The Deal Detective is SmarterTravel’s resident bargain hunter, Kate Hamman. She’s always on the lookout for new travel deals and invites you, dear reader, to submit your own questions.
Lynn writes, “Basically, my boyfriend & I would like to go relax on a beach for five to seven days, sip cocktails, eat good food, meet nice people, etc. Our schedules are pretty flexible and we would like to go sometime in mid-late February/early March. We would prefer a hotel/resort that isn’t too big (ie. avoid Disney Land or Walmart concept—nothing too touristy). I don’t think I am opposed to all inclusive resorts. Ideally, we’d like to spend a maximum of $1000 each on air fare and accommodations (if this includes food and cocktails—even better). No where sub-par. Initially, I wanted to go somewhere in the South Pacific (Bali, Fiji, Tahiti, Bora Bora, etc.) but I don’t think these are feasible. I am not at all interested in Mexico. My list of Caribbean destinations is: Grenada, Anguilla, St. Lucia, Barbados, or St. Croix. I also wouldn’t mind somewhere different like Morocco or Costa Rica … I hope you have some suggestions on potential vacation packages. I would be open to places not [on] our list as well. I would like to book ASAP. Flying out of Kansas City, Missouri (MCI).”
I appreciate questions that are filled with so many details, because it makes it easier for me to find exactly what you need. One thing to note, however, is that most places that are off the beaten path lean towards a higher price tag. You can sometimes find a hidden gem for the right price, but it does take quite a bit of searching savvy. With this in mind, you may have to sacrifice a bit of solitude to save. I agree with you that the South Pacific may be a bit overboard for your budget, but there are plenty of deals to the Caribbean well within your reach. Plus, we’ll look at alternative ways to plan without booking a bundled package.
First let’s see what the vacation providers are offering. CheapCaribbean is a one-stop shop for packages to the tropical isles, and it offers a slew of incentives to book in one place. For instance, you can book a four-night vacation to the Barbados starting at $639 ($869 with flights from Kansas City, Missouri) per person (without taxes and fees). The package includes airfare from New York (other departure cities are available for a higher price, including Kansas City for an extra $230), accommodations at the Cocunut Court Beach Hotel, breakfast buffet, Tripmate weather insurance, and a $100 coupon if it rains during your stay. You must book by February 3 for travel through March 31.
If you’d prefer a bit more variety, you can pick and choose between destinations with Expedia’s Winter Sale, which offers deals to places all over the Caribbean for travel by March 31. For example, you can find 16 different deals to St. Lucia, with four-night hotel and flight vacations starting at $551 per person (with taxes and fees), including accommodations and flights from New York. Prices vary by travel dates, departure cities, and destinations. You can try to cut corners by booking the lowest price with Expedia from the departure city it chooses, and then book a flight from your hometown to there. For instance, I priced round-trip flights from Kansas City to New York in February starting at $193 per person (with taxes and fees). This brings your grand total for the trip to $744, well within your budget.
Lastly, you can try to book items individually and see if you can find a better rate. Start by comparing airfare for your travel dates. I priced round-trip flights from Kansas City to St. Croix in February starting at $520 per person (with taxes and fees).
Once you find the right flight at the right price, you can start searching out places to stay. There are two ways to go about doing this.
First, start by reading reviews on our sister site, TripAdvisor, where you will find real traveler’s top picks of hotels, B&Bs, and vacation rentals for your destination. When you have a place in mind, try calling directly to see what prices they have available. From there, you can then either book or compare prices online.
The second way is based on picking a place by how much it costs, or in other words, “price first, read reviews later.” Hotel rooms in St. Croix start at $112 per night through a provider like Hotels.com. A four-night vacation starts at about $448 for lodging, bringing the grand total for airfare and hotel for two to $1,488.
If you plan on spending more than a few days, a vacation rental can be a money saver. For instance, I priced a two-bedroom rental in St. Croix starting at $625 per week, and it includes a full kitchen, balcony, and a shared pool. The total cost for airfare and lodging for two people comes to about $1,665, which leaves you with a bit of spending money for water activities, dining out, or drinks on the beach.
Each of these strategies will help you find what you’re looking for at a price that’s right for you. It just takes a bit of patience and flexibility. Knowing what you want is key when booking, but also being able to sacrifice certain things for the good of the wallet is a surefire way to have an outstanding trip on a modest budget.
As for my other readers: What do you think? Did I forget a particular strategy when it comes to finding the best prices to the Caribbean? Would you like me cover a particular place in more detail? Leave your comments below.
Get Help With Your Next Vacation
Let me help you plan your next trip, whatever your budget might be. Submit your request using the form below, and please remember that the more compelling and specific your question, the better the chance you’ll be selected for an upcoming case. Be sure to also include your place of origin.
(Editor’s Note: SmarterTravel.com is a member of the TripAdvisor Media Network, an operating company of Expedia, Inc. Expedia, Inc. also owns Expedia.com and Hotels.com.)
All prices, dates, and booking details listed here were valid at the time of publication. Some information may have changed since that time.
We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.
Top Fares From
Today's Top Travel Deals
Brought to you by ShermansTravel
Morocco: 9-Nt Guided Tour, Incl. Casablanca,...
Wisconsin Dells Water Park Resort w/Meals,...
Rome to Istanbul: Luxe, 11-Night Mediterranean...
Oceania Cruisescruise $3999+