Experience · Clearwater
Clearwater Arts & Elegant Date Night
Begin your evening with a refreshing drink and waterfront views, setting a relaxed tone before heading to a captivating performance at the historic Capitol Theatre. Conclude your date with a refined dinner featuring sophisticated New American cuisine.
A 4.5-hour Clearwater evening plan for couples — The Nash Keys Dueling Piano Bar & Restaurant, Nancy and David Bilheimer Capitol Theatre, Caretta on the Gulf.
- Duration
- 4h 30m
- Cost
- $100–$250
- Stops
- 3 stops
- Area
- Downtown + 1 more
- Walking
- Light walking · Total 2.1-mile driving route
- Best time
- 5:00 – 10:00 PM
- Ideal for
- Couples · Adults · Solo
The plan
The plan
- 1The Nash Keys Dueling Piano Bar & Restaurant(1 hr)→
- 2Nancy and David Bilheimer Capitol Theatre(2 hrs)→
- 3Caretta on the Gulf(1 hr 30 min)
Why this plan works
The 3 stops cover about 2.1 miles total, which keeps you in one pocket of Clearwater instead of crossing town between them. Nancy and David Bilheimer Capitol Theatre is the main event and takes the biggest block of time; the other stops are built around it. It finishes at Caretta on the Gulf — a short, low-effort stop you can skip if you're ready to call it. Best suited to couples, adults, and solo who want a planned Clearwater outing without improvising between stops.
The story
Overview
Begin your evening with a refreshing drink and waterfront views, setting a relaxed tone before heading to a captivating performance at the historic Capitol Theatre. Conclude your date with a refined dinner featuring sophisticated New American cuisine.
The itinerary
3 stops, one great day
- 11 hrThe Nash Keys Dueling Piano Bar & Restaurant
Nightlife · Downtown
What to do — Arrive early for a cocktail and some light entertainment before walking to the nearby Capitol Theatre. Check their schedule for happy hour specials.
Book it · The Nash Keys Dueling Piano Bar & Restaurant
Private Tandem Kayak Tour To Clearwater Island With Beach Setup!5.0 (10)2.5 hrFrom $2000.1 mi away
Check availability
0.1 mi · 3 min walk or 3 min drive
Then A short walk brings you to the Capitol Theatre, just around the corner.
22 hrsNancy and David Bilheimer Capitol TheatreArts & Culture · Downtown
Art deco-style venue hosting a mix of events, from comedy acts to musicals, plus film screenings.
What to do — Immerse yourselves in the cultural experience, whether it's a concert, comedy show, or a classic film. Pre-book your tickets for a specific event.
Scout Side QuestBefore the lights dim, find your favorite architectural detail in the hall and share it.
Book it · Nancy and David Bilheimer Capitol Theatre
2 mi · 7 min drive
Then Stroll down to Clearwater Beach for a special dinner with water views.
3Optional 1h 30mCaretta on the GulfFood & Drink · Clearwater Beach
Luxurious beachside resort eatery offering carefully sourced, sophisticated New American cuisine.
What to do — Savor a memorable dinner at this luxurious beachside resort eatery, enjoying the refined menu and elegant ambiance. Reservations are recommended.
Scout Side QuestBefore opening the menus, each guess the exact dish the other person will end up ordering.
Scout Stories
People who did this
Be the first to leave a Moment.
Did this outing? Hit "We Did This" up top and share a photo.
The route
On the map
Common questions
Planning this outing
- Is this a good Clearwater itinerary for couples?
- Yes. It's built for couples, adults, and solo and runs about 4 hr 30 min across 3 stops, starting at The Nash Keys Dueling Piano Bar & Restaurant.
- How long does this outing take?
- Plan on 4 hr 30 min door to door, including time between stops.
- How much does this Clearwater itinerary cost?
- Roughly $100–$250 per person, before parking and tips. Free and low-cost stops are marked on each card.
- Is this itinerary walkable?
- Not entirely. The stops cover about 2.1 miles, so you'll drive or rideshare between at least one pair.
- Do I need reservations?
- No. Every stop on this plan takes walk-ins, though weekends move faster if you arrive early.
Keep exploring
More ways to spend time in Clearwater
Different moods, same city.
FamilyClearwaterClearwater Downtown Park & BreakfastStart your family morning at the newly redeveloped Coachman Park, offering expansive green spaces and waterfront views perfect for kids to explore. Afterward, enjoy a casual and kid-friendly breakfast at Maggie Mae's Waterfront, conveniently located and offering hearty morning meals for everyone.
- Duration
- 3 hrs
- Cost
- $30–$60
- Ideal for
- Families · Kids
Arts & CultureClearwaterClearwater Pirate Adventure & Beach EatsSet sail on Captain Memo's Pirate Cruise for a swashbuckling adventure on the Gulf waters, a signature local experience. After your sea journey, enjoy a casual, beach-themed meal, then unwind with stunning panoramic views at Pier 60.
- Duration
- 3h 45m
- Cost
- $75–$125
- Ideal for
- Adults · Friends
OutdoorsClearwaterClearwater Park Stroll & Budget BitesEnjoy a tranquil morning starting with a peaceful walk along the trails of Crest Lake Park. Follow it up with a delicious and affordable breakfast at a local cafe, ensuring a satisfying start to your day.
- Duration
- 3 hrs
- Cost
- $15–$25
- Ideal for
- Solo · Friends
Date NightClearwaterDowntown Clearwater Arts & Dinner DateBegin your afternoon date with a light bite at Clear Sky on Cleveland before heading to a matinee or performance at the historic Nancy and David Bilheimer Capitol Theatre. Conclude your evening with a romantic, Italian-inspired dinner at SeaGuini at the Opal Sands Resort, enjoying exquisite food and breathtaking water views.
- Duration
- 4h 30m
- Cost
- $120–$250
- Ideal for
- Couples · Solo
FamilyClearwaterClearwater Family Aquarium MorningStart your day with an educational adventure at the Clearwater Marine Aquarium, where the kids can marvel at marine life. Afterward, enjoy a casual breakfast at a nearby bakery. Conclude your family morning with some active play at a local park, letting the kids burn off energy before heading home.
- Duration
- 4 hrs
- Cost
- $50–$100
- Ideal for
- Families · Kids