Destination
8 weekend itineraries available
Galena, Illinois pulls in everyone from couples craving a romantic reset to friend groups after something more adventurous, and we've mapped out 8 different itineraries to prove it works for all of them. Solo travellers and families both show up in the mix too, which says something about how flexible a weekend here can be depending on who you're bringing along and what pace you're after.
Budgets span the full range, from super budget to luxury, so the trip reshapes itself around what you want to spend rather than forcing one experience on everyone. The themes running through these plans, foodie, wellness, relaxing, off-the-beaten-path, nature, give a sense of the variety on offer. Most trips are built for a quick run from Chicago, making it an easy weekend escape without much planning overhead.
Aug 7 – Aug 9· 2 nights
from Chicago, Illinois, United StatesJul 10 – Jul 12· 2 nights
from ChicagoInterests: Travel personality: The Curious Drifter. Remoteness: 7/10. Pace: fast. Accommodation: wild. Loves: coastal, road-trip, hidden-gems, local-food, scenic-drives, off-the-beaten-path, small-crew. Avoid: all-inclusive, tourist-trail, guided-tours, resort.
Jul 10 – Jul 12· 2 nights
from ChicagoInterests: Travel personality: The Curious Drifter. Remoteness: 7/10. Pace: fast. Accommodation: wild. Loves: coastal, road-trip, hidden-gems, local-food, scenic-drives, off-the-beaten-path, small-crew. Avoid: all-inclusive, tourist-trail, guided-tours, resort.
Jul 17 – Jul 19· 2 nights
from ChicagoInterests: Travel personality: The Curious Drifter. Remoteness: 7/10. Pace: fast. Accommodation: wild. Loves: coastal, road-trip, hidden-gems, local-food, scenic-drives, off-the-beaten-path, small-crew. Avoid: all-inclusive, tourist-trail, guided-tours, resort.
Interests: Travel personality: The Quiet Drifter. Remoteness: 7/10. Pace: medium. Accommodation: wild. Loves: coastal, scenic-drives, local-food, golden-hour, off-the-beaten-path, quiet-villages, photography. Avoid: group-tours, all-inclusive, nightlife.
May 29 – May 31· 2 nights
from ChicagoInterests: Travel personality: The Solitary Drifter. Loves: coastal, wild-camping, off-grid, cliffs, solitude, fire-pits, local-food, spontaneous-routes. Avoid: group-tours, city-breaks.
May 8 – May 10· 2 nights
from Chicago