Finding the Perfect Vacation Accommodation

We all look forward to our annual vacation, a time to kick back, relax, and forget about the everyday world. However, there’s usually weeks’ worth of preparation put into planning for your getaway, even if it is as simple as renting a cottage. Questions like “lakefront or forest?”, “do I need to bring propane for the BBQ?”, “mom, where’s the Frisbee?”, are enough to warrant setting aside three vacation days to simply recover from the effort of getting there.

If you are wondering whether this is normal, we can hazard a “yes”. If you ask whether it should be normal, you will receive a resounding “NO”. Planning a vacation should be fun and easy, full of exciting possibilities, not a drudging chore.

Finding the perfect vacation accommodation is usually half the struggle since there are so many variables to consider. From cost, to location, to the actual rooms, it seems like one could spend hours online and on the phone maximizing the options for something which seems “ideal” but you aren’t really sure of until you check in.

If you want to make the best use of your planning time and start enjoying your vacation the moment it starts, follow this process to easy vacation accommodation booking:

  1. Consider Your Party

Before you even head towards the computer, consider who you are vacationing with. Will it just be you and your significant other? Is it a large group of friends looking to bond over an adventure? Or is it a family trip for the books? Who your company is will partially dictate the type of accommodation you will be looking for, whether it’s a full house rental, a romantic B&B, or a cosmopolitan hotel downtown.

  1. Plan the Budget

The budget can be a great (though sometimes unpleasant) way to limit your accommodation options. Decide how much of your total travel budget you can dedicate to where you are staying, and then divide it by the number of days you are away for a daily spending average. For some this will mean searching for listings in Turks and Caicos, the most beautiful place to rent a luxury villa for an unforgettable holiday, while for others that might mean a stylish AirBnB in a trendy district in Toronto.

  1. Define Your Needs

Everyone expects different things from their vacation accommodation. Some can’t fully relax without a deep soak tub, while others need to feel at home and have access to a kitchen. Get together with your vacation party and decide on what you “need” and what you “want”. This way it’s much quicker to find something which satisfies all the needs and then you can choose between the ones that also cover the greatest number of “wants”.

  1. Ask for Recommendations

If you are looking for the perfect child-friendly ocean-side resort in Mexico, or are looking for the best roof-top pool in New Orleans, sometimes it’s as easy as asking around. Reach out to your colleagues, friends, family members, and travel buddies for advice. Chances are that you will have a more similar taste to your friends than you will to those random strangers leaving reviews on the internet. Sometimes a personal recommendation might even lead to a discount if brought up at the time of reservation. It’s worth a try!

Once you go through these four steps, you are very close to finding the ideal vacation spot for you. Instead of scrolling through websites for hours looking for something to pop out at you, take control of the situation so that you can get to your “paradise” sooner and with less stress.

Updated: How I Used Free Frequent Flyer Miles to Get $9,000 Worth of Airfare — Twice!

Update: I just booked another trip using frequent flyer miles. This time I’ll be flying to Japan, India, and Nepal — for just $120! The real cost was just 80,000 miles that I earned from a couple of credit card offers.

For those who missed it last year, here’s my strategy that I posted in October 2012. Enjoy!

I’m excited to share how I’m spending a month traveling to Paris and Bangkok – and spending only $140 on airfare (just the taxes). How? It was really easy, actually: Free frequent flyer miles.

No, not the kind you earn from flying around from flights you paid cash for. And I don’t spend a ton of money on credit cards, either. Here’s how.

Earning Free Frequent Flyer Miles

For me (and many others), the best way to earn frequent flyer miles is to apply for credit cards that offer big bonus miles for opening a new account. I routinely earn anywhere from 30,000 to 100,000 miles for each new card I open.

To earn these rewards, you’re basically only required to spend $500-$2,000 within the first few months of activating your account. Most cards have an annual fee that’s waived for the first year, too.

Of course, the most common question is: “Doesn’t this hurt your credit score?” But, like many others have reported, the answer for me is “No.”

Using Credit Karma, you can see my credit score (from TransUnion) has been pretty stable the past 2 1/2 years. I’ve bounced back and forth between 740 to 765, but I’d hardly call that much of a change.

(Update: Since October 2012, my score as actually INCREASED to ~759. This is despite opening several new credit card accounts while closing several other credit cards, too. Lesson: there are many myths out there about your credit score and opening and closing new accounts, so beware.)

While I don’t normally endorse credit cards, I feel this can offer a lot of value to people like me that:

  1. Always pay off their balance in full
  2. Want to travel, but don’t have thousands of dollars to do it (hence the need for the free frequent flyer miles)

If you meet both these criteria (and ONLY if you don’t have credit card debt problems), check out to find some of the best cards for travel. You can do this easily by going to their “Airline Credit Card” page.

