Recommendations for escaping the forthcoming freeze as a family

When the Beach Boys debuted their famous ode to the Caribbean, I learned the lyrics as a six year old taking the bus to school in Massachusetts. Even then, Aruba and Jamaica conjured an air of escape that “Woburn, Jamaica Plain, oh I want to take ya (on the train),” never quite could match. (Perhaps beachier shoutouts like “Good Harbor, Wingaersheek, baby, why don’t we meet?” might have worked?) Now thirty years later, friends in New England recently asked if we had any thoughts on destinations for a winter getaway as they plan to travel for the first time with their six-month-old baby. The challenge got us brainstorming about what would make for some ideal spots to visit and, even more importantly, the planning that’s necessary for each.

Cathlin and I have found it to be especially productive to discuss our respective hopes and expectations in advance of any travels. And when we begin to make plans, it can also be revealing for each of us to handwrite — and only then discuss — what matters the most to each of us, and what we’re willing to accept along the way. For a baby’s first adventure, thinking through the following stages will hopefully help you to refine what choices you even consider:

1. Getting there: How much time are you willing to travel? If you’re flying, don’t forget to budget how long you need at the airport (hint: more than you did when you didn’t have a baby) and how long you need to get to the airport (hint: more than your online map tells you). Are you okay to take a connecting flight to save money and to expand the choices? And how far is your arrival airport from your actual destination? How will you get there? As a quick rule of thumb for airfares: for every day you have, add one hour to the flight time: If you’re looking for a two-day getaway, exclude flights longer than two hours; three days away, flights less than three hours; and so on. Of course, adapt as you wish.

2. Being there: Do you want to experience a favorite spot with a fresh lens or go somewhere entirely new? Is your dream for the trip to stay put at your hotel or rental or to use it as a base and set off to explore with your little one? Do you want to feel remote (i.e., bringing plenty of diapers and baby food in your luggage) or are you craving the hustle and bustle (i.e., needing to buy diapers and baby food nearby) that’s likely found in a town or city? If you’re traveling with only a baby carrier, make sure you don’t need to rely on cars. If you need your stroller, look online to see if there are paved sidewalks.

3. Getting back: It’s often tempting to leave as little slack as possible on your return trip. After all, who wouldn’t rather squeeze in a few more hours of vacation? But be careful about cutting the journey home too close to when you need to start work again. With this in mind, revisit the same questions you posed with “getting there.” Nothing can thieve the calm of a beach vacation like needing to navigate a flight delay with an overtired baby while calling in to work to say you won’t actually be there and need another day off.

With these framing questions in mind, we’d give some serious thought to the following locations:

Prioritizing warmth first and foremost, with direct flights: Listen to “Kokomo” and jump at the first recommendation. It helps that my good friend and former roommate grew up in Aruba, but what a manageable and relaxing destination with a rich and layered history and natural environment to explore! We haven’t been to Puerto Rico since before the Zika outbreak of 2016 and the devastation of Hurricane Maria one year later, but we’re eager to get back again. As for other Caribbean destinations, we certainly wouldn’t pass up a chance to experience any of the options served by direct flights, which includes Barbados, the Bahamas, Costa Rica (Liberia, but not San José), Dominican Republic, Haiti, Jamaica, Mexico (Cancún), St. Lucia, St. Maarten, St. Thomas, and the Turks and Caicos. If you’re willing to make one stop on the way, Cartagena, Colombia is absolutely entrancing. And don’t forget Florida: even if it feels like everybody else is fleeing winter in the Northeast for the same annual destination, you can carve off whatever kind of trip you want, taking in the Salvador Dalí Museum in St. Petersburg, a street-art walk in Miami, Disney World before you have to pay for your child’s entry (plug: our friend Sumana keeps up a great blog on all things Disney with kids), and quite an array of tasty breweries, coffee roasteries, and restaurants as well as expansive beaches all over the state.

Finding the spirit of a beach, even if it’s not the beachiest time of year: The downside to planning a winter getaway to any of the destinations mentioned above is that the price of airfare tends to spike with demand, especially around the holidays. Being willing to take a connecting flight can drop those costs, but why spend your extra hours sitting at another airport if you could find yourself taking an even more reasonably priced flight to Europe instead. Fly direct from Boston to Lisbon or Barcelona (or, if willing to accept a few more hours of travel time: Rome) and head immediately onward to a smaller fishing village or seaside town in Portugal, Spain, or Italy. Or savor Paris for a night or two followed by a leisurely train down to the French Riviera. And if you’d like to keep the flight shorter but are intrigued by the Azores or Cabo Verde, Azores Airlines flies five nights per week from Boston to Ponta Delgado and once per week to Terceira and Cabo Verde Airlines has a weekly flight to Sal. And if you’re keen to travel roughly the same distance, just the opposite direction, you can fly from Boston to Long Beach, Los Angeles, or San Diego and introduce your little one to Southern California’s taco scene, either staying put in one destination or renting a car and driving up and down the coast. And yes, Arizona is far from a beach destination, but its temperatures tend to be perfect in winter.

