Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Why travelers choose Greetwell

Curated by our team

Every experience is hand selected and approved by Greetwell.

Personal concierge

Real humans available to help before, during, and after your booking.

Intimate & authentic

Including unique in-home experiences you won't find anywhere else.

Easy booking & cancellation

Reserve in minutes with free cancellation on most experiences.

Greetwell

Experiences that stay with you long after the trip

Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

About

  • Our Story
  • For Experience Providers
  • For Hospitality Partners
  • For Developers

Resources

  • Travel Guides
  • Destinations
  • Categories
  • Experience Gift Cards
  • Help Center
[email protected]1-877-GREET-WELL

Safe & Secure Payments

© 2026 Greetwell, Inc. All rights reserved.
Privacy PolicyTerms
Free Concierge Service
Text or call 1-877-GREET-WELL
Ask AIAI
Ask AIAI
Best results for

Sailing in Yarmouth, ME

Showing 1-24 of 24 results
Sailing Charter on Casco Bay Aboard 36' Sailboat

Sailing Charter on Casco Bay Aboard 36' Sailboat

Enjoy a private sail aboard Endurance with views of Casco Bay’s islands and lighthouses

$89/ person
Custom Private Sailing Charter in Boothbay Harbor

Custom Private Sailing Charter in Boothbay Harbor

Make your time on the water your own

$558& up
2-6 Hour Sailing Cruise in South Portland

2-6 Hour Sailing Cruise in South Portland

Celebrate or unwind aboard Endurance on a custom sail

$500& up
Private Sunset Sailing Charter in Boothbay Harbor

Private Sunset Sailing Charter in Boothbay Harbor

Unwind on the water as evening settles over the coast

$558
Sunset Sailing Cruise in Casco Bay

Sunset Sailing Cruise in Casco Bay

Sail Casco Bay at sunset past islands, lighthouses, and local wildlife

$100/ person
Private Full-Day Island & Cove Sailing Charter in Boothbay Harbor

Private Full-Day Island & Cove Sailing Charter in Boothbay Harbor

More time to sail, relax, and explore the Maine coast

$1,115
Private Half-Day Sailing Charter in Boothbay Harbor

Private Half-Day Sailing Charter in Boothbay Harbor

See Maine's lighthouses and islands from the water

$558
Wednesday Night Sunset Cruise With Live Music

Wednesday Night Sunset Cruise With Live Music

Sail Casco Bay at sunset with live music and a BYOB vibe

4.9 • 160 reviews
$48/ person
Private Sailing Charter on Saco Bay, Maine

Private Sailing Charter on Saco Bay, Maine

Reserve the boat for an intimate Maine coast sail with your own group

5.0 • 453 reviews
$694& up
Portland Harbor 2-Hour Sailing Cruise

Portland Harbor 2-Hour Sailing Cruise

Sail Portland Harbor with your own snacks and drinks

5.0 • 162 reviews
$90/ person
Schooner Sail Past Burnt Island Light in Boothbay Harbor

Schooner Sail Past Burnt Island Light in Boothbay Harbor

Help sail Boothbay Harbor’s oldest windjammer

4.9 • 181 reviews
$64/ person
Sail Boothbay Harbor on a 1.5-Hour Guided Cruise

Sail Boothbay Harbor on a 1.5-Hour Guided Cruise

Sail Boothbay Harbor aboard the Friendship Sloop Bay Lady on a 1.5-hour trip

4.7 • 190 reviews
$45/ person
2-Hour Sailing Lesson in Saco

2-Hour Sailing Lesson in Saco

Build confidence on the water with a lesson shaped around your goals

5.0 • 453 reviews
$801& up
Portland Sunset Sailing Cruise

Portland Sunset Sailing Cruise

Sail Portland Harbor at golden hour with room for your favorite snacks and drinks

5.0 • 162 reviews
$101/ person
Classic Schooner Sail in Boothbay Harbor

Classic Schooner Sail in Boothbay Harbor

Take in Maine’s rugged coastline with open views from every seat

4.9 • 181 reviews
$58/ person
Private Sailing Tour of Wood Island Lighthouse

Private Sailing Tour of Wood Island Lighthouse

Sail Saco Bay and tour Wood Island Lighthouse from tower to Keeper's House

5.0 • 453 reviews
$1,707& up
Sunset Schooner Sail in Boothbay Harbor

Sunset Schooner Sail in Boothbay Harbor

Take in Maine's rugged coast with 360-degree views from your seat

4.9 • 181 reviews
$74/ person
Private Sailing Charter on Saco Bay, Maine

Private Sailing Charter on Saco Bay, Maine

Sail the Saco River and Maine coast on your own private boat

5.0 • 453 reviews
$941& up
Boothbay Harbor Sunset Schooner Sail Past Burnt Island Light

Boothbay Harbor Sunset Schooner Sail Past Burnt Island Light

Take in Maine's rocky coast with 360-degree views from your seat

4.9 • 181 reviews
$74/ person
Sunset Sailing Charter in Kennebunkport

Sunset Sailing Charter in Kennebunkport

A private evening sail with ocean sunset views

5.0 • 453 reviews
$801/ boat
4-Hour Sailing Lesson in Saco

4-Hour Sailing Lesson in Saco

Build sailing confidence with a lesson tailored to your experience and goals

5.0 • 453 reviews
$1,279& up
Private 6-Hour Sailing Charter in Saco

Private 6-Hour Sailing Charter in Saco

More time to explore the Saco Bay coastline by private sailboat

5.0 • 453 reviews
$1,921& up
4-Hour Sailing Charter in Saco Bay

4-Hour Sailing Charter in Saco Bay

Sail Saco Bay with island, river, and coastal route options

5.0 • 453 reviews
$1,172& up
Private Sunset Sail in Kennebunkport

Private Sunset Sail in Kennebunkport

Set sail for an extended evening on the ocean

5.0 • 453 reviews
$1,493& up
Yarmouth Things To Do
SailingBoat Tours50Kayaking Tours14Bike Rentals8Brewery Tours6
More
  • Ghost and Haunted6
  • Yacht Charters6
  • Bike Tours5
  • Dinner Cruises5
  • Escape Games5
  • Historical Tours5
  • Boat Rentals4
  • Equipment Rental4
  • Fishing Charters4
Food Tastings
4
  • Food Tours3
  • Speed Boating3
  • Trolley Tours3
  • Zip Lining3