Birthday/Anniversary Getaway - Happy Hour/Dining/Music Tips?

Question

Hello! My wife and I (39 years of age) are coming to town in early October. We get in during the late afternoon on a Friday. Leave Monday late afternoon. So a fairly short trip.

Details:

We are staying at the Conrad Orlando at Evermore. The plan is to spend most of morning/early afternoon lounging and relaxing by the pool. Then late afternoon we love finding spots to explore! We will not have a car but Uber will be accessible, but also prefer to stay fairly close. We love a good happy hour spot. As for dining, definitely not food snobs. We prefer atmosphere and a great view over having the best of the best food! As for after dinner, we are looking for places with some live music and awesome atmosphere and views!

Looking forward to any and all ideas on how we can make this our best anniversary trip yet! Thanks in advance!

Answer

Congratulations on your anniversary, and it sounds like you have an exciting trip ahead! Orlando has plenty to offer in terms of relaxing spots, great happy hours, and lively atmospheres with live music. Since you’re staying at the Conrad Orlando at Evermore, you'll be in a prime location to enjoy the area without needing a car. Here's how to make the most of your weekend getaway with your preferences in mind:

1. Happy Hour Recommendations:

For a great start to your evening, here are some excellent happy hour spots near your hotel:

The Lobby Bar at the Waldorf Astoria Orlando: Located just next door to the Conrad, the Lobby Bar is a chic and relaxed spot to enjoy a signature cocktail during happy hour. The ambiance is upscale and cozy, perfect for a pre-dinner drink.
Enzo’s Hideaway at Disney Springs: This Italian-themed bar offers great happy hour deals and an intimate atmosphere. It’s only a short Uber ride away and offers both indoor and outdoor seating with a cozy vibe, ideal for unwinding after a relaxing afternoon by the pool.
Wine Bar George at Disney Springs: This stylish bar has a great wine selection, and they offer wine flights during happy hour. It’s a great place to kick back with a glass of wine, paired with small bites or cheese plates.
Rooftop Bar at the Four Seasons: If you’re in the mood for views, this rooftop bar has a stunning 360-degree view of the area. You can enjoy a drink while taking in the sunset and the Orlando skyline. It’s an excellent choice for an evening drink before heading out for dinner.

2. Dining with Atmosphere and Views:

For dinner, you mentioned that you prefer atmosphere and great views, so here are a few spots that combine both excellent settings and delicious food:

The Boathouse at Disney Springs: Offering beautiful waterfront views, this restaurant has an upbeat vibe with live music and a great selection of seafood. The outdoor seating is fantastic, and it’s perfect for an evening with views of the water and a lively atmosphere.
STK Orlando at Disney Springs: A modern steakhouse with a great vibe, STK offers a chic, upscale dining experience with a vibrant atmosphere. The DJ and trendy ambiance make it a great spot for a special evening out.
Capa at the Four Seasons: For a high-end dining experience with an amazing view, Capa is a rooftop steakhouse offering Spanish-inspired cuisine. It’s perfect for a romantic dinner with fantastic sunset views and a lively, upscale atmosphere.
Riverside at Disney’s Port Orleans Resort: A bit more laid-back, this spot offers beautiful riverside views and an atmospheric setting, perfect for a more relaxed dinner. It’s also a short ride from your hotel and provides a quieter alternative to more bustling spots.

3. After-Dinner Drinks and Live Music:

For a nightcap and some live music, there are several great places near your hotel to enjoy Orlando’s vibrant nightlife:

The Edison at Disney Springs: This industrial-chic bar and restaurant has a fabulous, lively atmosphere with live music and a unique, vintage vibe. You’ll find a mix of cocktails and excellent food, with nightly entertainment, making it a great place to continue the celebration.
Jaleo at Disney Springs: A fun, colorful spot serving tapas with a great selection of cocktails, and the atmosphere is buzzing, especially during the evening. After your meal, you can head to their bar area for live music and drinks.
The Roof at the JW Marriott Bonnet Creek: This rooftop lounge offers incredible views of the skyline, with a laid-back but lively atmosphere. They often have live music, and the setting is perfect for enjoying a drink while taking in the evening vibes.
House of Blues at Disney Springs: If you’re looking for more live music, the House of Blues is a great option. It’s known for hosting live bands and offering a fantastic atmosphere. You can enjoy cocktails, listen to some blues, and even dance if you’re in the mood.

4. A Relaxed, Romantic Atmosphere for Your Trip:

Since you’ll be staying at the Conrad Orlando, you’re already in a beautiful location to unwind and enjoy a peaceful time together. Here are a few other suggestions to enhance your relaxing getaway:

Relax by the Pool: The Conrad’s pool area is perfect for unwinding, so spend a few hours there in the afternoon before heading out for happy hour. The poolside service is excellent, and it’s a great place to enjoy a cocktail or two.
Spa Time: The Conrad offers a luxurious spa experience, so consider booking a couple’s massage to relax before heading out for dinner. A spa treatment will elevate the experience and set a tranquil mood for the weekend.
Stroll Around Disney Springs: Disney Springs is a great place for a post-dinner walk. It has a lively atmosphere with live music, street performers, and great shopping. It’s fun to walk around and enjoy the sights, especially in the evening when it’s beautifully lit up.

5. General Tips:

Transportation: Since you’ll be relying on Uber, don’t hesitate to use the app to get to your destinations. The rides are generally affordable, and most places are within a short distance from your hotel.
Make Reservations: Orlando can get busy, especially on weekends, so it’s a good idea to make reservations for dinner and for live music spots ahead of time. This will ensure you get a good spot and avoid any long waits.
Plan for Flexibility: You’ll want to stay flexible since your interests and energy levels might change throughout the day. If you feel like staying in one place longer or exploring a new area, go with the flow!

It sounds like you’re going to have a wonderful anniversary getaway! With great food, music, and plenty of opportunities for relaxation, this trip will surely be a memorable one. Enjoy every moment!