The Real Chic Life

Late summer is that magical stretch where the days are still long and warm, but there’s a subtle shift in the air hinting at autumn. It’s a perfect time to slow down, soak in golden sunsets, and take a quick escape before fall routines fully set in. I’m planning to head back to my hometown for a weekend beach trip. If you’re also craving a last splash in the ocean, a peaceful countryside retreat, or a chic city break, these getaway ideas will help you make the most of the season’s final weeks.

1. A Coastal Cottage Escape

There’s something about late summer by the sea—crowds thin, the water is at its warmest, and the sunsets are pure magic. Book a charming coastal cottage where you can sip coffee on the porch, stroll the beach barefoot, and collect shells in the quieter morning hours. Or if you have a beach nearby, plan a fun day trip. Bonus points if you pack a basket for a sandy, seaside picnic.

Chic spots:

• Cape Cod, Massachusetts

• Martha’s Vineyard, Massachusetts (check out our recent guide to Martha’s Vineyard here).

• Tybee Island, Georgia

• Cannon Beach, Oregon

2. A Vineyard Weekend

Harvest season is just beginning in many wine regions, which means late summer is prime time for wine tasting and vineyard strolls. Sip chilled whites or bold reds as you wander rows of sun-drenched grapes, then enjoy an alfresco dinner under the stars.

Chic spots:

• Sonoma County, California

• Willamette Valley, Oregon

• Finger Lakes, New York

• Charlottesville, Virginia

3. A Lakeside Cabin Retreat

If you’re craving peace and stillness, a late summer cabin getaway by a lake is perfect. Spend your days kayaking, swimming, or simply lounging on the dock with a good book. Evenings are for grilling fresh fish and toasting marshmallows by a campfire.

Chic spots:

• Lake Tahoe, California/Nevada

• Lake Winnipesaukee, New Hampshire

• Flathead Lake, Montana

4. A Chic City Staycation

Cities often quiet down in late summer, making it an ideal time for exploring museums, rooftop bars, and hidden neighborhood gems. Treat yourself to a boutique hotel stay, dinner at a new restaurant, and an afternoon wandering art galleries or vintage shops.

Chic spots:

• Charleston, South Carolina

• Austin, Texas

• Chicago, Illinois

• Nashville, Tennessee

5. A Mountain Escape

Late summer in the mountains means cooler nights, crystal-clear skies, and trails still lush with greenery. Go hiking during the day, then cozy up by a firepit with hot chocolate in the evenings.

Chic spots:

• Asheville, North Carolina (Blue Ridge Mountains)

• Jackson Hole, Wyoming

• Lake Placid, New York

6. A Spa & Wellness Getaway

If your summer has been non-stop, unwind with a trip centered around self-care. Book a spa resort where you can enjoy massages, saunas, yoga classes, and nourishing meals. Late summer’s slower pace makes it easier to truly relax.

Chic spots:

• Sedona, Arizona

• Ojai, California

• Palm Springs, California

• Berkshires, Massachusetts

7. A Historic Town Wander

Spend a weekend in a charming small town filled with cobblestone streets, antique shops, and centuries-old architecture. Late summer light makes every building look like it belongs on a postcard.

Chic spots:

• Savannah, Georgia

• St. Augustine, Florida

• Newport, Rhode Island

• Williamsburg, Virginia

8. A Garden & Flower Tour

Late summer blooms—think dahlias, sunflowers, and hydrangeas—are spectacular. Visit botanical gardens, flower farms, or countryside estates for a colorful, fragrant getaway.

Chic spots:

• Skagit Valley, Washington

• Longwood Gardens, Pennsylvania

• Nantucket, Massachusetts

9. A Road Trip Along Scenic Byways

The heat has mellowed and the roads are less crowded—perfect for a spontaneous road trip. Pack snacks, queue up a great playlist, and explore scenic drives dotted with farmer’s markets, fruit stands, and small-town diners.

Chic spots:

• Pacific Coast Highway, California

• Blue Ridge Parkway, North Carolina/Virginia

• Great River Road, Mississippi River

10. An Island Escape

Before fall schedules take over, treat yourself to a few days on island time. Swim, snorkel, lounge on the sand, and watch the sun melt into the horizon.

Chic spots:

• Block Island, Rhode Island

• Mackinac Island, Michigan

• Kauai, Hawaii

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Tips for Planning a Late Summer Getaway:

• Book mid-week for better rates and fewer crowds.

• Pack layers—nights can be cooler even if days are warm.

• Embrace local, seasonal flavors—look for popular local restaurants and hidden gems.

• Take photos in golden hour—late summer light is famously flattering.

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Late summer is the season’s soft landing—a moment to pause and savor before autumn’s busyness really sets in. Whether your idea of relaxation is sipping wine in the hills or swimming in the sea, now is the time to make those lingering summer memories.

Do you have a favorite late summer getaway location? Let us know in the comments.

Xo, Courtney