Farewell to Summer: Family Getaways Before School Starts
Before the routines, homework, and packed schedules begin, there's still time for one more adventure. The best end-of-summer trips don't require weeks of planning—they're close enough for a long weekend, easy enough with kids, and memorable enough to make summer feel complete.
1.
A Weekend on the Waterfront
Tailored for: Families looking for a relaxing, low-key getaway that balances outdoor fun with plenty of time to simply be together.
There's something about being near the water that instantly slows the pace. Whether it's a charming coastal town, a lakefront resort, or a harbor city, a waterfront getaway is the perfect way to squeeze in one last family adventure before school begins.
Spend the days renting bikes, strolling along a boardwalk, building sandcastles, kayaking, or simply watching boats drift by. In the evenings, enjoy fresh seafood, hunt for ice cream, and end the day with a sunset walk along the shore. It doesn't have to be a big vacation—sometimes a simple weekend away is all it takes to make summer feel complete.
A Few Getaways to Consider -
St. Michaels, Maryland
Where I’d Stay: Inn at Perry Cabin
A charming harbor town on Maryland’s Eastern Shore with sailing, bikes, seafood, and an easygoing waterfront pace. The Inn at Perry Cabin makes the weekend feel special without requiring a packed itinerary.Duck, North Carolina
Where I’d Stay: Sanderling Resort
For a classic beach weekend, The Outer Banks offers wide beaches, bike paths, water sports, and an easy walkable town. The Sanderling Resort gives you the simplicity of an oceanfront resort while still feeling relaxed and family-friendly.Sea Island, Georgia
Where I’d Stay: The Cloister at Sea Island
If you want the full resort experience, Sea Island combines beach time with pools, bikes, boating, children's activities, and plenty for adults to enjoy as well. The kind of place where the resort itself becomes the vacation.Carmel, Monterey & Big Sur, California
Where I’d Stay: Carmel Valley Ranch
Use Carmel as a home base for exploring California’s Central Coast. Spend time in Carmel-by-the-Sea, visit the Monterey Bay Aquarium, explore the coast, and take a scenic drive toward Big Sur. Carmel Valley Ranch adds the family-resort element with pools, outdoor activities, and plenty to do between coastal adventures.Rent a Beach or Lake House
Simply head to the beach town or lake closest to home and settle into a beach house or lake house for a long weekend by the water. A waterfront getaway doesn’t have to be elaborate - the goal is simply to find somewhere that lets your family slow down for one last stretch of summer.
2.
A Historic Town or City
Tailored for: Families who enjoy walkable destinations, local restaurants, unique shops, and creating memories through slow, intentional travel rather than a packed schedule.
Some of the best family trips aren't built around theme parks or packed itineraries—they're built around simply wandering. A weekend in a charming historic town offers the chance to slow down, explore at your own pace, and discover the character that makes each destination unique.
Spend your days strolling brick-lined streets, browsing locally owned bookstores and boutiques, hunting for antiques, visiting museums or historic homes, enjoying outdoor cafés, and letting the kids run through town squares or waterfront parks. Many historic towns also host seasonal festivals, farmers markets, and live music, making each visit feel a little different.
The beauty of these destinations is that there isn't a checklist. You can linger over breakfast, stop whenever something catches your eye, and end the day with dinner at a local restaurant before taking one last evening walk through town.
A Few Getaways to Consider -
Middleburg, Virginia
Where I’d Stay: Salamander MiddleburgSet in Virginia’s horse and wine country, Middleburg pairs a charming historic downtown with a true luxury resort experience. Salamander Middleburg sits on 340 acres just outside town and offers horseback riding, pools, hiking and biking, ziplining, lawn games, a children’s camp, and a full-service spa. Spend part of the day wandering Middleburg’s brick-lined streets and boutiques, then retreat to the resort for an afternoon by the pool or an evening around the fire pits.
