Travel advice sought for a 40th birthday getaway.
April 23, 2013 1:54 PM   Subscribe

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?

3. West Palm Beach: PROS: It might be fun to get a room at a fancy place in Palm Beach like the Brazilian Court for an off-season rate. Lots of good food. Lots of direct flights. CONS: She’s turning 40, not 80. The old money crowd isn’t really our thing. The Worth Avenue shops don’t appeal. UNKNOWNS: Are there good beach options in the area?

4. Jacksonville: PROS: St. Augustine is cool (but an hour away). Quiet. Slightly shorter flight. CONS: Jacksonville proper isn’t terribly exciting from what I’ve seen. UNKNOWNS: Quality of resorts/hotels and food. Are there good beaches in the area?

5. Ft. Walton Beach. PROS: From what little I’ve seen, it seems like there are nice beaches in the area. CONS: Is there too little to do, even for a short and mellow trip like this one? Will we run into issues with the Eastern and Central time zones if we want to go to, say, Destin?

6. Ft. Myers/Naples: completely unknown to either of us. Might this work?

7. Ft. Lauderdale: PROS: Proximity to Miami, I guess? CONS: An urban south Florida vacation is not what we’re after.

8. Orlando: PROS: Disney? CONS: I’ll go here with kids, but not without them.

I will turn to TripAdvisor and similar sites if necessary, but I am looking forward to answers from MeFites first! Thank you very much in advance for any travel ideas, for suggestions about places I’m not aware of, for disabusing me of any prejudices that I may have, and for making this a fabulous trip for my wife and me!
posted by cheapskatebay to Travel & Transportation (10 answers total) 4 users marked this as a favorite
How about Amelia Island? It's reasonably close to the Jacksonville Airport, it's beachy, and it would be good for a long weekend of relaxation. Plus, it's easier to get to than Key West, and has significantly less sprawl than Clearwater/Tampa/St. Pete or Orlando.
posted by 2or3things at 2:18 PM on April 23, 2013

1. The whole Sarasota area is very nice. It has been several years, but I think Lido is more developed than Longboat. 1 hour south of Tampa. Closer is Clearwater Beach, Treasure Island.

2. Once you get out of Miami-Dade, it is a very pretty drive through the Keys. If you just want relaxing on the beach, you do not need to go as far south as Key West; many of the northern islands can be nice places to relax.

6. The southern gulf coast is more known for fishing & boating than for beaches.

On preview - I've heard good things about Amelia Island.
posted by neutralmojo at 2:21 PM on April 23, 2013

I am completely Florida-agnostic; however I can offer guidance on Charleston and potentially offer a very nice, drivable location.

Charleston is absolutely wonderful (though it will probably be fairly sweltering in June). It's a great city to walk in, especially in the evening—relatively low car traffic on most streets, nice architecture, pleasant gardens, etc. You can also just sit and watch the ocean. The food culture is great—I highly recommend Husk (or Sean Brock's other restaurant, McCrady's), among lots of other great places. Budget is usually the main concern for Charleston, but since yours is unlimited, I think Charleston would be great for a vacation.

Now, the other spot I'll recommend is a place that is maybe in the Southeast, depending on your definition: Lewisburg, WV. It's a very small town, absolutely charming, and there is good food to be had there. You could stay at one of the incredibly nice hotels nearby (e.g. the Greenbrier), though I stayed in a nice B&B in town when I went. The primary attraction there would be hiking around the mountains—there are some very nice, well-maintained trails around there. There's also a lot of Civil War-era history stuff to poke, if that piques your interest.
posted by Maecenas at 2:38 PM on April 23, 2013

what about Key Largo? you can fly into Miami, rent a car at the airport and drive down in about an hour and a half. If you're staying at one of the big hotels, there may even be a shuttle. there's lots of neat things to do - snorkeling or glass bottomed boat ride from Pennecamp state park, for example.
posted by 5_13_23_42_69_666 at 3:22 PM on April 23, 2013

I've been to Tampa, Key West, West Palm Beach, Ft. Lauderdale, and Jacksonville (why yes, I do travel to Florida a lot!) and I'd definitely go for St. Augustine, especially if she hasn't been there before. It's the perfect scale for a weekend, lots of interesting but non-crowded stuff to walk around and see, and it would be romantic as well as low-key so long as you stayed in a nice place. It is an hour from Jacksonville, but when I flew in and out of there for a weekend in St. Augustine the traffic was totally manageable. I was there in June and it was a bit hot for hanging out on the beach, but very nice to walk around the lovely town and laze about in gardens and coffee shops.

