Fun Travel ideas for 40th birthday

40th birthday party was a
My awesome wife will be turning 40 soon. Help me plan a surprise weekend trip, probably to Florida!
I would like to take a trip with my wife to celebrate her 40th birthday. The weekend that would work for this trip would be Saturday, June 1 through Monday, June 3. There is a chance we could leave the evening of Friday, May 31, but we’ll probably need to leave early June 1. It’ll just be the two of us. This would be a surprise trip for her and I want to make it special. For purposes of this question, you can imagine a very generous (nearly unlimited) budget for this trip.

We live in Baltimore. We rarely travel without our kids but, when we’ve done so in the past, we’ve stayed at a B&B in Virginia, a hotel in Rehoboth Beach, an all-inclusive resort in Mexico, and in various cities across the country, mostly in the northeast and mid-Atlantic. We like beaches, walking, hiking, fine dining (and tasty cheap eats, too!), museums, attending baseball games (minor and major league), warm weather, and history. We aren’t golfers (other than miniature golf!) or boaters and don’t particularly care to shop. I’d anticipate that she’d have the best time in a place with some fun and quiet activities, but nothing too strenuous. Lounging on a beach for most or all of the trip would be just fine. An upscale resort or B&B would be great fun. I don’t think this should be one of our “go to a big city and see all the museums and galleries” type trips.

If there is something within driving distance of Baltimore that you’d recommend, I’d be interested to hear about it. I’m generally thinking, however, that it might be fun to fly someplace a little further from home. If we were to fly, destinations that are readily accessible via Southwest Airlines from BWI would be strongly preferred.

The southeastern U.S. would hopefully have nice weather and wouldn’t be too far via air. Other than a brief trip to the Miami airport, she’s somehow never been to Florida, and I think that might be a nice place to spend a quiet weekend, based on the criteria listed above. (Am I nuts to be thinking of going there in early June, though, from a weather perspective?) I’m also open to Charleston if someone is willing to make the case. She’ll be in New Orleans for a conference later in the year, so I’m ruling that out. I travel to Florida periodically for business, so I have some of my own thoughts about possible Florida vacation spots. Here are the Florida cities that one can reach via BWI on Southwest, ranked more or less in descending order as I see them. Let me know what you think!

1. Tampa/St. Pete. PROS: Nice airport with many flights in and out. There may be good resorts on Longboat or Lido Keys, if that isn’t too far to go. I’ve heard great things about Caladesi and the Clearwater beaches. The Rays are on the road but it might be fun to go to a Blue Jays game in Dunedin. CONS: Sprawling, can take a while to get different places. UNKNOWNS: Quality of resorts/hotels and food.

2. Key West. PROS: Neither of us has ever been and it sounds awesome in all respects and would probably be #1 on my list but for ... CONS: Seems rather hard to get to. No direct flights. Will we get much bang for the buck if we don’t arrive until mid-day Saturday, and have to leave mid-day Monday?

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