Family Road Trip from Florida to Connecticut with Beach and City Adventures

Day 1: Miami Exploration

Miami, Florida on June 25, 2025

9:00AM

Breakfast at Big Pink

Enjoy a hearty breakfast with family-friendly portions and classic American dishes in Miami Beach. Opens at 8AM, perfect to start the day.
USD20pp, 1h

10:30AM

Visit Miami Seaquarium

Explore marine life with shows and exhibits; ideal for kids to learn about dolphins, sea turtles, and more. Open from 10AM to 5PM.
USD50pp, 3h

2:00PM

Lunch at La Sandwicherie

Grab a quick and fresh French-style sandwich, popular for light tasty meals before continuing the day. Open till 10PM.
USD15pp, 1h

3:30PM

Stroll along Miami Beach Boardwalk

Enjoy a relaxing walk along the scenic boardwalk, great for family photos and sunset views.
Free, 2h

6:00PM

Dinner at Joe's Stone Crab

Savor famous stone crab claws and fresh seafood in a family-friendly setting, available from 5PM onward.
USD60pp, 1.5h
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Day 2: Scenic Drive and Savannah Arrival

Miami, Florida to Savannah, Georgia on June 26, 2025

7:30AM

Early Breakfast at hotel or local café

Fuel up early with breakfast to begin the road trip north. Consider fresh fruit, bagels or eggs.
USD15pp, 1h

8:30AM

Drive from Miami to Savannah

Start the scenic 6.5-hour drive north, taking breaks at rest stops or small towns along the coast.
Gas approx. USD50, 6h30m

3:30PM

Check into Savannah accommodation

Settle in and get refreshed after the long drive.
Varies, 30m

4:00PM

Walk around Savannah Historic District

Discover charming cobblestone streets, beautiful squares, and historic homes — a perfect family stroll.
Free, 2h

6:30PM

Dinner at Mrs. Wilkes' Dining Room

Enjoy traditional Southern cooking served family-style in a welcoming atmosphere. Open until 7PM.
USD30pp, 1.5h
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Day 3: Savannah and Charleston

Savannah, Georgia to Charleston, South Carolina on June 27, 2025

8:00AM

Breakfast at Collins Quarter

Taste Australian-inspired breakfast with coffee specialties, open at 7AM.
USD20pp, 1h

9:30AM

Visit Savannah Riverfront

Explore the lively riverfront area with shops, street performances, and river views.
Free, 1.5h

11:00AM

Drive to Charleston

Begin the 2-hour scenic drive towards Charleston, enjoying picturesque Lowcountry landscapes.
Gas approx. USD15, 2h

1:00PM

Lunch at Fleet Landing Restaurant & Bar

Eat fresh seafood with views of Charleston Harbor, open 11AM-9PM.
USD30pp, 1h

2:30PM

Explore Charleston Historic District

Visit historic sites including Rainbow Row and Waterfront Park, perfect for family exploration.
Free to walk, 3h

6:30PM

Dinner at Poogan's Porch

Enjoy Southern cuisine in a cozy heritage house open till 9PM.
USD40pp, 1.5h
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Day 4: Charleston to Washington D.C.

Charleston, South Carolina to Washington D.C. on June 28, 2025

7:00AM

Early Breakfast at Callie's Hot Little Biscuit

Try famous Southern biscuits with variety of fillings, open from 7AM.
USD10pp, 30m

7:45AM

Long Drive to Washington D.C.

Prepare for approximately 7-hour drive with breaks for food and stretch.
Gas approx. USD60, 7h

3:00PM

Check-in and Rest

Arrive and unwind at Washington D.C. accommodation.
Varies, 30m

3:30PM

Visit the National Mall and Monuments

Explore landmarks such as the Lincoln Memorial, Washington Monument; open outdoor spaces, great for families.
Free, 3h

7:00PM

Dinner at Founding Farmers

Locally sourced American cuisine suitable for families, open until 10PM.
USD35pp, 1.5h
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Day 5: Washington D.C. Museums

Washington D.C., USA on June 29, 2025

8:00AM

Breakfast at the accommodation or local café

Grab a quick breakfast to prepare for a full day of exploring museums.
USD15pp, 1h

9:00AM

Visit Smithsonian National Air and Space Museum

Discover aviation and space exploration exhibits; perfect for family interest. Open 10AM-5:30PM.
Free, 3h

12:30PM

Lunch at Mitsitam Native Foods Café

Enjoy unique Native American dishes inside the National Museum of the American Indian, open 10AM-5PM.
USD20pp, 1h

