Looking to trade the cold for an iconic sunny location?
I'm Hannah, Product Manager at Guess Where Trips, and today I'm sharing my most favorite mystery road trips to help you escape the cold!
These trips are all about easy drives, feel-good stops, and destinations that make you want to linger a little longer.
Take a look at the map below to get a general idea of where these road trips end.
My Favourite Sunny Road Trips...
Here are my tips for 'The Southwest Quest':
- Important note: we don't recommend traveling on a Sunday as both of our farm market options on stop #1 are closed!
- You can spot manatees at our park suggestion on stop #1: They are best seen between mid-December and March, so this is the perfect time of year to visit!
- Enjoy complimentary freshly-squeezed orange juice: our citrus option on stop #2 offers free samples. Mmm tastes like sunshine!
- We promise you've never had tacos as good as the ones on stop #3: they're inside a hidden taco stand at a gas station that you definitely would drive right by if you didn't have us telling you where to go!
- Enjoy a relaxing day at the beach (Optional Detour): there are tons of beaches along the coast that you can enjoy pre- or post-road trip. Some of our favorites include: Delnor-Wiggins Pass State Park and Little Hickory Island Park.
- Visit a botanical garden and bird refuge (Optional Detour): this whimsical spot is near your 4th stop!
- Visit Sanibel Island (Optional Detour): it's nearby and worth a visit if you have extra time! Especially well-known for its world famous shell beaches, wildlife refuges, and amazing biking trails!
Recommended Stays for 'The Southwest Quest'
1952 Old Florida Cottage (Air bnb)
The Bonita Bitty Beach Cottage (Air bnb)
Here are my tips for 'Seaside Legends':
- You can turn this trip into a multi-day getaway: This itinerary is packed making it perfect for spreading out over multiple days!
- Don't forget to bring some cash: a few of our park suggestions are cash-only for their parking fees.
- Be sure to wear good walking shoes: the trails and parks on stops #2 and #3 will definitely help you get your steps in.
- You'll want to spend lots of time exploring at the last top: it's an iconic town with tons of history, beaches, and great eats that is worth traveling for.
- Visit a funky castle (Optional Detour): drive just up the coast from your 4th stop to see this funky Castle with the weirdest name (yes there are three t's!). Tours by appointment only.
- Indulge in amazing BBQ (Optional Detour): but don't judge a book by its cover! This epic BBQ spot is 30 minutes from your final stop and is totally worth the drive!
- Visit a nearby botanical garden (Optional Detour): Looking for a floral escape? This botanical garden is worth a visit if you have time!
Recommended Stays for 'Seaside Legends'
Romantic Historic 1888 Cottage
Designer Island Studio
Here are my tips for 'Hill Country Harvest'
- You can turn this trip into a multi-day escape: This iconic road trip route is perfect for a weekend getaway, especially for wine lovers!
- Love history? Don't miss these free walking tours: our optional historic home suggestion on stop #1 offers free walking tours at 10am every day; worth trying to join the tour if you're a history buff!
- Wine lovers will enjoy our featured winery on stop #2: they also offer Guess Where Trips travelers a complimentary Winemarkers' Tasting if you show your itinerary booklets!
- Don't Miss the Old West photo op: More great wines await on stop #3, but for a truly Texan experience you should visit our "photo op" suggestion for a taste of the Old West.
- Our final stop is a town that you could spend a few days exploring: Stay a while and enjoy all that this area has to offer!
- Visit this magical state park (Optional Detour): it's just 20 minutes from your final stop and is worth a visit to climb the ancient dome and get incredible views of Hill Country.
- Have a quirky picnic (Optional Detour): drive 30 minutes south of your final stop to visit this quirky roadside picnic spot that is sure to fill your camera roll!
- Visit an old railroad tunnel (Optional Detour): nearby is another cool state park with an old railroad tunnel that is home to millions of bats!
- Watch free glassblowing demonstrations (Optional Detour): this cool artist studio & gallery offers these demonstrations every day through January 10, 2026.
Recommended Stays for 'Hill Country Harvest'
Cozy 2 bed log cabin (Air bnb)
Post Oak Treehouse @ A-Frame Ranch (Air bnb)
Here are my tips for 'Quirky & Colorful'
- Visiting Dallas or Fort Worth?: This is a perfect easy day trip from the city!
- You'll love the quirky museum on stop 2: I promise you have never seen a museum that is as quirky as this! Use our fun eye-spy game to search through all of the colorful creations.
- Don't miss the brews on stop #3: whether it's a delicious coffee or latte from our cafe suggestion or a pint from our featured brewery. If you do visit the brewery, be sure to look across the way at the historic flour mill with its huge painted silos!
- Spot the colorful murals on your last stop: As you explore our 4th stop town, search for the colorful murals and see how many you can find.
