How to Plan a Honeymoon

I have to admit that one of my favorite parts of the planning process was actually planning our honeymoon. Don’t get me wrong, I loved planning the wedding but it was just different. There were times when it feels like you are planning the wedding for other people. Parents, grandparents, aunts, uncles, friends, etc. all have expectations of what your wedding will be. And realistically, they are all coming to this event for you, so it is kind to keep  them in mind when planning. But, the honeymoon. The honeymoon is different. The honeymoon is truly just for you and your special someone. I love traveling in general, so this was even more fun.

It took us a while to figure out where we even wanted to go. Initially we really wanted to go to Europe. Then, we were thinking somewhere more tropical. Ever time we came up with an idea, it just didn’t seem quite right. We didn’t want to travel too far and waste precious time on a plane. We also wanted to visit somewhere that neither of us had been by ourselves previously. One day Riley suggested New England and I was automatically like… YES! That is perfect.

It was perfect for a lot of reasons. It was only a quick direct flight across the country, rather than having to deal with layovers or trans-Atlantic flights. We had both been to places in New England in the past but not to the specific places that we were going (other than New York City). Each place had a wide variety of activities from museums to the beach to shopping. We decided we were going to have a three part honeymoon. Part 1 in Kennebunkport, Maine. Part 2 in Nantucket, Massachusetts. Part 3 in New York City, New York. We thought this would give us time in places with three different speeds and types of things to do.

Once we decided where we were going, the planning started. My planning process ultimately broke down into three parts as well; part 1 was accommodations, part 2 was  logistics, and part 3 was things to do. I am going to focus on how I planned rather than what I planned in this post! In the coming weeks, I am going to talk about each leg of our trip!


Places to Stay. Out of everything related to planning our wedding, I was probably the most nervous about finding great places to stay… Your accommodations and having a comfortable place to stay can really make or break a trip. Granted, you end up not spending a lot of time in your room on vacation, but coming back to a bad room or being in a bad area can be a bit frustrating. Because of this, I did SO much research when finding places for us to stay. I checked travel guides, maps, multiple review sites, etc. I was determined to find us great places to stay. I think I did a pretty good job when it was all said and done.

  • Check TripAdvisor and Google Reviews. Any hotel/inn’s website will only highlight positive reviews, these places will review everything.
  • Look at a map. Get familiar with the area a bit. Figure out where the clumps of restaurants and shops are. In general, you will probably want to find something close to one of those clumps.
  • Check blogs or travel websites! This is a great place to start, as they will normally have suggestions. I love looking on Pinterest to find great local blogs/travel websites.

Flights. After figuring out where we wanted to go specifically, it was time to book flights. Because we were doing a three part honeymoon, we were flying into one airport and out of another one. This made finding flights just a bit more difficult. Instead of being able to do one search for a round trip flight, I had to do two searches for two individual one-way trip flights. In general, here is my process for finding flights:

  1. Finalize your trip dates. Note if there is any flexibility with these dates. If you can leave a day earlier or a day later on either side of the trip, that can be helpful.
  2. Decide what your priorities are for the flights. Your priority may be to leave after 8:00 am, but before 12:00. It may be to have a direct flight both ways. It may be that you want the least expensive flight possible.
  3. Do an initial search for flights. I like to use Kayak as my starting place. I will see what is available. I will check what they have listed against the individual airline websites, just to make sure there aren’t discrepancies.
  4. After I see what is available, I will reevaluate my priorities. They may stay the same, but they may change if the flights are more limited than I thought or the prices are higher than I thought, etc.
  5. After I narrow down the flight I would like to book, I will start monitoring the flight to look for the best price. Always use an incognito browser tab when doing this! Once the prices seem to become stagnant, I will go ahead and book!


Transportation. For us, the next big question was transportation while we were on the honeymoon. If you are going on a one destination honeymoon, that may be as simple as whether or not you are going to rent a car. Maybe you’re going to a city with good public transit and don’t need it. Maybe you are going somewhere more rural where you do.

If you are going on a honeymoon like ours, where you aren’t staying in the same place the whole time, this becomes a whole other question. We were going from a more rural area (Kennebunkport) to an island (Nantucket) to a big city (New York), so I had a bit of work cut out for myself in figuring out how we would get from place to place and how we would get around when we were there. What we ended up deciding on was renting a car un Kennebunkport, driving it to the ferry port to get to Nantucket, take the ferry to Nantucket, walk or ride bikes around the island, take the ferry back, rent a new car to drive into Connecticut (we were originally going to stay for a night in Connecticut), then take a train into New York City and get around in cabs or on the subway in the city. In hindsight, this wasn’t the most well thought out plan because we had never done it before. If I were to do it all over again, I would still rent the car in Kennebunkport, return it at the ferry terminal and take that into the city. Then I would rent bikes for the whole time we were there. We only had them for about half the time and I wish we had had them a bit longer. Then I would have taken the ferry from Nantucket to New York (which I didn’t know would be more efficient at the time). At the end of the day, I think it is just super important to think through what is the easiest and most efficient way to get from point A to B and work through the issues that could come up. I think if I has done that we would have had a bit clearer path.

Airport Accommodations  Another detail to not forget about is how you will get to and from the airport. You may live in a place where this is a no brainer. But airport parking can be expensive, airport parking can fill up (especially in the summer), Ubers can be unreliable in the morning, so on and so forth. Think through your plan and make reservations ahead of time. The last thing you want to happen is to miss your flight because you couldn’t find parking or an uber. If your airport parking allows you to make a reservation, do it. If you are going to take a cab or shuttle, book it far in advance. Just make sure you know how you will get there and home!


Restaurants. Now you are onto the fun things, in my opinion. Now you get to find all the yummy places you will eat and fun things you will do. Finding great restaurants is one of my favorite things to find. I always start on Pinterest. I will just search the place and restaurants. I will start opening different blog posts and articles and reading through them. When I come across something that is of interest I will write it down, noting when more than one place suggests it or if the articles have any specific suggestions about the restaurant. Once I feel like I have gone through enough Pinterest finds, I will also just Google the town/city and see what I can find there. As I go, I try to organize the suggestions by breakfast/brunch, lunch, dinner, take-out and drinks. After I have my list together, I will note if there is anywhere I definitely want to go and will make reservations as needed.

Despite all of my careful research, it sometimes goes out the window the minute we get there. I will take a suggestion from a local over internet research any day of the week. I always try to ask people we meet or even servers at restaurants if they have any suggestions. In my experience, this is how you find the best places in town that may not make it in manicured travel guide.

Activities. Last but definitely not least, is activities. Both Riley and I love to explore, go to museums, check out art galleries, etc. While we love the beach or lake, neither of us are the types that can sit on a beach or be on the lake all day. Maybe for a morning or an afternoon, but we need something to break it up. So, finding activities is definitely important! To find activities, I take the same approach as restaurants. Research on Pinterest and Google, make reservations as needed, be prepared to change things up when you get there.

When I am looking for activities, I try to look for things in a wide variety of categories. I will look for things like museums, art galleries, hikes/bike paths, tourist attractions, drives/bike rides, spas, other outdoor activities, boat rides and shopping districts. I will get my list together so we have a few things to pick from on any given day.

Planning all of this can feel a bit overwhelming. Consider using this Honeymoon Planning Worksheets to work through all of the details.

Honeymoon LogisticsHoneymoon Fun

Hopefully this is helpful when you are planning for your honeymoon (or really any big trip)! I absolutely love planning trips. I probably have more trips planned in excel documents than I will ever be able to take. This was definitely the most special trip I have gotten to plan. Until next time, friends… CML