Family Trip to Europe with Miles Tutorial: Adding a “Cheaper Than Free” One-Way from the Caribbean

My parents and sister are planning a two week trip to Europe this summer. The vacation will be for three people and cover three different cities in Europe. As an added bonus, they decided to include a trip to Saint Martin in the Caribbean taking advantage of a “better than free” one way trick to save on American Airlines miles. Just about everything (flights, hotels, fuel surcharges) will be paid for with points. This post is part of a tutorial series to follow along step-by-step how I planned their trip!

Series Index:

• Overview

• Finding American Airlines Award Space to Europe

• Adding a “Cheaper Than Free” One-Way from the Caribbean

In my last post, I had found my family three tickets to Rome connecting in London from JFK airport. These were American Airlines award tickets and would cost 30,000 American Airlines miles in economy class for each person plus taxes and fuel surcharges. Although they’re happy to be going to Europe, they decided to stretch their miles even further by pulling off one of my favorite miles tricks: Booking the 20,000 American Airlines miles for a combined one-way trip from the Caribbean in Spring and a one-way trip to Europe in Summer!

Saving 10,000 Miles by Booking An Additional Trip to the Caribbean

Because my family is not stopping anywhere else in North America after leaving New York (their next stop is London), New York becomes my family’s North American gateway city. According to American Airlines award rules, all awards are booked as one-way and allow a free stopover at the North American gateway city. This can be a very long stopover – up to a year from the day you buy your ticket. To take advantage of this, they can actually extend their one-way to Europe to include a free one-way to New York from anywhere else in North America first. But in reality, it’s even better:

They can fly from Saint Martin to New York in April and then fly from New York to Rome in June for 20,000 miles total per person!

Let’s give an overview of why this works:

• Provided they can find award space, they can add a one-way flight from anywhere else in North America to New York at no extra cost.
• The one-way award from elsewhere in North America to New York and the trip from New York to Europe count as one ticket with a stopover in New York and will still price as a single one-way trip.
• American Airlines charges off-peak pricing to Europe for travel between October 15 and May 15. At this time, award tickets will cost 20,000 miles each way in economy.
• Provided the trip starts between October 15 and May 15, the whole thing will cost 20,000 miles each way.
• This means that, by adding a one-way trip from the Caribbean between October 15 and May 15, the whole thing will price at 20,000 miles. That’s two one-way trips: One from the Caribbean in the Spring and one to Europe in summer.

I explain all this in far greater detail, including how to book these kinds of awards, in the posts:

• From Caribbean in Winter + to Europe in Summer for 20,000 American Airlines miles TOTAL
• How to Add Free One-Way Trips on American Airlines Awards

Choosing an Island

My parents wanted to take a trip to the Caribbean in mid-April and they wanted to fly non-stop. Because it’s a little bit tiresome to check every single island for award availability, they used the American Airlines Award Map Tool to check which island they could visit with American Airlines miles:

Search American Airlines Caribbean Award Space To Every Island At Once!

They found convenient non-stop flights for all three people to Saint Martin and Antigua. While both islands are beautiful, Saint Martin has two hotels they can use points while Antigua has none.

The Westin Dawn Beach Resort & Spa, St. Maarten is on the Dutch side and costs 12,000 points a night in low season or 16,000 points a night in high season. The Radisson Blu Resort Marina & Spa is on the French side and, in my opinion, one of the best deals for hotels in the Caribbean! With the Club Carlson credit card, they have plenty of Club Carlson points and are happy to use them there!

Booking the Ticket: From Saint Martin in Spring and to Rome in Summer for 20,000 Miles Total

Once you decide on your individual segments, you can actually book all your segments right online (unless, of course, you are flying Iberia as part of your itinerary and you’ll have to call customer service for that.

To book the ticket, simply visit the American Airlines website and start in the Flights section under Plan Travel

On the next page, simply type in your dates for each of your legs one at a time. Since you’ve already searched availability, this part should be easy. In my example, I can type in that I want to travel from Saint Martin to NYC in April and NYC to Rome in June.

Your date options then come up showing that both legs together cost just 20,000 miles! It even says

This international award allows a stopover at New York – NYC for no additional miles. Mileage required for both flights is displayed on the Award Legend for the international flight.

An amazing savings, if you ask me!

Getting Tickets to the Island

My parents save miles by adding a one-way trip back from Saint Martin. Instead of the flight to Rome costing them 30,000 miles per person, they lower the cost to just 20,000 miles. That is, by going to Saint Martin, they save 10,000 miles over the cost of what they’d already be paying to Europe.

While this takes care of their trip back from Saint Martin, they still need tickets to Saint Martin as those are not included. That does cost additional miles or money to get there, but let’s look at why this may be a good deal:

• By adding the trip from the Caribbean, my parents free up 10,000 miles from each ticket.
• These miles can then be used to fly to the Caribbean.
• American Airlines charges 17,500 miles each way to the Caribbean from New York. If they use American Airlines miles to get there, the additional round-trip to the Caribbean only costs 7,500 miles per person.

You may be able to get an even better deal by using British Airways miles to fly to the Caribbean. Or not. In my parents’ case, they could not find award availability to Saint Martin that worked for their dates and opted to use a combination of fixed-value points to get there. I’ll be covering that in a later post.

Summary

So now that we have found a flight from Saint Martin, let’s see where we are in our plan:

• Find a flight to Saint Martin.
• Book a hotel in Saint Martin.
• Find award flight from Saint Martin: Three American Airlines non-stop award tickets included with the trip to Europe.
• Find award flight to Europe: Three American Airlines award tickets New York to Rome connecting in London.
• Find award flights from Europe.
• Find flights and train tickets within Europe.
• Book hotels in each city.

Miles spent so far: 60,000 American Airlines miles (20,000 per person).