Florida airport. We rented a car (this is a must if you are flying into the region, because there isn’t an easy way to get around). It took us about 45 minutes to get from the airport to our hotel in Naples.

We first stopped for lunch at a chain I had never heard of before called Jason’s Deli. The food was amazing. They don’t allow food that has dyes or msg or artificial colors and flavors.  I had the Zucchini Grillini sandwich on toasted herb focaccia with roasted zucchini, Muenster cheese, organic spinach, red onions, Roma tomatoes, kalamata olives, and roasted red pepper hummus with a side of fresh fruit. Everything was fresh. The best part is after you have your sandwich you get free soft serve ice cream. If you ever get a chance to go to Jason’s Deli I highly recommend going. They have a variety sandwiches that are healthy, fresh and delicious.

By the time we got to the hotel and got settled in it was 4 p.m. so we decided to check out the downtown region and we drove down Fifth Avenue. This area is very upscale. It felt like we were in Beverly Hills with several high-end stores and financial institutions lining the street.


Because it was nearing sunset we decided to go to the Naples Pier, which I had read was one of the best places to see the sunset. It did not disappoint. Besides being able to view the Gulf of Mexico and the sunset from the Pier you can also go fishing here and there is a public beach. The pier stretches out very far into the water. It was very windy the day we went so we didn’t get to see any wildlife in the water, however others have said this is a good spot to see dolphins. Below are two videos I took at the pier.

After viewing the sunset we drove to Third Street in the downtown district just to check it out. This area is very expensive so we decided not to have dinner here. There are several different upscale restaurants to pick from and they have indoor and outdoor seating. It was nice to just walk around and observe the buildings, the palm trees that were covered in sparkling white lights and fountains with sculptures scattered throughout the area.

Next we went to dinner. I had spent some time researching various places to eat prior to the trip. We generally like to eat at places that are off-the-beaten-track. These places usually have reasonable prices and great food. This night we at at a Tex-Mex eatery called Tacos and Tequila Cantina. It was amazing. They have dozens of different tacos to pick from and they are not your ordinary tacos. For examples, one of the tacos I tried was called the Idaho Taco. It was filled with smashed potatoes, cheddar jack and Cotija cheese, jalapeño cilantro slaw, quest blanco and green tomatillo sauce. If you prefer a meat taco you might like the Backyard Taco, which is filled with barbecue pork, grilled cartelized sweet onions, fried pickles and Maker’s Mark BBQ sauce. If we were visiting longer on this trip we would have gone back for another meal – that’s how good it was.

Day 2

On day two of our trip we started off the day with looking at properties. The main reason for our trip was to look at condos to purchase as a second home. Some of the properties we saw with the agent were amazing. I am still in awe of the communities they have available. One resort community we looked at had everything you could possibly need within the community from restaurants, spa, resort style pools, gym and fitness classes and two golf courses. After being in Naples for five days we realized why so many communities offer these types of amenities – it is because the traffic in the area is insane and it a lot easier if you can just stay in your community versus trekking out into the city.

After looking at potential properties for a few hours we decided to make a visit to Marco Island. We have been to the area before and we absolutely loved Marco Island. We went back during this visit as well. Marco Island is located approximately 15 minutes outside of Naples. It is a lot less busier than Naples, and is filled with waterways, marinas and large white-sanded beaches. We only went to go to the beach during this visit. I had read that Tigertail Beach on Marco Island was a great place to go shell hunting and it did not disappoint. It was a bit of a hike to the beach from the parking lot – about a mile, however it was well worth it. There were tons of amazing shells. We were there on a colder day (it was about 65 degrees out) so there were not a lot of people on the beach. We got to see some amazing wildlife, I found tons of shells (see the pics) and we even caught a very brave man who went out in the cold water to go windsurfing (see the video below).

Pelican Bend Naples FL
Pelican Bend Restaurant. Photo courtesy of Pelican Bend.

It was now dinner time, so we took a short 10 minute drive to Isles of Capri. This area is considered part of Naples, however it is off the beaten track so it isn’t overly crowded like Naples. We went to a dockside seafood restaurant called Pelican Bend. It kind of looks like a dive, however the food was great and the prices were very reasonable. We had two seafood meals, appetizers, soup and salad for under $50. The seafood was fresh and service was very quick.

Day 3

No trip is complete to a southern state without a trip to Waffle House

On the third day of our trip we started off the day with a trip to Waffle House. We always visit a Waffle House when visiting the south – it is a must do. After having some waffles and hash browns it was now time to start exploring again. One of the areas we had looked at the previous day for real estate is a region called Port of the Islands. It is part of Naples, but very much outside of Naples proper. The region is quiet and relaxing. There is a large marina and hotel and the waterway at the marina goes directly to the Gulf of Mexico.

