4-day trip in May w/ SO; looking for somewhere warm, relaxing, good food and drinks, ideally mostly walkable and adult oriented

My fiancee and I are fully vaccinated and will be taking a 4-day/5-night trip at the end of May and are looking for recommendations! We're currently leaning towards Key West since it seems to cover a lot of what we're looking for:

• Warm
• Good food & drinks (we don't eat meat but we LOVE seafood)
• Relaxing (poolside and/or beach; bonus for poolside/beach bar)
• Geared towards adults but not a heavy "party" destination (guessing we can avoid this by spending a little more money)
• Ideally most bars & restaurants in walking distance (willing to Uber somewhat but don't want the hassle of renting/driving a car)
• Bonus for live nightly entertainment (live music, outdoor shows, etc)

Under other circumstances we'd likely be going to an all-inclusive resort out of the country as we love the worry/hassle free, relaxing atmosphere. Don't have to do think much about where to eat/drink, make reservations, rent a car, etc. We just want to spend time together, relax, drink, and eat some good food. Maybe do one or two activities such as a sunset cruise, visit a museum or historical monument but this would be a bonus and not the focal point of our trip.

We'll be flying from the Midwest and total budget is $5k or less. We're currently leaning towards Key West but would love some recommendations as we don't travel too often so we're not really in touch with travel destinations. Thank you! :)

Submitted March 28, 2021 at 07:49PM by Keetonicc https://ift.tt/3u3aKjz