Tropical destination

Belize or Hawaii. Possibly Uruguay if you want to travel that far. The Azores won't be tropical, but could be fun.

Having lived on the right coast for 30+ years I know how December can stoke those fires-picture warm breezes, palm trees, the sound of the ocean. But, as you are finding out, you’re not the only one. February is peak season for tropical getaways. You are closer to the Caribbean so I’d keep looking, but don't give up on Hawaii. With Southwest about to enter that market other carriers are a bit jittery so you might find an airfare you can manage. We love Kauai. We do our share of beach time but love to hike and spend a lot of time in the Waimea canyon area. If you go, stay in The Poipu area-less rain. Get a condo, but you’ll need to get cracking no matter where you wind up, as places fill. We’ve been to Martinique and St. Martin. Martinique was memorable, but a long time ago. We stayed out of the tourist zone and we were surrounded by French speakers, little English. Our French was nearly non-existent. So we hiked, dined, swam and listened to people around us not knowing what they were talking about. It was great. St. Martin was just a stop on a cruise, so can’t recall much.

Yes, finding reasonable flights are the problem. I'd look at airline websites and look at vacation packages. Bahamas (the outer islands, not Nassau or Freeport); Grand Cayman; Turks and Caicos; Aruba. All places that are popular enough to have direct flight connections from the US. Noting that most (not all) of the Caribbean islands are dead flat and not mountainous, so all the scenery is at the beach. Dominica I recall was mountainous, as was St Kitts, and St Lucia, but Aruba is interesting because it is cactus-desert dry and different from the palm-tree tropical of the others. Not stayed there, but Costa Rica sounds interesting.

You don't need to stay in an all-inclusive in Mexico or be confined to the very narrow slivers of the country where most Americans go. The Yucatan is quite interesting and there are plenty of really neat hotels in places like Tulum, Valladolid, Merida, and even some in Cancun (here's an example: Hotel El Ray del Caribe http://www.booking.com/Share-5mp3zP). Lots of Mayan ruins to see and sinkholes to swim in, and gorgeous beaches. Not hard to get around, excellent long-distance buses that connect the towns. Grab a Lonely Planet book and check out your options. The only downside, if you're not used to it, is that it's blazing hot and humid and can feel downright uncomfortable.

Also, a Caravan tour of, say Costa Rica or Panama or Guatemala, may be a good value if you don't want a "do it yourself" trip (assuming the tour dates coincide with your constraints, of course).

Puerto Rico, easy, it's all there. Not a very physically active place though, so hiking is what you make for yourself.

Hawaii is too far for me, so for you it's really a trek, and major jet lag. Is Dubai closer to Boston than Hawaii? At least Dubai is nonstop, so maybe similar travel time even if farther.

Jet Blue is the airline to the islands out of Boston. I've never seen so many flights to the Caribbean from any city.
They fly to Aruba, Barbados, Bermuda, Cancun, Havana, Montego Bay, Nassau, Punta Cana, San Juan, Santiagos de los Cabelleros (Dominican Republic), and Santo Domingo las Americas (Dominican Republic.) Seasonal flights go to Grand Cayman, Port au Prince, Liberia (Costa Rico), Provindenciales (Bahamas), Puerto Plata (Dominican Republic), St. Lucia, St. Martin and St. Thomas.
I have been to a bunch of these islands, and my favorite hands down would be St. Lucia. There are a number of all inclusive resorts there that are beyond fabulous. If you're looking for something a little less expensive, the all inclusive resorts of the Dominican Republic are great values.

I agree with Tom, Puerto Rico is perfect. I know there are still lots of infrastructure issues but most tourist areas should be in decent shape and would welcome visitors. If you rent a car you can see much of the island and explore a few different beaches. There are forests and mountains and hiking opportunities. I spent two weeks there a few years ago in March and the weather was perfect and we had a marvelous time. Definitely check it out. There should be reasonable flights to San Juan.

