It sounds like you’re planning a fantastic getaway for a group of 10. Let’s create an ideal 5-day itinerary in a charming, walkable town. I’ll suggest a destination that fits your criteria: Savannah, Georgia. It’s known for its beautiful historic district, boutique hotels, and walkable streets. Here’s a fun and engaging itinerary for your group!

Day 1: Arrival and Exploring the Historic District

Morning:

• Arrive in Savannah and check into your boutique hotel. I recommend The Gastonian or The Brice Hotel for their charm and great locations.

Afternoon:

• Grab lunch at Mrs. Wilkes’ Dining Room for a true Southern experience. Be prepared to wait, but it’s worth it!
• After lunch, take a leisurely stroll through the historic district. Don’t miss Forsyth Park with its iconic fountain and beautiful oak trees.

Evening:

• Dinner at The Grey, a trendy restaurant in a restored Greyhound bus station. Make a reservation to ensure you get a table!
• After dinner, enjoy a ghost tour to explore Savannah’s spooky history. It’s a fun way to bond with your group!

Day 2: Art and Culture

Morning:

• Start your day with breakfast at Collins Quarter, known for its Australian-inspired menu.
• Visit the Savannah College of Art and Design (SCAD) Museum of Art to appreciate contemporary art.

Afternoon:

• Lunch at The Collins Quarter again or try B Matthew’s Eatery for a cozy vibe.
• Spend the afternoon exploring the River Street area. Check out the shops, galleries, and the beautiful views of the Savannah River.

Evening:

• Dinner at Cotton & Rye, a farm-to-table restaurant with a great atmosphere.
• After dinner, enjoy some live music at The Jinx or The Wormhole, both popular local spots.

Day 3: Day Trip to Tybee Island

Morning:

• After breakfast at your hotel, take a short drive (or arrange a shuttle) to Tybee Island.
• Spend the morning at the beach! Relax, swim, or take a walk on the pier.

Afternoon:

• Have lunch at The Crab Shack for a casual, seafood-filled experience.
• Visit the Tybee Island Light Station and Museum to climb the lighthouse and enjoy stunning views.

Evening:

• Head back to Savannah and freshen up.
• Dinner at The Olde Pink House, a historic mansion turned restaurant. Make sure to try their Southern specialties!
• If you’re up for it, take a night stroll through the historic district to see the beautiful homes lit up.

Day 4: History and Shopping

Morning:

• Breakfast at The Breakfast Club on Tybee Island (if you want to revisit) or back in Savannah at Clary’s Cafe.
• Visit the Savannah History Museum to learn about the city’s rich past.

Afternoon:

• Lunch at The Public Kitchen & Bar for a relaxed atmosphere.
• Spend the afternoon shopping at the boutiques along Broughton Street. Don’t forget to check out the local artisan shops!

Evening:

• Dinner at The Florence, a trendy spot with a great vibe.
• After dinner, consider a riverboat cruise for a unique view of Savannah at night. It’s a lovely way to wrap up the day!

Day 5: Relax and Reflect

Morning:

• Enjoy a leisurely breakfast at your hotel or at Back in the Day Bakery for some delicious pastries.
• Take a final stroll through Chippewa Square and snap some group photos!

Afternoon:

• Have a farewell lunch at The Grey Market, a casual spot with great sandwiches.
• Spend your last few hours visiting any spots you may have missed or simply relax in one of the parks.

Evening:

• Head back to your hotel to pack up and check out.
• If time allows, grab a final drink at The Rooftop at The Peregrin for stunning views of the city before you depart.

And there you have it! A delightful 5-day itinerary in Savannah that balances relaxation, exploration, and plenty of delicious food. Enjoy your trip with your group! If you have any specific interests or adjustments, feel free to let me know!