A week in Southwest Florida can go in many directions. The coast, the Everglades, the golf courses, the restaurants — there’s more here than most visitors realize. Here’s an itinerary that packs in the highlights without feeling rushed.
Day 1: Arrive and Settle In
Get to your rental, unpack, and take a slow first evening. Walk to the nearest beach for sunset (Naples sunsets are genuinely worth the effort), grab dinner nearby, and get to bed early. The best mornings here start before 8am.
Day 2: Naples Beach and Fifth Avenue
Spend the morning at Naples Beach — the pier area is ideal for first visits. In the afternoon, explore Fifth Avenue South for coffee, galleries, and shopping. Dinner reservations somewhere nice tonight.
Day 3: Everglades Day Trip
Book an airboat tour in the Everglades and get an early start — tours are better in the morning before heat builds. This is one of those experiences that justifies the drive. Back in Naples by mid-afternoon; low-key evening.
Day 4: Kayaking the Mangroves
Morning guided kayak tour through the mangrove tunnels near Rookery Bay or the Ten Thousand Islands. Peaceful, beautiful, and a complete change of pace from beach days. Afternoon is yours — pool time, a spa visit, or simply relaxing.
Day 5: Marco Island
Day trip south to Marco Island. Tigertail Beach for shelling in the morning, then lunch on the island and an afternoon exploring the waterways by paddleboard or boat tour. Return to Naples for dinner.
Day 6: Golf or Spa (Your Choice)
This is your dedicated leisure day. Golfers: book a round at Lely’s Flamingo Island Course. Non-golfers: a morning at the spa, afternoon at the pool, and an early dinner somewhere new. Naples Botanical Garden is also excellent if you haven’t visited.
Day 7: Slow Morning, Departure
One last beach sunrise, a proper breakfast, and a final walk around your favorite neighborhood. Most flights out of Southwest Florida International (RSW) are in the afternoon, giving you a full morning.
Book the right home base for this itinerary. Browse our Southwest Florida properties — centrally located rentals make every one of these days easier to pull off.
