Getting the Most from a Long Weekend

Enjoying Miami Beach

My daughter and I just returned from a long weekend get-away. We flew to Miami, boarded a cruise ship for a three-day cruise, and when we were back on land, we enjoyed an extra day in Miami.  For our almost five-day vacation, my daughter only took one day off work. I work from home with a flexible schedule, so it was easier for me to get away.

We had a great time on our weekend away. I’ll tell you more about it in a future post. Today, I’m going to explain a little about our rationale in planning.

Choosing the Right Weekend

When planning a long weekend away, the first dates that come to mind are the weekends of Labor Day and Memorial Day.  These are good options, but since they work for so many people, attractions may be busy and flights may be more expensive than normal.

Check your work schedule and calendar to see if you have other holidays that might work better. Many people are off work on Martin Luther King Day, Presidents’ Day, Columbus Day, Veteran’s Day, or Good Friday. One of my daughters got married on Columbus Day weekend last year. She and some of the guests were able to enjoy an extra day for the wedding weekend.

The daughter who went with me on the trip this past weekend has Good Friday off. This year, her birthday falls on the same weekend. She thought it would be fun to take a little trip to celebrate her birthday – especially since she had an extra day to add to the weekend.

Why a Cruise?
The Norwegian Star

A cruise can be a great way to spend a long weekend, although other destinations can fulfill the same criteria. We were looking for something close and easy to get to – the flight was only a couple hours.

The destination should be one where we would not have to pack and unpack. We wanted to stay in the same hotel or other accommodation for a majority of the time. In this case, we weren’t as successful since we are staying in a hotel for one night before and one night after the cruise. However, the three nights in the middle will be in the same place.

Palace Restaurant on the Cruise Ship

Since we didn’t start our planning long in advance, we looked for something simple. On a cruise, the meals and many activities are planned for us.

We could have visited family that lives a few hours away. Our relatives would have helped plan activities and meals, making it simpler for us. We could have chosen to go to an all-inclusive resort which would have had a similar feel to the cruise. After considering all our options, we decided to cruise.

Planning the Itinerary

The cruise we chose left the port of Miami on Friday afternoon, sailed to the Bahamas for a couple days, and returned to Miami on Monday morning. Usually, I suggest flying to the port city the evening before a cruise departs. If a flight is delayed or cancelled, there would be options for changing to a different flight.

When my daughter and I started looking at flight possibilities this time, though, we saw that our options were much better on Friday morning. We needed to be on the ship by 3 pm. If we took an early morning flight, we would still have some time available if the flight was delayed.

The flight we chose was scheduled to land at 9:30 am, so we felt relatively confident in booking it. The flight was delayed, but only by about 30 minutes, so we had plenty of time to get to the port and on the ship.

Starting the Night Before

In the past, as soon as my husband came home from work on the day before a trip, he would say, “I’m on vacation now!” If you pack the majority of your items ahead of time, you can add an additional evening to your vacation.

Since we had an early flight on Friday, we chose to travel to an airport hotel on Thursday evening. Our flight left at 5:30 am. We usually try to arrive the recommended two hours before the flight, even though we often spend most of that time waiting at the gate.  It takes about an hour and a half to drive to the airport from my home, so I would have had to leave at 2 in the morning to get to the airport on time.

Since my daughter and I have TSA Pre-check, we didn’t go to the airport until 4 am – that is when Pre-check opens and with Pre-check we usually get through security more quickly. It was still early, but there was less driving.

Giant Pretzel – Hofbrauhaus Chicago

The Hofbrauhaus Chicago is one of our favorite restaurants located near the airport. Starting our vacation early, we ate dinner there on Thursday evening.  If you don’t know, the Hofbrauhaus Chicago is patterned after the famous Hofbrauhaus in Munich, Germany. Our family ate at the German restaurant in 2009 – when we visit the Chicago restaurant, we are reminded of that experience.

Another option, especially for families with children, might be to spend the first night at a hotel with a nice pool or indoor water park. Adding an extra evening can make a vacation seem longer.

Staying an Extra Day at the End

Again, when looking at return flights, we saw that returning mid-day would cost much more than flying early or late. Since we were scheduled to disembark the ship around 9 am, we wouldn’t be able to book a flight until at least 1 in the afternoon.

Looking at this schedule, my daughter knew she would have to take Monday off work. If we stayed in Miami for the day, we could fly home early Tuesday. We could save money and enjoy another day of vacation. When our flight landed on Tuesday morning, my daughter drove home and went straight to work, working almost a full day. In all, we had four days and five nights of vacation using one vacation day.

Making the Most of a Long Weekend

My daughter and I packed a lot into our weekend. We started with a fun restaurant meal on Thursday evening. We boarded the cruise ship before noon on Friday and were able to enjoy the rest of the day exploring the ship.

Dessert on the Little Havana Food Tour

Saturday and Sunday were spent cruising and visiting the Bahamas (more on that later). When we got off the ship on Monday morning, we took a Lyft ride to the Little Havana neighborhood, where we participated in a food tour.

We spent time in the afternoon in the South Beach area – including some time on the beach and in the water. After a nice dinner on the west side of South Beach, we headed to the hotel near the Miami airport.

We had a great time on our long weekend!




    1. Yes, we did have points to fly this time. Southwest often has great prices for flights around the country. This time they did not, so we flew in basic economy on American. Basic economy is cheaper, but does not include a checked bag – which we didn’t need for the short trip. We also could not choose our seats. The flight price would have been quite reasonable using cash, but we also looked at non-flight options for the weekend like visiting family or driving to St. Louis or another close city.

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