Add to above: JetBlue also flies Boston to Aguadilla (for Rincon and Rojo Cabo areas) and Ponce, both in Puerto Rico, connection in Orlando. The times can be odd, though. It's a big place so you won't run out of things to do. Also the convenience of no passport, dollars, and home car rental insurance being valid.

I've heard that AirBnBs in condos attached to all-inclusives in Punta Cana allow restaurant meandering if the all-inclusive doesn't appeal. And Mexico is all that Agnes states, but with better food than anywhere else in the Caribbean.

Edited to correct incorrect driving observation.I was in Sint Maarten (the Dutch Side) a few weeks ago. It was on a cruise, but I did a day outing with a local, so saw a good amount of both sides. Roads are tricky and steep. Manual transmission is the norm. Just something to keep in mind. But, small enough to stay inland at some sort of short let apartment, condo or hotel. Sure you might need to make some meals and clean up after yourself, but privacy is often the trade off.
As stated, there are always options to AIs for accommodations.

One last thing to consider is that the UK has a 2 week February break so it is a double hit for demand - particularly those islands with direct Virgin Air access....like Barbados.

Maria, Why would you drive on the 'wrong' side of the road on Sint Maarten/Saint Martin - it's shared by Netherlands and France, neither of which drive on the left? When I was there they drove on the right just like the US and Canada. The roads may be narrow and/or steep but I didn't notice our driver having any problems and we were all over the island (both sides).

Maybe you're thinking of Barbados - they were an English colony so drive on the left.

Chatting with Nancy:

Sometimes places that were never British drive on the left because the home countries switched to right side drive but their colonies didn't, for example the US Virgin Islands (Denmark), Indonesia and Suriname (Netherlands), Mozambique (Portugal). At least that's what I have heard.

Also Japan and Thailand (never colonized) chose left side driving for some reason.

Edit: I guess Denmark never drove on the left, nor did the Netherlands, just a rumor. Portugal did, though.

Nancy, I stand corrected. Antigua, Tortola, and St. Kitts drive on left. The other ports on that itinerary. Manual transmission and steep still applies for Sint Maarten.

Tom, I understand that about the colonies sometimes being different from their original parent countries. I only mentioned Barbados because Maria happened to mention that island in her post.

I don't know anything about the cost of airfare but you might consider Costa Rica which has it all: mountains, beaches, incredible wildlife and natural beauty and should be warm that time of year.

I would add that although San Juan is the major cruise ship starting point, cruisers do not spend very much time there and have no impact on the vast parts of the island away from San Juan.

Don’t give up on HI. I’m seeing round trip from Boston to Lihue at around $700 on select dates in Feb. AA has a one stop in PHX. Yes, long ride, but wen you get there you are really in Paradise!

Brazil! I don't know when carnival occurs in 2019, but you'd probably couldn't get a reservation during that time. Nor have I researched airfares, etc. But there are lots of warm/tropical destinations that you and your teen would enjoy! Have a great trip!

There's a great big, diverse, interesting - and warm - country right next door called Mexico you might want to check out. And there's a whole lot more to it than the famous, over-touristed little slivers that are marketed to North Americans (eg Cancun). We're lucky to have this amazing place so close. Don't overlook it.

Having spent a few winters in Boston, I understand the desire to escape. I also advocate for Mexico, we spent a week in merida in April. The beach is a 45 minute drive, we rented a house w pool thru vrbo for 37$ a night

Try checking up on the Philippines. This February is a near-season to summer there and you might find it a good tropical spot as well. Been there 3 years ago.

As several have noted, the Yucatan in Mexico (outside of Cancun) is fantastic. We took our teenagers there for a spring break and they loved Merida, Chichen itza, Playa Del Carmen, and Tulum. You could also visit cenotes. And you will have much less of an issue with jet lag going there from Boston than trying to go to Hawaii. Barbados is also an interesting island, with good beaches and gardens.

And I meant to add we didn't stay in any all-inclusives, but in charming medium-priced hotels (with pool in Merida and Chichen Itza).

