Turn a night out into a city‑wide challenge: an app‑led bar crawl in Naples that blends trivia, photo challenges and local stops. Self‑guided and flexible, it’s designed for groups who want active evening fun without a guide.
Turn a night out into a city‑wide challenge: an app‑led bar crawl in Naples that blends trivia, photo challenges and local stops. Self‑guided and flexible, it’s designed for groups who want active evening fun without a guide.
The sun bends low over the Gulf as your group gathers near the Naples Pier, palm fronds whispering and the ocean breeze daring you to trade a quiet evening for a loose, competitive run through town. This is an app‑led bar crawl and scavenger hunt: you follow prompts on your phone, solve quick trivia, and snap photo challenges as you move between classic bars, plazas and pocket parks along Old Naples.
Verified experiences and guided adventures in the surrounding area.
Operated by Let's Roam · Naples, Florida
The sun bends low over the Gulf as your group gathers near the Naples Pier, palm fronds whispering and the ocean breeze daring you to trade a quiet evening for a loose, competitive run through town. This is an app‑led bar crawl and scavenger hunt: you follow prompts on your phone, solve quick trivia, and snap photo challenges as you move between classic bars, plazas and pocket parks along Old Naples.
Naples began as a late‑19th‑century resort town; the pier and downtown blocks grew around oyster boats and early hotel development. Geologically the area is coastal barrier plain — sandy beaches backed by mangroves and low limestone — which keeps the walking level but exposed to sun and wind. Culturally the downtown centers—Fifth Avenue South and Third Street South—blend gallery windows, seafood counters and polished cocktail rooms, so the route mixes historic markers, public art and storefront clues.
Practically, expect 1.5–2 hours of walking (roughly 1.5–2.5 miles) on sidewalks and flat streets with short detours to piers or boardwalks. The Let’s Roam app guides the route; redeem your voucher in the app before you start. Bring ID if you plan to drink, keep your phone charged for navigation and photo tasks, and respect local businesses when stopping for a drink or a selfie. Start at dusk for better light and more lively venues; start earlier if you prefer quieter streets. The experience is social, self‑paced and designed to be playful — treat it as a fast urban adventure that pairs easy walking with city discovery.
moderate.
1.5–2 hours.
Moderate fitness: able to walk 1.5–2.5 miles and stand for short photo challenges
Download the Let’s Roam app on your mobile device, sign in, tap “3rd Party Vouchers” and enter your TripAdvisor voucher number; the app will then let you begin the Naples hunt.
Yes—the game itself is family‑friendly and includes photo challenges; however this specific listing is a bar crawl so alcohol venues expect patrons to be 21+. You can play without drinking and include younger players.
The downtown walking route uses sidewalks and boardwalks and is marked wheelchair accessible, but check individual venue access if you plan to enter bars with steps.
Full refunds are available if you cancel at least 24 hours before your scheduled time; the activity is self‑guided and is not automatically canceled for rain—reschedule or cancel per policy.
Naples developed as a resort town in the late 1800s; the Naples Pier and downtown blocks date to those early tourism years and remain focal points for the city.
Coastal habitat and sea turtle nesting are sensitive; stick to marked beach areas, avoid disturbing wildlife and support local beach‑clean efforts when possible.
Let's Roam operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.




The sun bends low over the Gulf as your group gathers near the Naples Pier, palm fronds whispering and the ocean breeze daring you to trade a quiet evening for a loose, competitive run through town. This is an app‑led bar crawl and scavenger hunt: you follow prompts on your phone, solve quick trivia, and snap photo challenges as you move between classic bars, plazas and pocket parks along Old Naples.
The sun bends low over the Gulf as your group gathers near the Naples Pier, palm fronds whispering and the ocean breeze daring you to trade a quiet evening for a loose, competitive run through town. This is an app‑led bar crawl and scavenger hunt: you follow prompts on your phone, solve quick trivia, and snap photo challenges as you move between classic bars, plazas and pocket parks along Old Naples.
Naples began as a late‑19th‑century resort town; the pier and downtown blocks grew around oyster boats and early hotel development. Geologically the area is coastal barrier plain — sandy beaches backed by mangroves and low limestone — which keeps the walking level but exposed to sun and wind. Culturally the downtown centers—Fifth Avenue South and Third Street South—blend gallery windows, seafood counters and polished cocktail rooms, so the route mixes historic markers, public art and storefront clues.
Practically, expect 1.5–2 hours of walking (roughly 1.5–2.5 miles) on sidewalks and flat streets with short detours to piers or boardwalks. The Let’s Roam app guides the route; redeem your voucher in the app before you start. Bring ID if you plan to drink, keep your phone charged for navigation and photo tasks, and respect local businesses when stopping for a drink or a selfie. Start at dusk for better light and more lively venues; start earlier if you prefer quieter streets. The experience is social, self‑paced and designed to be playful — treat it as a fast urban adventure that pairs easy walking with city discovery.