Looking to head somewhere warm in Feb, Mar, or early April even, some place that’s not too expensive (maybe in the $2500 range for 4-5 days?). Bonus if there are nonstop flights from the northeast to the destination. Will be me, my husband, and 17 yo son. We enjoy seeing cultural sites, hiking/outdoorsy things to do, nice beaches/water, good food and drinks. Open to anywhere, really, as long as temps are 70s or above. Would prefer airbnb/apartment style lodging vs hotel, but open to either. Thanks in advance!
We did a last minute trip like this once…and i would say that planning now for year is last minute.
At the time, we went to a travel agent and said “just send us someplace warm”.
The issue was getting us there! Airlines even that long ago were really booked. We ended up driving to Williamsburg, and had a great time. Stopped in DC on the way and did some sightseeing there too. If you go in April, the weather could be nice!
If you can get to Atlanta, there is plenty to do there too. Huge airport so maybe lots of flights with unbooked seats.
What about Charleston? That would be lovely in April and some good history there.
I’m in San Diego and many like to come here to escape the cold. Our water isn’t warm enough for swimming, but it’s still nice to walk along our miles of beaches. We have lots of hiking, museums in Balboa Park and a wonderful zoo. Lots to keep you busy over 4-5 days. Jet Blue has a direct flight from Boston.
Early April in Bermuda is nice and it’s a 2 hour flight from Boston. I wouldn’t go in March as it can be quite windy.
Bermuda’s is expensive when it comes to food/drinks. With a budget of 2500, I would start the search with airfare. For 3 people it most likely will run $1000-$1500.
No beaches here, but Phoenix/Scottsdale offer a lot of what you’re looking for and are near a major airport. Sedona and Flagstaff are both beautiful and fun but a bit too far north for the temps you’re looking for.
Phoenix/Scottsdale’ lack of beaches is easily mitigated by plentiful swimming pools. 
Lots of great hiking in the area, I agree.
Three of us absolutely loved this place in March 2019:
For us it came in within your budget too. We’d easily return if there weren’t more places on this planet that we want to explore.
Bonus points if you speak any Spanish, but it’s fine if you don’t. Enough people around speak English. I also used my French for some conversations.
I am in the northeast too and, starting around Jan 1, I start the search for a warm-weather (and cost conscious) getaway for March/April. We did go to Scottsdale one year. Good price in flights usually, nice pools, horseback riding in Caves Creek. We’ve been to Tampa, lots of nonstop flights from Boston/Hartford. West Palm Beach is lovely. We have rented a couple of the Casa Coco homes. (These were a bit of a splurge, but so nice to get your morning coffee and head out to your little private pool.) Charleston has amazing food and cultural sites, temps will be prob 70s. We’ve flown into Daytona and rented a house near Flagler Beach. Not a whole lot to do but beach is nice, and Flagler Fish Co is a favorite. This year I’m looking at flying into Miami (very cheap flights) and driving to the Keys, maybe Islamorada. Trying to find a nice but affordable resort.
Lots of good suggestions so far. I would add Marco Island, FL. Fly in to FT Myers. The beach is beautiful- check AirBnB or Vrbo. JW Marriott, Hilton, etc have resorts on beach but are pricey. Plenty of condos for rent right on the beach. State parks not too far away for hiking, plenty of golf and loads of restaurants. Weather would probably be great.
For 4-5 days, not worth dealing with expense, travel time, jet lag, etc to go outside of your time zone.
I think you’re definitely looking at something between Tampa and Naples.
Once I stayed at the Walkabout Beach Resort at Hollywood beach just north of Miami. It’s a misnomer because it’s a tiny, art deco boutique hotel.
Only stayed there as an add-on to an international flight out of Miami but found I loved Hollywood Beach. It developed in the art deco period and was then neglected during the years of high-rise construction in other areas of Florida…recently resurrected as a quaint family beach. The Walkabout looks straight out onto the palm-tree-lined ocean and a narrow brick walkway that runs to the little center bandstand of the beach (just under a mile away.) No street separating you from the ocean. Nice little garden/patio/tiki bar on the oceanside. I think all rooms have kitchenettes.
I didn’t rent a car…just caught the shuttle from Miami Airport but learned that Ft Lauderdale is closer. There’s a little local bus as well. Lots of little open-air beach eateries, and close to the attractions to Miami/West Palm Beach, and nature preserves if you need more to do. I’m not normally a Florida fan at all, but loved the quainter “Old Florida” vibe there. That was ten years ago…not sure if it’s different now.
If you’d consider Tampa, then Clearwater Beach just a bit south is a nice and easy option with its own airport. I think Alliant Air is the only airline there, but runs cheap flights from many small cities in the U.S. The water tends to be very calm (Eastern Florida is better if you like waves) but the sand is white and the water gorgeous.
I was feeling the same way and early last week booked a 3 night trip to Cocoa Beach so DH could surf. A bday gift. It would be $1,300 for air, hotel, car and surf board rental (exl food). I thought a decent enough deal. I took advantage of the bundle Allegiant offers where for $66, I can change my flights once. It would be $300 otherwise.
Weather now looks bad and high enough winds no surfing next week. We are so bummed to have to cancel. Have to decide by Wednesday. But at least we can. We are so disappointed.
Friends from Midwest got very sick of the cold and snow one winter. Wanted a place that was cheap to get to and stay at…but wanted hiking and biking.
They went to Vegas. There is a ton of great hiking very nearby. Hotels and food are modestly priced, and the weather would be decent end of March/April. Lots of places have pools. Easy to rent bikes. Close drives to some nice national parks.
And if you decide you are dying to catch a show…you can.
Except for the expensive resort hotels with names you can recognize…hotels can be $40 a night.
We went to Vegas a couple of Decembers ago, and there is plenty of hiking close by. No beach, but plenty of pools.
We just went to San Diego this last December. We flew non-stop from the east coast and stayed 5 nights. We stayed plenty busy.
Palm Springs/Palm Desert. Warm, very different from the northeast, lots of airb&b rentals within your budget. No ocean, but lots of pools and great desert hiking and resort-type attractions in the area.
We are going to St Augustine later this year for a girls trip. Looks like a nice mix of historic sites, warm weather, and fun restaurants.
St. Pete Beach. Southwest, JetBlue and Delta were having great airfare sales last week into Tampa, (St. Pete is 30 min. from airport). Allegiant air flies into St. Pete/Clearwater, (PIE), about 20 min from St. Pete Beach. A wide range of places to stay from family owned sm. hotels/motels on the beach, condos, and small hotels up to resorts. We live in St. Pete Beach and can offer insight into restaurants, things to do and specific places to stay.
Miami Beach, plenty of AIRBNB choices. Miami Airport is 8 miles ways. Ft Lauderdale airport is 45 minutes away. Great beaches, restaurants and vibe. Family friendly.