15 Day Trips & Weekend Getaways From Naples You Need to Know
Naples is a pretty incredible home base.
You can spend one day on the Gulf, the next exploring the Everglades, and by the weekend be somewhere that feels completely different from Southwest Florida.
And some of the best escapes aren't necessarily the obvious ones.
Whether you want to spend the day on a remote island, take the boat somewhere for lunch, escape to an old-Florida beach town, or get out of Southwest Florida entirely for the weekend, there are so many places within easy reach of Naples.
So I put together 15 of my favorite day trips and weekend getaways, including a few that I think are worth knowing about even if they aren't the first places that come to mind.
At a Glance
Boat day: Cabbage Key
Remote beach: Cayo Costa
Old-Florida weekend: Boca Grande
Easy beach escape: Sanibel + Captiva
Adventure: Everglades City
Romantic getaway: Palm Beach
Girls' weekend: Sarasota
A weekend out: Miami
Best "I need to get out of Naples" escape: Key West
BOAT DAYS
1. Cabbage Key
Best for: A boat day + old-Florida vibes
Cabbage Key is one of those places that makes you appreciate having access to the water in Southwest Florida.
It's only accessible by boat, and the journey is part of the fun.
The main attraction is the Dollar Bill Bar, where the walls are covered in signed dollar bills. Grab lunch, have a drink, explore the island and enjoy being somewhere that feels completely removed from the mainland.
The whole place has that old-Florida feeling that can be harder and harder to find.
Make a day of it: Pair Cabbage Key with Cayo Costa if you're already out on the water.
My take: If you have a boat and haven't been, put this one on the list.
2. Cayo Costa
Best for: A remote beach day
If Cabbage Key is about the destination, Cayo Costa is about the escape.
Cayo Costa is accessible by boat, and once you arrive, the experience is much more about slowing down. Anchor up, spend the day on the beach, swim, shell, explore and bring everything you need for a few hours in the sun.
There aren't the restaurants and conveniences you have on the mainland, which is exactly why I like it.
Bring: A cooler, plenty of water, sunscreen and everything else you'll want for the day.
Best part: It actually feels like you've gotten away.
3. Keewaydin Island
Best for: A spontaneous beach day
Keewaydin is one of my favorite options when you want a beautiful beach day without committing to a full weekend away.
The barrier island sits between Naples and Marco Island and is accessible by boat.
Pack a cooler, bring your beach chairs and make a day of it.
You don't need a complicated itinerary here. The whole point is to get on the water, find a good stretch of beach and stay there for a while.
It's also a great reminder that living in Naples gives you access to experiences that feel like vacations without actually having to go very far.
4. Useppa Island
Best for: A slower, more polished boat day
Useppa is a little different from Cayo Costa.
It's private, historic and has a distinctly old-Florida atmosphere. The island has no bridge connecting it to the mainland, so getting there is part of the experience.
This is one I'd save for when you want your boat day to feel a little more like an occasion.
Best for: Lunch, exploring, a little history and a slower pace.
5. Boca Grande by Boat
Best for: Turning a beach town into a boating day
Boca Grande is great by car, but getting there by boat is an entirely different experience.
Spend the day on the water, head into Boca Grande, grab lunch, explore the island and enjoy the fact that you can combine a boat day with one of Florida's prettiest old-Florida towns.
And if you love it enough to stay overnight, even better.
EASY DAY TRIPS
6. Sanibel + Captiva
Best for: A laid-back beach getaway
Sanibel and Captiva are an easy choice when you want to get out of Naples without making a huge production out of it.
If you're driving, make a stop in Sanibel along the way. The island is famous for its shelling, and shellers will tell you it deserves the reputation.
Bring a bag, head to the beach and see what you find.
And because this is me, I'm also going to tell you to stop at Cheeburger Cheeburger for a milkshake.
Then continue on to Captiva.
Spend the afternoon at the beach, explore the island and make a stop at The Bubble Room, which is one of those places that's worth seeing simply because it is so uniquely Captiva.
If you have a boat: You can also make the trip by water, which turns the whole experience into more of a boating day.
7. Everglades City
Best for: Something completely different
And then there's Everglades City, which is probably the biggest departure from the other trips on this list.
Instead of another beach day, head into the Everglades.
Take an airboat ride, explore the mangroves and waterways, and experience a side of Southwest Florida that feels completely different from Naples.
It's also a great opportunity to experience the area's fishing and seafood culture.
If you're going during stone crab season, that's something I'd absolutely work into the trip.
My take: If you want a day trip that makes you feel like you went somewhere completely different, this is it.
8. Marco Island + Goodland
Best for: An easy change of scenery
Sometimes you don't need to drive three hours to feel like you got away.
Head south to Marco Island, spend some time at the beach and then continue over to Goodland.
Goodland has a completely different personality from Naples. It's casual, funky and very much its own thing.
This is an easy option when you want to get out of your normal routine without turning it into an entire weekend.
