Most online tools are ill-equipped to help with a spontaneous trip on the cheap, since you have to search specific dates and locations. Kayak's Explore tool is great, because you can choose departure dates as vague as "any month" or as specific as a season ("fall 2013") or a month ("September 2013"). Then you can set a maximum you're willing to spend on airfare and see where in the world that money can take you.
I searched for flights under $400 during "summer 2013" and the tool spat out a world map with fares in my range. I was surprised that Bermuda was much closer than I'd thought (the flight is less than two hours from NYC) and how cheap the tickets were ($280 per person roundtrip, total). I was sold.
Weigh Your Accommodations
The flights may have been cheap, but Bermuda is an expensive resort town. Being on an island means most products have to be imported, which makes everything much pricier. We decided to offset the high Bermudian prices by staying at a private property via Airbnb, which lets regular people rent out their properties. Our host had a multilevel home with about four separate units that she regularly rented out through Airbnb and similar sites like VRBO.
Not only was this less expensive than a resortwe paid $110 a night, whereas a resort would have cost a few hundredbut it also gave us more local flavor. Our accommodations were basically a fully fledged one-bedroom apartment, complete with living room furniture, Internet and cable TV. Our host, Sabrina, even offered to take us clubbing on our last night there ... though I sheepishly have to admit that we begged off because we were tired.
Although Sabrina's accommodations lacked amenities like a pool or in-house restaurant, she lived close to a high-end resort. We didn't have access to the resort's private beach, but we were welcome to buy cocktails and hang out at the restaurant, on the veranda overlooking the beautiful beach and crashing waves. Not bad considering that we paid about a third of the price.
Make Your Food Really Count
This is especially important in a place as expensive as Bermuda, where a simple strawberry smoothie easily costs $9 and an unremarkable restaurant breakfast can run $15 a person. Because we had a full kitchen in our Airbnb apartment, we started our vacation with a visit to the local supermarket. Although prices were still high ($7 for a box of cereal even trumps Manhattan!), we were able to buy the foods we liked and avoid eating out three times a day for a week. Cooking for ourselves also meant we could control our food from a health perspective. I recently became gluten-free, so buying my own groceries meant I didn't have to interrogate waiters non-stop.
All told, we spent around $200 on groceries during our week, for both of us. That may sound like a lot for a week's groceries, but it pales in comparison to the $400 plus we would have spent per person if we'd eaten out for every meal.
The best part? The few times we did eat out, it felt special and intentional, and we enjoyed it all the more.
Know Your Travel Style
As it happens at many destinations, there's a lot of conflicting info on the best ways to navigate Bermuda. Many people recommended renting a moped, while others were in favor of the bus. In the end, our decision came down to knowing how we travel. While a moped sounded like fun, my husband and I don't like feeling encumbered. Having a moped would be like having a car: It's only convenient until you wander off and have to backtrack just to get your vehicle. Plus, renting a moped for seven days would have cost around $200.
Instead, we chose to walk as much of the island as we could and used a bus or ferry where we couldn't. Most people recommended multi-day bus passes, but we did the math and realized it would be better for us to get a ticket booklet, since we didn't need the bus that often. Meanwhile, we knew of one traveler who loved the flexibility of hopping on and off the bus wherever she wanted, so she got an unlimited pass. Both choices were right for each of us, because we travel differently.
Our total transportation costs around the island? $40 between both of us, and we even had a few bus tickets leftover. When making any travel decisions, know thyself.
Don't Deprive Yourself
It's easy to praise everything cost-cutting, but if spending zero money were the highest goal of all, you would have just stayed home. In many ways, being smart about saving just means you can spend in other ways without feeling crunched for money. We aimed to eliminate mindless spending and replace it with intentional spending that would add to our overall experience.
One of the coolest things we did in Bermuda was afternoon tea at an expensive resort famous for its English-style tea time (Bermuda is a British territory, after all). Yes, we paid around $40 a person for afternoon tea, but it was worth it. Neither of us had ever experienced a proper British tea: the hotel was beautiful, the service was impeccable and we sat by the windows looking out on the perfectly groomed (tropical) English garden. Oh, and the mini sandwiches, cakes and sweets weren't so bad, either.
After tea, we went to the hotel's happy hour, which is one of the most acclaimed in Bermuda. We sat by the water at sunset, sipped our cocktails and, despite spending a good chunk of change that day alone, felt absolutely no guilt about enjoying ourselves. That's what a vacation is all about, after all.
--Written by Allison Kade for MainStreet