Biggest problem ever: where do we go for our 'free' vacation?
August 24, 2017 6:49 AM   Subscribe

I have 140K+ points on Southwest and some must be spent by Dec 31, 2017 or I will lose them all (I don't think I need to spend them all). And we need a vacation. So my husband and I decided to take a long weekend....somewhere. I also have a good number of Marriott points so we could potentially use those if it works out. But we cannot decide...a lot of destinations sound 'nice' but nothing is particularly attracting us and since we will need to layout some cash for things like rentals, food, etc., we are just paralyzed. WHERE should we go? Constraints and wishes inside....

Here are the constraints:
1. We can leave from BOS, PVD, or MHT and we'd hope for a direct flight if possible.
2. Nashville is out. A hundred business trips there, including some where my husband tagged along to make it a vacation too, is how I earned all these points.
3. Hurricane season? That has made us hesitant to book Caribbean options; also we have never been to the Caribbean and have no idea where to start.

Here are our wishes:
1. I love structure! If there's some key itinerary for a destination, even if it's an activity I've never really looked into, it will be attractive to me! I love active/busy/interactive vacations, where someone has mapped out what we will be doing. I don't like sitting passively on a bus tour; I love biking-around-city-with-a-guide tours.
2. Do-nothing, lay on the beach weekends are also great, but I still need that go-here-specifically direction. For instance, another vacation in Germany included a day of lolling around, but specifically in a recommended bath facility. Beach in the Caribbean sounds fun but I am overwhelmed by options...
3. Bonus points for adult-centric, but not required.

What awesome experiences have you had in the Sept to December timeframe at any of the locations reachable non-stop from Boston/Providence/Manchester on Southwest?
posted by Tandem Affinity to Travel & Transportation (15 answers total) 2 users marked this as a favorite
Fly to Las Vegas, rent a car, and drive up to Southern Utah to check out some rad national parks. Fall is the best time to be there. Not too hot, not cold, less crowds. Zion, Bryce, Canyonlands, Arches and Moab are all great spots.
posted by trbrts at 7:17 AM on August 24, 2017 [10 favorites]

San Diego is great in December, and you can get there with just one stop. Spend half a day at Cabrillio National Monument, some time on Coronado Island and maybe hit up La Jolla, too.
posted by soelo at 7:18 AM on August 24, 2017 [3 favorites]

Chicago is a direct flight. Chicago has oodles of museums and restaurants and experiences. Plus it wouldn't be a long flight.
posted by mmascolino at 7:19 AM on August 24, 2017 [6 favorites]

Trade 110k of them in for a Southwest Companion Pass and one of you can fly for free with the other until December 2018.
posted by caek at 7:36 AM on August 24, 2017 [13 favorites]

Things around El Paso are surprisingly interesting, if you can rent a car. There are White Sands National Monument and Guadalupe Mountains National Park within two hour drives, and the city itself, on both sides of the border, can also occupy a day or so. Carlsbad Caverns is a three hour drive, but if you like caves it can occupy the entire trip.

Do not, I repeat not, go in the summer.
posted by ubiquity at 7:38 AM on August 24, 2017 [1 favorite]

I apologize for not directly answering your question, but Southwest Rapid Rewards points don't expire as long as you have earning activity through flights with Southwest or partners every 24 months.
posted by DanSachs at 7:48 AM on August 24, 2017 [7 favorites]

Puerto Vallarta. On the west coast of Mexico, so a much safer bet regarding hurricanes.
posted by greta simone at 7:48 AM on August 24, 2017 [1 favorite]

Not doing airline research, but if Asheville is on that list, I highly recommend it during October if you can still find a room available. The Grand Bohemian Asheville is a Marriott and has a lovely spa, so you could rent a car and drive out on the Blue Ridge Parkway to see the leaves, hike woods and/or waterfalls, come back for a massage, visit the Biltmore. Asheville is a great town to visit.
posted by headnsouth at 7:52 AM on August 24, 2017 [2 favorites]

Logan to San Juan, Puerto Rico. If you don't use your Marriott points AirBnB is very reasonable there. We had a 3 bed / 2 bath house 5 minutes from the beach for $125. Studio beachfront condos were available for under $100 a night, and this was high season at Christmas 2015.

Review of our trip.
posted by COD at 7:54 AM on August 24, 2017 [2 favorites]

Trade 110k of them in for a Southwest Companion Pass

You don't actually lose the points, you just get the pass once you hit 110k. Tandem Affinity, if you don't already have the companion pass (there's a few rules on how the points are earned), it's worth checking online to see how close you are.

Of course, then you get into to the ridiculous US problem of having an absurd amount of free travel and not enough time to use it. That was an obnoxious year :)
posted by Nonsteroidal Anti-Inflammatory Drug at 9:05 AM on August 24, 2017 [3 favorites]

GeekGirlCon is in Seattle at the end of September/beginning of October. I had a blast last year, and enjoyed what I saw of Seattle.

I am non-touristy and didn't go to the Space Needle or other famous places (...there are some of those, right?), but I enjoyed the Pike Place fish market (which was near the con & where I was staying) and taking the bus to gaming stores and seeing the new Amazon dome, which was under construction back then.
posted by ErisLordFreedom at 9:58 AM on August 24, 2017 [1 favorite]

I get a lot of free travel on Southwest and I have this same problem of being overwhelmed. I solve it in one of 2 ways:

So, you've already got the flight map and you can see the non-stop cities: MKE, MDW, DEN, MCI, STL, IND, ATL, MCO, HOU, DAL, AUS, BWI, CMH, and a bunch of places in Florida. Then start eliminating. Cross off any city that is likely to be too hot or too cold. Cross off any city that you've already been to or that really makes you say "nope". Then, for each city that is left, google "3 days in [city]". You will get a lot of pre-planned itineraries in that city. Read through and see if any of them appeal to you. Pick one based on your interest, or do a random draw and call it an adventure.

The other way I travel is that I remember that I can come back later. So I take day trips. I pick 1 or 2 things to do in that city, have lunch, then come home the same day. No hotel charges, take public transit or uber, lunch is cheaper than dinner. If you have more points than money, consider taking a few day trips instead of a weekend. It feels extravagant to go to Kansas City just for the BBQ lunch, but I've done it several times.
posted by CathyG at 9:37 AM on August 25, 2017 [2 favorites]

Southwest starts flights to Turks & Caicos this fall.
posted by 2soxy4mypuppet at 9:58 AM on August 25, 2017 [1 favorite]

Thanks for all the suggestions! We definitely feel more focused now with some concrete leads. Unfortunately, it took me more than a year to get to 110k so the companion pass was not an option, but it's correct I was confused about the deadline and our actual deadline for use is 24 months from last earning, which for me will be July 2018. Thanks again!
posted by Tandem Affinity at 10:28 AM on August 27, 2017

Oh my gosh we finally managed to pick a place and went to.....drumroll... Denver and Estes Park with a pit stop in Boulder. We hiked in the Rockies and then soaked in our hot tub. We had fancy food in Lodo and accidentally caught Derby Day at the Brown Palace. We wandered in Boulder after an excellent lunch at the Sun Pub Brewery and caught a beekeeping class on top of the library. It was an excellent trip and I highly recommend if you have some Southwest miles (or otherwise) to burn.
posted by Tandem Affinity at 9:16 PM on May 9, 2018

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