One of the great things about New York is that getting to places that aren’t New York can be really easy. In this trip planning segment, our next adventure will be to Boston for the weekend. These write-ups should act as guidelines, and are not a promise that you can find these exact trips; however, I hope they are close enough to show that you can really do “expensive” trips for much less than you think.
As you’re probably aware by now, I’m pretty partial to Amtrak (to put it mildly), and using them to get between New York and Boston is super easy. To be honest, the worst part about Amtrak is Penn Station–jeez, what a dump.
That aside, you’ll want to take one of the later trains after work and one of the latest trains from Boston on Sunday, that way you have two full days in Boston. I’ve priced out the following on Amtrak:
The trip will run you 5,244 points (4,982 if you have the Amtrak card) per person, and is only about 4/4.5 hours in each direction. Note: you’ll be getting off at Back Bay, not South Station, as the hotel is much closer to the penultimate stop on this line. This saves you $136.80 in train fare per person. You could also take the bus (Greyhound, BoltBus, MegaBus, etc…), but honestly, treat yoself.
Next, your hotel. If you can manage, walk the .2 miles to the Westin Copley Place. You’ll be staying here for both nights, and using 40,000 SPG Starpoints to do it.
Note: The increased bonus for the Starwood SPG card expires today! If you want to take advantage of this deal, make sure to do it ASAP!
Once in Boston, use Saturday and Sunday to explore! Boston has a TON of great things to do–including Sox games. Unfortunately, the Sox are at Toronto that weekend. That shouldn’t stop you from exploring Chinatown, hitting up the multitude of excellent museums, or just ambling around some of Boston’s historic neighborhoods.
All in all, you’ll spend 49,964 points for your weekend in Boston:
| Items | Points Used | Cash Value of Points | Cash Spent |
|---|---|---|---|
| 2x Amtrak tickets NYP-BBY-NYP | 10,488 Amtrak Guest Rewards miles
(9,964 if you have the Amtrak card) |
$273.60 | $0.00 |
| 2 nights Westin Copley Place |
40,000 SPG Starpoints |
$611.92 | $0.00 |
Cost of trip: 49,964 points and $0.00 ($79.00 if you include the Amtrak card annual fee)
Cost of trip without miles/points: $885.52
Savings: $885.52, or 100% off!
So which cards make this possible? You’ll need two cards:
| Card | Annual Fee | Spending Requirement | Bonus Points | Notes |
|---|---|---|---|---|
| Bank of America Amtrak Guest Rewards World | $79 | $1,000 in 90 days | 20,000 points | You will still have 10,036 points for another trip. |
| American Express Starwood Preferred Guest | $0 for the first year, $95 every year after that | $3,000 in 90 days | 35,000 points | This is the highest the bonus has ever been. You will need to spend $5,000 on the card to get all 40,000 points. |
And that’s that, folks! Here’s to your free weekend in Boston!
A Point Earned 
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