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Status Match Perks: Free Dinners, Hotels, and Cruises

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I just returned from a mostly free trip to Las Vegas and have a free 7 night Bahamas cruise planned later this year.  Below is how I did it...read on for more.   If you need additional help with a personalized points/miles earning and/or redemption strategy, drop me a line at wheelsupwithpoints@gmail.com.   It all starts with Wyndham Diamond status, which small business owners (whether a side hustle sole proprietor or a real estate LLC) can earn with a single Barclays credit card that comes with a $95 annual fee.   The initial fee is immediately offset by the sign-up bonus of up to 100,000 points outlined below whereas the ongoing annual fee is further offset by a 15,000 point anniversary bonus every year as well as by the first step in our status match journey. 50,000 after spending $4,000 on purchases in the first 90 days  50,000 after spending $15,000 in the first 12 months.   Status Match 1 (Online) : Wyndham Rewards to Caesar's Diamond. Simply enter your Wyndham Rewards Numb
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FRA-JFK in Singapore's A380 Suites

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This is by far my most expensive booking for a one way flight, however I had really wanted to try this product as well as finally fly on an A380 and with limited options now out of JFK, Singapore offered me a chance to do so with significantly lower out of pocket costs (in the form of taxes and fees) than Emirates.  Miles were transferred to Singapore's Krisflyer program from American Express's Membership Rewards, which are relatively easy to earn.  You can browse their sign-up bonuses here . My return trip home from Europe started with a visit to Lufthansa's Senator Lounge, as Frankfurt is obviously an outstation for Singapore and my flight being a rare Fifth Freedom flight between two countries other than the airline's home country.  Fifth freedom flights are allowed so long as it originates or terminates in the home country, so technically my flight was just an extension of the earlier flight from Singapore to Frankfurt.  This lounge had a much nicer vibe than I was
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Wanderlust? Save Up For Future Travel Now...

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Did you know that you can fly coast to coast on Southwest for as little as 13,000 points and you can earn 40,000 Southwest Rapid Rewards Points with the  Chase Southwest Visa  card?  All you have to do is spend $1,000 within the first 3 months of opening your account!   If you're new to points and miles and want to learn more before getting started, send me a message at wheelsupwithpoints@gmail.com .
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The Sun Has Not Set On Award Travel...

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With many of us not planning to travel any time soon, now is an opportune time to stock up on miles.   My wife recently signed up for two new American Airlines credit cards which will net her over 120,000 miles to add to her 126,000 mile balance.  This is almost enough for two round trip partner awards in Business Class all the way to Bali or the Maldives! That said, with a two year old, I think we'll just settle on our favorite tropical destination:   Hawaii ! American Airlines recently ditched their award chart and moved to dynamic pricing so travel with flights on American isn't the best deal when it comes to AAdvantage miles.  However, they have been running "web specials" and currently, First Class from Philadelphia to Maui is around 100,000 miles per person round trip.   Best part is that on itineraries connecting in Dallas, the ~8 hour leg is in lie flat first class! For hotels, I think we'll try something new a
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