The Southwest Quest
Home / Trips / The Southwest Quest

The Southwest Quest

The Southwest Quest

Regular price $65.00 USD
Sale Sold out

One trip is required per group.

* "PDF Instant Download" means the trip will be sent by email as a PDF document, and not by mail (the email is sent immediately after completing your purchase)


Plenty of sun, strolls and citrus make this the ultimate Southwest Florida road trip. From unique eateries and boardwalk trails to an eerie ghost town and a sunset beach stop, there is truly something for everyone!

Trip Highlights

  • Easy boardwalk trails
  • A ghost town with a wild past
  • Tasty local eateries and breweries
  • A beach for sunset
  • Donkeys, goats, and tortoises - oh my!


This trip is best done from Tuesday - Sunday throughout the year.


  • Families with older kids
  • Outdoor enthusiasts



A morning park or pick-me-up, the choice is yours! We've recommended two great trails or spots to grab a bite. Drive time to the second stop is 10 minutes.


Wander along a 1.5 mile boardwalk, stop for some citrus, or sip a beer (weekend only). Drive time to the third stop is 20 minutes.


An eerie ghost town awaits! Explore historic buildings and learn about its spooky past. Drive time to the fourth stop is 15 minutes.


Get your toes in the sand and enjoy a beach sunset or grab a tasty cocktail to end the day.



Can depart from

Fort Myers Area, Naples Area, Tampa Area

Before you go

What You'll Need to Bring

  • Bathing Suit
  • Beach Towel
  • Water
  • Walking Shoes
  • Cash
  • Camera
  • Road Trip Snacks
  • Sunscreen (lots of easy outdoor activities)

Additional Details

  • Kid-Friendly
  • Accessible


We're here to help!

From Fort Myers:

1 hour and 45 minutes / 72 miles

From Cape Coral:

2 hours and 5 minutes / 72 miles

From Naples:

2 hours and 5 minutes / 92 miles

From Sarasota:

3 hours and 35 minutes / 208 miles

From Tampa*:

4 hours and 50 minutes / 307 miles

*We recommend booking an overnight hotel if the driving distance is greater than 4 hours round-trip.

This trip is best done between Tuesday - Sunday throughout the year. Please note: your best bet to see Manatees at one stop is from December - May.

We do not recommend traveling on Monday.

We recommend leaving between 10:00 and 10:30 am if you are leaving from the Fort Myers area.

Stops #1, #3, and #4 have pet-friendly options available!

Please remember to keep your pet on a leash at all times, and if you’re unsure about pet-friendliness, we encourage you to contact businesses ahead of your visit to double check.

We recommended bringing up to 5 people on your surprise road trip.

If you're bringing a larger group, we highly recommend having one person in charge of booking reservations at restaurants and attractions in advance. Please see the previous page for a copy of the digital itinerary.

First Stop: Our featured stop is free to explore. One alternative has a $2 per hour parking fee.

Second Stop: Our featured stop has a $1 per hour parking fee.

Third Stop: Our featured stop is $5 per vehicle. Alternative food options available.

Fourth Stop: Our featured beach stop is $2 per hour. Brewery suggestions are free.

*Please note: gas, tolls, and food may be additional costs.

After booking your trip, we'll send you a confirmation email with a few recommended accommodation options.

Customer Reviews

Based on 1 review
Overall, how would you rate this trip?:
I would not recommend this trip
Excellent! I would definitely recommend this trip
Rate how active the trip was:
Not very active
Very active
Rate how accessible the trip was:
Not very accessible
Very accessible
Rate how 'unique' the stops were:
Not really
Yes, very unique!
Unexpected exploring in the Sunshine State

We've been in Florida for years and stopped in at so many fun and unexpected places. Given the variety of places at each stop we doubled up on a few, opting for 6 stops and a full day of exploring. Tip: make sure you have lots of water on hand.
This was our first Guess Where Trip as it was gifted to us but won't be our last!