- Destination -

Connecticut

Welcome to the charming little powerhouse of the Northeast: Connecticut (aka “The Constitution State”). If you’ve ever thought “New England is all coast, lobster shacks, and leaf-peeping,” Connecticut says: “Hold my cider mill.” With a coastline on the Long Island Sound, storybook small towns, lively cities, forests galore, and even some “okay yes we are still east of NYC” swagger, Connecticut packs variety into a compact footprint. You’ll find seaside breezes, inland farms, university towns, historic mansions, craft breweries, and plenty of cute cafés where your over-packing jokes will fit right in. Whether you’re after a crunchy fall foliage snapshot, a lazy beach stroll, or a quirky castle visit, Connecticut delivers. So pack your comfy sneakers, your “I love New England but don’t make me freeze” layers, and let’s dive into when to go, what to do, how to get around, and all the travel tips you’ll want for your next Connecticut adventure.

Best Time to Visit

  • Fall (September to October): Peak leaf-peeping season—fiery maples, cooler nights, pumpkin spice everywhere. This is Connecticut at its most iconic.

  • Late Spring to Early Summer (May to June): Flowers bloom, coastlines warm up, and crowds are lighter than midsummer.

  • Summer (July to August): Beach season along the Long Island Sound, small-town festivals, and all the coastal charm. Expect more visitors and higher prices.

  • Winter (December to February): Quiet and cozy. Ideal for fireside cafés, snowy strolls, and small-town charm (if you don’t mind bundling up).

If you’re picking one season to highlight—make it fall. Connecticut’s autumn colors and crisp air make for incredible photos and the perfect long-weekend vibe.

Top Things to Do

  1. Explore Mystic: Visit the seaside town that feels straight out of a movie, complete with boats, cobblestone streets, and a pizza legend or two.

  2. Visit Gillette Castle State Park: A quirky, medieval-looking castle tucked into the hills of East Haddam—part history, part fairytale.

  3. Stroll Litchfield County: Home to charming town greens, antique shops, and the kind of small-town energy that makes you want to linger.

  4. Wander Yale University and New Haven: Museums, architecture, and a surprising foodie scene make it worth the stop.

  5. Relax Along the Shoreline: The Long Island Sound beaches give off relaxed coastal energy without the chaos of Cape Cod.

  6. Hike and Explore Inland Trails: Connecticut’s countryside is full of lush trails and scenic overlooks perfect for a half-day escape.

  7. Eat Local: From New Haven-style pizza to cozy farm-to-table restaurants, Connecticut’s food scene holds its own.

Blogs & Itineraries

Travel information

Getting There

  • By Plane: Fly into Bradley International Airport near Hartford—it’s the main hub for Connecticut.

  • By Car: The easiest way to explore. Connecticut sits conveniently between New York and Boston, making it ideal for a road trip.

  • By Train or Bus: Amtrak and regional rail lines connect major towns like New Haven, Hartford, and Stamford. Great if you want to skip driving.

Because the state is compact, travel times are short—perfect for long weekends or mini getaways.

Travel Tips

  • Pack Layers: New England weather can change from warm to chilly in a blink.

  • Plan for Seasonal Events: Fall festivals, summer concerts, and winter holiday lights add extra magic.

  • Book Lodging Early: Especially in autumn when leaf-peeping crowds roll in.

  • Try Local Eats: Don’t miss New Haven pizza or local cider doughnuts.

  • Budget for Tolls: If driving, bring a card or E-ZPass for highways.

  • Stay Central: Connecticut is small enough to base in one town and take easy day trips.

  • Give It Time: Plan at least three to four nights to explore coast, countryside, and city life.

Getting Around

  • Rent a Car: The best option for exploring both coastal towns and inland trails at your own pace.

  • Public Transportation: Available in major cities like New Haven and Hartford, but limited in rural areas.

  • Rideshare Options: Uber and Lyft work well in urban centers, less so in smaller towns.

  • Bike or Walk: Many towns are pedestrian-friendly with scenic trails and parks.

If you want the freedom to stop at every adorable café or covered bridge, rent a car and take the scenic route.

Thinking about the Waterfalls of Damajagua in Puerto Plata for your Virgin Voyages excursion?🌊 Important context: I am not a thrill girl. Roller coasters make me queasy. And I still loved this.

The 27 Waterfalls of Damajagua are like a 5/10 intensity. Adventurous but very doable. Guided. Safe. Not extreme.

You can choose your comfort level and that’s what makes it so good.😍

#damajagua #puertoplatacity #dominicanrepublic🇩🇴 #waterfalls #adventure
If you’re docking in Puerto Plata and don’t want to book an excursion, this is such an easy way to spend a few hours. You can walk straight from Taino Bay. It’s flat, manageable, and felt safe with a really good mix of colorful photo ops and actual city energy.

If you only have 1–2 hours, prioritize:
📍 Umbrella Street
📍 Pink Street
📍 Centro Histórico

Have more time? Add the Malecón de Puerto Plata. Into history? Stop by Fortaleza San Felipe. We were there during La Vega Carnival, which made everything feel extra lively, but even without a festival, I’d still recommend this route.

It’s simple. It’s realistic. And it gives you a look at Puerto Plata beyond just the cruise port. 🌴✨ Save this for your next stop.

#travelling #puertoplata #dominicanrepublic #downtownpuertoplata #travelitinerary
I wouldn’t recommend @virginvoyages to everyone…🫢

If you’re Googling who Virgin Voyages is really for, you’re probably wondering if it fits your travel style, or if it’s just great marketing. I’ve sailed multiple times, taste-tested the ship (for research, obviously), and paid attention to the details that actually matter. 

Here’s the honest answer, no cruise brochure fluff. Head to my blog to read more about planning your trip!🚢

#travelling #travelvlog #cruisevlog #cruiseship #virginvoyages
Day 2, Puerto Plata… waterfalls, city walks, and zero rush.🌴

Port day in Puerto Plata and we truly packed it in waterfalls, wandering through town, and actually having time to explore. One thing @virginvoyages does so well? Long port days. No sprinting back to the ship. No watching the clock all day.

Dinner at Extra Virgin tonight (yes, included). Fresh pasta, made to order, a menu that feels like a real restaurant not cruise food. No constant upsells. No nickel-and-diming. Dining, drinks, Wi-Fi… it’s all just handled.

You really start to see what you’re paying for and what you’re not. Ending the night with Scarlet Night! Full day out. Full night in. This is the sweet spot.✨

Virgin Voyages Cruise Vlog | 📍Puerto Plata, Dominican Republic

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Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.

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