Southwest Florida packs two completely different landscapes into one easy weekend loop: the sawgrass marsh and mangrove-tunneled backcountry of the Everglades, and the white-sand, postcard Gulf Coast just a half-hour away. Three days is enough to drive the Tamiami Trail into gator country, take a boat out through the Ten Thousand Islands, and still get two full afternoons on the beach — starting and ending in Naples, with a detour out to Marco Island.
Day 1Naples — Fifth Avenue South & the Pier
Settle into Naples’ walkable downtown, then catch one of the Gulf Coast’s best free sunsets off the end of the city pier.
🏨 Check-In — Inn on Fifth
Check-in 4pm · from $320 USD/night
A grand European-style hotel right on Fifth Avenue South, Naples’ main strip of restaurants, galleries, and boutiques — walk everywhere for the rest of the evening, no car needed.
Inn on Fifth · +1-239-403-8777 · www.innonfifth.com
🛍️ Stroll Fifth Avenue South
Free · shops close ~6–9pm
Naples’ main downtown strip of palm-lined sidewalks, art galleries, and outdoor cafés — easy to fill an hour before dinner without a plan.
🌅 Sunset — Naples Pier
Free · best ~30 min before sunset
A 1,000-foot fishing pier at the end of 12th Avenue South where locals gather most evenings to watch the sun drop into the Gulf of Mexico — dolphins and pelicans show up often enough that it’s worth the short walk from downtown.
🍽️ Dinner — Tin City
Dinner · $25–45 USD/person
A cluster of waterfront seafood restaurants in a converted 1920s cargo warehouse on the Naples Bay waterfront — walk the docks after dinner to see the charter boats come in.
Day 2Tamiami Trail — Airboats, Big Cypress & the Ten Thousand Islands
The whole point of the trip: a drive straight into the Everglades on the historic Tamiami Trail, an airboat through sawgrass marsh, a roadside photography gallery inside Big Cypress, and a boat out through a maze of mangrove islands.
🚗 Drive — Naples to Ochopee via Tamiami Trail (US-41)
~45 min
The two-lane highway that first crossed the Everglades in 1928, running dead straight through cypress swamp and sawgrass prairie with almost no development — roll the windows down.
🐊 Wooten’s Everglades Airboat Tours
~30–50 min tour · from $37 USD/person
A family-run outfit on the Tamiami Trail in Ochopee running airboat rides out into open sawgrass marsh since 1953, plus swamp buggy tours and a small animal sanctuary on-site — book online ahead to skip the ticket line.
Wooten’s Everglades Airboat Tours · www.wootenseverglades.com
📸 Clyde Butcher’s Big Cypress Gallery
Free (donation welcome) · ~20 min down the road
A roadside gallery inside Big Cypress National Preserve showing the large-format black-and-white swamp photography of Clyde Butcher, the Everglades’ best-known photographer — the swamp walk out back (seasonal) lets you wade into the cypress he shoots.
⛵ Ten Thousand Islands Boat Tour — Everglades City
~1.5 hrs · from $45 USD/person
A narrated boat tour out of Everglades City through the mangrove-studded Ten Thousand Islands, the watery maze where the Everglades meet the Gulf — dolphins and manatees turn up often, and it’s the easiest way to see the backcountry without your own boat.
🏨 Check-In — JW Marriott Marco Island Beach Resort
Check-in 4pm · from $450 USD/night
A full beachfront resort on Marco Island’s wide white-sand coastline, about 45 minutes from Everglades City — the splurge night of the trip, with a long stretch of Gulf beach right outside.
JW Marriott Marco Island Beach Resort · +1-239-394-2511 · www.marriott.com
Day 3Marco Island Beach Morning & Back to Naples
One unhurried morning on Marco Island’s beach before the short drive back up the coast.
🏖️ Tigertail Beach
Parking ~$8 USD/day
A county beach park on a lagoon-and-sandbar system a short drive from the resorts, with calmer, shallower water than the open Gulf beach and good shelling at low tide.
🚗 Drive — Marco Island to Naples
~30–40 min
A quick final drive back up the coast, with time to stop for lunch in Naples before heading home.
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