By Amy Angelilli, GoGirlfriend Contributor

How to travel with your lover...

There are certain things that appear over and over again in online dating profiles. The majority of singles claim to appreciate a sense of humor, fun activities and travel. Many of them neglect to clarify what kind of travel they appreciate though. Because I had been told my kind of travel isn’t mainstream, I made sure to include anecdotes from my trip to South Africa, as well as my general travel values, when I explored online dating at age 40. Five months later I was on my first international trip with Chris – the man who would become my husband. While I’d like to say the adventure in the Virgin Islands went off without a hitch, I’d be lying. Even though we thought we were clear on each other’s travel styles, likes/dislikes and rules of the road, it wasn’t until we were actually traveling that our values became clear to each other.  

If you’re planning a getaway as a Valentine’s Day celebration with a new someone special, here some areas to discuss before you pack your suitcase:

Budget vs. convenience

I admit it. I booked the ferry from Tortola to St. Thomas to St. John instead of going directly to St. John because it cost less. My not-yet-husband thought that was ridiculous, as he had always opted for convenience over budget. The jockeying around took quite a bit of extra time, but I was proud of myself for having saved money that could be spent on other trip expenses. Now, when this kind of routing situation comes up, we discuss it before I book. I’ve learned to always go for the non-stop option, even if it cost a few extra dollars. The time vs. money discussion is so important whether you’re planning a local road trip or an international adventure, as these decisions will help guide your trip planning process well into the future.

Division of duties

Normally I like to be responsible for planning all of my travel. Partly it’s because I enjoy the process and partly it’s because I’m a budget traveler. (See #1.) However, because this was our first major trip together, I split the duties between us. While I had been the one to find the guesthouse on the organic farm via airbnb.com, it was Chris who actually handled the booking.

Once we arrived, Chris realized he neglected to bring the caretaker’s contact information, so we had no idea how to find the cottage. A few hours later, based on my hunch, we finally spotted the cottage tucked away in the foliage on a dirt road off another dirt road. Chris asked me to please be responsible for bringing along all the travel details in the future. So noted! Even if you’re not yet sure who likes to do what, prepare a checklist so you’re sure all the details are taken care of and all the information is with you when you arrive.

With or without you and you and you?

The cottage on Tortola was so secluded that once we got into the 4x4 required to get to and from the property, we did all of our activities in one drive. To go out and back more than once a day was a huge undertaking as the roads were horrible and the cottage was so secluded. Chris loved it. When we moved over to St. John for the last leg of the trip, we only needed a car for our one day of exploration around the island’s rim as the rest of the time we spent walking from our small hotel to the village. I loved that.

What became clear was that Chris valued seclusion in nature where he could minimize his interactions with others while I thrived in small towns and villages where a bike – or two feet – are all that’s needed to enjoy the local culture (and people). In what environment do you thrive when traveling? A busy city? A rural community? Nature? And if you don’t have the same thrivability as your special someone, can the trip be saved? Of course – by compromising! Now I try to create itineraries where even city stays include a remote leg in nature.

How many legs are too many legs?

The trip to the Virgin Islands included three legs over a 12-day period with the focus being Tortola. It was a nice pace that that both of us were pleased with – in theory and in reality. Fast-forward two years to our 12-day self-guided driving tour of England (Bath to Cardiff to the Cotswolds to Liverpool to Manchester to York to London). Even typing it makes me exhausted!

Since the UK is so small, we had been advised – even by guidebooks – that this was doable. In theory, yes. The reality was much different. Factor in jetlag, driving on the other side of the road and actually having a desire to spend some time soaking in each of the stops, and it became clear we has created an overambitious itinerary. But, at least we both agreed! How fast or slow you want to – or are able to -- experience an area is a real issue. Get together on how to approach this part of the planning, so no matter what your pace, you’ll both be on the same page about it – even if it means kicking yourselves for attempting to pack too much into one trip.

It’s coming up on the three-year anniversary of our Virgin Islands adventure and I continue to negotiate travel options with my husband. There are some things I know will never fly and, almost always, they are things that wouldn’t work for me either. Chris always tries to weasel a small luxury experience into the trip. I usually veto it as budget trips mean more trips! But, once in a while I’ll give in (one night at the Hard Days Night Hotel in Liverpool, for example) and consider it a compromise to keep us both enjoying happy travels together – for years to come.

Traveling with someone new – girlfriend, friend or lover – for the first time can be a logistical challenge. What other conversation points would you like to add into the mix. Drop a comment below or connect with us on Facebook or Twitter … we’d love to hear your ideas!

About Amy Angelili

Amy Angelilli is a socially responsible lifetime adventurer who’s visited at least 24 countries – and she continues adding a new one to that list every year. Between trips, she moved from Philadelphia to Denver in an RV filled with rescue pets, and opened a low cost spay/neuter clinic for stray cats so she wouldn’t have to adopt any more. Now, as Chief Adventure Officer of The Adventure Project, she uses improvisational theater techniques to play with others so that they may discover and create their own adventures – at home or abroad. She performs regularly in “3 Blind Dates” and “It’s All About Amy” – improvisational theater experiences she created and produced. When not on stage, she’s usually packing, planning or putting her frequent flier miles to good use on a new adventure. Catch up with Amy on Twitter, Facebook, LinkedIn, Pinterest or Instagram.