Tim Cranch wearing blue shirt

Tim Cranch

Ellie Penaranda

Day Trips from Naples, Florida

We live in Paradise and we’re thankful every day for that! However, it doesn’t mean that a change of scenery and a completely different vibe isn’t welcome every now and then. Here are some of our favorite day trips and destinations for that refreshing day off but a reminder that Naples is the only place on the planet that we would live full time.

St. Armands Circle in Sarasota (110 miles)

Sarasota shares some common ingredients with Naples but the area has a totally different feel. The common ingredients are a touch of sophistication, some culture and arts, beautiful beaches and lots of water all around, good restaurants. The city is a real city, but St. Armands Circle has a special thing going on with all of the restaurants, shops, and boutiques all an easy stroll as you make your way around the circle. We go up for day three or four times every year.

The go-to restaurant is ShoreIf you want to linger longer in the area, then take a drive up the length of Longboat Key from St. Armands Circle and go to the waterfront Shore restaurant at the north end of Longboat Key.

Siesta Key (105 miles)

Siesta Key gets voted best beach in America and it’s a popular destination for that reason. The sand is soft and white with the beaches being very wide. Good destination for a family day at the beach. That said, there is a lively bar and party scene – nothing crazy – but it is active. The restaurants, bars, and shops are all within walking distance along the strip in Siesta Key Village.

You can hit any of the restaurants in the Village for your expected beachy lunch sitting outside on the front porch of one of the restaurants. The go-to place for an upscale dinner (dinner only) on the bayfront water is Ophelia’s on the Bay. You have to drive south on Midnight Pass Road to the south end of the island but it’s worth it for the lovely view and excellent food.

Venice (90 miles)

You drive to Venice to kick around the one main street with shops and restaurants and walk to the beach looking for fossilized sharks teeth. They have bragging rights for being The Shark Tooth Capital of the World. Sidewalks roll up early here.

The go-to restaurant is Sharky’s on The Pier which is located at the south end of the beach. The upscale sister restaurant in the same location at The Pier is Fins at Sharky’s. Another favorite restaurant in Venice is at the north end of town near the jetty and overlooks a marina is The Crow’s Nest (order the fish sandwich at lunchtime).

Anna Maria Island (125 miles)

We love this place. The vibe is a world away and it’s a completely beach vibe. Gorgeous beaches and the color of the tropical water is Carribean. Cool little town with interesting shopping and a city pier. No honky-tonk, just a great beach vibe. Several waterfront and beachfront restaurants.

The go-to restaurant is Sandbar and ask if Aaron is working as a server. Complimentary valet parking. No reservations and you might have to wait a bit but it’s worth it. Some of the tables are totally toes-in-the-sand. Same people operate Beach House and Mar Vista Dockside Restaurant & Pub just down the road to the south (Bradenton Beach and Longboat Key, respectively) and both are also very good.

Miami (100 miles)

You want a change of scenery? You’re anywhere in Miami within a couple of hours when you cross over on Alligator Alley from Naples. As you would guess, there is a ton of things to do here. It’s not just hanging out to check the scene at South Beach. Go see the graffiti in the Wynwood neighborhood. Take a boat cruise around Biscayne Bay. Visit Little Havana. Art Deco architecture. Plenty of sightseeing, plenty of nightlife, plenty of waterfront views, and plenty of things to do that you won’t find anywhere else. Click the links below for some ideas of the variety in Miami.

It’s a big city with every cuisine, every atmosphere and every budget for restaurants. We’ll let you pick.

Miami Things to Do        More Miami Things to Do        Even More Miami Things to Do

Homestead for the Nurseries on Krome Avenue (130 miles)

If you like gardening and working outside as much as we do, then you will enjoy a drive down Krome Avenue in Homestead to check the nurseries. Many of these are huge nurseries with a variety of plants, trees, shrubs and flowers, some of which you will not have seen before. Some of these nurseries provide our local nurseries and landscapers with wholesale materials as well as delivery service to your own yard here in Naples.

We have used their services on some of our renovation projects because it’s cost effective, they will install for a modest fee, and we look forward to driving down there to pick out and tag particular specimens. Combo this trip with a meal in Key Largo as the beginning of the Florida Keys is just down the road.

Here are a few places that we have frequented:      

Kendall Nursery

Santa Barbara Nursery at (305) 256-7577

A Heavenly Garden (Orchids) at (305) 247-7628

Key Largo (180 miles)

A world apart but a doable distance driving in the car is Key Largo at the top of the Florida Keys. You have just entered the Keys but everything changes when you have crossed into the Keys. The Atlantic Ocean is on one side of the road and the Gulf of Mexico is on the other. A great destination to charter a fishing trip, kick around the area, and stop at a few waterfront restaurants and bars for a drink or a snack. Great diving and snorkeling including John Pennekamp Coral Reef State Park at Mile Marker 102.5 on the Overseas Highway.

The go-to restaurant and bar is located on the Gulf side of the road at Mile Marker 104 and appropriately named Sundowners. Outside dining and tiki bar, patio seating overlooking the water, a small marina, lots of boating activity, and awesome sunsets.

Jupiter and Jupiter Island (170 miles)

We have friends in Jupiter and the other side of Florida is definitely a change of scenery. There is not the concentration of shops, boutiques, and restaurants in the form of a walkable village setting but Jupiter has a lot to offer. The beaches are beautiful (both in Jupiter and Jupiter Island) but I would warn you the sand is a different color so it gets very hot in the warmer months. The lighthouse in Jupiter adjacent to the inlet is as picturesque as it gets. 

The go-to restaurant is the newest waterfront restaurant and you have options within the location. Developed along with Joe Namath and overlooking the Jupiter Lighthouse, it’s called Charlie and Joe’s at Love Street. Other favorites are the riverfront Guanabana’s and The Food Shack which have been regular places for us and highly recommended. 

Palm Beach (160 miles)

Swanky Palm Beach is worth a visit because of the change in atmosphere. Drive around, appreciate the local architecture as well as the estates along the beach. The beaches are beautiful but can be crowded. Cultural venues, events, and things to do with a different twist from what you would find elsewhere.

The go-to restaurant for us is a Middle Eastern restaurant located in West Palm Beach called Agora Kitchen. Call ahead.

Sanibel Island / Captiva Island (40 miles)

The nearest destination to Naples on this list are the barrier islands of Sanibel Island and Captiva Island. One road, one bridge in and out so plan accordingly and try to time it so you don’t get hung up in the long string of traffic during high season. Just up the road from Naples but a totally different vibe. Even the two connected islands have different vibes. More action on Sanibel with shops, etc., but both have a natural setting. Look up J.N. “Ding” Darling National Wildlife Refuge. Beautiful beaches on both islands with shelling a favorite pastime.

The go-to restaurant for us is the Mucky Duck which sits on the Gulf of Mexico in the village of Captiva. Pub feel, toes in the sand, laid back, tropical sunsets and great spot as a getaway from the usual.

When you have more than a day…….

A bit farther down the Overseas Highway, there is a unique world waiting for you to explore…….the Florida Keys and, of course, Key West. Although you can make Key West a day trip by traveling on the Key West Express (high speed ferry boat), you would not be giving its due. The Keys are for relaxation and decompression. Take it easy. Switch over to “Island Time” and take a few days when there is no schedule. Another blog for another day.

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Tim Cranch at 239-272-4848    or    Ellie Penaranda at 239-776-5077