Williamsburg, Virginia
Where I’d Stay: Williamsburg Inn
Williamsburg is an easy choice for families because the history itself becomes part of the entertainment. Stay at the Williamsburg Inn and spend the day exploring Colonial Williamsburg before returning to the resort for the pool, spa, golf, or a slower afternoon on property. It gives you the charm of a historic getaway with the amenities of a true luxury resort.Newport, Rhode Island
Where I’d Stay: The Vanderbilt, Auberge Resorts Collection
Newport combines Gilded Age history with everything I love about a coastal New England getaway. Tour the mansions, wander the historic streets, walk along the harbor, and spend an afternoon on the water. The Vanderbilt is a historic mansion itself, right in downtown Newport, which makes it a beautiful home base for exploring the city on foot.Charleston, South Carolina
Where I’d Stay: Zero George Street
Charleston is perfect for a weekend built around simply exploring—historic homes, beautiful architecture, great restaurants, shopping, and plenty to see on foot. Zero George Street feels especially fitting for this kind of trip because the hotel itself is part of the historic experience, set within restored early-1800s residences and carriage houses surrounding a quiet courtyard. From there, you can walk or borrow one of the hotel’s bikes to explore downtown Charleston before returning for an evening on the piazza.Woodstock, Vermont
Where I’d Stay: Woodstock Inn & Resort
Woodstock has everything you picture when you think of a charming New England town: historic buildings, covered bridges, locally owned shops, farms, and beautiful countryside. Woodstock Inn sits right in the village, and families can bike around town, visit Billings Farm, hike nearby trails, swim, play games, and finish the evening with s’mores by the fire.Mackinac Island, Michigan
Where I’d Stay: Grand Hotel
With no cars, horse-drawn carriages, bikes, Victorian architecture, and views over the Great Lakes, Mackinac Island makes the trip itself feel like stepping into another time. Grand Hotel adds to the experience with its famous porch, pool, mini golf, bikes, lawn games, and plenty of family activities—which makes this one especially fun with kids.Santa Fe, New Mexico
Where I’d Stay: Rosewood Inn of the Anasazi
Santa Fe gives this list something completely different, with centuries of history, adobe architecture, art galleries, Southwestern food, and the historic Plaza at the center of it all. Rosewood Inn of the Anasazi sits just steps from the Plaza and makes it easy to explore the city on foot or by bike while still giving you an intimate, beautifully designed luxury hotel to come back to.
3.
A Mountain Escape
Tailored for: Families looking for fresh air, outdoor adventure, and a slower pace—with the flexibility to make the trip as simple or as luxurious as they want.
Trade busy schedules for fresh air, mountain views, and a slower pace. A mountain escape is an easy way to squeeze in one last summer adventure before school starts, whether that means checking into a full-service resort or renting a cabin somewhere close to home.
Spend the day hiking, horseback riding, swimming, biking, fishing, or exploring a nearby mountain town. At a resort, you may have pools, kids’ activities, great dining, and plenty to do without ever leaving the property. In a cabin, the experience can be much simpler—morning coffee on the porch, afternoons outside, board games after dinner, and s’mores around the fire.
What I love about this kind of trip is that it can be as active or as relaxed as you want it to be. You can fill the day with adventure or do very little at all, and either way, the setting naturally encourages everyone to slow down and spend more time together.
A Few Mountain Escapes to Consider -
Blue Ridge Mountains, Virginia
Where I’d Stay: The Lodge at Primland, Auberge Collection
Primland feels like the kind of place where you could arrive for a long weekend and barely need to leave the property. Set on 12,000 acres in the Blue Ridge Mountains, there’s hiking, horseback riding, fishing, archery, and even stargazing at the resort’s observatory. It still feels special for the adults, too, with beautiful dining, a spa, and incredible mountain views.
Park City, Utah
Where I’d Stay: Montage Deer Valley
Park City is just as fun in the summer as it is during ski season. Spend the day hiking, mountain biking, horseback riding, or exploring town, then head back to the resort for an afternoon by the pool. I especially love that Montage has Daly’s Pub & Rec with bowling and games - it makes the resort feel genuinely fun for kids, not just beautiful for adults.
