The Southwest Quest

5.0 (6 reviews)

From $39

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!
When to Go Tues - Sat
ends near Bonita Springs, FL

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  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges
  • No Booking Required

essentials for your trip

Mint Road Trip Journal

Mint Road Trip Journal

Track all your local adventures - big or small - in one place. With space...

Road Trip Tote Bag

Road Trip Tote Bag

An essential tote bag for your road trip ahead. Carry everything from your surprise package...

Trip Highlights

  • Beaches & boardwalk trails
  • A ghost town with a wild past
  • Tasty local eateries and breweries
  • Donkeys, goats, and tortoises - oh my!
  • Multiple recommendations included on every stop

How Long Is This Trip?

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.

When Can I Go?

Days of the week: Tuesday through Saturday

Seasons: Year-round

Not recommended: Mondays and Holidays

Travel Tips

Can be done on a Sunday; however, you'll need extra road trip snacks as our farm market options on stop #1 are closed.

Shipping & Returns

Shipping: Free shipping on orders over $100. Standard shipping takes 4–10 business days. Need it faster? Choose the fastest option at checkout for 2–4 business day delivery.

Returns: Not the right fit? Reach out within 30 days of purchase to start a return. Products just need to be unopened, unused, and in their original packaging, return shipping is your responsibility. Digital trips, gift cards, and opened products can't be returned.

Exchanges: Want a different trip instead? Email us at questions@guesswheretrips.com within 30 days of your order, there's a small $8 reshipping fee to send your new pick out. Digital trips cannot be exchanged.

Read our full return policy →

The Southwest Quest

5.0 Physical Package

Here's How It Works

Browse by location and find a surprise trip that fits your day. Every route is road-tested by our team.

Your surprise destinations stay sealed until you're ready for them. One envelope at a time on the road, all day long.

Hidden gems, local favorites, and stories you won't find on Google. That's what's waiting for you.

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Road Tested by Our Team

Our team spends 40+ hours researching, driving, and vetting every route: talking to locals, discovering hidden gems, and making sure every stop is worth your day.

We Remember Experiences, Not Things.

Research consistently shows that spending time together creates more lasting happiness than buying more stuff. Every Guess Where Trip is thoughtfully planned to help you reconnect, explore, and create memories that last long after the day is over.