Sign in display at Everglades City Museum showing damage from Hurricane Irma in 2017.

We then decided to drive further south to the last town before hitting the Everglades. This town is called Everglades City. It is literally in the middle of nowhere and is known as a fishing region. I felt like we were driving into a ghost mining town as we entered the “city.” There seemed to be several abandoned homes and businesses. We drove up to a museum called Everglades City Museum so we decided to check it out. While visiting the museum we learned this area was hit very hard by Hurricane Irma in 2017. There were even watermarks within the museum to show how far the water surge came up. The area was hit with 8-10 foot surges. The town is very remote and was apparently a hot spot of activity back in the early 1900s. Today people who are avid fishermen visit the region because it has direct access to the Gulf of Mexico and several small islands. Although there wasn’t much to see when we arrived in town the drive was very pretty. Because there are no other towns in the area all we saw was tropical vegetation and beautiful birds.

We went out to dinner with family that lives in the area on this day of our trip. This is when we really learned how crowded this area is during January. My husband kept saying he felt like we were driving in New York City. A drive that would normally only take 20 minutes took us well over an hour. When we got to the first restaurant we were going to eat at there was an 1 1/2 hour wait so we ended up finding a different place to eat. We went to an Italian Restaurant called Nino’s Thick and Thin in Fort Myers. There was also a wait here – about 40 minutes. The food was reasonably priced and the portions were huge. We both ordered pasta dishes that came in huge bowls. We ended up getting two meals out of it (we saved the leftovers for lunch the next day). It was good, but of course it wasn’t Connecticut Italian food good.

Day 4

On our last full day of vacation we checked out a tourist spot called Tin City in downtown Naples. It is located in Naples Bay and there are several tourist stores where you can get t-shirts and other souvenirs. There were also a few seafood restaurants and you could purchase excursions to take a cruise out through the canals or even out to one of the islands to go shelling and see dolphins.

After this we drove to go to the beach one final time. It wasn’t warm enough to go swimming – the ocean water was around 60 degrees, however the sun was warm enough to enjoy and we went shelling again. On the drive to the beach we drove on Gulf Shore Blvd. which was filled with multi-million dollar mansions. We went to Lowdermilk Beach. There was a very long stretch of white sand here. We walked quite a ways down the beach for about an hour. The water was clear, there were plenty of shells to find and several sections of the beach were empty. It felt good to get some sunshine on our last day here. Below is a video of Lowdermilk Beach in Naples.

On our last night we stayed a hotel closer to the airport in Fort Myers. I was a little hesitant about this hotel at first because I had never heard of the chain, however I have nothing but fabulous things to say about this chain now – it is called Drury Inn & Suites. They are a chain located in the southern states. The hotel was extremely clean and the staff was very friendly. Not only was it reasonably priced, they had several amenities that were included. There was a large pool and hot tub area. In the evening hours from 5:30-7 p.m. guests are given tickets to get up to three free “adult beverages” each. They also put out a large food spread that included a salad bar, two types of soup, nachos bar, hot dogs, baked potatoes, pasta and chicken tenders. We had plans already to go out to dinner so we decided to have some salad before we left.

We decided to have pizza on our last night and went to a large shopping plaza called Gulf Coast Town Center. The restaurant was called Amore Brick Oven Pizza. Based on reviews it was supposed to have New York-Style pizza. It was thin crust and it was decent for pizza that was not from Connecticut – I am a pizza snob having grown up on New Haven pizza.

Day 5

Our trip ended the following morning with a large breakfast that was included with our hotel stay. They had biscuits and gravy, sausage, eggs, potatoes, waffles, donuts, bagels, yogurt, cereal and of course coffee.

After eating we checked out and headed to the airport. When we returned home it was 30 degrees, gloomy, grey and depressing. We may need to look into purchasing that condo sooner rather than later – the seasonal depression is already kicking back into high gear!

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11 responses to “Winter Getaway to Southwest Florida”

    • It is very beautiful and it was nice and warm compared to where I live in Connecticut!

    • You should do it. This next storm that is coming is making me wish I was still visiting down in Florida.

  1. What a great idea to take a trip to get away from the cold… and an even better idea to live in FL half the year! I keep telling my husband we need to move down south becuase I cannot take the cold anymore. Lol!

  2. Everything looks beautiful! With the polar vortex sweeping the country right now, I’m definitely craving some warm weather!

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