Best for: A low-key day when you don't feel like planning much.
9. Matlacha
Best for: Art, color and something a little quirky
Matlacha is tiny, colorful and completely different from Naples.
The fishing village has colorful buildings, local galleries, shops and a very relaxed atmosphere.
It's a fun choice when you want something that isn't another polished beach-town experience.
Pair it with a trip through Pine Island and make a full day of exploring the area.
10. Fort Myers
Best for: Food, history and a change of pace
Fort Myers is close enough that it doesn't feel like a major trip, but there's plenty to do if you want something other than the beach.
Explore the River District, grab lunch or dinner, check out the historic architecture and spend some time downtown.
This is an especially easy option when you have visitors who have already seen plenty of Naples and want to see another side of Southwest Florida.
WEEKEND GETAWAYS
11. Boca Grande
Best for: A romantic weekend + old Florida
For a proper weekend getaway, Boca Grande is one of my favorites.
Stay at the Gasparilla Inn, rent a golf cart, explore the island and spend the day at the beach.
You don't need an overly complicated itinerary here. That's part of the appeal.
Boca Grande has a slower pace and a sense of old Florida that makes it feel like you've actually left Naples for a little while.
It's polished, beautiful and easy to settle into for a weekend.
One thing to know: The Gasparilla Inn is seasonal, so check its operating dates before planning your trip around it.
My pick: This is the one I'd choose when you want a proper getaway without getting on a plane.
12. Sarasota
Best for: A girls' weekend or a food-and-culture escape
Sarasota gives you a completely different Gulf Coast experience.
Spend the day at the beach, explore St. Armands, have dinner downtown and build the weekend around restaurants, shopping and the arts.
It's a particularly good option when you've done the Naples routine a hundred times and want somewhere that still feels distinctly Florida but has a different energy.
Best for: Girls' trips, couples and a weekend with friends.
13. St. Petersburg
Best for: Art, restaurants and a livelier weekend
St. Petersburg is another Gulf Coast option, but it feels much more urban than Naples.
There are galleries, museums, restaurants, bars and a much more energetic downtown.
You can still get your beach time, but the appeal here is having more to do once you're off the sand.
My take: If you want a weekend where you aren't planning your entire day around the beach, go here.
14. Palm Beach
Best for: A polished, romantic weekend
If you want to get a little farther away, Palm Beach is one of my favorite Florida weekend escapes.
It's an easy place to spend a couple of nights without needing to create a massive itinerary.
Stay somewhere beautiful, walk around Worth Avenue, have a long lunch, go to the beach, get dressed up for dinner and enjoy the change of scenery.
It's particularly good when you want something that feels elevated and completely different from your normal Naples weekend.
15. Key West
Best for: When you actually want to get away
Key West is not the kind of trip I'd recommend squeezing into one day from Naples.
Make it a weekend.
Drive down, stay for a couple of nights and actually enjoy the island.
Spend time on the water, walk around Old Town, have dinner, catch the sunset and let yourself slow down.
It's touristy in parts, obviously, but that's also part of what makes Key West fun.
Best for: A birthday, girls' trip, couples' weekend or when you just need a change of scenery.
BONUS: for late nights out
Miami
Best for: Shopping, restaurants and nightlife
If you're looking for something completely different from Naples, Miami is an obvious choice.
It's close enough for a weekend but different enough that it feels like you've left Southwest Florida entirely.
Spend the weekend between Miami Beach, Brickell and Coconut Grove, depending on what kind of trip you're after.
This is the one to choose when you want restaurants, shopping, nightlife and a little more energy.
A Few Things to Know Before You Go
Florida travel can look deceptively simple on a map. A destination may look close, but traffic, bridges, boat conditions and seasonal crowds can change the equation.
A few things I'd keep in mind:
For boat days: Check marine conditions before you leave and make sure you have everything you'll need once you're away from the mainland.
For remote islands: Don't assume you'll be able to grab lunch or water when you arrive. Pack accordingly.
For weekend trips: Check hotel availability before building your itinerary, especially for seasonal destinations like Boca Grande.
For the Everglades: Book your airboat or other activities ahead of time if you're going during a busy period.
For Sanibel and Captiva: Give yourself extra time if you're traveling during a busy season. Florida traffic has a sense of humor.
The Best Part About Living in Naples?
You don't necessarily need to leave Florida to feel like you've gone somewhere.
That's one of my favorite things about Naples.
You have the Gulf, the islands, the Everglades and some of the most distinctive little towns in Southwest Florida all within reach. And when you want a bigger escape, you're still within driving distance of places like Palm Beach, Miami and Key West.
So the next time you feel like you need a vacation, you might not need a plane ticket.
You might just need to leave Naples for the day.
Save this guide for your next escape, and send it to your favorite travel partner.
And if you're thinking about making Naples your home base rather than just your vacation destination, I'd love to help.
Email me at [email protected] or reach out to start a conversation about what a move to Naples could look like.