Lake Tahoe, California
Where I’d Stay: The Ritz-Carlton, Lake Tahoe
Lake Tahoe is a great choice if you can’t decide between a mountain trip and a waterfront getaway. Hike in the morning, then spend the afternoon swimming, kayaking, or paddleboarding at the lake. The Ritz-Carlton gives you the mountain resort experience while still making it easy to enjoy everything that makes Tahoe so special in the summer.
Big Sky, Montana
Where I’d Stay: Montage Big Sky
If you want the trip to feel like a true Western adventure, Big Sky is hard to beat. Families can spend their days hiking, biking, horseback riding, fly-fishing, or simply taking in the scenery, and Yellowstone is close enough for a day trip. Back at the resort, the pool and children’s programming give everyone a chance to slow down after a full day outside.
Or keep it simple with a cabin.
Rent a cabin in the mountains within a few hours of home and build the weekend around hiking, scenic drives, swimming, local towns, and slow evenings on the porch. You don’t need a full-service resort to get the feeling of a mountain escape - sometimes a cozy cabin, a fire pit, and a beautiful view are enough.
4.
Cruise from a Nearby Port
Tailored for: Families who want an easy getaway with plenty to do, minimal day-to-day planning, and something for everyone in the family.
If you want one last trip without a lot of planning, a short cruise can be an easy way to fit in a getaway before school starts. Once you’re on board, your room, meals, entertainment, and activities are all in one place, which takes a lot of the logistics out of traveling with kids.
Look first at the cruise ports within driving distance—or an easy direct flight—from home. Depending on where you live, that might mean Port Canaveral, Fort Lauderdale, or Miami in Florida; Galveston, Texas; Baltimore, Maryland; the New York/New Jersey area; San Diego or Los Angeles in California; or Seattle, Washington. Sailings vary by season, but many major ports offer shorter itineraries that work well for a long weekend or quick family getaway.
Spend the day by the pool, catch a show, join a family activity, or simply relax while the ship takes you to the next stop. Depending on the itinerary, you might spend a day at a beach, visit a private island, explore a new port, or enjoy a full day at sea.
If you’re considering Disney Cruise Line, I especially recommend 4-night cruises for this kind of trip. They’re long enough to feel like a real vacation without requiring a full week away, and there is so much built into the ships for both kids and adults. Disney currently offers short Bahamian sailings from Florida, including 4-night cruises from Port Canaveral and 4-night options from Fort Lauderdale, with destinations such as Nassau, Castaway Cay, and Lookout Cay depending on the itinerary.
A shorter sailing is also a great way to try cruising for the first time and see whether it fits your family’s travel style before committing to a longer itinerary.
5.
Your Own City Bucket List
Tailored for: Families who want the excitement of a city getaway without a long travel day - and anyone who has a running list of local museums, restaurants, games, and experiences they’ve been meaning to finally try.
You don’t have to travel far to fit in one last adventure before school starts. If you live in or near a major city, consider spending a weekend experiencing it the way you would if you were visiting for the first time.
Book a hotel downtown, leave the errands and chores at home, and build a mini itinerary around the things you rarely make time for in everyday life. Go to a baseball game, spend a morning at a museum, take a boat or sightseeing tour, explore a neighborhood you don’t usually visit, and make reservations somewhere you’ve been wanting to try. Let the kids choose an activity or two and turn the weekend into your own family bucket list.
And if you don’t live in a big city, make a staycation out of the closest one. A night or two at a centrally located hotel can give you enough time to pack several experiences into one weekend without the expense or logistics of a bigger vacation.
Sometimes the places closest to home are the ones we put off exploring the longest—and looking at a familiar destination through the eyes of a visitor can make it feel surprisingly new.
One last summer trip doesn’t have to be elaborate—or even take you very far from home. Whether you check into a beautiful resort, rent a cabin for the weekend, board a short cruise, or finally explore your own city like a visitor, the goal is simply to carve out a little more time together before the routines of the school year begin.