1:45PM

Visit National Museum of Natural History

Explore dinosaur skeletons, oceans, and gems; open 10AM-5:30PM.
Free, 2.5h

4:30PM

Relax at the hotel or visit local park

Rest before dinner or have light outdoor activity.
Free, 1.5h

7:00PM

Dinner at Carmine’s

Family-style Italian dining great for groups, open till 10PM.
USD40pp, 1.5h
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Day 6: Travel to Westport, Connecticut

Washington D.C. to Westport, Connecticut on June 30, 2025

7:30AM

Breakfast at hotel

Start the day early with breakfast before hitting the road for Connecticut.
USD15pp, 1h

8:30AM

Drive to Westport, Connecticut

Approximately 5.5-hour drive northeast to the family’s accommodation, including breaks.
Gas approx. USD40, 5h30m

2:00PM

Check-in and settle at Westport accommodation

Get comfortable and unpack for the week-long stay.
Varies, 30m

3:00PM

Explore downtown Westport

Walk around the charming town center, visit local shops and cafes.
Free, 2h

6:30PM

Dinner at The Whelk

Enjoy fresh seafood and coastal-inspired dishes in a contemporary setting.
USD40pp, 1.5h
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Day 7: Westport Relaxation Day

Westport, Connecticut on July 1, 2025

8:30AM

Breakfast at Blue Moon Café

Start with locally loved breakfast and bakery items, opens at 7AM.
USD20pp, 1h

9:30AM

Visit Compo Beach

Spend the morning enjoying family beach time with sand and water activities; beach opens at dawn.
USD10 parking, 3h

12:30PM

Lunch picnic at Sherwood Island State Park

Relax in a scenic beachside park with picnic facilities.
USD10 parking, 1.5h

2:00PM

Afternoon visit to Westport Historical Society

Learn about local history through exhibits suited for family educational time; open 1PM-5PM.
USD5pp, 1.5h

4:00PM

Relax at accommodation

Downtime before dinner.
Free, 2h

6:30PM

Dinner at Bartaco

Enjoy casual, healthy tacos and bowls, family-friendly and open till 10PM.
USD30pp, 1.5h
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Day 8: Westport Family Adventures

Westport, Connecticut on July 2, 2025

8:00AM

Breakfast at Nourish Westport

Try organic, healthy breakfast options with smoothies and bowls, opens at 8AM.
USD18pp, 1h

9:30AM

Visit Pez Visitor Center in Orange (30 min drive)

Fun and quirky tour about the history of PEZ candies, very entertaining for children; open 10AM-4PM.
USD15pp, 2h

12:00PM

Lunch at Longshore Clubhouse Grill and Bar

Enjoy casual lunch near the golf course with outdoor seating options.
USD25pp, 1h

1:30PM

Afternoon boating or fishing at Longshore Park

Rent kayaks or take a fishing trip suitable for the whole family.
USD30 rental, 2h

4:00PM

Return to accommodation

Rest and refresh.
Free, 1h

6:30PM

Dinner at The Spread

Vibrant, trendy spot offering creative American dishes and pizza, ideal for families.
USD35pp, 1.5h
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Day 20: Westport Final Day and Departure Preparation

Westport, Connecticut on July 14, 2025

8:00AM

Breakfast at Lucy’s Kitchen

Breakfast café with homemade pastries and fresh coffee, opens at 7:30AM.
USD18pp, 1h

9:30AM

Morning walk at Sherwood Island State Park

Enjoy natural beaches and walking trails for last morning relaxation.
USD10 parking, 2h

12:00PM

Light lunch at The Cheese Wheel Sidewalk Café

Grab artisanal sandwiches and snacks before packing up.
USD20pp, 1h

1:30PM

Pack and prepare for departure

Organize belongings and rest before road trip home.
Free, 3h
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Day 21: Return Road Trip Start

Westport, Connecticut to Richmond, Virginia on July 15, 2025

7:30AM

Breakfast at accommodation

Early start with breakfast before the road trip southward.
USD15pp, 1h

8:30AM

Drive to Richmond, Virginia

Approximate 6-hour drive with stops for rest and lunch.
Gas approx. USD50, 6h

2:30PM

Check-in and quick exploration of Richmond

Stretch legs and enjoy brief visit to Carytown area for shops and snacks.
Free, 2h

6:30PM

Dinner at The Daily Kitchen & Bar

Health-conscious American fare with options for all ages, open till 9PM.
USD35pp, 1.5h
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Day 22: Richmond to Florida

Richmond, Virginia to Florida on July 16, 2025

7:00AM

Breakfast at hotel

Light breakfast to start final day of travel.
USD15pp, 30m

7:30AM

Drive back to Florida

Approximate 10-11 hour drive depending on final destination in Florida; plan breaks for comfort and meals.
Gas approx. USD80, 10h30m

6:00PM

Arrival and dinner at hotel or home

Relax and enjoy meal at destination after long drive.
Varies, 1.5h
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