Again, you’re looking for cards that offer at least 25,000 miles to sign up. Make sure you can earn at least this much without increasing your spending in any way.

Redeeming Miles for Great Value

Earning the free miles was the easy part. But when I wanted to book a trip, I honestly had no idea how to go about it.

So I emailed my buddy, Mike, who runs where he literally takes your miles and desired destination and sets up the entire itinerary for you.

I just told Mike “I want to go to Thailand. Can you get me here?”

Mike said, “Sure. But why don’t you stop in Europe for free on the way?”

My reply: “Um, what?!”

Thanks to Mike’s knowledge of how redeeming miles worth, I tacked on 3 nights in Paris to my journey at no extra charge.

Mike’s next piece of advice “Would you like to fly into Chiang Mai, Thailand and fly out of Bangkok? It will save you an extra trip between the two cities, and it doesn’t cost any extra.”

Of course, I said “Hell yes!” to this, too.

After settling on this, Mike worked his magic and came up with an itinerary for me that told me exactly which flights to book. His trip gave me  3 nights in Paris followed by 3 weeks in Thailand.

I went ahead, following Mike’s instructions, and booked by entire trip. Right before I booked, United asked: “Would you like to book your travel with cash instead? Pay $9,000.” I said “No, thanks” of course.

Instead, I paid just $140 in taxes and 65,000 United MileagePlus miles.

I would note that redeeming miles for domestic flights almost certainly won’t get as much value as going for international trips like this one. This is totally fine for me since I’ve been eager to make my first trip to Asia.

So to get started earning free frequent flyer miles, you’ll need to sign up for credit cards that offer great rewards, such as ones offered here on the Airline Credit Cards page. Then check in with Mike at – he’ll even give you a free email consultation!

Note: Mike agreed to provide me his $80 service for free for this trip and post about it. However, I would definitely recommend his service so much that I’ll gladly pay him from now on. This post also contains affiliate links, but these are services I use myself and recommend to others.

Travel When Retired? No! Travel Now!

I just don’t buy into the whole “travel when you’re retired” thing. It seems like such a waste to wait my whole life to travel (and, not to be morbid, but assuming I make it to retirement age).

I just got back from my latest trip to Montreal, which was fantastic. It was my first visit, and it definitely won’t be my last.

Despite the cost $400 and the fact that I’ll soon be jobless, I took the trip on my own for a few reasons:

1) I really wanted a getaway from New Haven and

2) I wanted to test out traveling on my own.

I definitely cut back on spending in some areas

  • I stayed at an AirBnB rental for $30 a night
  • I ate homemade sandwiches for lunch
  • I travled by bus (the least-expensive option by my calculations)

But I didn’t sacrifice on everything. I had a couple of nice $30+ dinners (including one awesome vegan meal with cheesecake for dessert). While I’m all about frugal trips, I do like to live it up a bit, especially while I still travel only infrequently.

Although I’m only a few weeks from quitting and with a smaller paycheck, I’m still glad I took the time and the money to travel. Even though I could probably use that $400 much more once I lose my full-time income, travel is a priority right now (at age 26) whether I have a ton of money or not.

Travel at age 26 does not equal travel at age 65

It’s highly unlikely that I’ll be able to travel at the same cost and with the same flexibility that I can now as when I’m 65. I definitely can’t imagine staying in the same accommodations that I did this time. It just wouldn’t make sense as an old man.

Plus, I walked over 15 miles this weekend, including up and around Mont Royal Parc (see the photo!) While I’m optimistic that I’ll still be in good shape at my old age, the average retiree probably have that level of endurance.

Finding balance

I always wonder: What does saving for retirement really mean? Am I trying to save up so that I can just sit on the couch or play golf every day? Or spend winters in Florida? Or travel in a tour group of retirees? Those things hardly sound exciting to me.

But the answer can’t possibly be to do the things at age 65 that I wanted to do at age 26 but that I chose to save for retirement instead. That doesn’t make sense to me.

Obviously, I’m not advocating depleting every dime of my savings and funding travel with a credit card. But, I hate the idea of not going anywhere exciting right now.

It’s hard to say how much to spend on travel now and if I should sacrifice retirement savings, so I’ll just leave it at this: Travel all you can afford now. Spend wisely in trips. Don’t go into debt.

How do you feel about travel? Do it while your young, or save for it when you retire?

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photo by: me!