The Keys are awesome, but June is starting to get into roasting-hot territory and if you only have two days there is no way that drive is worth it. I've done it flying in and out of Miami (driving down to Key West once, and Key Largo once) and even though I'm huge fan of road trips and driving-for-the-sake-of-driving, I thought it was way too much. Plus both times I did this I ran into epic traffic and it just sucked all around.

West Palm Beach and Ft. Lauderdale are nice, but somewhat crowded and neither would really strike me as special enough for a big birthday, particularly if you're walking types. Both are very car-oriented sprawling areas with little pockets of walk-ability on the beach or a boardwalk, but not really fun places if you'd like to just wander around on foot. Beaches will be VERY HOT this time of year; I'm not sure I'd want to assume I could just hang out on the beach all day as a vacation plan. I'd actually put Tampa/St. Pete's in this bucket too; there were some cool things I saw when I was there but my overall impression was vast tracts of suburbia that weren't particularly differentiated from other places where you'd see a lot of suburbia. Plus, June is not really the nicest time to be visiting Florida in general; none of those cities or associated beaches strike me a nice enough for what you're wanting to do. (I've also traveled a bit in the islands and maybe that is what has made me so unimpressed with many Florida beaches.)

If St. Augustine isn't right, I'd actually try to focus on nearby islands where the flight wouldn't be too brutal. Nassau, Bahamas is only a 2.5 hour direct flight from BWI. Or, if you wanted to head north (given the time of year), I think Montreal could be romantic, and that's under a two-hour flight from DC.
posted by iminurmefi at 3:30 PM on April 23, 2013

I am not a fan of Florida but I find Fernandina a treat--a respite from the rest of Florida and a place to which I would definitely return. I think these Google Images give a flavor of the town and surrounding area.
posted by rmhsinc at 3:45 PM on April 23, 2013

Native Floridian here - based on your list, it seems like St. Augustine would be all but perfect for you and your wife:

- The beaches are beautiful, bountiful, and even at the height of summer, relatively uncrowded.

- The downtown area is wonderfully walkable and full of great locations to explore on foot. It's also full of great restaurants (The Floridian on Cordova Street is my new favorite) in a range of price points.

- The historic downtown area is basically a giant museum. Amazing history as far as the eye can see.

- St. Augustine is surrounded by lots of nice nature preserves that feature excellent hiking. Guana River State Park and Moses Creek Conservation Area are two in particular that I'd recommend.

- The weather in June will be plenty warm: 80's during the day, although generally not too humid if you're downtown or at the beaches (further inland things get muggier during the day).

The only hole that I see is the lack of baseball, but if you're dying for a game the Jacksonville Suns play at Bragan Field, which is only about 40 minutes away from downtown St. Augustine via I-95.

Feel free to give me a shout if you're got any questions about St. Augustine. My email address is in my profile.
posted by saladin at 5:59 AM on April 24, 2013

Another Florida native piling on for St. Augustine. Stay at one of the B&Bs near the historic district and enjoy walking around.
posted by Shoggoth at 6:24 AM on April 24, 2013

Response by poster: Thank you to everyone who has responded! I sincerely appreciate your comments and suggestions. Based on these answers, I think I'll focus on St. Augustine or Amelia Island for this trip, and I'll look forward to exploring the other locations that have mentioned on other trips.
posted by cheapskatebay at 8:11 AM on April 24, 2013

I'm going to dissent.

If I were you and I had a couple of bucks, I'd go to Miami. There's an express bus from the airport to the beach, and then take a cab from there to your hotel.

If you can get into the Fontainbleu for a decent rate, that. The resort is gorgeous and while it's not the 'old school' place of yore, it's still a great location. Sit on the beach, have a spa day, and if you're in the mood to walk around and people-watch, go to Lincoln Rd and do that. Lots of little cafes and such.

It's a completely different vibe than St. Augustine. More urban and funky, but really fun if you're into that sort of thing.
posted by Ruthless Bunny at 9:21 AM on April 24, 2013

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