Portland ME Adventure 5 Days Itinerary

Begin your second day with a visit to one of Portland's iconic lighthouses on the Portland: Maine Lighthouses Sightseeing Cruise with Drinks. This tour offers breathtaking views of the coastline and informative commentary about the area's maritime history. Afterward, grab breakfast at Standard Baking Co., renowned for its freshly baked pastries.

In the afternoon, explore Rising Tide Brewing Company. Take a tour of the brewery and sample some of their finest craft beers. For lunch, head to Eventide Oyster Co. for some fresh seafood delicacies.

Spend your evening on an unforgettable adventure with the Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks. Witness the stunning sunset over Casco Bay while enjoying drinks on board. For dinner, visit Central Provisions, offering innovative small plates that are perfect for sharing. Conclude your night at The Bar of Chocolate Cafe for some decadent desserts.

Kick off your third day by visiting Fort Gorges, an old military fort located on an island in Casco Bay. Accessible only by boat or kayak, this site offers a unique glimpse into Portland's military past. Enjoy breakfast at Becky's Diner, a local favorite known for its hearty meals.

In the afternoon, delve into Portland's lesser-known stories with the Portland, Maine: Hidden Histories Guided Walking Tour. This tour will take you through hidden corners of the city while sharing intriguing tales from its past. For lunch, try out The Highroller Lobster Co. for some delicious lobster rolls.

End your day with a visit to New England Distilling, where you can learn about traditional distilling methods and sample their handcrafted spirits. For dinner, head to Street & Co., known for its seafood dishes made from fresh local ingredients. Finish off your evening at Liquid Riot Bottling Company, which offers both craft beers and spirits in a lively setting.

Start your fourth day with an exciting Fall Foliage Paddle on the Presumpscot River. This tour offers a unique way to experience the stunning fall colors of Maine while paddling through serene waters. Afterward, enjoy a hearty breakfast at Hot Suppa, known for its Southern-inspired dishes and cozy atmosphere.

In the afternoon, explore Portland's vibrant food scene with the Portland: Old Port Culinary Walking Tour. This tour will take you to some of the best eateries in the Old Port district, where you can sample a variety of local delicacies. For lunch, visit The Honey Paw, which offers a creative menu featuring Asian-inspired dishes.

As evening falls, embark on the Portland: Sunset Windjammer Cruise Along the Coast. This cruise provides a picturesque view of Portland's coastline as the sun sets over Casco Bay. For dinner, dine at Scales, a waterfront restaurant known for its fresh seafood and elegant ambiance. End your night with drinks at Nova Res Bier Cafe, which boasts an impressive selection of craft beers.

Begin your final day with a historical exploration on the Portland: West End Neighborhood Walking Tour. This guided tour will take you through one of Portland's most charming neighborhoods, offering insights into its architectural and cultural history. Afterward, enjoy breakfast at Tandem Coffee + Bakery, famous for its delicious pastries and excellent coffee.

In the afternoon, take in more coastal beauty with the Portland: Casco Bay Afternoon Lighthouse Cruise. This cruise will give you another opportunity to see Portland's iconic lighthouses from a different perspective. For lunch, head to J’s Oyster, a beloved local spot known for its fresh oysters and seafood dishes.

Conclude your trip with an immersive experience on the Portland: Crime & Injustice Guided Walking Tour. This tour delves into some of Portland's darker history, providing fascinating stories about crime and justice in the city. For your final dinner in Portland, visit Chaval, offering a menu that blends Spanish and French cuisine in a cozy setting. Finish off your evening with cocktails at The North Point, known for its creative drinks and lively atmosphere.