Maximizing Weekend Getaways For Fun While Minimizing Cost

weekend-getawayWeekends! The joy of anyone living in the workaday world. We’ve got to make the most of them because sometimes it’s the only thing to work for. Although I can’t really complain about the ~5 weeks I’ve had off this year, this basically means doing my best to make the weekends a blast. And I sure do a good job of that. I’m rarely at my apartment in New Haven on weekends. In fact, I’ve been gone the last four weekends, and I barely spent a weekend at home the past summer, too.

But it’s not about shelling out a ton of money on flights, hotels, and restaurants for these short getaways. It’s really about leveraging the connections that you have to make the most of what’s close by. Some of my recent trips have been to Vermont, Boston, Rhode Island, and Chicago. Here’s how I manage to do it all.

Travel with friends

This was the best part about our recent trip to Vermont. We rented an awesome house that went for about $500 per night! But we split the cost 11 ways, so it ended up only costing $90 each for the weekend. We enjoyed the 8-person hot tub, pool table, fireplace, large kitchen and more for a budget price. Plus, it was a lot of fun to just hang out with friends.

Cheaper accommodations

I’m always up for camping, and it’s always a deal compared to just about any other way to stay. We camped during my trip in August, and most campgrounds are only $10-$20 per night. Of course, staying for free with people you know can’t really be beat, either.

Stretch the weekend

When I’m heading out of town for  the weekend, I want to make it’s worth my while if I’m going to travel for 2+ hours. Lately, I’ve been leaving work as early as possible on Friday (around 4pm) and traveling back Monday morning. It’s a little tiring to head straight from the bus to work on, but it’s totally worth it to have a great weekend. Plus, I can always rest up during the workweek, which is usually less exciting than the weekend anyway.

Find deals

More and more deal sites, like Groupon, are coming out with travel options now. I took advantage of a Groupon deal last year to get a night at a nice little B&B in Western Massachusetts for only $80, including breakfast for two. I’m also loving Travel Zoo these days. They send out a “Top 20” email every week that outlines some of the best deals they have to offer. I’ve seen several deals for cheap tickets to Broadway shows, and I think I’ll take them up on that very soon.

Go off-season

This is nothing new, but it’s a great way to save. We went to Cancun in August and the place was deserted! I can understand that people don’t want to travel to warm locations when it’s summer and it’s already warm where they live, but it was great to take advantage of the cheap food and drinks without having to fight crowds.

Travel to nearby friends and family

I take advantage of this all the time when I visit my cousins in Boston and my parents on the water in Rhode Island. My cousins have an apartment in a prime location located right in downtown Boston. There’s no shortage of things to do around there, so it’s always a great time. My parents are near Newport, which is a popular location in the summer.  It’s great to have my family so close!

Use cheaper transport

I’ve been living it up on the MegaBus lately and loving it! (Donna at GRS loves Megabus, too) I can’t stop talking about their $1.00 tickets, and I often just buy a bunch if I have any plans to go to Boston. Occasionally I’ll take Amtrak when it’s worth it, especially when I can use rewards for free or cheap Amtrak tickets. Carpooling works great, too, for the group trips.

Cook meals and carry food

While I don’t mind eating out when it’s worth it, I hate buying food simply because I’m traveling and I’m hungry. Prime example: I can’t stand eating at Subway. Their vegetarian option is essentially a lettuce sandwich, which isn’t appealing whether you’re a meat eater or not. I try to hold off on this stuff as much as possible and carry trail mix or cereal bars instead.

For meals, I enjoy mixing it up between eating out and cooking wherever I am. In Vermont again, we cooked two fantastic dinners that I don’t think could’ve been matched by any restaurant around. Eating out is great when it’s something unique and special, but I never underestimate how good a home-cooked meal can be, too.

Stay in

Even though we were in Vermont with lots of stuff around, I mostly enjoyed hanging out by the fire, enjoying some beers, and playing some pool. Sitting by the pool in Cancun under the umbrella with a drink in hand was awesome, too. I even like playing games or just chatting with whoever I’m with. Going out just to go out gets old quickly to me, and I usually don’t do it unless I’m really feeling like exploring somewhere new.

Those are my secrets to mastering weekend travel without overspending. The only downside: I haven’t exactly mastered my working time on the weekend, but that’s next on my list to figure out.

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photo by: Margo!

Coworking Spaces: For Getting Out of Your Apartment and Working on the Move

coworkingSince I first heard of it, I’ve been really interested in the idea of coworking spaces. Until about a year ago, I’d never even heard of it (and maybe you still haven’t either). The basic idea behind coworking is that it’s an office with desks and other spaces for working, except other people, running their own businesses, share the space with you. It’s ideal if you want to spend less money on office space, try working someplace else other than your apartment or home, or want to meet, talk, and collaborate with other entrepreneurs.

