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.
Jump to a section:
- Gifts for Couples
- Gifts for Families
- Gifts for Seniors
- Gifts for Winter Lovers
- Gifts For Everyone
- Spice Up Your Gifts
Bridges & Beauty (Cleveland)
Must love: 🌉 Bridges | 🍷 Wine | 🛍️ Boutiques
Seasons: Year-Round
Along the River (Philly, Trenton, Baltimore, Allentown, PA, Newark, Wilmington, DE, NYC)
Must love: 🏘️ Charming Towns | 🌉 Bridges | 👟 Easy Trails
Seasons: April-November
Waterside Bliss (Washington DC, Baltimore, Alexandria VA)
Must love: 🏖️ Beachfront Boardwalks | 🍷 Wine | 📜 History
Seasons: Spring-Fall
All Things Charming (Chicago, Milwaukee)
Must love: 🏘️ Cute Small Towns | 📜 History | 🦙 Animals
Seasons: Year-Round
Whimsical Wonders (Philly, Trenton, Baltimore)
Must love: 🌸 Picturesque Gardens | 🏘️ Charming Towns | 🧚 Fairytale Stops
Seasons: Year-Round
Mountain Marvels (Atlanta, Chattanooga)
Must love: 🏘️ Small Towns | 🖼️ Quirky Art & Museums | 🍺 Breweries
Seasons: Year-Round
Elegant Estates & Outdoor Art (Indianapolis)
Must love: 🏘️ Adorable Small Towns | 🖼️ Art | 🐔 Farm Animals
Seasons: Year-Round
Antique Adventures (Charlotte, Winston-Salem)
Must love: 🕰️ Antique Shops | 🍷 Wine/Beer | ☕ Bakeries & Cafes
Seasons: Year-Round
Covered Bridges & Baked Goods (Philly, Trenton, Baltimore, Allentown, PA, Wilmington DE)
Must love: 🌉 Bridges | 📜 History | 🥐 Baked Goods, Chocolates, Bread
Seasons: Year-Round
Vibrant Vistas & Picturesque Towns (Hartford, New Haven, Springfield MA)
Must love: 🏘️ Small Towns | 🍺 Beer | 🏞️ Scenic Lookouts
Seasons: Year-Round
Charming Curiosities (Washington DC, Baltimore, Winchester, Alexandria VA)
Must love: 📜 History | 🍺 Brews | 👻 Spooky Stories
Seasons: Year-Round
Waterfall Wanderings (Cleveland)
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
