On any given day at Free Fly HQ, at least a couple people are out on PTO, using up those hard-earned vacation days. But it’s not your typical sit-by-the-pool vacation… it’s usually some far-flung, offbeat adventure involving cliff jumping, RVs, and empanadas. So we’ve rounded up a few of the coolest, most memorable, action-packed vacations (and hot tips) from our own Free Fly staff, and added them to our Bucket List Vacations. Take a look and get inspired—just remember us when you’re packing for your next trip.
_____
Boat Camping on Casco Bay, Maine
Nathan, Product Team
Why did you choose that destination?
Casco Bay has hundreds of islands, known as the “calendar islands.” Many of them are uninhabited and managed by Maine Island Trails, making them available for camping and exploring with arrival by your own boat/kayak the only way to get there. A perfect off the grid adventure.
Any adventures that made it unique?
Packing our 15 ft Whaler for a family of four (and a dog) for three nights took some careful planning. We had tents, coolers, firewood and food. Waking up to the beauty and silence of the bay was magical. We hosted 20 friends for a lobster bake one evening, they all arrived by boat, we built a big fire and cooked a pot of lobster and shared cold beer as the sun set. It was EPIC.
Any hot tips or useful info you learned while visiting?
Arrange boat trailer parking with the town of Yarmouth at the Royal River launch. Don’t miss a day trip to Dolphin Marina for lunch and ice cream. Bring an inflatable SUP and both bow/stern anchors to keep your boat secure and have an easy way to land as tides change.
What to pack:
 |
 |
_____
Rincón, Puerto Rico
Mary Chelsea, Ops Team
Why did you choose that destination?
It's a water lover's nirvana. There's killer surf, an incredible reef to snorkel right off the beach, pristine waters to swim, and it's a fishing paradise—if off-shore is your thing. Also, who doesn't love $2 Medallas!
Any adventures that made it unique?
The fact that you can do all of the above within a 2-mile radius. Minus the off-shore fishing, but the marina you take off from is within that 2 mile span. Not to mention, Puerto Rico itself is only 100 miles wide, and each town offers its own unique culture and adventures.
Any hot tips or useful info you learned while visiting?
Get ready for a wild ride in. Literally. Most people pass on the shoulder. Also if it's nighttime and you're outside of the city, red lights don't mean “stop.” They mean “slow down” and if you don't see a car, just go!... Not that I'm advising this.
Another local tip: go to the Lighthouse and order a mojito and empanada—preferably make those plural. The mojitos are the size of your head and the perfect compliment to the epic view you have overlooking Domes beach.
What to pack:
 |
|
_____
Big Island, Hawaii
Scott, Brand Team
Why did you choose that destination?
Many years ago, Outside Magazine did an issue about the “50 best vacations in the world.” The Big Island was rated as the 2nd best adventure-based vacation, including the recommended B&B to stay at. So, we booked it and it absolutely delivered.
Any adventures that made it unique?
The coolest part of the Big Island is that every single day you can do something different. Hiking all over Volcanoes National Park is amazing. Discovering black sand beaches where you can see sea turtles up close. Cliff jumping off the southernmost tip after driving through beautiful grassy plains. Driving to the 14,000 ft peak of the tallest mountain in the world, Mauna Kea, to catch an amazing sunset (fun fact: it’s the “tallest” mountain in the world because of how deep the sea floor is where it rises… but yes, Everest is still the “highest elevation” mountain).
Driving or walking down (probably a safer bet) one of the steepest roads in the US to check out Waipio Valley. Off-roading the back way to naturally lava heated tidal pools. We were there a week, put 1,000 miles on a rented Jeep traversing the island, and still don’t think we got to really see everything it had to offer.
Any hot tips or useful info you learned while visiting?
Don’t go the standard route of staying in Kona and hanging out at coffee farms. Do that for a day but fly into Hilo and find a place to stay near Pahoa. It’s an eclectic town and the perfect base camp for sending it every day. Two of the coolest things we experienced on the whole trip were reco’s from our B&B host and completely free.
The first: grab stuff for a picnic lunch at the local grocery store and some loaner snorkeling gear, then find a neighborhood where you can walk in to get access to incredible lava rock tidal pools. Park outside the neighborhood to avoid issues but it’s well worth the walk—incredible snorkeling for a chill day.