I was excited to learn that there’s not one, but TWO (The Grove and The Bourse) coworking spaces in New Haven (it’s a small city, so having 2 of anything is pretty amazing). The Grove is only one year old, and they’re already expanding.

Better than the local cafe

“Why not just work at a coffee shop?” you might ask. First off, coworking offers a much more comfortable space. After all, these spaces are geared towards getting work done rather than selling coffee and pastries. Typically, you get a real desk (and not some funky setup at a cafe) plus the internet is more reliable because so many people are really depending on to do work. I’m not sure about internet speeds, but I would bet that you’re better off in the coworking space than the coffee shop in most cases. You also won’t have to keep buying coffees to stay at coworking spaces. In fact, most provide complimentary coffee and sometimes food, too. Plus, you can actually talk to others that are working in the same space. This is the area that I’m least sure about in terms of how it would benefit me, but it has great upside potential and would probably help me more than I think it would. The local spaces offer different events for members to learn different skills (like social media). Most coworking spaces are open 24 hours, which makes them accessible at any time, too.

What’s it cost?

Coworking spaces are far from free, but can still be a good value. For 24/7 access, the two spaces in New Haven cost $197 and $250. There are also part-time options for about $75 for 50 hours a month, which is probably what I would consider for myself right now. I think if I was going to consider coffee shopping it, the coworking space would still be a good deal at about $1.50 an hour instead of spending money on coffees and drinks for 50 hours of cafe time!

Workspace for the traveler

Another aspect of coworking that gets me excited: there’s an international network of coworking spaces! It’s called Coworking Visa, and there are 30 U.S. states and about 90 countries listed with spaces. Basically the deal is that if you belong to a coworking space in your hometown, you can use any other coworking space on the Visa list for 3 days (and sometimes longer) at no charge. This is really cool if you’re traveling somewhere for a short period and need a space to work in temporarily. There are many awesome coworking spaces around the U.S., and I could definitely see myself using this when I visit Boston and want to stay past a weekend. Of course, if you plan to stay longer than 3 days, you’ll need to work something else out. Most coworking spaces have a variety of plans, so you can simply buy a cheaper hourly membership in your destination of choice to make it worth your while.

I’m thinking of testing out a coworking space very soon. I think it will definitely help my productivity with my freelance work, plus give me the opportunity to meet others that are doing awesome things. The only reason I haven’t tried it yet is that I still have the 9-5, and the coworking spaces here have some restrictions on dropping in outside of regular business hours. Since I really want to report back to you and let you know if it’s any good, I’ll make it my goal to go in and check one of them out by year’s end!

Have you ever tried (or thought of trying) coworking?

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photo by: achimh

Crafting a Bucket List For an Awesome Life

crafting-bucket-listAfter being inspired by my Location Rebel comrade Sean’s bucket list and his post explaining how it got him on a TV pilot (awesome!), I decided it’s time that I start working on my own. I definitely got some inspiration from Tyler’s 1% Club, too. Aside from being a really fun idea, I think it makes a lot of sense for goal setting, too. If I’m going to do this whole location independent thing and travel thing, I should at least have some ideas of where I want to go and what I want to do!

Here’s what I’ve come up with so far: (this will be going up on it’s own page soon, as well)

– Live on the beach in another country for a month

– Learn to surf

– Enjoy a local beer in 30 different countries

– Overcome my fear of heights

– Tour Europe by bicycle

– Run a marathon

– Compete in a triathlon

– Learn to ice skate and join a hockey team

– Learn to speak Spanish fluently

– Take Salsa and swing dance lessons

– Go vegan for 6 months

– Visit every state in the U.S.

– Visit every national park in the U.S.

– Go white water rafting (again)

– Visit each of the seven wonders of the world

– Hurl tomatoes at La Tomatina

– Learn to make wine

– Spend a whole week without speaking a word

– Attend a PGA major golf tournament

– Attend the Super Bowl (and watch the Patriots win)

– Attend the Winter Olympics (and watch a ton of hockey!)

– See a football game in Europe

– Learn to sail

– Live on a boat for 6 months

– Fly first class

– Create a video that gets more than 1 million views on YouTube

– Get interviewed by a major publication

– Write a book and have someone tell me it’s changed their life

– Teach/mentor someone to become more successful than I am

– Leave more than $1 million to charity in my will

That’s what I’ve got for now, and I’m sure I’ll be building on this a bit. After making this list, it seems a bit daunting. But I can’t imagine ever completing this list if I lived the traditional employed life. I’m also going to make it a goal to check off at least one item a year on this list, although I’d definitely like to pick up the pace on that once I get going 🙂

 Do you have your own bucket list? Is there anything you’d suggest that I add based on your experiences?

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photo by: Redeo