DISCOVER

Was it catching fireflies with your Uncle Joe or was it watching your mom performing a picture perfect cannon ball to the applause of the family? Was it the late night laughter you heard between your parents and your aunts and uncles as you listened through the screened windows and cool summer breeze? Was it a time when you heard stories from your grandfather that taught you that he was once a boy too? These gatherings are where so many of the memories that hold the tapestry of our lives and family identities together.

If only we had understood the effort and planning that goes into them when we were kids, perhaps our gratitude might have been a bit more boldly expressed. Here is what we can do – we can make them happen for the next generation, aware that we too need that time with those who have known us the longest – away from the obligations of our everyday, where we all set aside our worries and enjoy each other. Did you only dream of these leisurely vacations as a kid, and want to make these memories for your own family? We certainly understand that and are here to lend a hand.

We know families come in all sizes and personalities, but we took have an approach that can make the planning lift a little lighter – and a few destination ideas that we can share! We’re all about community, connection, fun, great times, memories, and discovery here at MoxieTowns, and we know a thing or two about planning trips.

*Photo cred: Federico Giampieri @ unsplash*

Set a Date!

Setting a date months ahead will save you so many headaches – but we still love a spontaneous excursion! Pay attention to school schedules. This is important even if you are in a season without school-age children. Taking advantage of shoulder seasons and the week of finals can assure that you get that cottage with a view of the lake. We love using Doodle for getting a date on the calendar if your group is sizable! Are you having trouble getting everyone to commit to a week? Sometimes a 4-day long weekend can fit more readily onto today’s packed schedules.

Start with a Family Huddle (Yes, Really!)

Once you find dates that work for the fam, gather your crew—virtually or in person—and ask: What does everyone want from this trip? Grandpa may dream of a hike near a trout stream, the little ones might vote for pool time, and you? Maybe you’re eyeing the spa menu. By letting everyone share their “must-dos,” you set the stage for a getaway where every voice matters. It is also a great way to set expectations!

Since you are tasked with planning, stir up the conversation as. you suggest some meals where everyone gathers and knows what to expect in advance. Perhaps the inn can arrange a BBQ buffet by the pool one evening or book a special dinner at the town's favorite restaurant. Get everyone’s buy-in before you even crack open that travel app!

We put together a little questionnaire to help you get the answers back in workable order. Download it below. Tech Tip: If you are on the techie side, you can drop in Google Forms and collect your answers there!

Download form here

Gather your tribe’s requirements for accommodations

Book suites, cottages, or adjoining rooms so everyone can gather for morning coffee or share late-night stories, while also enjoying some solo downtime. Accessibility matters too—make sure grandparents and little ones can navigate the space easily.

Is this the year the kids move into an adjacent room? Does your younger sister need a crib for her newborn? Are the stairs becoming a challenge for your grandfather? You will need all of this when you identify your destination. You will find that the best destinations to choose will be those where the inn’s manager knows each room like the back of their hand.

Once you have a list of who is coming and their needs organized, you can hand it off to your new best friend, the inn manager, and benefit from that inside expertise to make everyone happy!

Choose a Destination That Wins Everyone’s Heart

While we know there are big city destinations and all-inclusive resorts – our heart lies with the magic you find in a small town inn, or a historic resort in the countryside near one of our small town treasures. Most of these destinations have a long history of blending adventure and leisure.

Look for places with:

Spacious common areas for gathering, playing games and drinking your morning coffee – front porches can do the trick!
Pools, spas, and cozy corners for unwinding
Biking and hiking trails, lakes, and creeks, or zip lines for your adrenaline junkies
Golf, tennis, & pickle ball courts for your competitive ones
Playgrounds, game rooms, and kid clubs for the young (and young at heart)
Charming downtowns for strolls, shopping, and local bites
Local entertainment such as summer theaters, concerts at the amphitheater, or a local live music joint

Make sure everyone can get there with ease

This becomes more complicated when gathering people from all over. Consider that some will be driving, others flying in. Choosing a place that accommodates all of these, easily and affordably, is ideal. If you and your tribe are from the same region, this is much easier as everyone will likely be traveling using the same means.

Small towns and the resorts located there are usually remarkably walkable and bikeable, making it easy to stay out of the car. Public transport is usually not readily available, so fortunately, one of the delights of small towns is that parking and traffic typically aren’t a challenge.

Make Friends with the Hotel Manager (Your Secret Weapon!)

As we mentioned earlier, your relationship with the hotel manager or group coordinator begins when you book, and it continues well before you arrive. These hospitality heroes are the keepers of local secrets and can help you:

Reserve the best tables for family meals
Book spa appointments, tee times, or kids’ club spots in advance
Suggest off-the-beaten-path adventures or quiet picnic spots
Arrange for a professional family photographer
Solve last-minute hiccups with a smile

The more information that you can provide in advance will help you and the hospitality team ensure a fabulous getaway. Think of them as your family’s vacation fairy godparent!

MoxieTowns Pro Tips for Family Bliss

Book ahead: Spa treatments, kids’ clubs, and special dinners fill up fast—your hotel manager can help!

Ask about local events: Festivals, farmers markets, and outdoor concerts are the heartbeat of small towns.

Capture the moments: Assign a family “photojournalist” each day for a fresh perspective (and fewer group selfies). Hire a professional photographer for those timeless portraits where everyone looks their best.

Leave room for serendipity: The best small-town stories start with, “We just wandered in and…”

Ready to Plan Your Next Family Adventure?

Looking for some small-town ideas? These first picks will get you started!

Barrows Inn & Restaurant

Dorset, Vermont

This is one of our favorite small towns for family getaways as everything is so close and walkable and yet for such a small town there’s something from almost every appetite. A heated, saltwater pool, exceptional dining, live music on the patio and coffee on the front porch - and that is for starters. Flying into Albany, NY makes it accessible for those outside of driving distance. The inn owners run two inns in this small town and have a few historic homes that can remarkably hold a good size extended family.

We visited this inn last year so check out the blog here.

Horseshoe Farm Inn

Hendersonville, North Carolina

Right outside of Hendersonville, NC, this 85-acre destination even comes with a family reunion package for a party of 15 or more! A spa, outdoor games, excellent dining, are just appetizers. Close to Asheville, Charlotte, and a reasonable drive from the Atlanta metro, this one may have your name on it!

The Omni Homestead Resort

Hotsprings, Virginia

This sprawling resort in the Allegheny Mountains of Virgina has just received a massive renovation. Offering rooms and amenities to meet every appetite you can imagine, the inn has been welcoming guests for over 250 years. Whether your family is focused on sports or sunning by the pool, or tooling around the charming town of Hot Springs, we are betting you will be able to meet everyone’s “must have” desires here.