The second: visit the local farmer’s market. Happens once a week and is the most interesting collection of locals, transients, and I-gotta-get-the-hell-out-of-mainland retirees I’ve ever seen. The time we went, there was a legendary local family playing incredible Hawaiian music, all kinds of interesting and delicious food and drinks, and legit mementos you won’t find at a tourist trap gift shop. The people watching is a lot of fun but it’s better to embrace the vibe and hit the dance floor.
What to pack:
|
 |
_____
Ring Road and Westfjords, Iceland
Kimberly, Ecomm Team
Why did you choose that destination?
When it comes to planning vacations, I have a rather spontaneous and random approach. I head to Google Flights and search for the cheapest international flight available for my chosen dates. If it's a destination I haven't been to before, I hit that ‘buy’ button like my life depends on it.
Having a wanderlust-y spirit, I thought Iceland would be a cool experience because of the beautiful scenery, the aurora borealis, active volcanoes, (plus some of my favorite Icelandic athletes are from there). I stumbled upon a fantastic deal in September 2022: round-trip flights for just $279. Consider taking your trip in early September, so you can see the mesmerizing aurora borealis and still get to drive the Ring Road before winter sets in. Plus, it’s at the tail end of the summer, meaning there are less crowds and deals are abundant!
Any adventures that made it unique?
Firstly, be prepared to be swept away by Iceland’s awesome beauty. Honestly, sometimes it feels fake, like someone photoshopped in the views. Also, fun fact: this nordic country is known for its 1:2 ratio of humans to sheep.
We drove along the Ring Road in an RV, and saved a few days for the Westfjords. The Westfjords are only accessible by 4WD, and you won’t run into too many people there. Just deserted beaches, dramatic cliffs, glaciers, and treeless landscapes.
Here’s a few of the most unique, must-see spots we stopped by:
- Seljalandsfoss: A massive waterfall you can actually walk behind, but be prepared to get delightfully drenched.
- Jökulsárlón Glacier Lagoon: A surreal spot, especially during the golden hour when photo opportunities abound.
- Vatnajökull National Park: Filled with glaciers, volcanoes, and black sand beaches.
- Godafoss: The "Waterfall of the Gods" makes for an awesome sunset view. Get up close by walking to the base and prepare to be overwhelmed by its size.
Any hot tips or useful info you learned while visiting?
Let me share some valuable lessons I learned the hard way while exploring Iceland:
- Prepaid Gas Cards: Your savior at the pump! Outside of Reykjavik, paying for gas with a credit card sans PIN can be a nightmare. Stock up on prepaid gas cards to save on fuel costs and ensure you have access to gas even if your credit card fails or isn't accepted. Buy them in bulk for peace of mind!
- Skip the Blue Lagoon: While the pictures may tempt you, trust me, it's a tourist trap. There are better hot springs to experience in Iceland that offer a more authentic and enjoyable soak.
- Take a Plunge Into Arctic Waters: If your chosen hot spring is near a river or lake, take a dip. Few can boast of swimming in such icy depths (I am one of those lucky few). Then, relax in the comforting warmth of the hot spring—a moment of pure bliss.
- Indulge in Local Farm Ice Cream: Don't be afraid of unique flavor combinations. Iceland's local farm ice cream is some of the best you'll ever taste, and by indulging, you're also supporting the local economy. A win-win!
- Food Exploration: Visit local grocery stores to stock up on breakfast and lunch items. Icelandic oatmeal and Norwegian crackers were my go-to staples!
- Camera Gear Essentials: While drones are prohibited in many tourist areas, you can still find opportunities to fly in Iceland. Windy conditions can be challenging, so be prepared. Essential gear includes a sturdy tripod, extra batteries, large memory cards, and microfiber cleaning cloths. I found my wide-angle lens to be the most useful for capturing the vast landscapes and those breathtaking northern lights.
- Rent an RV: We rented an RV for our travels and it was stellar. We could roll into a campsite at 10pm and go to bed. These campgrounds have restrooms, showering facilities, laundry and more. It is also a cool opportunity to meet others to share your adventures with
What to pack:
0 Comments