Scenic Road Trip from Hollywood, Florida to Virginia Beach, Virginia

Day 1: Hollywood to Savannah

Hollywood, FL to Savannah, GA on May 27, 2025

8:00am

Breakfast at The Field Irish Pub & Eatery

Start your day with a hearty breakfast at this popular Hollywood spot known for classic Irish breakfast fare and comfortable ambiance.
USD20, 1h

9:30am

Drive to Savannah, Georgia

Embark on the drive north via I-95, approximately 6.5 hours covering around 460 miles. Enjoy scenic views and plan for breaks along the way.
USD30 (gas estimate), 6h30m

4:00pm

Check-in at Hyatt Regency Savannah

Settle into your hotel located right on the historic riverfront, perfect for exploring the charming city of Savannah.
USD180, 30m

5:00pm

Explore Savannah Historic District

Wander the picturesque squares and streets lined with Spanish moss and historic architecture; great for photography and light walking.
Free, 2h

7:30pm

Dinner at Mrs. Wilkes' Dining Room

Enjoy traditional Southern cuisine in a family-style dining room that captures Savannah’s culinary heritage.
USD35, 1h30m
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Day 2: Savannah to Charleston

Savannah, GA to Charleston, SC on May 28, 2025

8:00am

Breakfast at Clary’s Cafe

Relish a classic American breakfast with a Southern touch at this bustling local favorite in Savannah.
USD18, 1h

9:30am

Drive to Charleston, South Carolina

Enjoy a scenic 2-hour drive of about 110 miles north along the coast to charming Charleston.
USD12 (gas estimate), 2h

11:30am

Tour Historic Charleston City Market

Explore this vibrant market featuring local crafts, food vendors, and historical exhibits open from 9am to 5pm.
Free to browse, 1h

12:30pm

Lunch at Fleet Landing Restaurant & Bar

Enjoy fresh seafood with river views at this waterfront spot open daily from 11:30am to 9pm.
USD30, 1h

2:00pm

Visit Fort Sumter National Monument

Take a ferry from Liberty Square to Fort Sumter, notable for its Civil War history. Ferry runs 10am-3pm; plan ahead.
USD25, 3h

5:30pm

Check-in at The Vendue

Stay in Charleston's historic French Quarter, offering a boutique art hotel experience.
USD220, 30m

7:00pm

Dinner at Husk

Savor refined Southern dishes prepared with local ingredients at Husk, open for dinner from 5:30pm to 9:30pm.
USD50, 1h30m
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Day 3: Charleston to Richmond

Charleston, SC to Richmond, VA on May 29, 2025

7:00am

Early Breakfast at Toast!

Grab a quick but delicious breakfast known for creative spins on classic dishes, open from 7am.
USD15, 45m

8:00am

Drive to Richmond, Virginia

Enjoy a longer 6-hour drive of approximately 430 miles heading north through scenic landscapes.
USD40 (gas estimate), 6h

2:30pm

Lunch at Perly's – Jewish Deli

Experience unique Richmond flavors with a modern take on Jewish deli classics, open 11am-3pm weekdays.
USD25, 1h

3:30pm

Visit Virginia Museum of Fine Arts

Explore one of the top comprehensive art museums in the US, open from 10am to 5pm, closed on Mondays.
Free, 2h

6:00pm

Check-in at The Jefferson Hotel

Stay at this luxurious historic hotel in Richmond's heart known for architectural beauty and excellent service.
USD250, 30m

7:30pm

Dinner at L’Opossum

Enjoy eclectic French-inspired cuisine in a quirky atmosphere, open for dinner from 5:30pm to 9:30pm.
USD45, 1h30m
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Day 4: Richmond to Virginia Beach

Richmond, VA to Virginia Beach, VA on May 30, 2025

8:00am

Breakfast at Perch Bistro & Bar

Enjoy fresh and casual breakfast fare close to downtown, open from 7am.
USD18, 1h

9:30am

Drive to Virginia Beach

Take a relaxing 2-hour drive east covering about 110 miles towards the coast of Virginia Beach.
USD12 (gas estimate), 2h

11:30am

Visit Virginia Beach Boardwalk

Enjoy a scenic stroll or bike ride along the famous 3-mile boardwalk, featuring shops, art, and ocean views.
Free, 2h

1:30pm

Lunch at Waterman’s Surfside Grille

Savor fresh seafood with views of the ocean at this highly-rated restaurant open daily 11am to 9pm.
USD30, 1h

3:00pm

Explore Back Bay National Wildlife Refuge

Relax with nature walks and bird watching in this peaceful refuge open during daylight hours.
Free, 2h

6:30pm

Check-in at Hilton Virginia Beach Oceanfront

Enjoy oceanfront accommodations perfect for relaxing after your journey.
USD200, 30m

7:30pm

Dinner at Terrapin Restaurant

Dine on upscale American cuisine with a coastal twist in a cozy setting, open until 9pm.
USD50, 1h30m
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