I wear my cuddle duds under my dress and lose them when I get off in Cancun. Then on the way back, put them back on once we land. Wool toe socks with my sandals. haha which everyone laughs about but I am warm.
Not strictly on topic, but I pack our pool bag with our sunscreen, refillable cups, sunglasses, swimsuits, sandals and cover-ups, and then put the pool bag at the top of our suitcase, so when we arrive at the resort, we don't have to rummage thru suitcases to round up all our pool gear. We just open 1 suitcase, haul out the pool bag that has everything we need, and book it to the pool top speed.
We always just suck it up when we leave/get back and leave coats and blankets in the car. For travel, I usually wear yoga pants and hoodie and tennis shoes; Hubby usually wears shorts on the way there because he’s so excited that the cold doesn’t bother him. We typically wear the same clothes back that we wear on the way there to cut down on luggage. Maybe pack a small blanket or jacket in your carry-on in case you’re chilly on the plane??
This also works best for when you arrive early and your room isn’t ready yet!!!! No sense wasting even a minute of time while there!!!
We travelled to Las Vegas one time... +20C when we left and -20C when I returned (and found a flat on my car!). I had a light jacket... that was fun. It always seems like I’m leaving in the cold to warm places. Generally if I cab to the airport I just leave my jacket at home or if I drive we leave it in the car and suck it up. For the last few trips I’ve had a packable down jacket, I bring it along and use it as a pillow. I always wear pants when I fly. It’s the blowing air and the cramped spaces. I use a pair of light travel/hiking pants.
I dress for the beach!! I put my swim trunks or shorts on under a pair of sweat pants, tennis shoes, and a hoodie. I put my flip fops in my carry on and when I know it's about the last time to get up before we land I go to the bathroom ditch the sweat pants and swap out shoes and put all my winter stuff in my carry on. Then I do exactly the opposite on the way home. My wife usually dresses like it's fall and not winter so she looks nice, but isn't uncomfortable when we hit the heat. She always has a suit and a cover up in her carry on and changes in the hotel bathroom the second we get there. Every time we have been to TTR it takes 2 to 4 hours to get a room so we are always both beach ready so we can enjoy the pool and beach while we wait on our room. I'm sure it's possible to get a room faster, but the flight we take usually lands at about check out time so no rooms are clean yet.
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I'm always rocking the Shorts and Hoodie easy for security and then I'm close to being ready to party when the plane touchdown in Cancun. We travel in Feb from up here in MI so its pretty cold and shitty. LOL
When we have gone in the dead of winter, I'll wear a pair of thong panties and no bra under clothes that arent too heavy, but warm. Sam will wear jeans with sexy underwear and a long sleeve shirt. We'll leave home wearing coats. In a carry on, I'll have a pair of light shorts and a next to nothing top. Sam will have a thin short sleeve fishing shirt. (Neither of us like the bunchiness of layers.) When we get to the airport, we'll leave the coats in the car and just tough it out until we get in the terminal. Once we get in the USA Transfers van in Cancun, I'll ask the driver if he minds if I change clothes in the van. (None of them have said "No" yet! Lol!) Once we're moving, I strip down to just a thong and put on the shirt and top. Sam changes shirts. Once we get there and our room isn't ready, we check our bags and head to the Sexy Pool. We find a chair (or get permission to store our stuff under someone else's chair) and strip down to our underwear and jump into the party. Easy transition!
We travel from Chicago, so I have to do this a lot! From Chicago to Cancun: bikini under a maxi dress. Light cardigan or jean jacket. Lightweight puffy coat. Thigh high socks and boots (keeps the legs warm!) ---In the carry-on: sunscreen, Todd's trunks, sandals/flip flops On plane: jacket becomes a pillow, cardigan becomes a blanket if needed. Arrival in Cancun: jacket, cardigan, socks and boots go in the carry-on, exchanged for the flip flops. Can be done in line waiting for customs. Arrival at TTR--whip the dress off, run out to the pool! Voila--comfortable the whole trip, and no time wasted getting to the pool!