Considering the (chillier) possibilities closer to home: Perhaps going for a beach walk in freezing temperatures is the furthest thing from your ideal vacation, in which case: got it! But if you simply love being near the beach and don’t mind missing out on any semblance of beach weather, you’ll likely find off-season steals without needing to worry about booking a flight. A few weeks after Labor Day or a few weeks before Memorial Day may sound more enticing than during the depths of winter, but keep an eye out for year-round resorts in Maine, Cape Cod, New Hampshire (a Rye/Portsmouth combo), or the Hamptons on Long Island. If you find the right place, you’ll be happy to sacrifice outdoor heat for indoor coziness. And be sure to ask the hotel if they have a fireplace — and if they might be able to upgrade you given it’s your first trip with your baby and it’s a quiet time of year for them! This choice might feel less adventurous because it is, but you’ll end up with more time to read, chat, and even catch up on your sleep deficit (and less time applying, and re-applying, sunscreen). And if you’re having a difficult time imagining how to travel without your Pack ‘n Play or a box of diapers, throw both in the back of your car and only unpack what you actually need.

Doubling (or even tripling) your vacation with creative bookends: If you’re finding it tricky enough to plan one vacation already, you might look at me sideways if I were to suggest you should consider taking a second (or even a third) at the same time! Some less-than-beachy destinations like Amsterdam, Dublin, London, Madrid, Paris, and Reykjavik often have extremely reasonable direct fares from Boston. (For example, a roundtrip ticket between Boston and Dublin currently costs as low as $470 on Aer Lingus.) From these cities, you can often find dramatically cheaper (and shorter) flights to seaside dreamscapes in Croatia, Greece, Malta, the south of Spain, or Turkey. If you’re only able to claim a week away, this can feel like an overly stressful option. But if you’re lucky enough to have 10-14 days and wanted to leave in late December and return in early/mid-January, you could fly Norwegian to London-Gatwick for $230, enjoy 3 nights in London, fly onward to Seville for $25 each or Malta for $35 each or Faro for $37 for a full week, then find a cheap flight to Barcelona for a 3 night wrap-up and fly back direct to Boston for $196 on Iberia. Downside: lots of hopping about. Upside: so much!

Keep in mind that while Boston’s Logan International Airport serves the greatest number of routes for New England, it doesn’t hurt to look into other regional airports. T.F. Green Airport (serving Providence) offers directs to Fort Lauderdale, Fort Myers, Orlando, Punta Gorda, Tampa, and West Palm Beach in Florida. Bradley Airport in Hartford flies to Cancún, Mexico and San Juan, Puerto Rico as well as six destinations in Florida (same as Providence, except replacing Punta Gorda with Miami). Even tiny Pease Airport in Portsmouth, New Hampshire has seasonal flights with Allegiant down to Orlando, Punta Gorda, and St. Petersburg, and JetBlue connects Worcester Airport daily with Fort Lauderdale and Orlando. And depending where you live, you could be reasonably close to the airports in Manchester, New Hampshire; Bangor and Portland, Maine; or Burlington, Vermont as well. While these smaller airports might have fewer back-up flights if there’s a cancellation or delay, you can often find better ticket prices and/or long-term parking costs if you expand your search a little wider.

Last year, we detailed the items that helped us while traveling with our baby, but a SPF protective hat and baby-safe sunscreen should be at the top of your list. Also, read up on the CDC’s latest guidelines for vaccines and preventing mosquito-borne illnesses, though it’s good practice to avoid mosquito bites anywhere. (I write this as Massachusetts deals with its own bout of Eastern equine encephalitis.) And before going abroad, don’t forget to ensure your passports are up-to-date (i.e., they shouldn’t expire for at least six months after you’re due to return from your trip) and that you have one for your baby too. (We met a couple in Michigan once who’d been turned away from their connecting flight to Mexico after they had shown their infant daughter’s passport card, which had been issued instead of a passport booklet based on faulty advice they’d been given. Awful.)

Long story short: depending on how much travel you wish to incorporate into your first trip with a baby, you’ll have ample choices. Figure out the kind of experience you’re hoping to have, play around with different dates and airports to find the best airfares, do the same with finding ideal accommodation, and then prepare your own beachside soundtrack and enjoy your time there.