How to Spend a Week in Naples, Florida | Travel Guide

January 4, 2017

Sunset in Naples, Florida image.

My family has been vacationing in Naples for as long as I can remember. I can only wish that I was referring to Naples, Italy. Alas, it is merely Naples, Florida (still amazing, I know, don’t hate me for making that comment). Nonetheless, it will forever remain one of my favorite spots to visit. Everything is slower here. The pace of life slows down, the time passing seems to wind down, and even the drivers slow it way down (there are a lot of elderly people, so you must also learn patience). This post is an in-depth guide of how to spend a week in Naples, Florida.

WHERE TO EAT when you spend a week in naples, florida:

To save money for more activities and better dinners, we typically make a big Publix (grocery store) run to stock up on some food. We get items for breakfast and lunch and typically eat those meals at the condo. If we don’t have a “big” activity planned, we’re usually at the pool or beach anyways. We pack a picnic and take that with us. This is definitely a more cost-effective option.

Coconut Jack’s – This is one of my favorite restaurants. It’s a bit north in Bonita Springs but so delicious. Get a seat on the patio and gaze at the natural setting on the waterfront. My personal recommendation is to start with the ceviche to share and then load up on the grouper sandwich.

Doc’s Beach House – Located directly on Bonita Beach, this is a great, affordable dinner spot to watch the sunset. Parking nearby can be a bit of a nightmare since so many people come to this spot to watch the sunset, so I recommend taking advantage of Doc’s valet parking. A window seat will give you the best view, but this place starts to get crowded about an hour before the sun goes down. Did I mention this place has some of the best pizza in town?  Once you finish your meal, head downstairs and outside. If you care to grab a beer to enhance your sunset viewing pleasure, there is a walk-up window connected to the building where you can buy one. Then you can wander over to the beach and try to snag a spot at one of the tables or stand/sit on the sand. Make sure you look out for the Green Flash!

Visit Doc's when you spend a week in Naples, Florida image.

Sunset in Naples, Florida image.
View from Doc’s onto the beach.

Sunset in Naples, Florida image.

MASA – This restaurant is located in the Mercato. If you choose to have a slightly earlier dinner, you can take advantage of a great happy hour here, which is daily from 3-6pm. Select appetizers and entrees are $6 and select margaritas are $5. I ordered the Margarita De Diabolita (regular price – $12) and it was hands-down one of the best – if not the best – margarita I’ve ever had. I highly recommend this if you like a little spice! Tyler ordered the Cucumber Margarita which he vowed was equally as delicious. The food was fairly average for Mexican. So if you plan to dine somewhere else in the Mercato, I’d at least come early to get a pre-dinner margarita here!

The Village Pub – After enjoying The Village Shops on Venetian Bay, you’ll want to grab another waterfront meal. The Mahi tacos are amazing! For a fun rooftop patio atmosphere, walk over to Bayside Seafood Grill and Bar for an after-dinner drink. It’s another great spot to watch the sunset from.

Rooftop bar in Naples, Florida image.

What to Do when you spend a week in naples, florida:

Everglades Airboat Ride – The drive down to Everglades City is worthwhile, especially to take an airboat ride. We took the Everglades City Airboat Tour and it was great! This one has some of the best reviews on travel websites and is also the only airboat company with two-way communication. The airboat ride itself was SO FUN and well worth it. You’re on the water for about an hour cruising through the mangrove jungle. All of the airboat company drivers communicate the entire time to make sure no one is going to cross paths. You fly down the windy waterways and don’t know if you should smile or scream.

Alligator Viewing – You’ll see countless alligators on the side of the road as you drive the roads in the everglades. However, there are a couple spots that are especially great. Head to HP Williams Roadside Park. There is a viewing boardwalk with plenty of wild alligators in the water below. Some are massive! It’s a cool way to see these giant beasts from a safe distance.

Alligator in Naples, Florida image.

Art Festivals – Throughout the year there are a variety of art festivals in the area. Local and national artists come and display their funky – typically Florida-esque – art for all to enjoy. If you’re going to spend a week in Naples, Florida you should at least bring home some items to prove it. Now that I have my own place to decorate, I now understand the obsession with some good wall pieces! My family is obsessed with artist Kelly Tracht. She has colorful and creative pieces that scream Florida. I was able to meet her at the Southwest Florida Art Festival and slightly fan-girled as Tyler and I bought a couple of her prints. If you think these are cute, check out her Etsy page or look up when she will be attending another art fest. So many of these artists are SO talented – and how cool you get to meet them?

Kelly Tracht artwork image.

Naples Princess Sunset Cruise – If you’re like me, you’re obsessed with HGTV and imagining a future dream home (that would require millions of dollars you may not have). I love going on drives to marvel at big houses – their architecture, their landscape – and imagining the people who live in them and what their lives are like. It’s my ideal fantasyland. Therefore, this cruise was perfect for us! You drive past enormous mansions while enjoying some drinks. You make your way in and out of the canals until you reach a passage into the ocean. I recommend getting food before or after at Tin City.

Princess Cruise image.

Sunset on Princess Cruise image.

The Beach. If you spend a week in Naples, Florida, there is one necessary item you must do. Hello! The beach! There are a bunch of great beaches in this area: Vanderbilt Beach, Barefoot Beach, Bonita Beach, and Lovers Key to name a few. Try a new one each day to see which one suits you best!

Vanderbilt Beach image.

Sunset in Naples, Florida image.
Sunset at Barefoot Beach.

If you find yourself planning a trip to spend a week in Naples, Florida – enjoy it! I am envious. Hopefully this post can help you determine some of the different offerings in the area.

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