Live Your Best Lives
  1. Travel FAQs
  2. United States
  3. Florida (FL)
  4. Clearwater

Anniversary/Birthday Weekend Trip Recommendations

My wife and I are making our first trip to Clearwater in a couple of weeks. We are staying at Opal Sol. I am trying to find the best places to fit into our long weekend. We are there Thursday-Sunday night. We are by no means food snobs. We are looking for places with great views, live music, maybe a rooftop bar, and then one really nice seafood/steak meal. If you have any recs on any of those categories, throw them our way! We are both 40 and we will not have a car and will be relying on Uber/walking/biking. Thanks!

Clearwater is a fantastic spot for a long weekend getaway, especially for a celebration like an anniversary or birthday. Staying at Opal Sands puts you right on the beach and within easy reach of several dining, nightlife, and entertainment options, even without a car. You can rely on walking, biking, or Uber to get around comfortably.

For places with great views, live music, or a rooftop vibe, here are some suggestions:

  • Clear Sky Beachside Café: Just a short walk from Opal Sands, this spot has ocean views, a relaxed vibe, and occasional live music. Great for breakfast, brunch, or casual drinks with a sunset view.
  • Frenchy's Rockaway Grill: A classic Clearwater beachfront spot with live music most nights. The deck overlooks the sand and water, perfect for a laid-back evening.
  • Sea Critters Café: While more casual, it’s great for grabbing drinks and enjoying live music right on the beach. Perfect for starting the evening.
  • Rooftop or scenic bars nearby: Consider the Hyatt Regency Clearwater Beach rooftop bar for sunset cocktails and sweeping views, or Jimmy’s Crow’s Nest for panoramic waterfront scenery.

For one really nice seafood or steak meal, these are highly recommended:

  • Columbia Restaurant Sand Key: Renowned for seafood, Spanish-inspired dishes, and a classy atmosphere. Ideal for a special occasion dinner.
  • Caretta on the Gulf at Sandpearl Resort: Upscale dining with fresh seafood, steaks, and stunning Gulf views. Perfect for a romantic anniversary dinner.
  • Salt Cracker Fish Camp: A local favorite for seafood with a cozy, slightly rustic vibe. Known for fresh catch and creative sides.
  • Island Way Grill: Combines seafood and steak options with a sophisticated ambiance, located in Clearwater Beach for easy Uber access.

Other activities and tips to enhance your weekend:

  • Take a sunset stroll along Clearwater Beach and Pier 60, which also hosts nightly sunset festivals with street performers and music.
  • Consider renting bikes to explore the beach area and nearby Causeway for scenic views.
  • Check local schedules for live music at Sand Key Park or nearby bars; some places feature jazz, blues, or acoustic performances in the evenings.
  • If you have time, a short Uber ride can take you to nearby Clearwater Harbor for boat tours or dolphin-watching excursions.

In summary, Clearwater offers a perfect mix of beach relaxation, scenic views, live music, and excellent dining. You’ll be able to celebrate in style without needing a car, relying on walking, bikes, and Uber. Your anniversary and birthday weekend should be memorable and stress-free!

More Clearwater Travel Questions

The attractions mentioned in this question

beach
Rooftop

Popular Destinations

Ming Changling
Lishi Clock Tower
Jietai Temple
Shapowei Art West District

Popular Travel Questions