Our Favorite Small Towns
1. Hood River, OR
Pat Graham is our luxury cruise advisor, and he lives on a scenic bluff in one of the most adorable towns in North America. Hood River, Oregon is known as the "Windsurfing Capital of the World" — the perfect home base for an adventure traveler like Pat and his wife. It's basecamp for outdoor adventure, agritourism, and craft beverages in the Pacific Northwest, where the river meets the Cascade range. The result is stunning views of Mount Hood at every turn.
We attended a travel show there last spring, and Pat showed us around, including a drive up to the peak of Mount Hood for lunch at Timberline Lodge. Look familiar? If it reminds you of a scene from The Shining, that's because it is one — the lodge was used in the film.
We also enjoyed a bike tour along the historic Columbia River Highway State Trail, a car-free path repurposed from America's first scenic highway. The most iconic stretch, the Hood River to Mosier Twin Tunnels segment, is absolutely stunning.
We ended the day at a lovely wine tasting overlooking the river, where everyone knew Pat by name — and I loved every single wine🍷we tasted.
There is so much history, so many legends, so much to see and do - you should GO! Pat will be happy to help you plan for the best adventure! [email protected]
🍁Ask about our Columbia & Snake River sailings, including Hood River!
2. North Conway, NH
We escaped for a long weekend to North Conway, New Hampshire, for spring break. Tucked into the White Mountains, the town has that classic New England charm we came to love—historic architecture, beautiful mountain scenery, locally owned shops, cozy restaurants, and plenty of places to wander. We wished we had more time.
We centered our stay around the five unique nearby ski slopes and Funspot, the largest arcade in the world! With hundreds of games—including an incredible collection of vintage arcade games—it’s just as much fun for adults who remember playing them as kids as it is for the kids discovering them today. We spent four hours here, had so much fun, and only spent $20!!!
Make a long weekend out of scenic drives, fireplaces and historic inns, shopping, great meals, breweries, and mountain views. Whether you visit for winter skiing, a spring getaway, or New England's spectacular fall colors, it has that rare combination of nostalgia, scenery, adventure, and small-town charm that makes a few days away feel like a real vacation.
3. "Port A" Port Aransas, TX
When my cousin's oldest son was in the Coast Guard, we took our five boys on the 18-hour road trip to Port Aransas, TX. There’s something wonderfully laid-back about Port Aransas, Texas—or “Port A,” as the locals call it.
Getting there is part of the fun: if you arrive from the north through Aransas Pass, you’ll drive right onto the free car ferry for the short ride across the channel, and suddenly vacation mode begins.
Once you're there, golf carts are practically the preferred mode of transportation! As a matter of fact, many vacation rentals include a golf cart. Cruise around town to colorful little shops, boutiques, and galleries, stop for fresh seafood or tacos at one of the casual, locally owned restaurants and bars, and then hop back in the cart and head for the beach. It’s quirky, friendly, and just feels like a beach town should.
We loved the freedom of driving the golf carts on the beach. We carried firewood down in the evening, dug a hole, and had some awesome bonfires on the beach, where the kids enjoyed meeting other teens.
When it's time to call it a day, accommodations range from colorful beach cottages and vacation homes perfect for families to condos, small inns, and full-service beachfront resorts.
If you would like to visit Port Aransas, TX, reach out! We know all the best spots!
PS We stopped at Magnolia 😍 in Waco, TX, on the way there, and the River Walk in San Antonio on the way back. It helped us break up the trip and make the drive worthwhile.
Ready to plan a trip? We would love to hear from you! 🥰
Gather inspiration at IslandTravelGroup.com
Reach out via email at [email protected] or call 217-202-3406.