Costa Rica: Beaches on both Atlantic and Pacific, decent infrastructure, democratic government, lots of concern for the environment, flora and fauna.

Easiest would be any Caribbean island that appeals to you and is easy to reach. US or British Virgin Islands might be easiest re language and culture, or another one with a different history.

As David says, Mexico is a big warm (temperature and culture) easily-reached country nearby. Yucatan would be fun and interesting, fly to Cancun and get outta there right away. Playa del Carmen has beaches, cenotes, nearby Tulum ruins.

My favorite Mexican place is Oaxaca, farther south and west but incredible if you can forego the beach, i.e. deflect the teen from the Hawaii thing. (There are good beach towns on the coast south of the city but they're harder to reach). United flies nonstop from Houston to Oaxaca at least daily in winter, but overall airfare from the east coast might be a problem. Prices in Oaxaca itself will be a bargain compared to Hawaii and most US destinations.

Not to overlook the obvious -- south Florida isn't really "tropical" but it's pretty close, the Keys and Everglades have lots of fun stuff to do (not mountains though).

Thank you all for your detailed responses. I’m looking at Madrid or San Diego because they have a better chance at decent airfare at this point. Not tropical but would be better than home and we haven’t visited them yet. If that doesn’t work out, next year I will plan earlier and consider all your suggestions!

Madrid in February is likely to be cold. Not as cold as Boston but not far.

San Diego is a great choice. Don't write off LA either. Great weather all year round and lots to do.

February nonstops to San Juan are cheaper than San Diego.

February isn't December, but spent a week last December in San Diego/LA/Death Valley and it was always sweatshirt weather, not one warm day the whole week. Puerto Rico is never not warm.

Thanks for the feedback, maybe we should just wait for a future trip.

I lived in SoCal for 20+ years and can vouch that, whatever the weather in February, it will be pure heaven compared to Boston in February. You can always drive out to Palm Springs where it's warm and sunny almost every single day (it's still the desert so it can get a bit cold in the mornings though).

It’s all relative. Sure, it won’t snow in San Diego, but February is far from tropical. The high during the day is around 66, and February is the height of the rainy season. I was there for a meeting last February and it rained all day, every day for 5 days straight. Most of what you’d want to do in San Diego is outdoors, so a bad few days will see you searching for museums and malls. I would not fly that distance to San Diego for a warm/tropical vacation. You are unlikely to have that there.

Note that the El Niño weather pattern has finally kicked in this winter so there will be a tendency for a sunnier, mild northern US winter and gray, rainy southern US winter.

There seems to be a reluctance to book Puerto Rico, but it is a gorgeous, safe, middle class society destination. This is my photo from the west coast between Rincon and Mayaguez. Paradise!

https://scontent-ort2-2.xx.fbcdn.net/v/t1.0-9/48369217_1263535463785859_5583414844364685312_o.jpg?_nc_cat=103&_nc_ht=scontent-ort2-2.xx&oh=dcf8912add5f418389fa93a6343bbaa8&oe=5CD5E7E6

Some places that sound interesting are St Martin and Martinique... but
can’t find reasonable flights. Mexico and the Dominican seem to be
better values, but don’t really want to stay in an all inclusive. Any
ideas would be appreciated, I’m overwhelmed!

I bet you're overwhelmed. It's now December 21. If you haven't made your plans yet, you will have a hard time finding discounts during the February school holidays. Perhaps consider the beaches of the Florida panhandle which is typically cheaper than southeastern FL. See where Jetblue flies as that is your best bet out of BOS. Remember you could be snowed in before you leave BOS so try not to prepay for lodging.

New Orleans ? Not tropical, but LOTS to do. And Southwest flies there.

Another vote for Costa Rica. If you want a tour, check G Adventures. They have loads of options and price ranges. IF you want a single destination, fly into San Jose and then arrange transportation down to the area near Manuel Antonio park. It's gorgeous. Beaches. Monkeys. Birds. Sloths. Jesus Christ lizards. It's incredible.