Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Luxury Weekend Getaway in Portland, Maine

Viewed by 78 travelers
Friday, October 20:

Morning: Start your luxurious weekend in Portland with a visit to the historic Old Port district. Explore the charming cobblestone streets lined with upscale boutiques, art galleries, and chic cafes. Indulge in a delectable brunch at one of the renowned local restaurants, such as Hugo's or Street & Co.

Afternoon: Treat yourself to a leisurely yacht cruise along the picturesque Casco Bay. Marvel at the stunning coastal views, lighthouses, and even spot some wildlife. Charter a private yacht for an intimate experience or join a luxury group tour with Maine Sailing Adventures.

Evening: Experience an exquisite dining experience at Fore Street, a renowned farm-to-table restaurant located in a beautifully restored warehouse. Indulge in their seasonal menu featuring locally sourced ingredients and complement your meal with a fine selection of wines.

  • Old Port District: Free, 2-3 hours
  • Brunch at Hugo's or Street & Co: $40-60 per person, 1-2 hours
  • Casco Bay yacht cruise: $200-500 per person, 2-3 hours
  • Dinner at Fore Street: $80-120 per person, 2-3 hours
Saturday, October 21:

Morning: Start your day by visiting the Portland Head Light, one of the most iconic lighthouses in the United States. Enjoy a peaceful stroll along the cliffside and capture breathtaking views of the rugged coast. Afterward, treat yourself to a luxurious spa treatment at the award-winning Inn by the Sea.

Afternoon: Immerse yourself in the rich maritime history of Portland by visiting the Maine Maritime Museum. Explore fascinating exhibits showcasing the state's seafaring heritage and learn about shipbuilding and lobstering. For a unique experience, take a private tour of a lobster boat and even try your hand at hauling traps.

Evening: Conclude your luxury getaway with a memorable fine dining experience at Tempo Dulu. Located in an elegant boutique hotel, this upscale restaurant offers a fusion of Southeast Asian and international cuisines, complemented by an extensive wine list. The opulent ambiance and impeccable service create a perfect end to your weekend.

  • Portland Head Light: Free, 1-2 hours
  • Spa treatment at Inn by the Sea: $150-300 per person, 2-3 hours
  • Maine Maritime Museum: $15-20 per person, 2-3 hours
  • Lobster boat tour: $100-200 per person, 2-3 hours
  • Dinner at Tempo Dulu: $100-150 per person, 2-3 hours

Hidden Gems and Local Favorites

For a luxurious twist away from the usual tourist spots, consider visiting the Portland Hunt & Alpine Club. This upscale cocktail bar combines Scandinavian design with craft cocktails, offering a cozy and sophisticated atmosphere.

If you're a wine enthusiast, make sure to pay a visit to The Wine Bar. With an impressive selection of wines from around the world, this chic bar provides an enjoyable wine tasting experience accompanied by delicious small plates.

For a unique shopping experience, head to the Treehouse Toys boutique. This upscale toy store offers a carefully curated selection of toys, games, and collectibles that appeal to both children and adults alike, making it a great place to find luxury gifts.

Lastly, indulge in a pampering spa day at The Spa at The Press Hotel. This boutique hotel boasts a tranquil spa offering a range of luxurious treatments that will leave you feeling rejuvenated and relaxed.

For hotel and flight prices, check here.

0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version