- Hop aboard a vintage train (Optional Detour): If you've got extra time or want to come back to the area, we recommend booking a vintage train ride at this historic railroad near stop #1.
- Visit this stunning outdoor mall (Optional Detour): Transport yourself to Europe at this beautiful outdoor mall which is worth a visit even if you're not ready to shop!
- Try some of the best of Texan BBQ (Optional Detour): this spot just a few minutes from our final stop.
Recommended Stays for 'Quirky & Colorful'
The Honey Pot: A Tiny Pyramid Suite for Two (Air bnb)
Tranquil Country Escape
(Air bnb)
Here are my tips for 'Joshua Tree Journey'
- Visit during the winter months: Cooler temps in January make hiking and exploring these unique desert landscapes ideal, avoiding summer heat and the crowds!
- This the best time of the year for stargazing: as the skies are really clear and there are longer, darker nights. You'll probably spot the Milky Way in the sky above!
- Note that it can get quite chilly here in the winter months at night time, so bring lots of cozy layers to stay warm after the sun goes down.
- We've got a fabulous lunch option for you on stop #3, but they do recommend reservations as it gets quite busy. Book a time around 1pm or so.
- This is a perfect trip to pair with a visit to Palm Springs; an easy day trip while you're there!
- Consider these amazing hikes (Optional Detour): There is a good variety of hikes in Joshua Tree that range from a few hundred yards to several mile treks. The most famous hiking route is the Arches Rock Trail, where, at the end of the 1.2-mile hike, you will find one of the park’s fantastic rock formations.
- Go on a challenging hike (Optional Detour): For those looking for a more challenging endeavor, the Willow Hole hike is an amazing 6.8-mile hike through some of the most beautiful parts of the park. January is the perfect time to walk the trail, as the cooler climate makes it much easier to complete the entire hike.
- Visit this peaceful Boulder Garden Sanctuary: it's near your 2nd stop on the road trip.
Recommended Stays for 'Joshua Tree Journey'
Joshua’s Treehouses
1950s Homesteader Cabin (Air bnb)
Here are my tips for 'Ojai Oasis'
- Winter is the best time to visit: With highs of 63-70°F, this is a lovely time to visit this popular area with fewer crowds.
- Avid cyclists will enjoy this road trip: there is a bike path all the way from stop #1 through to stop #3. Bring your own bikes or rent bikes at our suggested shop on the first stop. The milder temperatures this time of year make cycling a little bit easier!
- Our featured winery on stop #2 is so beautiful: it even has cornhole and bocce ball to enjoy outside while you sip.
- We highly recommend the olive oil tasting on stop 4: We've got some fabulous options to choose from on stop #4, but my personal favorite lets you taste all kinds of olive oils and you can even walk through the olive groves!
- Go whale watching (optional Detour): The early months of the year are great for whale watching, so head out on a wildlife cruise and see how many you can spot!
- If you're a movie fan, we highly recommend this restaurant (Optional Detour): The iconic diner scene in the movie Erin Brockovich was filmed at this restaurant near stop #1, where the real Erin Brockovich herself made a cameo appearance as the waitress.
- This rustic farmhouse-style restaurant and cafe is worth a visit (Optional Detour): and it's near your 3rd and 4th stops!
Recommended Stays for 'Ojai Oasis'
The Chapel | Luxury Historic Ojai Villa
Caravan Outpost Ojai
Here are my tips for 'Sonoma Sips & Strolls'
- You'll love the downtown area of Sonoma: it's quaint and charming, and it is super lovely during the quieter months of the year for a slow-paced wine & food-focused holiday with fewer crowds.
- A note about the winter months: Though you may not get very high temperatures, the days will be comfortable and the nights will be perfect for cozying up in a sweater and with a hot beverage!
- Don't miss our on the way option on Stop 1: If you have time, our "on the way" farmstand option is really cute and worth a visit! Generally open Thrusday - Sunday.
- Grab a bite at the cutest cafe on stop #4: before heading to our park suggestion on the final stop which is one of my all-time favorite destinations with so much history and beauty! It's worth coming back to again and again.
- Take advantage of whale season in the winter months (Optional Detour): You can easily pair a trip wine tasting in Sonoma with whale watching excursions along the coast as winter is peak whale season.
- You can also easily pair this road trip with a visit to Napa (Optional Detour): Napa is also quieter this time of year and has tons of fabulous world-renowned wineries!
- Visit this funky diner (Optional Detour): It's just a few minutes from stops #2 and #3 and worth a visit for their delicious fried chicken!
Recommended Stays for 'Sonoma Sips & Strolls'
Gaige House
Beltane Ranch
Author: Hannah Elias
Hannah is the Product Manager at Guess Where Trips. From product launch strategy to research & development (and even writing our Detour Diaries book!), she continues to find new ways to improve our road trip products for customers.
