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hotel milano terrace san juanWe often talk about travel bucket lists filled with big-budget trips that require a lot of planning. They’re stressful, at times, because so much goes into them and we have such big expectations. There’s a reason these trips often stay on the bucket list for many years; it’s much easier to just escape, spur of the moment. So we keep a few trips in our back pocket. Not mega-bucket-list trips, but cheap and easy trips we could take without much planning and with minimal damage to our savings.

San Juan has been calling me lately. For about $520 total, my husband and I could fly there on AirTran. I’d stay at the Hotel Milano, only 15 minutes from the airport, but in the middle of the old city. The family-owned property has free Wi-Fi throughout the hotel, a necessity for me. I can imagine having coffee on the rooftop terrace.

Since this isn’t a bucket list destination for me, I wouldn’t feel any pressure to do anything except wander, eat empanadillas and drink rum. Since it is hurricane season in the Caribbean, I could most likely continue to do at least two of my intended activities should the weather turn foul.

A completely different, yet equally satisfying back-pocket trip, for me, would be Acadia National Park in Maine. I want to challenge myself on the Dorr Mountain trail, a series of granite steps up the mountain, much of it through the forest. (Can you imagine the autumn foliage?)

I’d fortify my hike with popovers on the lawn at Jordon Pond House. I’d stay at the Moseley Cottage Inn, preferably in a room with a working fireplace. Sure, the rate is a bit high for my strict budget, $205 per night, but my husband and I would drive to Maine, saving on airfare.

The qualifications for a back-pocket trip are simple: cheap, quick and no stress. Not much of an itinerary is required. Need inspiration? Check out our travel deals.

We’re all about extensive travel, with plenty of planning and packing. But sometimes we just have to throw a few things in a bag and go. That’s why we need a couple of trips in our back pocket. Which destinations are in yours?

– written by Jodi Thompson

3 Responses to “Keep a Trip in Your Back Pocket”

  1. Rod says:

    The San Juan deal sounds like a steal. I’m not typically a beach guy, but at that price it would be worth it. And I agree – I’ve got a big bucket list trip I always talk about but never undertake. A quick, and frankly affordable trip like the one to San Juan, would be a great, fun and affordable escape. Thanks for sharing!

  2. CAROL JEAN says:

    San Juan is ideal for a short getaway. PLUS no need for a passport. Beach and culture make a good mix for a 1st time visitor.

  3. Geri says:

    I can’t believe you just gave away our most favorite hike- Dorr Mountain! ;-) Another tip for that area is 2 Cats B&B. The rates are reasonable and nowhere on earth will you get a better breakfast- which is included- of anything off their menu.

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