The Ultimate Summer 2026 "Drive-To" Guide

The best summer stories don't always require a passport or a long-haul flight. For Summer 2026, we're seeing a beautiful shift towards "Close-to-Home Luxury" escapes. We've removed the stress and friction of airport terminals and tight connections and replaced it with either a drive or a short flight so that you maximize your PTO and arrive as your best self. These regional treasures prove that a total reset is just a scenic drive away. I've curated domestic escapes where intentionality meets world-class service, ensuring that your summer is significant, elevated, and sensational! These special offers are available to Pineapple7 clients, so please contact us directly to take advantage of these options. Please note that availability is limited!

The Dunlin, Auberge Resorts Collection, Johns Island, SC

The Dunlin, DUN Dine Willet Room | 📷 Virtuoso

This NEW riverfront retreat on the Kiawah River is the quintessential summer sanctuary. It captures the soul of the Lowcountry with its wrap-around porches and a slow-living pace that is perfect for families looking to unplug together among the marshlands.

• The Offer: 3rd Night Free for 2-night stays (excludes Sat or Sun check-outs)

• Pineapple7 VIP Perks: Upgrade on arrival (subject to availability), Daily Breakfast for two, and a $100 Resort Credit.

Miraval Berkshires Resort & Spa, Lenox, MA

Paddle boarding at Miraval Berkshires, Lenox, MA | 📷Virtuoso

While famous for wellness, Miraval’s summer season is an incredible time for families with older teens to focus on mindfulness and shared growth. Their expansive desert campus offers everything from equine therapy to culinary workshops designed to foster deep connection. It's so much fun at Miraval. It's like summer camp! Go hiking, paddle boarding, zipline. yoga, hang out at the pool. The food is made-to-order delicious and the beds are the most comfortable beds ever!

• The Offer: 5th Night Free + $175 nightly resort credit per person.

• Pineapple7 VIP Perks: Additional $100 Resort Credit, Welcome Amenity, and priority for room upgrades.

Inn at Perry Cabin, St. Michaels, MD

Nestled along the Miles River on Maryland's Eastern Shore, The Inn at Perry Cabin, St Michaels MD | 📷 Virtuoso

Just a short drive across the Bay Bridge (it's taken me 2-hours from Ashburn in non-rush hour traffic), this iconic maritime estate is the gold standard for a Chesapeake summer. Whether you are taking the kids out on a luxury sailing excursion, playing a round of Pete Dye golf, or cracking blue crabs by the water, it is an intentional escape that feels worlds away from the DMV.

• The Offer: 30% Off select 2-night Suite stays or the "Greens & Grandeur" golf package.

• Pineapple7 VIP Perks: $100 Resort Credit per stay, Daily Breakfast for 2, Welcome Amenity

Montage Palmetto Bluff, Bluffton, SC

Guest Rooms lit up at night, Montage Palmetto Bluff, Bluffton, SC | 📷 Virtuoso

Nestled between Hilton Head and Savannah, this sprawling estate is a family favorite for its "Southern Gothic" charm. From roast-your-own s'mores at the fire pits to exploring the river by boat, it is a destination where the schedule is entirely yours to design. You can stay in the main building or larger families and groups can reserve a cottage or home! It's also where Justin Bieber and Hailey Baldwin got married! Reaching Montage Palmetto Bluff is convenient for a getaway. You'll take a quick flight from IAD to Savannah and then you can rent a car or take a taxi to the resort.

• The Offer: Up to 20% off your stay when booking 4 nights or more.

• Pineapple7 VIP Perks: $100 Spa Credit, Daily Breakfast for two, priority for free room upgrade

Pendry Natirar, Peapack, NJ

First look at the Pendry Natirar, Peapack, NJ | 📷 Virtuoso

This NEW historic estate retreat is located an hour outside of Manhattan in Somerset, NJ. The 500 acres include a Tudor-style manor home, an organic farm, and 68 comfortable rooms and suites. Sip cocktails or afternoon tea in the mansion, take a cooking class, relax at the pool, decompress at the spa. It's a 4-hour drive from Ashburn.

• The Offer: 3rd Night Free on select Summer 2026 dates

• Pineapple7 VIP Perks: $100 Credit, Daily Breakfast

Salamander Resort, Middleburg, VA

The NEW RESORT POOL, Salamander Middleburg, VA | 📷 Virtuoso

Heading to VA Wine and Horse Country is the perfect escape for couples, a girls trip, families. Go horseback riding, zipline, relax by the NEW RESORT POOL that just opened (!!), relax at the spa, take a cooking class, visit local wineries (there are 50+ wineries within an hour's drive), and visit with Cupcake, the resident miniature horse. Salamander is a short drive from Ashburn. Fly into IAD and it's a 36-min taxi or Uber.

• The Offer: 4rd Night Free on select 2026 dates

• Pineapple7 VIP Perks: Upgrade on arrival (subject to availability), Daily Breakfast for two, and a $100 Resort Credit.

Schedule your Summer 2026 Discovery Call with Pineapple7 today to lock in these exclusive rates and design your ultimate drive-to adventure.

Grace A Cular Yee is the founder and lead travel strategist at Pineapple7, where she transforms the chaos of modern travel into seamless, intentional exploration. With a focus on bespoke curation and precision logistics, she helps high-achievers reclaim their time and reconnect with the world through meaningful, high-integrity journeys. Ready to plan your next chapter?  Let's start the conversation!