Why You Need to Haggle On Your Trip

Being on hold for the majority of two hours was not on my itinerary for this trip. Starting the day with fresh coconut water and pineapple, wasn’t officially, but it was a welcomed breakfast.

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Following the theme of this trip, today started with a few knuckleballs. I have started to reluctantly await each day’s plot twist, a la Scrooge and his spirits in A Christmas Carol, whether it’s a restaurant that’s closed or a ferry that filled before we could get our tickets.

Today was transition day from Fajardo to Old San Juan. That meant checking out, returning the rental car and checking in at our new hotel. On our way to the airport we stopped to get fresh fruit from the coco frio man. Not knowing Spanish well enough to barter or attempting to, we got hosed on the cost of the fruit. To save some toll money we took the 3 all the way to the airport instead of getting on 66. That saved at least $7. The first two legs were relatively smooth, minus creating my own roundabout trying to find a gas station before returning the junk bucket.

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We meandered to find ourselves a cab. There’s a stand and the fares are fixed. A man gives you a paper detailing your destination area of town and costs. Ours was $23 to Old San Juan. The driver dropped us off and we went to check into the Sheraton Old San Juan. The front desk woman couldn’t locate a reservation under my name. Plot twist: there is another Sheraton in new San Juan, which is across a bridge and away from all the attractions we wanted to see. We asked if we could walk it and she suggested we take a cab, not because it was far, but for safety. I asked her an estimate of what the fare would be and she said $10.

While in the new cab, I started mentally flagellating myself for not giving the cab driver the address of the hotel. The money saved on avoiding the toll road was now wiped away. During the drive across the bridge we discovered the other hotel wasn’t that close to Old San Juan and the route wasn’t an easy one if we opted to walk it. We exited the cab and I gave the cabbie $5. He said the fare was $18. We did a bit of back and forth and we settled on $15. I wouldn’t call that success, but progress from this morning.

Before checking into the new hotel, I sat for a moment to think and discuss options with Leann. This wasn’t the area I booked when researching options and it wasn’t convenient for our vacation plans. I booked the trip through Expedia and called them to find a solution. My first call was 52 minutes, most of which was waiting on hold for a manager that never arrived. I hung up and re-dialed. This time I asked for a manager. I explained the situation and the manager assisted me in exploring options, including a credit to cover cabs to the desired area and alternate hotels. After a few more managers and calls to corporate, she was able to find a hotel in old San Juan with a room for the same duration. That call took another hour until final resolution.

What at did we do next, you ask? Back into a cab to return to Old San Juan. This time the bellhops at the hotel assisted in establishing the cost of the cab and notified the driver that we needed a receipt to get reimbursed. This cab ran us another $17. That’s nearly $60 in taxis in 3 hours.

Arriving at our new hotel, El Convento, we quickly lost all concerns over the costs of the cabs being worth it. So far, it’s near the top of any hotel I have ever stayed in. It’s the type of place that if asked to dispose of s body, wouldn’t ask questions. It’s the type of hotel that looks like the after for every HGTV show. It’s the type of hotel where you feel you shouldn’t concern yourself over someone over charging you for a pineapple.

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We were early for check-in so we left our bags and explored Old San Juan. Wandering around the narrow streets, my eyes darted from colorful home to sweeping aquatic vistas. The architecture is reminiscent of new Orleans’. After an irritating morning, the warm sun and cobblestone roads helped me forget about the uncertainty in where we would sleep tonight. Popping in for one of the claimed original piña coladas also helped eased those frustrations.

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We checked into our room and figured out how to spend the afternoon. One of the forts is right by the hotel, so we explored the grounds. While my timing may be off for ferries, it is impeccable for sunrises and sunsets.

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El Convento used to be a convent so I’ll be saying prayers of thanksgiving this evening that everything was resolved and that everything worked out, as it always will, even if I am bad at haggling.

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