Long weekend - Portland, Ogunquit and Kennebunkport?

Question

Trying to plan a long weekend road trip in Maine - probably 3 or 4 nights beginning in Portland and driving south. I was looking at staying a night each in Portland, kennnebunkport and Ogunquit but also considering Portsmouth NH. Any recommended itineraries- is one night per spot enough or should I plan for , for example; 2 nights in Ogunquit etc?

Answer

A long weekend road trip in Maine sounds like a fantastic idea, especially exploring Portland, Ogunquit, and Kennebunkport! With 3 or 4 nights, you can definitely have a relaxed pace while visiting these charming spots. Here are a few suggested itineraries based on your preferences:

Itinerary Option 1: One night in each spot
This option allows you to see each destination but keeps the pace moving quickly. Here's how it could look:
- Start in Portland: Explore the historic Old Port district, visit the Portland Head Light, and enjoy a seafood dinner at one of the local restaurants.
- Head south to Kennebunkport: Walk around Dock Square, visit the Seashore Trolley Museum, and enjoy the coastal scenery. If you're a fan of history, stop by the Bush family compound.
- Finish in Ogunquit: Walk along the Marginal Way, a scenic coastal path, and enjoy some time at the beach or in Perkins Cove.
This itinerary can work if you're short on time, but you might feel like you're rushing from one place to the next.
Itinerary Option 2: Two nights in Ogunquit
If you want to take a slower pace and truly enjoy a destination, spending two nights in Ogunquit would be a great choice. Here's a potential plan:
- Night 1 in Portland: Enjoy Portland's food scene (it’s a foodie’s paradise), visit the Portland Museum of Art, and check out the waterfront area.
- Night 2 in Ogunquit: Spend more time here, walking the Marginal Way, visiting Ogunquit Beach, and enjoying local art galleries and seafood restaurants.
- Day trip to Kennebunkport: This allows you to enjoy the coastal charm without feeling rushed. You can still explore the town, have a nice lunch, and visit the local attractions. Then head back to Ogunquit for your second night.
This gives you a chance to explore Ogunquit in greater detail and still hit the major spots in Portland and Kennebunkport.
Itinerary Option 3: Include Portsmouth, NH
If you want to add another city to the mix, Portsmouth in New Hampshire is only about 45 minutes south of Ogunquit, and it offers a great balance of history, waterfront views, and food options. Here's how this itinerary could look:
- Start in Portland: Explore Portland’s Old Port, have a bite at one of its many top-rated restaurants, and check out the lighthouses.
- Head to Kennebunkport for the second night: Walk around the town and visit the Bush compound if you're interested in presidential history.
- Spend your third night in Ogunquit: Relax on the beach, walk along the Marginal Way, and enjoy the art galleries and shops.
- End in Portsmouth, NH: This town has a beautiful waterfront and plenty of colonial architecture. Visit Strawberry Banke Museum and explore the downtown area before heading home.
This option adds a little more travel time but could be a great way to experience another charming coastal New England town.

Ultimately, it depends on your travel style—whether you want to slow down and spend more time in one place or see everything quickly. If you're looking for more relaxation, I’d recommend spending two nights in Ogunquit, but if you’re keen on seeing as much as possible, one night in each spot should be doable!

Long weekend - Portland, Ogunquit and Kennebunkport?

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