Best time: Late spring (May-June) and early fall (September-October). Although hotter summer is my preferred time to visit (Late June-End of August).
Why: Blooming gardens in spring; crisp air, vibrant foliage, and Red Sox games in fall.
Best time: June to September.
Why: The beaches are warm, the seafood’s fresh, and the summer vibe is electric.
Best time: Fall for foliage (late September to mid-October) and summer (July-August) for festivals and hiking.
Why: Leaf-peeping at its finest, plus Tanglewood concerts and farm-to-table dining.
Boston Logan International Airport (BOS): The state’s major hub, with flights from all over the world. A quick hop on the T (Boston’s subway) or a rideshare takes you downtown.
Worcester Regional Airport (ORH): Small but mighty, great for central Massachusetts.
T.F. Green Airport (PVD): Located in Rhode Island, but often cheaper and just an hour’s drive to Boston or Cape Cod.
Many major cruise lines dock in Boston, making it a popular embarkation point for New England and Canadian itineraries. CruisePort Boston is centrally located in the Seaport District—just minutes from downtown hotels and attractions.
I-90 (Mass Pike): Runs east-west from the Berkshires through Boston.
I-95: Loops around Greater Boston and continues south.
Route 6: The scenic way to Cape Cod.
Amtrak’s Northeast Regional: Connects New York City, Washington D.C., and Boston.
MBTA Commuter Rail: Great for day trips to Salem, Lowell, Worcester, and more.
Pack Layers: New England weather can change faster than your GPS can say “recalculating.”
Book Early: Summer and fall are peak seasons — hotels, ferries, and B&Bs fill up fast.
Embrace Small Towns: Don’t just stick to Boston. Charming spots like Rockport, Concord, and Great Barrington are worth a detour.
Try the Local Eats: Clam chowder, lobster rolls, Boston cream pie, and cider donuts — it’s basically a food tour waiting to happen.
Visit Year-Round: Each season offers something different, from cozy firesides in winter to flower-filled gardens in spring.
“Outside Terminal 3” is not a pickup location at PHX.
Before your driver pulls in, text them four things: your terminal, north or south side, door number, and inner or outer curb. Grab your bags first, then call them in. Drivers can wait free in the cell phone lot instead of circling. Getting through security is easy; getting picked up is the hard part.
Save this for your Phoenix trip ✈️
Come for the architecture, stay for the view.
The Chapel of the Holy Cross has been built into Sedona’s red rocks since 1956. The outside overlooks get busy, but inside is quiet, with huge windows framing the rocks. It’s free, takes 30-45 minutes, and has a paved, wheelchair-accessible ramp. Make sure to bring water in summer.
Save this for your trip planning!
Order it well done. Trust me.🍑🍕
Peach & Pancetta Pizza at Hideaway House in Sedona: roasted peaches, salty pancetta, ricotta, basil, extra-crispy crust. Split the house salad, grab a prickly pear lemonade, and get a patio table facing the red rocks. Skip the bread if you want room for another slice.
Save this for your Sedona trip✈️
Pack your bags, Denver is not just a mountain layover. RiNo alone can eat a full day between the murals, food, and bars. Skip the concert and hit Red Rocks midday instead, you’ll basically have it to yourself. Golden’s a 30-minute trip if you want a change of pace, and if food drives your travel like it does mine, Denver Central Market and BRUTØ deserve real time on the calendar. Give it three days minimum, four if you’re eating your way through it. Save this.
Stayed at The Maven in Denver’s Dairy Block and the location alone sold me, walking distance to Union Station and most of downtown, string lights right outside at night. The room was spacious and quiet, even had a swing in it. Real talk though, there’s a $28 daily resort fee and parking isn’t cheap, valet ran us $59 a day. Bed was a little firm, but that’s the only complaint I’ve got. Save this before you book.
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
