Every time I start thinking about planning a trip with friends, my gut knots up as a reminder of all the hoops I have to jump through to make it happen. Forget about the difficulties of agreeing on dates and making reservations. That’s not what makes me panic. It’s the coordination of work and family responsibilities during the time I’ll be away that almost scares me into staying home. Almost, but not quite, because I know once the destination is in sight and friends are present, all the sweat equity that went into planning will be well worth the effort. My work and family always seem to get by without me for a few days, and best of all, I get to explore, recharge and reinvigorate with my friends. What could be better than that?
Now that summer is here and Covid-19 travel restrictions are easing up, I reached out to my friend and travel advisor Lisa Cohen-Dumani for expert guidance on trips with friends. Lisa specializes in luxury destinations through her company The Travel Fairy. Not only has she traveled all over the world, Lisa has learned through experience how to plan a fabulous trip.
LOF: Lisa, what constitutes a great destination for a trip with a friend, vs. a family or romantic vacation?
LCD: The goal of a great trip with friends is usually to get in enough hang time, explore a beautiful destination and then go home dreaming about the next time you will get together again. You could go back to one of your old haunts, like your college town, or explore a fun new destination like Nashville or Napa, or head to a resort, like a beach or a spa. So, the destination is important, but so are the accommodations. If you’re used to being woken up several times a night by your kids to get them water or a stuffed animal they dropped, you will want to sink into a comfortable bed, draw the blackout shades and sleep through the night after hours of stimulating conversation with wine and your friends. I love hotels that have suites with a great living area, a staffed villa where you can make yourself at home but don’t have to worry about doing the dishes, or rooms with two king beds where everyone can laze around in their PJs for some late-night catch-up sessions.
LOF: What kinds of things do friends traveling together need to get on the same page about in trip planning?
LCD: BUDGET! Not everyone can afford to do the same thing. Some people will be on a very restricted budget, while others may have no limit to their spending. Either way, you’ll need to find a price point everyone can agree on.
You should also figure out what kinds of activities you all want to be doing, and how much of the time you will want to have scheduled. Some of you might be looking for lots of unstructured time, while others will want to make the most of their time away. If you are flying all the way to Paris, do you want to have restaurant reservations in advance or do you want to stroll the streets and eat when you get hungry?
Lastly, what kind of traveler are you? Are you a carry-on-only person, or do you come with 10 pairs of shoes for the long weekend just in case you might need them? If you’re only happy when you’re dressed to the nines, absolutely bring what you need to enjoy yourself. But don’t forget these trips are definitely an opportunity to go with the flow and revel in your friendships without having to sweat the small stuff.
LOF: Anything to consider for bigger vs. smaller groups?
The more people there are in the group, the harder it is to agree on a destination. Decide on a budget and then propose two or three options.
If your group is big, decide on a leader who might want to pick the place and see who wants to come along. And, with a big group, there does have to be a leader or nothing ever gets decided. Also, in a large group, you need structure, but at the same time, free time, so planning half-day activities is best. That way, everyone can join the larger group for the planned events but then break off for some smaller group or individual time.
LOF: What were some of your favorite trips you’ve ever taken with friends?
LCD: I’ve been fortunate enough to have some great adventures:
- Jamaica – We rented a villa with staff and it was very luxurious and relaxing. We all had our own rooms, and the best part was that the staff took care of everything—the cooking, cleaning and even laundry. All we had to worry about was who was bringing the pina coladas down to the beach.
- Paris – We were there during fashion week. Oolala! I had lived there about 10 years earlier, and I speak fluent French. I really wanted to bring my friends over to experience Paris from the eyes of a former local.
- Napa Valley / Bourbon Trail – Both of these trips were a total blast, with fine food, drink and scenery. My most recent girls’ trip was right before the pandemic to Kentucky to explore the Bourbon Trail. The biggest thing I learned on that trip was that I LOVE my friends, but I still don’t like Bourbon!
- Palm Springs – I think you remember this one 😉
LOF: Oh yes! How could I forget?! Such a great long weekend away with our college friends. So many incredible memories we’ve had together. Lisa, thank you for sharing your travel wisdom with us. For more ideas, check out Lisa’s blog.