Planning the Perfect Short Summer Getaway

Summer has a way of making even a simple weekend feel significant.

Maybe it's the extra daylight. Maybe it's the collective agreement that work emails can wait until Monday. Or maybe it's the fact that some places simply come alive this time of year. (looking right at you Chicago)

When you're planning a bachelorette weekend, mini-moon, honeymoon, or just looking for an excuse to getaway for a quick weekend, it's easy to default to the usual suspects. The destinations everyone else is booking. The places filling your social feeds.

The kind of places where mornings start slowly with coffee and a waterfront walk. Where dinner reservations turn into sunset cocktails. Where the destination itself sets the tone, and suddenly everyone is lingering a little longer, laughing a little harder, and forgetting to check their phones.

These destinations know how to do summer exceptionally well.

Think sailboats and hydrangeas in Newport. Golden sunsets over Lake Michigan in New Buffalo. Storybook cottages in Carmel-by-the-Sea. Long bike rides and lobster rolls in Nantucket.

Beautiful hotels. Incredible food. The kind of scenery that makes every photo look accidental and every moment feel a little more cinematic.

Because if you're going to celebrate a once-in-a-lifetime season, you might as well do it somewhere unforgettable.

🌊 Newport, Rhode Island for Coastal New England Charm

Photo Credit: Cliffside views at The Chanler at Cliff Walk 

If summer had a dress code, Newport would be responsible for it.

This is the kind of place where sailboats drift across the harbor, hydrangeas spill over white picket fences, and every corner feels pulled from a Nancy Meyers mood board. Equal parts historic and effortlessly polished, Newport delivers all the East Coast summer energy without requiring a passport.

Spend your days:

Exploring Newport's Gilded Age mansions

Walking the iconic Cliff Walk with an iced coffee from The Nitro Bar in hand

Chartering a sailboat for sunset on Narragansett Bay

Shopping along Thames Street for coastal-inspired finds. Lunch at the iconic White Horse Tavern to soak up it’s history.

Lingering over lobster rolls and chilled rosé by the water at The Grill at Forty1North.

& it wouldn’t be a trip to Newport without a sunset at the iconic Castle Hill Inn

The pace here feels intentionally slower. Mornings stretch long, afternoons disappear on sunny patios, and evenings are best spent watching the boats come back into harbor.

It's classic New England summer at its absolute best.

Perfect For:
The bride who owns multiple striped sweaters. Coastal grandmothers in training. The group that loves a little history with their Aperol spritz.

Where to Stay:
The Chanler at Cliff Walk for an ultra-romantic splurge or Hotel Viking for classic Newport charm.

⛵ New Buffalo, Michigan for a Lake Michigan Escape

Dine waterside Harbor Grand’s Terrace Room

Sometimes the best getaways aren’t on the opposite end of a flight.

Less than 2 hours from Chicago, with a Metra stop that parks you in the heart of town, New Buffalo is full of new energy. Once an untapped sleepy town, new development delivered beach-town energy with boutique hotels, a James Beard nominated chef, and some of the best sunsets in the Midwest.

This is the destination for groups who want something easy without sacrificing charm.

Spend your days:

Shopping your way through downtown, grabbing souvenirs from Lakeside Goods and Eastern Standard Time to your to-do list. 

Dining al fresco at PostBoy, drinks to follow at Beer Church.

Reading your favorite summer romance with your toes in the sand.

Taking in a Lake Michigan sunset at Bentwood Tavern.

Exploring nearby antique shops and farmers markets. Farmette is a must and beach sandwiches at Whistle Stop in nearby Union Pier are well worth the 20 minute drive.

There's something refreshing about a trip that doesn't require a complicated itinerary. The lake does most of the work for you.

Simple. Relaxed. Surprisingly romantic.

Perfect For:
Chicagoans short on time. The group that values quality time over packed schedules. Sunset chasers.

Where to Stay:
The Neighborhood Hotel New Buffalo for a dog friendly weekend or Harbor Grand for a little luxury and waterfront views.

The patio at PostBoy also features a walk-up window for quick bites.

🌿 Carmel-by-the-Sea, California for Storybook Romance

The lobby at Le Petite Pali Carmel

Some destinations feel curated. Carmel feels enchanted.

Tucked along California's rugged coastline, this seaside village is full of winding pathways, ivy-covered cottages, art galleries, and white-sand beaches.

It feels like someone designed an entire town with one word in mind: WHIMSY.

Spend your days:

Driving the iconic 17-Mile Drive with a stop to see the bagpipers at The Inn at Spanish Bay

Dining alongside sheep at Clint Eastwood’s Mission Ranch

Breakfast at Katy’s Place before leisurely shopping through local galleries and boutiques

Golfing at Pebble Beach followed by fireside drinks at The Bench.

Exploring nearby Big Sur's dramatic coastline, stopping for photos at Bixby Bridge.

The beauty here isn't flashy. It's subtle. Thoughtful. The kind of destination that sneaks up on you and becomes everyone's favorite trip.

Perfect For:
The romantics. The creative types. The couple who'd rather spend the day wandering than rushing between reservations.

Where to Stay:
L'Auberge Carmel for European-inspired luxury or Le Petit Pali, perfect for the interiors enthusiast.

⚓ Nantucket for the Ultimate Summer Fantasy

The terrace at Faraway Nantucket

There are beach destinations, and then there's Nantucket.

Everything here feels like summer turned all the way up: weathered cedar shingles, sailboats bobbing in the harbor, bicycles lined up outside cafés, and enough hydrangeas to make your camera roll beg for mercy.

It's the epitome of coastal elegance and it lives up to all the hype.

Spend your days:

Biking to Siasconset through flower-lined streets. 

Live music at Cisco Brewers.

Taking a boat excursion with Endeavor Sailing around the island

Eating Blue Crab Fried Rice from Nautilus and late night eats at The Brotherhood of Thieves

Beach hopping, alternating between the famous Step’s Beach, Fisherman’s Beach and Miacomet Beach

Nantucket Bookworks to pick up an iconic Elin Hildebrand summer read.

Nantucket somehow manages to feel both luxurious and laid-back. It's polished, but never pretentious.

The kind of place where everyone immediately starts talking about coming back next year.

Perfect For:
The coastal chic crowd. The summer dinner party aficionado.  Wishbone Kitchens in training. The hydrangea chasers.

Where to Stay:
Greydon House or Faraway Nantucket , both offering boutique charm in the heart of town.

Photo: Jennifer Lake of Style Charade. Find her guide to Nantucket here.