From coastal escapes to charming small towns, our U.S. surprise road trips make it easy to give the gift of adventure. In this guide, we’ve rounded up our top picks for every type of traveler - couples, families, seniors, winter lovers, and more. Whether you’re after a cozy getaway or an unforgettable road trip, you’ll find the perfect surprise waiting here.
🎁 First Things First: Gift Cards Make the Perfect Gift
Not sure which trip they'll love most? A Guess Where Trips gift card lets them choose their own adventure - whether that’s a cozy small-town stroll, a scenic nature escape, or one of our bestselling mystery days.
The perks:
- Our gift cards never expire
- They can redeem it closer to the date of travel, so they have the most up-to-date information as possible
- Redeemable for any road trip on our site
- The easiest way to give an unforgettable day out.
Three easy ways to gift:
- Our new Road Trip Gift Card comes in an easy-to-wrap box, complete with a handy booklet to help them understand how our trips work, and how to redeem their gift card.
- Our Road Trip Gift Bundle includes a gift card, tote bag, and game pack - all packed up in a keepsake gift box that they can later use to store their road trip memories.
- Our Digital Gift Card can be emailed directly to the recipient (just click "I want to send this as a gift" before adding it to your cart!)
Jump to a section:
- Gifts for Couples
- Gifts for Families
- Gifts for Seniors
- Gifts for Winter Lovers
- Gifts For Everyone
- Unique Gift Add-Ons
Give them a day to reconnect - no planning required.
Bridges & Beauty (Cleveland)
Scenic tree-lined roads, charming covered bridges, cozy wineries, stunning trails, and maybe even a chill from a ghostly tale or two.
Must love: 🌉 Bridges | 🍷 Wine | 🛍️ Boutiques
Seasons: Year-Round
Along the River (Philly, Trenton, Baltimore, Allentown, PA, Newark, Wilmington, DE, NYC)
Tiny towns along the river that are brimming with hidden gems. Countless photo-worthy moments and memories to make on this easygoing scenic road trip.
Must love: 🏘️ Charming Towns | 🌉 Bridges | 👟 Easy Trails
Seasons: April-November
Waterside Bliss (Washington DC, Baltimore, Alexandria VA)
The ultimate waterfall adventure not too far from home! Historic paths, snap photos of four falls, local vino and a mysterious cave.
Must love: 🏖️ Beachfront Boardwalks | 🍷 Wine | 📜 History
Seasons: Spring-Fall
Keep the kids curious (and entertained) with family-friendly stops, treat shops, outdoor activities, and hands-on surprises. Perfect for families who want to try something new without straying too far from home.
All Things Charming (Chicago, Milwaukee)
From serene lakeside views and quaint small-town charm to playful animal encounters and a whimsical museum, this captivating road trip promises to create unforgettable memories for everyone!
Must love: 🏘️ Cute Small Towns | 📜 History | 🦙 Animals
Seasons: Year-Round
Whimsical Wonders (Philly, Trenton, Baltimore)
Hidden gem destinations that feel like a fairytale world. Lucious gardens, charming towns and whimsical photo ops make this the perfect road trip.
Must love: 🌸 Picturesque Gardens | 🏘️ Charming Towns | 🧚 Fairytale Stops
Seasons: Year-Round
Mountain Marvels (Atlanta, Chattanooga)
This family-friendly trip is the ultimate way to escape the city and head to some remote towns in the mountains. Stroll the streets of charming rural small towns, explore quirky art and museums, indulge in tasty bites & brews, and enjoy the surprise!
Must love: 🏘️ Small Towns | 🖼️ Quirky Art & Museums | 🍺 Breweries
Seasons: Year-Round
Well-paced road trips with lots to choose from for every walk of life and activity level. Retired? Skip the weekend road trips, and enjoy beautiful locations without the crowds.
Elegant Estates & Outdoor Art (Indianapolis)
Just a short drive from Indy, you'll find a world full of elegant estates, whimsical gardens, and colorful outdoor art. We'll tell you all of the quirky fun facts and historic moments that make these spots so unique!
Must love: 🏘️ Adorable Small Towns | 🖼️ Art | 🐔 Farm Animals
Seasons: Year-Round
Antique Adventures (Charlotte, Winston-Salem)
This leisurely trip packs a punch! Expect a variety of antique shops (both small and large), cozy cafes, funky eateries & effortless outdoor escapades and haunted stops along the way. The best part? It's only a quick jaunt from the city.
Must love: 🕰️ Antique Shops | 🍷 Wine/Beer | ☕ Bakeries & Cafes
Seasons: Year-Round
Covered Bridges & Baked Goods (Philly, Trenton, Baltimore, Allentown, PA, Wilmington DE)
This trip is like taking a step back in time! Wind through the peaceful countryside to a number of quaint covered bridges and locally owned bakeries, farmers markets, and shops.
Must love: 🌉 Bridges | 📜 History | 🥐 Baked Goods, Chocolates, Bread
Seasons: Year-Round
Give the gift of fresh air, scenic hikes, and unique winter wonderlands.
Vibrant Vistas & Picturesque Towns (Hartford, New Haven, Springfield MA)
Hit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls.
Must love: 🏘️ Small Towns | 🍺 Beer | 🏞️ Scenic Lookouts
Seasons: Year-Round
Charming Curiosities (Washington DC, Baltimore, Winchester, Alexandria VA)
With a few haunted stories, trails with a unique past, and charming historic mansions, we're confident you'll find new favorite spots to explore when you hit the road with this surprise trip.
Must love: 📜 History | 🍺 Brews | 👻 Spooky Stories
Seasons: Year-Round
Waterfall Wanderings (Cleveland)
The ultimate waterfall adventure not too far from home! Wander along historic paths, snap photos of four falls, enjoy a glass of local vino and explore a mysterious cave.
Must love: 💧 Waterfalls | 🍷 Wineries | 🌉 Bridges
Seasons: Year-Round
Can’t decide which trip to choose? Take the road trip quiz or use our interactive road trip map to be matched with a trip OR consider these gifts for those hard-to-buy for loved ones!
Road Trip Gift Card
Includes:
- A road trip voucher redeemable for one physical road trip including taxes & shipping
- A handy road trip guide
- Beautiful gift box with a slide out enclosure
Road Trip Gift Bundle
Includes:
- One gift card that can be applied to any trip with shipping & taxes included
- Guess Where Trips Tote Bag
- A Road Trip Game Pack
- Red Keepsake Gift Box
Add On: Gift Wrapping
Featuring a sleek magnetic closure, it’s perfect for gifting a surprise road trip - and even better for holding onto the memories afterwards.
More gift guides:
- The Northeast Gift Guide (From DC/Maryland to New England)
- The Midwest Gift Guide
- The Southeast Gift Guide (Florida, Georgia & North Carolina)
- The California Gift Guide
- 7 Great Experience Christmas Gifts
- The Ultimate Guess Where Trips Gift Guide
